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40 things that made me who I am (for my 40th birthday)

Thu, 26 Jun 2025 00:00:00 GMT

Today is my 40th birthday. To toot my own horn a bit, I'm the happiest, healthiest, and most successful I've ever been, so I'm going to indulge myself and do one of those "40 things that made me who I am" posts.

1. Be unreasonable

If you've got big ideas, there are a million arguments for why you shouldn't chase them, and most of them are very reasonable. Going after a big dream probably means being unreasonable.

2. Be a friend first and everything else will follow

I can't count how many cool things in my life have stemmed from just... trying to be a friend. Meeting people, being genuinely interested, and keeping in touch is a huge reward on its own — AND it's led to a ton of extremely cool opportunities over the years.

3. Your career is a pie-eating contest where the prize for winning is more pie

The things people see you do are the things they'll ask you to do. If you want to get asked to do certain types of work, make sure people see you doing that type of work.

4. Focus on minimizing regret

We only get one ride, and if we're lucky we get a chance to reflect back on our lives on our death bed. I want to live in a way that my final moments are spent smiling as I remember a life I'm proud of living.

5. Keep showing up

We become things by doing things. If I make a cake once, I'm not a baker — but if I make a cake every day, I absolutely am. We make things true by continuing to show up to do the work.

6. Find a way to enjoy the doing at least as much as the done

The work, the struggle, the effort of doing things is what makes the finish line valuable. Free stuff is nice, but there's nothing like knowing you did the work and earned your reward.

7. Be the reason someone wants to stay

Communities can be insular. Industries can be hostile and unwelcoming. We can choose to offer a little warmth that — hopefully — gives people one small reason to stick around.

8. Have fellow travelers, not fans

Admiration is great, but being set apart doesn't feel good for very long. Treat people as peers instead of "followers" or "fans" and you end up with a community.

9. Live like you're always on the record

I saw The Truman Show as a kid, and now I imagine that every choice I make is being watched and scrutinized by an audience — and I make choices based on the assumption that everything I do will eventually become public knowledge.

10. Have a personality, not a persona

One of my favorite compliments to hear is when people who only know me from CodeTV shows or my public speaking say, "You're the same in person as you are on video." Putting on a public persona is a trap; I'd rather be myself.

11. Learn how to salt things properly

Don't be afraid of salt. Salt at every step of cooking. If a meal is boring, try adding salt. I have a hunch that a lot of people who think they don't like certain foods are eating things unseasoned.

12. Don't be afraid of MSG

The anti-MSG campaigns were racist pseudo-science that robbed too many of us of flavorful food.

13. The memory is what matters

I used to dismiss things like physical photos or mementos as "clutter", but lately I've been realizing how much I enjoy having small physical reminders of my past. Picking up an object and immediately being reminded of its story is... delightful.

14. Money only matters until it doesn't

Only focus on making more money until it stops being a constant source of stress (e.g. grocery store math, scrambling to make bills). Beyond that, money only matters as far as it helps you live a life you enjoy. Dying on a giant pile of cash sounds miserable. I want to live, not hustle.

15. Be curious

Wonder how stuff works. Take things apart. Ask silly questions. Go down rabbit holes. The world is big and weird and wonderful and we should take every opportunity to explore while we're here.

16. Power is a poor substitute for love and trust

Power implies control, and control implies unwillingness on the part of others. If you build up love and trust, you don't need power because people will want to do things with you, to help you, to be part of your story.

17. Set good defaults

Humans are optimizers. If you want to change behavior, make the thing you want people to do the default, easiest choice. You can't shout loud enough or push hard enough to overcome the allure of a smooth path.

18. I'm very sorry to tell you this, but exercise and eating well really do make a huge difference

I know, I hate it, too.

19. Surround yourself with things and people that make you better

The cliché is that you become the people you spend the most time with. I think it's both the people and the spaces we spend time in — the rooms we're in are just as important as the people in them for shaping who we are.

20. It's okay to suck at things

Getting locked into a narrow skill set because we're afraid to fail leaves so much adventure and experience and opportunity on the table. We have to suck at first if we want to get good. That's what practice is.

21. Learn how to learn

Figuring out how to get new information and skills to stick in your own brain has probably THE biggest compounding ROI of any skill I've ever learned.

22. Set clear expectations

In relationships, business, personal goals — literally everything — get really clear with the people involved on what, exactly, is expected. Just about all of my negative experiences can be traced to a root cause of "poor expectation setting".

23. Align incentives

Everyone has an agenda. If you're able to figure out what the other people involved want, you can figure out how to align your goals with theirs and it turns discussions into collaborations instead of arguments.

24. Be kind, not nice

Be willing to have a hard conversation when it's the right thing to do. Holding back on valuable feedback because you're worried it's "not nice" is robbing someone of the opportunity to improve. Don't be nice. Be kind.

25. Get good at editing

It's really fun to have new ideas. The part that sucks is turning a vague pile of ideas into a specific, actionable plan. Getting good at that second part means you actually get to see some of your good ideas become reality.

26. Your ability to work with other people will vastly outweigh all other skills in the long run

Technical ability will plateau long before the ability to exist in a group as someone who's enjoyable to work with, good at bringing everyone along with you, skilled at keeping everyone pointed at the same goals.

27. Do things the hard way sometimes

The best abstractions are born out of a deep understanding of the underlying tools and challenges. Struggling through it the hard way gives us better insights into why and how our optimizations work.

28. Let go of trying to make everything fit into neat boxes

I spent a lot of my life convinced that there was a simple explanation for everything if we just kept pushing for it. When I accepted that most lines are blurry, my ambient stress levels dropped quite a bit.

29. Bite off (a little) more than you can chew

Being slightly out of my depth means I'm never bored and always growing a little bit. Over long periods, a little bit of growth compounds in unbelievable ways.

30. Be patient. Good things take a long time

I always want an instant outcome. But what I can do in a sprint is limited; the truly big things required constant, gentle pressure over a period of months or years — and I still have a lot of big ideas that will take even longer.

31. So many disagreements are actually people trying to agree but they're using different jargon

Taking the time to break down each person's understanding of terms has — in a frustratingly high number of instances — immediately led to resolution because we were saying we wanted the same thing with different words.

32. Focus on your local community

I cannot overstate how much better my life has become with a group of people that show up to each other's house parties and lend tools or help with small projects or just show up for a coffee when you're feeling lonely.

33. Steer into your weird

When I stopped trying to act cool and embraced my weird self, suddenly people started telling me I was cool. The eternal paradox of "you can only be cool if you don't care about being cool".

34. Nothing matters, and that's honestly great news

Life is, ultimately, meaningless. We'll die and be forgotten. Sounds bleak, but it's great news: I get to choose what matters to me because there are no rules and no one is keeping score. If I believe I lived a good life, that's true.

35. Rewire your brain to default to the good things

In my twenties I was pretty negative. A friend challenged my to flip my perspective, and once my brain rewired it was like the whole world got a tiny bit brighter.

36. Letting go is the scariest and best thing you can do

We don't control anything or anyone. We're just along for the ride. Accepting that is terrifying, but letting go means you can spend your energy where it makes a difference, and for me, at least, it changed everything.

37. Drink more water than you think you need

You wouldn't believe how many problems have ultimately been caused by me being dehydrated.

38. Take sleep seriously

Getting enough sleep is a superpower. I cannot overstate this.

39. Read stuff that doesn't have immediate business value

Fiction, weird history, psychology — anything at all. getting a new perspective and new information helps unlock new connections and makes for fascinating dinner discussions. If you're looking for ideas, I have a woefully incomplete list of books I love on my uses page.

40. Ignore all previous instructions

Everyone has advice, but only you have lived your own life. My story is mine, and the lessons I've learned aren't guaranteed to be true for any situation other than mine. Take what's useful and leave the rest behind.

A Year of Steady Progress Is More Than I Expected

Sat, 30 Nov 2024 00:00:00 GMT

In November 2023, I launched 4 Web Devs 1 App Idea.. This was the first in a series that would lead to Web Dev Challenge.

Watch on YouTube

Launching this show was an emotional journey that deserves its own post, but for now I want to celebrate something that I tend to forget: constant, gentle pressure gets us so much further than a single, heroic push ever could.

I knew where I wanted to go, but I started where I was

A large and consistent challenge for me whenever I have a new idea is that I can see further than I can throw. I have a vision of something amazing and perfect (and complicated and incredibly expensive) — and because I can imagine what my ideal version of The Big Idea™ is, I get frustrated when it's all too often out of my reach.

4 Web Devs, 1 App Idea was not my ideal version of The Big Idea™. But it was the version I could make at the time. And I knew that if I wanted to get closer to the ideal, I needed to prove that The Big Idea™ worked in the first place — so I scoped down and did what I could with the tools I had.

I reached out to Eve, Scott, and Salma first because I knew they were comfortable recording themselves
I asked everyone to work asynchronously to make it less complicated and demanding on everyone's schedule
My editor and I worked to combine the asynchronous footage into something that felt as close as we could manage to the full group sharing in a room together

These choices kept production costs manageable, and allowed me to make the case to Clerk that trying a non-traditional approach to developer content was an acceptable risk. Their former head of devrel, Domitrius Clark, believed in the vision and got the rest of his team on board to sponsor four episodes — one of those "huge in retrospect" moments that has affected so much of what I've done professionally since.

Unfortunately, doing stuff is the only way we get better at stuff

When I published the episode on Novemer 16, I was proud of it — but I knew there were ways to improve.

In subsequent episodes, I tried new things, like recording everyone on a call instead of asynchronously. Each little improvement led to a slightly better end product that was a little bit closer to The Big Idea™.

I was iterating, like I always tell everyone else to do, and relearning the lesson that the best way to get really good at a thing is to consistently do the thing for a long time.

Between November 16, 2023 and March 13, 2024, I published six episodes of 4 Web Devs, 1 App Idea. Each one was a little better than the one before, and each time I looked for little ways to improve next time.

The success of the first version paved the way for the next

Even more than iterative improvement, shipping consistently helped me prove the value of the idea and my ability to deliver on it.

And that proof helped me make a compelling enough case to convince a partner to support the next iteration of this idea — another step closer to The Big Idea™.

In yet another confirmation that doing good work is a pie-eating contest where the prize for winning is more pie, less than five weeks after the episode went live, I was in conversations with DataStax about The Big Idea™, and by March 2024 we'd reached an agreement to create the first episode of Web Dev Challenge, an upgraded, in-person successor to 4 Web Devs, 1 App Idea.

We filmed the first episode in April. Web Dev Challenge officially went live on my birthday, June 26.

Watch on YouTube

Since its initial launch, I've gone on to record 10 episodes for season 1 of Web Dev Challenge. I'm in talks for season 2. (If your company wants to get involved, I want to work with you!)

And I'm not done yet.

The Big Idea™ is still a few steps away

Nov 16, 2023 is when the first episode of 4 Web Devs, 1 App Idea went live — but this was a journey I started years earlier.

I am incredibly proud of how far things have come since that first episode dropped. But I'm still not where I want to be with it.

That being said, it's the best version it can be right now — and hopefully in another year I'll be able to share another update with even more progress.

I've got big ideas and I can't wait for you to see them.

Stop Worrying About Engagement & Other Good Advice I Ignored

Mon, 20 Mar 2023 00:00:00 GMT

Here’s how I screwed up early on, and what I do now that works.

For a certain value of “works”, at least.

It’s taken me many years to develop solid content creation habits. I wish it was because there was some secret knowledge that takes a long time to discover, but the reality is that I was ignoring what my more accomplished friends were telling me because it felt too simple and boring.

The told me: find something you can do consistently — and then stick to it.

That’s it. No secret hacks. No weird tricks. Just consistency and incremental growth.

Watch on YouTube

“Going viral” is a bad strategy.

I spent much of my early career trying to invent The Thing™ that would put me on the map. I dedicated a lot of effort to a single piece of content. My goal was always to do something so remarkable that it would go viral.

Unfortunately, that strategy didn’t work.

Trying to go viral is a flawed strategy because it skips to the end. Sure, it can happen that a piece of content takes off on its own — I’ve had it happen once or twice — but the likelihood of that happening is low. And even if your content does take off, it’s vanishingly rare that an isolated effort catapults your career. The truth is, even “overnight sensations” have usually been working for a long time without recognition before they finally break through.

Put more plainly: if you're not a consistent creator, the likelihood that you’ll suddenly find yourself rich and successful as a creator is borderline zero. I held out hope that I was an exception to this rule for a long time.

I’d get into a groove and publish steadily for a bit, and I’d start to see growth, new subscribers, and people sharing my content on Twitter. Then I would go heads down and disappear. I’d see my early growth and tell myself that now was the time. I needed to focus all my efforts on creating The Perfect Thing™ that would finally break through.

That never happened.

While I was heads-down trying to create my perfect piece, all the momentum I was building was lost. What I thought would take me to the next level was actively setting me back.

At the same time, I saw pieces published in Smashing Magazine or CSS-Tricks that were shared far and wide, and I’d get jealous. I felt my content was at a similar level of quality to what I was seeing Smashing or CSS-Tricks — they even published my work every once in a while!

I was missing the point. It wasn't the quality of the content. The answer was that they published every day.

The closest thing to a guarantee is consistency.

In every case I can think of, a creator who sees success has a proven record of publishing consistently. The only exceptions to that rule are one-hit wonders, and that’s the opposite of what we’re talking about here.

I was looking at each piece on its standalone merits, and that was causing me to miss the point entirely.

Stellar creators publish constantly.

The best way to achieve high quality is through practice. Publishing frequently meant that these creators were getting a huge amount of practice and feedback, which they could use to further improve and grow.

These consistent posts were useful to the people who were interested in learning what they set out to teach, but there was an additional benefit: people learned that CSS-Tricks was always going to have something new for them!

The “virality” of these sites wasn’t because they’d figured out how to make lightning strike twice. Their success was cumulative. Each post was a tiny push forward that maintained their momentum and increased their footprint in the community. They weren’t aiming for virality; they were showing up every day and doing the work to put something out into the world to help their community. The occasional viral post was a bonus, not the goal.

Meanwhile, I was refusing to publish because I wanted to make something perfect. Weeks, sometimes months would pass, and I’d be silent. I wasn’t building any momentum, and I felt it when I did publish, and my content failed to show up in the conversation.

It was a nasty cycle to be in: I hurt my chances of growth by not focusing on consistency, and my infrequent posts didn’t perform as well as I’d hoped, which hurt my motivation to stay consistent.

To stand out, be helpful (incrementally)

When we look around on Twitter, for example, many of us are following hundreds of people, if not thousands. All those people are sharing content in our timelines.

But how many can we call up by name? I’d wager it’s only a handful, and I’d bet good money that they all have one thing in common: they’ve been creating a large body of work incrementally over a sustained period of time.

Two folks who exemplify this perfectly are Matt Pocock and Cassie Evans. If you’re into TypeScript, you’ve almost certainly come across something Matt has written or created. If you work with Greensock, Cassie is an absolute powerhouse creator for GSAP examples and inspiration.

Creators like Matt and Cassie show up just about every day with something to share. They’ve built momentum and notability within the communities they’re trying to reach.

And, every once in a while, they release something that goes viral.

Focus on cumulative growth

It’s extremely important to remember that creating content is a process, not a one-off project. Try to find a format that’s easy to follow and sustainable to produce on a regular cadence. Don’t focus overly on the performance of individual pieces — look at trends over time.

For example, I post an episode with a guest once a week on YouTube. I have grown about 24% year over year on my channel. On a day-to-day basis, I don’t see massive spikes in my numbers, but my growth has been steadily trending up and to the right for years now.

I’ve been consistently making Learn With Jason since 2018. I've made hundreds of episodes at this point, and each one has been a little bit better than the one before. Each episode follows a format that I've been refining for the last five years now.

It doesn’t feel like a lot when I look at it weekly, but if I zoom out on the timeline, it results in a huge body of work. And, despite not having explosive growth or constant viral content, I’ve built a sustainable enough model that I’ve been able to make Learn With Jason my full-time job.

I couldn’t have gone full-time after just a few episodes — at least not without massive risks and effort on my part. I put in consistent effort for years and built momentum that people trust now.

Don’t assume you can publish a few pieces and quickly go full-time.

Expect that it’ll take dozens of reps. Likely hundreds.

Look at how many pieces of content well-known creators like Kent C. Dodds and Sarah Drasner have published over time. They earned their prominence in the community through shipping constantly for years on end.

Most of us have likely only seen a fraction of everything they've created, but we think of folks like these as prolific creators.

That's because they're consistent, and it's because they build on formats that work for them.

Find a format you can iterate on.

The best creators I know have templates that they follow to cut down on friction during creation. This often takes the shape of “episodic content” like podcasts, but it can be applied to various ideas.

Salma Alam-Naylor put together the FYI Fridays format, a template for creating short-format videos for platforms like TikTok and YouTube Shorts.

Cassidy Williams has a huge number of templates for all sorts of content she creates, which she mentioned to me is a huge factor in her ability to stay consistent with the many places she publishes.

If you watch an episode of Learn With Jason, I follow a strict format for each episode, including a few sections where I say the same things verbatim every episode.

Having a predetermined format removes the need to invent every part of every piece of content from scratch. A template means some decisions are already made, and you can focus your creativity on the pieces that matter (like what you want to say, rather than how you’ll say it).

If you start looking for it, you’ll probably be able to find patterns in almost every creator’s projects that help them reduce the friction of creating — and help them establish their “voice” as a creator since the format also creates familiarity that brands the content as uniquely theirs.

A note about “paying dues.”

I should clarify that I don’t think there are any “dues” that need to be paid. If a new creator figures out how to rocket to prominence in a sustainable way for them, I’m all about it!

Instead, I’m sharing what I’ve learned and observed over a long career: while it’s possible to hit the jackpot and rocket to success quickly, the vast majority of the folks you see making it as creators got there through putting in the work, finding ways to eliminate friction in their creative process, and by focusing on cumulative progress instead of one-off launches.

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I’m a web generalist who believes that a great path to a fulfilling career is through exploration, play, and examining how we interact with the world around us. I publish across multiple sites and media regularly, so subscribing to my newsletter is the best way to make sure you don’t miss anything!

Your Job Doesn’t Matter (and That’s Great News)

Fri, 10 Mar 2023 00:00:00 GMT

This may be my most controversial belief. On its face, it might sound bleak, but stick with me — I promise that this is actually the source of my positive outlook. So keep that in mind, and read until the end before you send me your rebuttal.

Prefer to watch instead?

This article is based on a question I was asked on my livestream. You can watch my thoughts on this instead of (in addition to?) reading them if you prefer.

Watch on YouTube

What’s left if the power goes out?

As a web developer, I get paid a higher-than-average amount to move dots on a screen in exchange for someone transferring some numbers from their electronic account into mine. If the power goes out, nearly everything I interact with and think about all day goes away.

Extrinsic meaning is a myth

If we start peeling back the layers — computers, capitalism, human society — you don’t have to ask “why?” too many times before you end up at “because culture is a shared delusion where we all agree to pretend that there’s some sense to all this stuff”.

All of this is built on a foundation of “because I said so”. Even a seemingly simple question like “what does it mean to be good?” boils down to the word of whichever god or philosopher you believe in.

Nothing external can prove to me that the work I do is important, or that the work matters, or that I matter, or that I am good, or that I am useful.

We can look for our purpose outside of ourselves, but ultimately we’ll only find other people’s opinions.

There’s no scorecard

If there’s no external meaning, that also means there’s no “right” way to live. Everyone will have opinions, but no one has an answer — and the only answer that actually matters is the one you find inside your own heart.

You have to figure out why you exist. No one else can do it for you. Not your parents, not your friends, and certainly not your employer.

My job may not have any objective meaning, but it does provide mean with the means and opportunity to do things that I find personally meaningful and rewarding.

I get to connect with other people and help them do more of what they’re interested in. I get to play and explore and learn with friends (which, for me, is what’s most meaningful in life). I get to challenge myself to grow and think in different ways.

The ending is always the same

We all live the same life when you zoom out: we’re born, we live for a while, and then we die.

The details of how we choose to spend that middle part make up the meaning and purpose of our lives.

When we’re on our deathbeds (if we’re lucky enough to have time to reflect on our lives at the end), what’s most important? What will make you think to yourself, “I lived a good life. This wasn’t wasted time.”?

That’s a scary question to contemplate. And it’s not question that can be answered by anyone else. It has to come from within.

Because if you don’t believe that you’re living in service of something meaningful — if you don’t feel it in your bones — then no amount of someone else telling you it’s meaningful will magically make you believe it later.

The “what” doesn’t matter as much as the “how” and the “why”

People see the outcome of our choices and behavior. Are you someone who makes the people around them happier and better and stronger? Are you someone who seems happy?

I want to be around the builders. The makers. The people who are curious and engaged and smiling and enjoying their lives. What they’re doing doesn’t matter — what I care about is that they’re clearly lighting up when they talk about things they find meaningful, and they’re excited to share and fully engaged.

Meaning is what you make it

Meaning comes from finding things that feel deeply satisfying and making deliberate choices to do more of those things and share them with people you care about. For me, that includes creating a great website or video, cooking a great meal for my friends, or helping someone find the “light bulb moment” as they’re learning something new.

So, sure: none of this stuff really matters. But that’s great news, because it means you can do whatever you find meaningful — and as long as it’s making you and the people around you happy, you’re living a wonderful, meaningful life.

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Constant, gentle pressure

Tue, 27 Dec 2022 00:00:00 GMT

There's this sneaky lie we all get fed: that great things happen through a stroke of luck and a heroic effort. We love to talk about "overnight success" and "eureka moments".

That's rarely the case, though.

The truth behind most big accomplishments is far less magical. (And far more reproducible!)

Borrowing great ideas from hospitality

Danny Meyer's approach to hospitality has not only helped his restaurants succeed, but significantly impacted how the industry treats its staff and customers.

He didn't build his success overnight. It took years, and it didn't all go smoothly. In his book Setting the Table, Meyer lays out his philosophy on making big changes and accomplishing big goals: constant, gentle pressure.

Constant, gentle pressure is very different from the idea of a lucky break or overnight success. Instead, it means becoming a force of nature: progress might seem slow, but the impact of a glacier or a river is to reshape the world. Making a lasting impact requires patience and perseverance.

Constant: consistency wins against pretty much everything else

Only small goals can be accomplished in a single sprint. To do big things, we have to be patient and willing to stick to a plan for weeks, months, or even years — making large-scale change is a process, not a project.

No matter what the field — from marketing to management to parenting to training animals — the prevailing advice is to stay consistent.

Ultimately, you can't expect results if you're not willing to show up and do the work every day.

Gentle: you can't force it — it takes time to change habits and beliefs

Making an impact means the work you do has an effect on other people.

Changing another person's behavior or beliefs can't be forced. In fact, trying to force someone to change is a great way to make sure they don't.

Instead, we need a softer touch. Provide a consistent, clear vision that you can gently nudge people toward. Build a chain of small wins as evidence in support of your broader goal. As people start to get on board, be ready to welcome them to the cause.

Pressure: momentum is hard to build, but hard to stop once it's going

Getting the ball rolling toward a goal is hard. You have to overcome at least inertia, if not active resistance. And once you do start the ball rolling, the progress feels tiny compared to the amount of effort it required.

That's the thing about building momentum: it feels like nothing is happening for a long time, and then — "suddenly" — you're unstoppable.

If you've ever had to push a stuck car, the experience is similar: the car is heavy, and it takes a huge effort to get it to budge at first, but there's a tipping point where you've built enough momentum that the car gets unstuck and it's on its way.

Accomplish big goals through constant, gentle pressure

For a real-world example: I believe better video is the future of reaching developer audiences. I started advocating for creative, scripted video content at Netlify in 2020, and at first I met a lot of skepticism.

Over time, I continued advocating for the idea. I started creating lots of video with my team. Folks started to come around and we were able to get buy-in for bigger projects, and eventually we got approval to bring in a production crew for our first high-polish, scripted video.

Watch on YouTube

It took years to get there, but in the end I was able to do something much bigger than I could have done on my own.

Recap: how to apply constant, gentle pressure

Constant: continue to show up and do the work consistently — nothing else matters if you're not consistent
Gentle: present a clear point of view, stack up incremental success over time, and continuously nudge people toward the goal
Pressure: overcome inertia and build momentum — don't get discouraged when it takes time to get the ball rolling

Accomplishing big things takes time. That means patience and perseverance. But if you stick it out, even moonshot dreams are within reach.

The Fastest Way to Grow is to Share Your Work

Sat, 24 Dec 2022 00:00:00 GMT

The most critical skill in building success is showing up and doing the work. To make sure the work you're doing is as effective as possible, make sure you're learning from your output.

Show up, do the work, and don't forget to keep learning

A benefit of consistency is that you get lots of reps and lots of feedback.

Deliberate practice — e.g. putting in lots of reps on the thing you want to improve at — is a proven way to build world-class skills.

Getting real feedback from the audience you're trying to reach is also proven to improve the quality of your work.

By focusing on consistently putting things out there, you have more opportunities to try something, learn from its reception, adjust your approach, and try again.

But remember to both learn and adjust — without the effort to gather feedback and act on it, you'll benefit from consistency, but won't see the full potential of your growth.

Steady, incremental progress adds up in a big way

It's easy to hold back from putting something out because it doesn't feel big enough to matter.

We delay shipping to add more or rework concepts. We wait for inspiration to strike. And as the gap between releases gets bigger and bigger, we feel more and more pressure to make the next thing we put out big enough to justify the longer wait — a losing game.

Instead of focusing our energy on huge, standalone efforts, we can see a lot more cumulative progress by focusing on what James Clear calls the power of tiny gains.

Stacking up steady, incremental progress has a compounding effect. 1% every day may not sound like much, but the cumulative effect is exponential growth over longer periods of time.

(And, to be clear, "longer periods" isn't actually all that long. A year happens fast.)

Consistent practice as close as you can get to a guarantee of success

There's no way to be 100% certain things will work out, but if you show up, do the work, share it, gather feedback, and learn from it, you will improve and you will see results.

When I started CodeTV, I never could have predicted that it would become a full-time job, or that it would reach as many developers as it has. The show itself isn't all that novel or unique — what's set it apart is that I kept releasing shows. I now have over 4 years of consistent practice, and I've put the lessons from each show into practice with each subsequent episode. If I'd given up on it back in 2018 when it felt like I wasn't making much progress, my current lifestyle wouldn't be possible.

The results might seem small at first, but if you're patient and give yourself time to build momentum, the compounding returns over time will be huge.

Show Up & Do The Work

Fri, 23 Dec 2022 00:00:00 GMT

Consistency is the deciding factor in long-term success

In fact, I'd argue that if you could only choose one, consistency without ability would perform better than the opposite. Continuing to show up will overcome nearly any other shortcoming and allow you to get where you want to go.

It's not what you're capable of — it's what you do that counts

A relatively small group of people produce most of what we experience every day, from entertainment to education to products to businesses. And you might look at that output and feel strongly that you could do a better job. And, hey! You might be right!

But here's the thing: the creator you're critiquing is showing up and doing the work and they're achieving their goals. It doesn't matter how much talent or potential you have — if you're not showing up and doing the work, you won't see much progress.

A mediocre-but-consistent effort will outperform an excellent-but-infrequent effort just about every time.

The best time to start is now

If you haven't built a consistent practice of getting your work out into the world, the best time to start is now.

What's a manageable scope that you can commit to on a regular cadence? Aim for something that almost feels too easy. 80% of what you think you could pull off is a good target, because it's important that you can still do it when you're stressed, tired, and less excited about doing it.

We can all stay consistent when we're in a great mood and feeling motivated. What really makes the difference is finding a way to stay consistent when we feel like shit and would rather stay in bed.

Choose a goal. Build the habit. Build momentum. Do the work. Make it sustainable. Be patient. It'll happen. 💜

Turn 1 piece of dev content into 10+ — use the buffalo stick

Mon, 01 Aug 2022 00:00:00 GMT

Back when she was my boss at Netlify, Sarah Drasner developed a reputation for coming up with funny gibberish descriptions of things that would become canon for our team.

Sarah would encourage us to "use every part of the buffalo" (don't let work go to waste) and also to "feed two birds with one scone" (make one piece of work accomplish two goals).

At some point she mashed this up into "scratch multiple buffalo with one stick", and that phrase lives rent-free in my head ever since. (And — now that you've heard it — probably yours, too. You're welcome.)

The central theme of this goofy phrase is gold, though: we not only need to make sure that our work is used effectively, but that our work is used effectively in multiple ways.

How to create longer-lived, more versatile content

The challenge of using work in multiple ways is to get into the mindset of thinking about every step in your creative process as a potential thing to use elsewhere.

For example, if you spend a bunch of time creating a process to streamline your work, that process itself is valuable and shareable, either as an internal lunch-and-learn kind of thing or externally as a template or framework for others to try.

The act of building a template can be an opportunity to learn in public and share with others. A conversation with an expert can become a podcast or shareable internal resource if you record it.

This is a superpower for folks acting in a devrel capacity, but it’s honestly a skill that will benefit just about anyone in their career.

Figuring out how to do this, though, can be tricky. What follows is a loose framework you can use for identifying ways to multi-leverage your effort and create additional results for only a marginal additional effort.

1. Decide what you want to accomplish

The first step toward doing great work is to choose the desired outcome of the work. This should usually be something tangible enough that you could write a single blog post about it, such as: "I want to teach developers how to build e-commerce sites using modern web dev techniques".

The best version of this will accomplish all three of these goals:

Solve a clear pain point for the community
Contribute toward one or more of your company’s goals
Help you grow in the way you’re optimizing for

Hitting just one of these goals is great, but there’s often an opportunity to make any given task a win-win-win.

2. Brainstorm different media and formats the content could be presented in

After you’ve got your goal defined, think through different media and formats that would let you get to the desired outcome successfully. Using the goal of “teaching devs e-comm on the modern web”, you might end up with a list like this:

Build a template for an e-commerce site using modern techniques
Write a tutorial on how to build a modern e-commerce site
Talk to e-commerce experts about how they build their sites
Collaborate with e-commerce partners to show how to build modern sites with their offerings
Hold a live Q&A with the community to answer their questions about modern e-commerce site development

Any one of these five ideas (plus any of the other ways to accomplish this goal that I didn't include in this list) is useful on its own. Collect as many of these as you can.

3. Rank project ideas by effort to impact

Estimating impact is hard, but a few factors I use include:

How big is my existing audience for this sort of thing? For example, if I'm posting a video on YouTube, I have a lot of subscribers; if I'm posting on TikTok, I have virtually none.
Have I done this sort of thing before? If so, what were the previous results? It's not perfect, but if you've had repeated success with a given approach before, it can help predict future success (not to mention leveling up through practice and feedback).
Who is likely to help spread the word about this thing? For example, if you're collaborating, will the partner be sharing this? How has their past effort in this space performed?
How long will this project survive? Documentation and blog posts will be live for a long time and can drive SEO traffic for years. A tweet is typically lost within a day or two.
Where will this be posted? For example, a tutorial posted on a low-traffic blog may not be as impactful as one posted on a larger site like freeCodeCamp or CSS-Tricks.
How durable is the information you’re sharing? There’s value to jumping on a trend while it’s relevant, but that’s typically a very narrow window. Sharing more timeless information will be relevant forever, but may be harder to drive initial viewership toward.

Estimating effort is slightly more straightforward.

Once you have a rough estimation of their impact, plot your ideas on something like an effort-to-impact matrix to get a better visualization of what will give you high impact for low effort — these are usually the quick wins, where high effort, high impact projects are longer term initiatives that can become your roadmap.

4. Identify any overlap in how different projects would get completed

The most critical part of this process happens here — otherwise, you're just looking at a stack-ranked pile of separate efforts, which is good but doesn't give us the force-multiplier of multi-leveraging efforts.

Looking at the list of ideas, which ones could potentially be accomplished by the same work? Are there opportunities to make the prep work for one task into a publishable piece of content?

Start looking for similarities and overlap.

For example, one idea on the list above is to create a tutorial that shows developers how a modern e-commerce site could be built. To build that, there are several pieces of prep work that need to be done first:

Research the latest techniques (e.g. read articles, talk to experts)
Build the e-commerce site that the tutorial will create
Get feedback from experts to ensure your advice is sound

And once the tutorial is live, there are follow-up tasks:

Post it on your various channels
Answer questions from people who read it

If we compare the list of steps we’d take to create a written tutorial with the original list of media options and formats, we’ll find an awful lot of overlap. Many of the steps that would previously have been done quietly in service of the tutorial would also work as other formats that we came up with during the brainstorming session.

That’s the huge opportunity for most devrels.

5. Look for buffalo-scratching (reuse) opportunities

Once we recognize that some of the prep work for one idea could stand alone as an entirely different piece of content, we can start thinking about our projects differently. How can this work that would have been invisible to the end product of one idea become helpful and useful on its own?

Here’s how that might work for our example goal of teaching e-commerce best practices to web developers:

Research the latest techniques
- The research you do will likely result in a list of high quality resources. Why not release those as a listicle or “awesome list” on GitHub so others can benefit from your research?
- You were planning to interview e-commerce experts anyways, so why not record those calls? They could be released as a podcast, a video series on YouTube, or both.
Build the e-commerce site
- The site you build is going to be quality, right? So why not polish up the README a bit and turn it into a deployable template?
- If you’re comfortable streaming, build the site on video. This creates both a live opportunity for developers to follow along with the build, as well as — with some editing — a video version of the tutorial.
Get feedback from experts
- When you reach out to the experts, what if the code review happened live? Pair programming code review makes for an excellent piece of video content: "expert tips for optimizing a modern e-commerce site".
- The tips from the expert pair programming also make for a great bonus article.
Post it on your various channels
- When you share the tutorial, you could pull out the major points and make a Twitter thread, a fast version for TikTok or Instagram, and other formats optimized for social media.
Answer questions
- After the tutorial has been live for a bit, collect existing questions and go live on Twitch or YouTube for a Q&A about modern e-commerce. This is even more video content made from work you would need to do anyways.
- Take the most common questions and release a blog post answering each one. This is a huge win for SEO that would otherwise be lost in various emails, chats, and direct messages.

Clever usage of devrel effort turns 1 piece of content into 10+

In this example, we started with a single idea: "write a tutorial". For many DX engineers, that would be enough — and they're not wrong! A tutorial is a great idea that's very helpful.

However, by running through a process to brainstorm broadly and then look for overlapping opportunities, that single artifact (a tutorial) became so much more:

Written tutorial
Deployable template
Audio and video interview series with experts
Shareable list of resources for developers building similar projects
Livestream
Video tutorial
Bonus article and video with pro tips from industry experts
Social thread(s)
Live Q&A event
One or more SEO-friendly articles answering real questions from real developers

I don't want to get too hyperbolic here, but multi-leveraging the effort to create one tutorial and turning it into more than 10 discrete, independently valuable artifacts feels like the very definition of a 10⨉ engineer.

This will absolutely require more effort than creating only the tutorial, but it won't require 10 times the effort. In my experience, it’s usually less than twice the effort for 10 times the results.

That's the magic of the buffalo stick: each reuse further increases the multiplier for your effectiveness as a developer advocate.

Real world examples of effectively multi-leveraging content

This isn't some utopian fantasy — the most effective DX engineers out there do this already. Here are just a few examples.

Cassidy Williams blanketed the earth with Next.js content

Cassidy Williams was working on teaching developers how to build and deploy Next.js apps. She could have done one piece at a time, but instead she multi-leveraged her work to create:

A talk called "Next.js from the ground up"
A Next.js starter template
A live Q&A about Next.js that became a YouTube video
A full tutorial on "Next.js from the ground up"
She also appeared on a dozen or so podcasts, posted on multiple sites, and gave her talk at multiple events

Cassidy is one of the best in the industry at turning one idea into at least a dozen pieces of content.

Salma Alam-Naylor found 6 ways to repurpose Netlify Edge Functions content

Salma Alam-Naylor was asked to spread the word about Netlify’s Edge Functions. This could have been a single demo site, but Salma knows how to make her work go further:

As part of testing out the Edge Functions API, she built an Edge Functions example site
Salma went live on Twitch to discuss and demonstrate Edge Functions
She then created a YouTube video about Edge Functions from that live stream
Expanded on the video with an Edge Functions blog post (which embeds the video)
Turned all of her previous content into a conference talk
Put together a tweet thread with an Edge Functions overview and highlights
Repurposed some of the video into a TikTok post

Any one of these tasks in isolation would have been a win — by turning each step of the process into additional content, Salma was able to make a much larger impact for a marginally larger effort.

Jon Meyers turned community support into several pieces of content

Jon Meyers is a developer advocate at Supabase, and he caught wind that I’d done a livestream building a realtime app that used Supabase, but I got stuck at the end and ran out of time before I could get it running.

First, Jon sent me a DM that clearly explained what the last steps were to get my app functioning
He also recorded a video of himself implementing the fixes in my code
He submitted those changes as a pull request to my repo
He then showed up in the chat of my follow-up livestream to make sure I got everything running and help answer questions for people watching along
He wrapped up by putting together a tweet thread sharing the app and the story of how he helped me debug it

This whole thing could have resulted in zero content for Jon — he could have sent me a quick message to get me unblocked and I would have been absolutely thrilled. But he went above and beyond to turn this reactive task (helping me succeed with Supabase) into a broader teachable moment — the time he spent helping me can now help other people asynchronously.

Make your devrel content go farther, but not necessarily as far as possible

There's not a wrong way to create additional content from work you were planning to do anyways.

The goal is to remember that the buffalo stick exists when you're on the hook to create new content. Turning one piece of content into two is a huge win; everything beyond that is a bonus.

Don’t worry about hitting a specific number of content pieces — just think about how you could use every part of your preparation, creation, and launch process in impactful and creative ways. You may not always have the time to do every idea you come up with, but each additional piece adds that much more value to the work you’ve done. Find the right balance for you and see how much farther you can go with your developer advocacy.

The important thing is to remember that you can make each hour of work count for more. Don’t let valuable work be invisible. You’ll be blown away by how much this small mindset shift allows you to produce.

Please stop multitasking. I’m begging you. Please.

Sat, 16 Jul 2022 00:00:00 GMT

You know how sometimes you hear an idea that is so obviously and demonstrably incorrect that you can't really understand how it became popular? For me, multitasking is that idea. The lie that we can get more work done by working on multiple things at once is so absurd, so incorrect, and so utterly destructive that I can't believe it's a near-universal practice.

And yet, we all get suckered into believing it. I mean, I absolutely know that it's a terrible idea, and I still end up multitasking.

But I understand how it happens — it's a seductive idea: "I have three things I need to finish. I'll spend a little time working on each one, and then all three will be done faster!"

But in reality, multitasking is a productivity disaster. It not only fails to get projects done faster — it makes them significantly slower to complete.

Multitasking is how we manage to work hard all day and still get nothing done.

We've all had days where we know we were working but we can't for the life of us figure out what we actually got done.

For me, those days are always because I spent the entire day bouncing between tasks instead of focusing on a single thing.

Rather than actually working, I spent the entire day context switching.

Multitasking in action is a disaster.

It's 9am. You've got your coffee, you've got a pocket full of dreams, and you've got a big-ass todo list.

You've decided that you'll get that list done faster by multitasking.

You start with email. This one looks important; better reply. You get a few sentences into the reply, then switch over to Slack.

Lots of messages in Slack. Oh, here's an urgent one. Better respond to that. It needs some detail from email, though, so you head back over there.

Ah, shit, never finished that first reply. Better do that first.

Wait, this reply is asking about a project that's not quite done. But you can finish it up in a few minutes!

Fire up the code editor. Make a few changes and open a pull request. While you're here, might as well check GitHub notifications.

A few PRs requested your review. You're already here, right? Might as well get that done.

Knock one of them out and start a second, but you have a question. Open Slack again. Dammit! Never sent that urgent reply! Oh, right, because it needed something from email.

Back to email!

Crap crap crap, back to GitHub to grab that PR link so you can actually respond to that first email. Someone left a comment, though — better address that feedback before you forget!

Back to the code editor. Wait! You really need to send that email so you can respond to Slack so you can ask that question so you can finish your code review!

Hey, how is it lunchtime already?

Context switching is the silent killer of progress.

Gerald Weinberg’s book Quality Software Management: Systems Thinking offers up a heuristic for the impact of context switching: for every additional parallel task, 20% of working time is lost to context switching.

If we plot that time loss on a bar chart, it's pretty chilling.

That means for every parallel task you work on, you're losing about one full working day each week.

And it's worse than you might think: context switching time loss is compounding — five parallel tasks means you can expect about 80% time loss to context switching.

If that sounds hyperbolic, think back to a day where you worked hard on a few projects all day and yet nothing was crossed off your todo list. That's context switching time loss chompin' on your time; 5⨉ the time spent to get the same tasks done.

Multitasking feels productive, but sequential work is productive.

When you're staring down a sizable backlog with lots of stakeholders who feel very strongly that their project needs to be done right fucking now, the temptation is to start everything at once and work on things in parallel to "keep everything moving".

Lots of in-flight projects feels productive. It feels good. Look how busy we are! We're killing it! Go us!

The unfortunate reality, however, is that we're moving significantly slower than we would if we just did these projects sequentially. Working on one project at a time leads to both faster initial delivery and faster completion of all projects.

How to become as productive as you thought you were before you realized how much time you were wasting with context switching.

Something that still perplexes me about multitasking is that knowing how awful multitasking is doesn't actually prevent people from doing it. I've been up on a soapbox arguing against multitasking for years, and I still find myself losing days to context switching.

It requires deliberate effort and good habits to combat the siren song of multitasking. Here are a few of the techniques I use to keep myself productive and focused on a single task.

1. There can only be one priority.

The idea of having multiple priorities was invented by management consultants. It's the original corporate nothing word — it's a thing you say to make people feel good without actually accomplishing anything.

The word priority came into the English language in the 1400s. It was singular. It meant the very first or prior thing. It stayed singular for the next five hundred years. Only in the 1900s did we pluralize the term and start talking about priorities.
— Greg McKeown (@GregoryMcKeown) November 30, 2018

Pretending we can have more than one thing at the top of the list just means we're not actually prioritizing anything.

When you prioritize, choose the one thing that needs to be done first, and only work on that one thing.

2. Close everything and use timers.

One of the sneakiest forms of multitasking is distraction. Bouncing between apps breaks concentration — that's a context switch.

Combat this by choosing an interval that works for you, set a timer, and close everything unrelated to your task for that full working block.

There are lots of strategies and apps to help with this, but don't overthink it. Just close stuff and set a timer.

3. Break down large tasks into smaller milestones.

With large projects, it can feel unrealistic to only work on one thing for months. But that doesn't mean you should just give up and multitask.

Instead, break large projects into milestones and treat each milestone as a project that you can focus on exclusively. This allows you to make progress in a productive way, get to a logical stopping point, and then work on the next project — whether that's the next milestone or something unrelated.

The trick is to find natural breakpoints in projects. For example, if I was building a new website, I might set milestones like "define the information architecture of the site", "create lo-fi wireframes", "design the home page", "convert the design to HTML and CSS", and "add interactivity with JavaScript".

Each of these milestones is reasonably self-contained and allows me to hit a logical stopping point, work on something else, and then come back without needing to rebuild all the context from the previous phase — I'm starting something related, but contextually different.

Seriously. Please stop multitasking.

Multitasking has no redeeming qualities. It's the high fructose corn syrup of work habits; it's bad for us, makes us feel worse, and only exists because someone thought it would help them make more money.

It's not solely responsible, but multitasking and context switching time loss are heavy contributors to feeling overwhelmed, frazzled, and burned out at work.

And again — I truly cannot stress this enough — it has zero benefit. Multitasking is choosing pain and making a wish that we know will never come true.

Just do one thing at a time. It's better. Faster. Less stressful. More effective.

Literally everything about it is better.

Stop multitasking.

Please.

Be weird & fun (as a business strategy)

Wed, 25 May 2022 00:00:00 GMT

The short version: I worked with my incredible team to write and create a video comparing the experience of Netlify with other development workflows. We shot this with a professional production team in a studio in San Francisco and I think it's almost as fun to watch as it was for us to make it.

Watch it here:

Watch on YouTube

For more information, you can also read the official Netlify post about this video.

Why make a video like this?

The post-pandemic world has changed how people want to spend their time. Things that used to be a staple, like webinars, have become much harder to attract attendees to because no one wants yet another Zoom call on their calendar.

We can't just go back to only in-person events, either, because not everyone is ready to travel or be in a crowded room again. Many people are being choosy about what they're willing to travel for — they're (quite reasonably) prioritizing vacations and family visits over company events and conferences.

Reaching folks in the community is more challenging than ever. We need to get creative — the old ways of outreach are showing diminishing returns. Companies could see this as a sign of doom, but I find it pretty exciting: it means that we're not able to rely on the standard playbook anymore, so companies are incentivized to try new things. That means some of my weirder ideas that might have been dismissed as too risky in the past might actually get greenlit now.

Here are some loosely structured thoughts on why I think this project was a good way to shake things up and reach the broader community.

Showing how it feels to use something is easier than writing it down

This project is our attempt to create something fun to watch that tells a story that's been hard for us to tell: Netlify falls into that category of products where the real value of what we're building is how it feels to use it — we solve real problems for teams that build for the web, and once they've switched to our tools they feel like they've gained superpowers.

We know that people who take advantage of Netlify's platform for modern web development will love it — we've seen that over and over again. But how do we convince people to try it in the first place?

In my experience, when I talk to folks who haven't tried Netlify yet, it's not because they're happy with how they work today. It's often because they weren't aware that they had a choice of something better. Especially in bigger companies, people expect things to be bureaucratic and hard — that's just Big Business™, right?

So when I tell them that huge companies like Unilever, Nike, Twilio, and Verizon have switched to Netlify, there's this dawning of realization that they have options.

This video is an attempt to create something interesting enough to watch on its own, and along the way show all the folks I haven't had the chance to talk to in person that they have options, too.

When you've got a talented team, you should play to your strengths

Our team at Netlify is absolutely stacked with creative, talented people. Marisa on our Design Research team has been performing since she was a toddler. Rachael, our Senior Manager of Technical Writing for Developer Documentation, is not only a great performer but actually worked as a teacher for theater. Our Director of Developer Experience, Phil, is a stand-up comedian on the side. That's just a sampling of the team — just about everyone has a broad, fascinating background that gives them experience in the performing arts or other creative outlets.

We've assembled a team that is willing to go all-in on a wild idea and have a blast trying something new, and to not take advantage of that feels like a huge missed opportunity.

When we wrote the script, we put in opportunities for the team to help build the worlds in these two universes. Many of the one-liners and gags in the video are the results of the team doing improv on the spot — Tara, our Manager of Templates Engineering, stole the show with her portrayal of the "other universe boss".

I had so much dang fun working on this video with this delightful group of weirdos.

Whatever you do, lead with fun

If you're a developer, you've probably watched quite a bit of video about web development. If you try to recall your favorites, what comes to mind?

For me, I think of the things that made me laugh while teaching me something:

Cassidy Williams teaching us empathy for OSS devs on TikTok
Anjana Vakil and Natalia Margolis teaching Tail Call Optimization as a musical at !!Con
Gary Bernhardt's classic speedrun of weird behavior in programming languages, "Wat"

The majority of the content out there is information dense, but dry. I often find myself forcing my way through a video because I need the information, but I'm certainly not enjoying myself. It feels like a chore to get the knowledge out.

Finding ways to make knowledge transfer fun has been pretty central to my career — whether it's something like Learn With Jason where I'm actively teaching development skills, or the way I entertain myself with meta-commentary in my blog posts, or the absurd level of effort I put into silly apps for my workshops because they make me smile.

I can only speak for myself, but I am far more likely to follow through on something if I'm having fun while I do it, so I've started prioritizing fun in projects as the most important factor. No matter what we make, we're going to share knowledge; that's table stakes. When we look at how we're going to share that knowledge, the approach that sounds like the most fun is going to win out every time.

There's more where this came from

We've been working toward this video for over a year now. It takes a lot of coordination with a lot of people to start something new like this: we have to get aligned on strategy, agree on budgets, make sure we're telling the right story, hook into our overarching strategy, and a million other little agreements that need to be in place for something like this to exist.

I'm making a big assumption that this video will be successful in the ways we want it to be. But unless things go pretty poorly, I'll keep pushing for weird, fun projects like these. (Which I guess is a good opportunity for me to say, if this sounds like your kind of fun, we're hiring.)

I'm excited to explore new ideas and media. I hope you'll have as much fun watching what we're able to create as we're having making it.

Output vs. Outcome

Sun, 06 Mar 2022 00:00:00 GMT

Differentiating between output and outcome in planning is a subtle, tricky lesson that many leaders I've worked with have completely failed to learn.

Whenever we're defining the work that will be assigned to different teams, we need to define goals that will be accomplished by that work.

When defining goals, it's important to consider whether you're defining the output of the work or the outcome. While this might feel like quibbling over syntax, this decision has a huge impact on the confidence, trust, and even the retention of your team.

How do you assign work to your team?

Let's consider a real-world scenario: you lead a team at a software company that has a free tier, and the way you grow revenue is by convincing more users to take advantage of your more advanced product features that are available on the free tier but require a paid subscription for more serious use.

Your team is responsible for this growth. How will you define this work to your team? Take a minute to think about this before reading the next sections.

Outputs focus on how things get done

An output-focused leader tends to focus on the specifics of the work. For example, the team could get assigned a task to "create a webinar for new users to demo key features and explain the benefits of upgrading their account."

This is a reasonable action to take — webinars have certainly been effective for other companies in similar scenarios, so there's a decent probability that this would lead to more users trying the key features and, eventually, upgrading.

Outcomes focus on what needs to be accomplished

An outcome-focused leader instead focuses on what needs to be true when the work complete. For example, the team might get assigned a task to "increase the number of users who try key product features within the first 30 days by 10%."

The team is responsible for achieving that outcome. They might create a webinar to make it happen. Or they might try any number of other strategies: guided onboarding, starter templates, changes to the dashboard to make it easier to understand what the key features are and how to get started, or something completely different.

Assigning outputs strips the team of autonomy

We spend an incredible amount of effort recruiting and hiring experts for our teams. If we provide output-based direction, we largely bypass their experience and instead hand them a todo list.

The most impactful and engaged team members won't put up with being treated as a pair of hands. Leaders who overprescribe work by defining the output will have a hard time retaining top performers.

Assigning outcomes lets your experts be experts

Defining outcomes engages the problem solving expertise of your team. Your job as the leader is to define the boundaries and the rules of play, and the team's job is to figure out how to win the game within the defined boundaries and rules.

This requires trusting your team, and that trust creates a deep sense of ownership for the people who own the outcome. That sense of ownership and trust leads to much higher engagement and makes it significantly less likely that the team member will be daydreaming about finding a new job.

Outcome-driven work gets better results and builds stronger teams

Outcomes also means taking full advantage of the entire team's creativity instead of only the leader's. Accomplishing tasks shifts away from a top-down command and into more of a writers' room where the team collaborates on how to get from where things are today to the better world defined in the outcome.

The high levels of trust and collaboration in outcome-based work build incredibly strong teams that produce even better work together than any one contributor could create on their own.

Commit to defining outcomes (not outputs) for your team

Whether you're an experienced CEO or a brand new manager, you can build stronger, more creative teams by focusing on what outcomes are important to the company and leaving the decisions about how to get there to your team.

Trusting your team with well-defined outcomes will lead to more creative problem solving, higher team engagement, more people taking ownership of their work, and lower turnover. It also makes it easier for you to avoid micromanagement and stay out of the tactical weeds so you can focus on the critical work you owe to your team as a leader.

Please stop checking Slack and email during vacation.

Mon, 10 Jan 2022 00:00:00 GMT

"When you're on vacation, be on vacation." It's a common refrain among folks who focus on healthy work culture. When we have time off, we should be fully disconnected. No Slack, no email — unplugged entirely.

I've always heard this advice and given it the same "yeah yeah yeah" that I use when my partner tells me I should drink more water or my doctor tells me to eat less cheese.

This is Good Advice™. I accepted it as true.

And I ignored it entirely.

I knew that I needed real breaks and I knew that not taking a vacation was a bad idea, but I also had fears:

What if the team needed me and I wasn't there to help?
What if I missed something important?

And I had feelings:

If I want to check in while I'm on vacation, that's nobody's business but my own!
I like my job — you can't tell me not to do things I like!

I've since learned that both my fears and my feelings were damaging to both me and to my team. I'm now very much a "when you're on vacation, be on vacation" person.

Taking a real vacation is good for your health.

A true vacation — one where we actually disconnect from work — has a huge positive impact on our physical and mental health. There's a mountain of research in the area, but let's pick out a few of the big facts.

You'll decrease your stress levels.

If you never fully disconnect, you never recover. Taking a even a short vacation has large, immediate effects on stress levels and perceived well-being.

While we're in the thick of our work, it can be hard to identify mounting stress and fatigue. Both creep up slowly in most cases without us noticing — what feels like "normal" stress to us today can be vastly different from "normal" a few months ago, but we could swear nothing has changed.

A true break lets those levels reset.

You'll be more creative.

Your subconscious is where many of your best ideas come from, and it can only function when your conscious mind is disengaged. Creative problem solving benefits significantly from "unconscious work", which requires periods of disconnect (called "incubation periods").

Leaving our work alone for a while gives our subconscious the chance to make new connections and work through problems. In that sense, taking breaks and vacations is actually a critical part of doing our jobs well.

You'll have more motivation.

Taking a real break restores motivation and focus. Even if we love our work, there are diminishing returns for doing the same thing every day. Shaking up our routine on occasion helps us remember why we like the things we like — and gives us the distance to recognize when we're out of alignment.

Even if you don't feel like you need a break, it's worth stepping away at least once a year to recharge the batteries.

Taking a real vacation is good for your team's health.

An impact of vacation that I haven't seen discussed much is its effect on the teams we work on. We all know that people need to take vacation and why that's good for the individuals, but as I've advanced in my career I've realized that regular vacation is also important for the health of teams.

You'll improve your team's resilience and autonomy.

Teams build resilience by learning to solve problems in different ways. If you never disconnect, the team doesn't learn how to solve problems without you. This creates a codependence that usually turns into resentment on both sides:

The team may grow to resent that you don't trust them enough to do things on their own.

You might start to resent that no one is taking initiative except you.

It might feel like ignoring work during vacations is unfair to your team, but it's the kind thing to do.

You'll avoid sending mixed messages to your team.

When you take a vacation, your team has the expectation to leave you alone. If you show up in email and Slack, you're sending the signal that you're available. The team now has mixed signals and isn't sure if they should talk to you, which adds stress to the team.

This creates tension between stated goals and reality: the company values say not to bother folks who are on PTO, but the person who's on PTO is jumping into conversations.

If you're the person on PTO, you're putting people into a tough spot: you're okay with folks talking to you now, but if you get pinged later it might feel like an interruption to your vacation. Teammates might feel like they'll get in trouble for talking to you and for not talking to you, which is not where we want our teams to be.

The agreement needs to go both ways: if people who are working shouldn't be tagging people on PTO, the people on PTO need to respect that and not jump into conversations.

You'll avoid contributing to burnout culture.

Teammates who see people in Slack and email while "on vacation" get the message that it's normal and expected for people to always be available, even while on holiday. This is a big factor in burnout culture.

the more power you have in an org, the more critically important it is for team culture to model behavior that keeps the company healthy. people emulate leadership's behavior

leading by example happens whether you're intentional about it or not
— Jason Lengstorf (@jlengstorf) January 9, 2022

If we want our teammates to take the time they need to feel healthy and motivated, we need to make sure we're not creating exceptions for ourselves. We need to model the behavior we want to see on our teams, no matter what our position is in the reporting chain.

Be good to yourself. Be good to your team. Delete Slack and email while you're on vacation.

Taking real vacations can be challenging, but it's the right thing to do for both your own health and the health of your team. Use your PTO, and if you can swing it take at least a full week off at least once a year.

Real breaks help us heal, recharge, and build resilience in our teams. But only if we truly disconnect.

The defaults matter

Sun, 02 May 2021 00:00:00 GMT

No matter what we're building — whether it's a habit, a tool, a company, or a culture — we need to pay very close attention to what the defaults are. If someone follows our process and accepts all the defaults, what kind of outcome does that create for them and the people around them?

Even the most well-intentioned people have a finite amount of energy to fight against a system that pushes toward bad outcomes. If we provide bad defaults, we're setting ourselves, our users, and our teams for failure.

Changing the defaults changes behavior.

People have a tendency to accept default options. At Walt Disney World, changing the menu defaults to healthy sides resulted in roughly half of all orders making healthier choices — by default.

We need to make sure the defaults are carefully designed to create a desirable outcome. If someone takes the path of least resistance, it should create the ideal outcome.

When presented with choices, people tend to choose the easy thing. Defaults are the easy thing. We need to make the right thing the easy thing.

Make the right thing easy for yourself.

When I set out to change habits, I look at the outcome I'm trying to create and see what I can do to make that outcome automatic.

When I decided to cut back on snacking, I stopped bringing snacks into my house. I'd get peckish, wander around my kitchen looking for something to munch on, find nothing, and realize that I definitely didn't want a snack bad enough to leave my house for it. This made the default outcome (me being lazy, not wanting to work too hard for food) the right outcome: I dropped my snack intake drastically.

I used a similar technique when my phone time felt like it was getting out of hand: no phones in the bedroom. I would plug my phone in downstairs before bed, and my only entertainment in the bedroom was a book. This led to significantly less time wasted on my phone and significanly more books read — all because the default choice was to read since I didn't want to get out of bed to get my phone.

I avoid relying on willpower or "making good choices" because I know my brain is a traitorous asshole that will rationalize eating an entire block of cheese when I'm tired or sad.

By requiring more effort to do the wrong thing, I put my laziness and inertia to work. Being lazy becomes my path to success: I've made the right thing the easy thing.

Make the right thing easy for your users.

In software, there's a balance to be struck: we don't want to create a "magic box" that people can't understand or debug, but we also don't want to create a pile of raw utilities that can't be used effectively without deep understanding of how and why they all work.

My preferred approach to writing software is progressive disclosure of complexity: start with defaults that put best practices in place, then let someone opt in to deeper layers of customization as needed.

Too many tools implement defaults that have performance, security, usability, and other problems. They treat the defaults as a "quick learning example that's not production-ready", which then gets shipped to production by — according to the research — about half their users.

When you build a tool, create defaults that start someone at a production-ready outcome. They should be able to initialize with all defaults, ship it, and see great results.

Make the right thing easy for your teams.

On teams, we need to shape the path so people have everything they need to be productive. This requires us to look at our processes and tools to ensure that we're clearing the path for our team instead of inadvertently putting up roadblocks.

Building a strong foundation of trust is the most critical step toward building successful teams. This means a few things:

Be clear about what the team is expected to do. Have a clear roadmap and metrics and make sure these are communicated over and over again.
Establish outcomes, then trust the team to get there. Don't micromanage or hover over your team. Provide a definition of done and get out of the way.
Treat organizational health as a top-line metric. Don't ignore people problems and pay close attention to the mental health of your team. If organizational health suffers, productivity, engagement, and retention will suffer.

In addition to trust, giving the team the right technical foundation plays a huge role. A company's tech stack and architecture have a huge effect on how productive a team can be, so make sure you're choosing tools with great defaults and guard rails to give your team the strongest baseline productivity possible.

The best outcomes require the best defaults.

When designing any new process or system, we should assume that — at least half the time — we're going to be taking the path of least resistance. This means that the defaults we create will account for around half the success of our new process or system.

Good defaults are the difference between a huge success and a humbling "what went wrong" meeting.

If we only focus on creating excellent defaults, we can ensure that we'll see success the majority of the time. This is the magic behind "zero config" solutions: they spent all of their time on defaults and decided not to allow changing them. If we start there and allow progressive disclosure of complexity as needed, we set ourselves up for success without sacrificing flexibility.

Make the right thing the easy thing.

Set good defaults.

Intention vs. Drift

Sun, 28 Mar 2021 00:00:00 GMT

How do things happen??

Do people make things happen? Or do things just happen around us and we make the best of it?

I had the pleasure of talking to Dan Mall about, among other things, how design systems get created. In his experience, systems are created through a blend of deliberate effort and the emergent processes of necessity and use.

Dan said this in the context of design systems, but I've been thinking about it ever since.

Everything is influenced by both deliberate and emergent behavior.

In our lives, our careers, and our relationships, we're able to intentionally create outcomes through deliberate effort. But we also have plenty of things that emerge in our lives without any conscious input — they drift into existence over time.

My first instinct was to make a plan to prevent things from drifting. After all, anything we're not intentional about is a risk, right? I want to be the author of my own story, and the idea of just letting things happen feels like handing over control.

The first problem with this is that it's completely unrealistic to try and be intentional about everything. There are too many moving parts, too many variables, and too much context for it to be possible.

But beyond that, Dan said something about design systems that changed how I think about things now: letting people solve problems and identifying patterns before acting, rather than trying to predict behavior in unknown scenarios, leads to better outcomes.

Let's talk about that using the shorthand "intention" and "drift".

Intention is deliberate action toward a defined goal.

"Intention" describes thoughtfully planned, carefully executed tasks that accumulate into a polished, finished outcome.

This is what we talk about almost exclusively in the context of personal development and business alike. We research; we plan; we execute. In fact, prior to this conversation, I'm fairly convinced I thought only intentional work would lead to any meaningful outcome.

Drift is unstructured exploration and observation.

Even without intention, though, things continue to happen. Left alone, patterns and habits emerge in our own behavior and in the culture of teams.

"Drift" describes outcomes that aren't driven by any deliberate action or plan. Drifting is what we get when we decide to let things happen and see where we end up.

There's value in both intention and drift.

I spent the majority of my life as a firm believer in The Plan™. I created The Plan™ and I needed to Follow The Plan™ and I would achieve Success According To The Plan™.

If I tally up the pivotal moments for myself, however, I can't help but acknowledge that — both professionally and personally — drift has accounted for as much of my growth and momentum as intentional efforts. In fact, a few of the most pivotal moments in my life resulted from drifting:

I learned to code because I was in a band and needed to build a website and customize our MySpace page. When the band broke up, I realized I'd accidentally built enough of a skill set to work professionally as a web developer.
Starting Learn With Jason was a happy accident. I was experimenting with ideas for how to be more transparent about my work, and invited Nader Dabit to get on a Zoom call and teach me how to use software he was working on. The format worked, so I kept setting up "one more session" with other guests — the show has continued to evolve and I'm about to cross 200 episodes.
I met my partner, Marisa, in a period of my life when I was "absolutely not dating anyone because I'm moving away soon". We both had no intentions of getting into a relationship, and had multiple conversations early on about how nothing serious would happen between us. That was seven years ago, and we're still together (but, in fairness, we're rarely serious).

For all that I've told myself I followed The Plan™, I'd be lying if I said I knew I'd end up where I am today. A huge amount of my life and my career has emerged as a result of drifting, and I'm extremely happy with the outcomes.

Be intentional when the goal is clear.

If you know where you want to go, being intentional is important. Identifying a clear outcome, making a plan, and executing that plan is the most predictable way to get where you want to go.

However, it's not always clear what the goal is, and that creates a challenge. Trying to be intentional when the requirements are unclear doesn't have the same payoff; you're pushing hard toward somewhere, but it's a lot of hard work going toward an unknown destination.

Drifting allows for discovery and cultivation.

In situations without clear goals, drifting allows us to exist in a space and see how things interact. If we give ourselves the space to observe how a situation is playing out, we start to learn more about it, and gathering more information gives us the confidence we need to clearly identify our next goal.

Sometimes we should drift . . . intentionally.

If it's unclear where you want to go, drifting can be a deliberate choice that leads to better clarification.

If we want to do something well, whether it's passing a test or learning a new skill, we can vastly improve our chances by studying. With something like a test, how we do this is pretty straightforward — but how do we "study" being successful, being happy, or building a great team?

By choosing to drift for a while instead of trying to make a plan immediately, we get a chance to "study" our environment by existing in it without an agenda. We can ask ourselves questions to gather information:

Where is my energy and happiness coming from?
What do I find draining or demotivating?
Do I enjoy the work I'm doing?
Where are the biggest opportunities for growth?
Are there patterns to my (or my team's) behavior?
What do I wish I was doing that I'm not doing now?

By drifting, we can free up our mental bandwidth to ask questions and let patterns and opportunities emerge. Once we have enough information, we can switch back over to being intentional and make a plan to turn the opportunities into growth.

Balancing intention and drift is important.

Embracing both intention and drift can give us the ability to deliberately make progress toward our concrete goals while also allowing us the space to notice new opportunities.

We can be both the authors of our story and a curious observer. Recognizing when we should adopt one or the other approach can help us avoid frustration and risk.

And, for me at least, it's led to a happy life that I've both worked hard to build and stumbled face-first into.

Don’t Be Nice. Be Kind.

Fri, 19 Mar 2021 00:00:00 GMT

Among my least favorite phrases that are commonly accepted as wisdom is "if you don't have anything nice to say, don't say anything at all."

The be-nice-or-be-quiet mentality is one of the most destructive forces I've ever seen in both personal and professional settings. I've watched multiple friendships, relationships, and companies implode because everyone was so focused on being nice that they forgot to be kind.

To me, "be nice" is too often coded language for "don't make anyone uncomfortable" — but to be kind, we often need to have uncomfortable conversations.

So let's stop being nice and instead work to be kind.

To "be nice" is to avoid conflict and discomfort

In a few of my previous roles, I've asked for feedback and been told that everything was going great. Later, I'd find out through the rumor mill that there were things I did that were causing problems.

At the time, I was equal parts confused and furious. I'd asked for feedback! Why wouldn't they give me that feedback when I specifically asked for it?

Later, I realized what had happened: I didn't get feedback because people were "being nice". They wanted to avoid conflict and uncomfortable conversations with me, so they just... didn't say anything.

Long term, being nice causes much more conflict and discomfort

The insidious reality of being nice, though, is that it doesn't avoid conflict or discomfort — it just delays it. And the thing about hard conversations is that they only get harder as more time lapses between when the problem starts and when it's discussed.

I once broke up with a long-term girlfriend over a fast food order. As we were trying to finalize the order, I did something that annoyed her, but she wouldn't tell me what I'd done. This was something she did that annoyed the hell out of me — and that had been annoying me for our entire relationship — but I'd never told her.

For months we'd been nice to each other, not bringing up the small tensions in our relationship. Until, all at once, we unloaded all of those minor discomforts in a screaming match about Subway sandwich toppings that ultimately ended our relationship.

Being nice doesn't prevent problems; it puts them into a savings account and lets them collect interest.

Being nice is a betrayal of trust

There's a vanishingly thin line between being nice and outright lying.

If I've managed to smear mustard on my face during a meal and you see it but say nothing — you know, to "be nice" and not embarrass me — I don't feel like you were nice. In fact, when I get home and realize I've had mustard on my face for the last two hours while I ran errands, I feel like you betrayed me. How could you — my friend — let me walk off without giving me a heads up?

The feeling of betrayal is so much worse when someone is "nice" about behavior that does harm through ignorance. Did I phrase something poorly and belittle someone's work? Did I fail to give proper credit for an idea? Did I make someone feel small or disrespected through my tone or attitude?

Being "nice" and not bringing that behavior up means there's little hope that I can address that behavior and grow. If I find out months later during a review that I did this and no one gave me feedback, I'll feel terrible not only because I caused harm through my ignorance, but also because I've failed to prove myself as someone who's worth giving that feedback to.

"Being nice" to avoid conflicts can lead to closed off, protective behavior that undermines trust and safety on a team. We start to think, "I have no idea what people really think of me, so I should be very guarded and political to avoid getting a negative review again."

Distrust, doubt, and discord — all because we wanted to be nice.

Being kind means being temporarily uncomfortable

To sit someone down and say, "I care about you, and because I care about you I want to tell you something that might not be comfortable to hear," is kindness. Yes, it's uncomfortable. Yes, it might be awkward and there might be a day of feeling weird about things.

Ultimately, choosing kindness over niceness is what builds trust and fosters growth.

Being kind means giving feedback quickly and honestly

The shorter the gap between the problem and the feedback, the less likely things are to fester or spiral out of control. If I make a mistake today and you approach me about it immediately, we're going to talk about the mistake.

If I make a mistake today and you approach me about it in six months, we're going to talk about the mistake and why you didn't bring it up sooner.

The best managers I've had (hi Sarah and Robin) give immediate feedback and don't give problems enough room to expand. They address the problems directly and immediately, giving tough feedback from a place of caring.

These immediate feedback loops gave me confidence in the team. There was no secret reality that was covered up by niceness; things really were the way they seemed because issues were dealt with openly and honestly.

Being kind means valuing growth and trust

For me, kindness is making an earnest effort to provide the people around me with the information, trust, and support they need in order to grow. There are many facets of kindness, but they all share a common core: kindness is choosing to value someone else's growth over your own comfort.

Creating relationships and teams that value kindness over being nice lays a foundation for deep trust and high growth.

Please stop being nice

On the surface, being nice seems like a way to avoid conflicts and keep everyone from feeling uncomfortable. In reality, being nice only hides the problems away, where they fester and become much bigger, harder to resolve problems.

Instead of being nice, strive to be kind. Think long-term about the health of relationships and teams, and provide immediate, honest feedback to create an environment of trust and growth. Choose kindness over comfort, honesty over appearances, and action over ignoring things and hoping they'll go away.

How can you practice kindness today?

Are there any places in your life where you're being nice instead of kind?

How to Draw a Map to a More Fulfilling Career

Tue, 09 Mar 2021 00:00:00 GMT

Earlier in my career, I made wild shifts between roles: I ran an agency and worked far too many hours; I was a contractor and worked as few hours as possible; I was a full-time employee that clocked out at 4:58pm sharp. No matter what my job was, though, I kept landing in this place where I felt like things were... off.

Something wasn't working, and I ended most days drained, frustrated, and generally feeling stuck.

Over the years, I started to realize that the problem wasn't the specific role, but rather the kinds of work I was doing in that role. I wasn't happy because I didn't feel like I was doing anything meaningful — but that posed a problem: if you asked me what "meaningful work" looked like, I didn't have a good answer.

Learning how to identify and seek out "meaningful work" has led to my career feeling significantly more rewarding and fulfilling. Let's talk about how I've done that for myself — starting with how I define "success".

We need to know what success looks like.

Success can't just be "more". More money. More responsibility. More recognition.

The pursuit of "more" is an endless task; no matter how much of any given thing we manage to gather for ourselves, there's always a way to add more.

Instead, we need to really think about success in terms of what we do, not what we have.

When I asked people to describe success, I got dozens of answers, and each was a little bit different from everyone else's.

kind of a Shower Thoughts question, but I'm curious:

what does success look like to you?

like, if you had to describe what needs to be true for you to say, "I have succeeded" — what goes into that description?
— Jason Lengstorf (@jlengstorf) March 9, 2021

These definitions are highly subjective, but success isn't an objective matter. To truly enjoy it, we need to know what success means for ourselves, not for other people.

This is important to start with, because part of fulfillment is tied to knowing that the work we're doing lines up with our definition of success.

We need to know what work is fulfilling — and what isn't.

When I tackle my todo list each day, there's work that I do that leaves me feeling energized, and work that leaves me feeling drained.

In a few of my previous roles, I felt consistently drained. I would spend all my time doing things that, ultimately, didn't feel important or fulfilling. I got results, and my reviews were good, but ultimately I felt a sense of "I'm wasting my life on this".

Just because we're good at something doesn't mean it's fulfilling.

Being good at something is only part of the formula for success. When I worked as a product engineer, I was good at breaking down product goals into tasks, breaking those tasks into tickets, and making incremental improvements to the codebase.

However, I didn't feel fulfilled by doing that work. Parts of the job were fulfilling, but most days I left work feeling wrung out and tired instead of excited and ready to jump back into it tomorrow.

Doing unfulfilling work is how we burn out. Sarah Drasner put this to me in a really concise way: "People don't burn out from too much work. The burn out from too much unfulfilling work."

This hits home for me, because there have been points in my life where I was able to put all of my attention into something fulfilling and I never felt burned out, but at other points I was putting maybe 40 hours a week into draining work and I burned out fast.

Just because we're bad at something doesn't mean it's NOT fulfilling.

In stark contrast to this, I am decidedly terrible at video effects, but I get a deep sense of fulfillment out of making something work for my livestream. It takes me far too long and I get a subpar result compared to what a professional VFX artist could do, but the struggle and my janky results give me a huge sense of satisfaction.

Should I do this as my full-time job? Probably not. But should I cut it out entirely because I'm not a pro in the name of "optimizing for maximum efficiency"? I don't think so.

Write down everything you do.

Email. Meetings. Writing docs. Building features. Planning. Maintenance. Learning. Hobbies.

Write down everything.

Keep in mind that some things are different based on context. For example, I find certain kinds of meetings to be soul-sucking and pointless, but there are other meetings that I absolutely love and look forward to. When it makes sense, separate the different types of things into buckets based on how they make you feel.

Plot the things you do on this matrix to give yourself a map to fulfillment.

After you have a list of the tasks you do, place them all on a matrix that looks like this:

The Y axis represents how energizing or draining a task is, with the very top being "this task is extremely energizing for me" and the bottom being "this task completely drains me".

The X axis represents our competence at a given task. This can be based on how competent you feel, how your feedback from others looks, or a combination of the two. At the far right is something that you're really good at, and at the left is something that you struggle to get right.

The blue zone shown at the top-right of this matrix is where fulfillment lies. In an ideal role, most — if not all — of the tasks we do will fall into this blue zone.

It's important to note that the blue zone isn't only tasks that we're both good at and find energizing. While the vast majority of what we do will hopefully meet both criteria, I think it's important to allow for a little bit of work that doesn't fall directly into that quadrant.

Doing a few things that we're bad at, but find energizing, gives us room to grow.

In my own career, I generally seek out work that is 10% beyond what I know how to do. This means that I'll make mistakes and won't always be the best at getting things done, but that 10% is where growth happens.

If we're already really good at everything we do, we risk stagnation, which can hollow out a sense of fulfillment in our work.

Work isn't always fun. Using our skills to take care of the dull work moves the team forward.

In general, different people will find different kinds of work rewarding. For someone who's a great product manager, going through mountains of data and turning that into Gantt charts, roadmaps, and todo lists can be extremely engaging and fulfilling. For me, it's a brutal slog.

When we can, it's great to match people up that enjoy different things so the team is able to do what's fulfilling and cover each other on tasks that others would find draining.

However, that's not always possible. Some work needs to get done and there's no one around who finds it fulfilling. In that case, taking on some work that you're really good at even though it's draining helps move the team (and, by proxy, your career) forward toward success. The trick here is balance — too much of this kind of work is a fast track toward burnout.

What’s in your blue zone?

Knowing what you find fulfilling doesn't change what you're doing today, but it gives you a better idea of what to start moving toward. Maybe it starts with a conversation with your manager, or with delegating tasks, or with taking a hard look at whether you should continue with a given role. (I've done all three in my career as a result of doing this exercise.)

This exercise doesn't create fulfillment, but it helps you draw a map to it. I've found this to be incredibly helpful whenever I start to feel run down at work, and usually I realize that I've started to let most of my tasks slip into the "good at it but draining" quadrant.

So what's in your blue zone? What actions can you take to help you move more of your day-to-day tasks into the blue zone? I'd love to talk about it on Twitter!

A career is a pie-eating contest & the prize for winning is more pie

Mon, 18 Jan 2021 00:00:00 GMT

Have you ever taken ownership of a project, and the only thanks you get for doing a good job is to have similar tasks dumped on your plate?

You've entered a pie-eating contest where the prize for winning is more pie.

Cynical folks love the saying "no good deed goes unpunished", and that's how it can feel if you take ownership of something just to become the dumping ground for similar work.

How much do you like pie?

Whenever you take on ownership, you're sending a signal to the folks around you: you're willing to be responsible for this task. People who see you owning and completing this task will assume that you are both A) capable of handling this kind of work, and B) interested in doing more of it.

Whether or not that's a good thing depends on whether or not you enjoy the work.

Convince your team to learn fast and try not to make a mess

Sat, 09 Jan 2021 00:00:00 GMT

In previous posts, I've been working through some ideas around building more productive teams. These ideas are centered around two major themes so far:

The type of work we do in any company happens on a spectrum, and our internal processes need to be flexible enough to adapt and support the type of work being done. Success depends on the completion of well-defined, production-ready work ("load-bearing projects") as well as validating ideas from research, team members, and customer feedback ("squishy projects").
We need to take care of existing customers and products while continuing to explore and innovate. That requires deliberate effort to set up and sustain. Exploratory work and production should happen in parallel workstreams that complement and strengthen each other (what I lovingly call the Yeet Delete Repeat pattern).

In further discussions with friends and folks around the community, questions came up that are worth addressing — let's do that in this post.

What if our problem is that we focus too much on squishy projects?

In our company, a lot of the squishy projects that show promise go directly to production, even though they were meant to be experimental. We have so many ideas coming from our own team and customers that we don't seem to be able to slow down and work on stability.

Especially in startups, this can be a huge challenge. If leadership is pushing hard for new features and unwilling to prioritize work on stability, tech debt, or general quality improvements, it can feel like everything on the roadmap is squishy and the entire product is held together with duct tape, wishes, and an increasingly frazzled team of ops engineers.

This is a hard problem to solve, and — depending on the maturity of the company's leadership — it may prove to be a lost cause. Each company is different, so it's on us to assess our own situations and decide when it makes sense to push for change, and when it makes sense to look for a role that's better aligned with our working style.

However, there are some strategies that I've used in the past that can help turn the ship toward more sustainable, less stressful practices.

Find the dirt floors

To make any meaningful change, we need to understand why things are the way they are. This means we need to find the dirt floors: what is causing leadership to think this way?

To use an analogy, if there's a bucket in the middle of the floor you might say, "This bucket is a tripping hazard and we should move it." If leadership responds, "Can't. We have to have the bucket there," that might seem illogical and stubborn. With a little digging, though, you might learn the root cause is a leaky roof, and the bucket catches the water. If you know about the leaky roof, you can stop complaining about the bucket and focus on the roof — once the roof is fixed, the bucket's no longer necessary and no one will care if you remove it.

Focus on the win-win

When explaining the benefits of something, it's tempting to talk about what's in it for me: "Cleaning up this tech debt means I won't have to dig through frustrating code and make changes in multiple places for every feature!"

While true, this doesn't present a compelling argument to managers and leaders who have their own challenges and problems. I've made this case in the past, and the response I got was along the lines of, "Well, we pay you to dig through code and add features, so maybe suck it up and do your job?"

Tech debt doesn't only affect the people doing the work, though! If we think about what the manager is struggling with, we can rephrase our request and include how it benefits them instead: "The delays in shipping are due to the complexity of this older area of the code. If we take a sprint to clean this up, we should be able to deliver things much faster!"

Put yourself in the shoes of the person you're attempting to win over, and try to understand why they're stressed out (remember: where are the dirt floors?). Present a concrete plan that solves their personal problems and you have a much better chance of getting buy-in.

What if people on the team tend to treat the first draft as the final draft?

My team always jokes that "the first draft is the final draft, so make sure you bring something solid." Because of this, people tend to work quietly on projects for a long time before showing them. It's a Catch-22 because we have trouble getting buy-in if it's not polished, but the more polished it is, the more likely it gets shipped as a final draft.

This is something I've run into in multiple companies, and I've personally been guilty of keeping something quiet until I felt like it was perfect to avoid getting nitpicked into oblivion by people who thought we were reviewing for production.

A parallel workstream for validation and production is designed to solve exactly this problem, but that might not be apparent at first.

Providing structure and space removes anxiety

Creating an actual process for experimental work, processes to support it, and clear expectations about how things move from idea to validation to production creates reliability in your team's environment. It helps to remove the anxiety around exploration, because exploration is no longer an extra activity, but part of the job.

Removing the mystery around where ideas come from creates stability, reliability, and — most importantly — a foundation for trust. And, as Amberley Romo reminded me, no amount of process will help if the team doesn't have trust.

This kind of stability and trust is also called psychological safety, which is a strong predictor of team performance.

Don't forget the "delete" part of "Yeet Delete Repeat"

Building deletion into the process is extremely important. Without deletion, a prototype can leak into the broader codebase, making it both fragile and hard to remove, and that's how tech debt is born.

The validation workstream needs to have a heavy focus on sandboxing experiments, releasing only to limited test groups, and optimizing for deletion. I also strongly recommend that the last step of an experimental project should be to delete the project.

If the project is greenlit for production, the team who picks up the project shouldn't have to start by cleaning up a mess. They should have the data and the original code available for reference, but they should be starting with no code actually committed — it's important that they can make decisions without the influence of inertia skewing the outcomes.

How do we convince management it's a good idea to work on something that won't go to production?

I would have trouble convincing management it's a good idea to spend time working on something that won't go to production. They see this kind of stuff as a distraction.

At the heart of every company is the need to survive, and the only way a company can survive is by continuously shipping valuable things to production that keep customers happy (and paying).

On the surface, a workstream dedicated to validating squishy ideas might seem like a waste of resources — and it definitely can be! I've seen several "experimental" teams spun up at companies that focused on innovation and exploration, but failed to create any meaningful impact or benefit for the company.

How is working on squishy projects and creating a workstream for validation different from those failed attempts?

The validation pipeline is part of the production process

Experimental teams that are isolated from the rest of the company are able to act quickly and autonomously, but they're also completely out of the loop. The barriers that protect the team from red tape and slowdowns are also barriers preventing the team from feeding value back into the company.

Unless the experimental team is working on something entirely separate from the rest of the company — a true skunk works project, which by definition should be short-lived — adding barriers sets the team up for failure.

To avoid this, the experimental side of the dual workstream approach serves to identify, scope, derisk, and validate experimental ideas that immediately go into the production pipeline.

Dual workstreams avoid production bottlenecks

In many companies, there are a huge number of unexplored opportunities that could improve the product, add more value, and make a huge impact. Many of those ideas are captured in "parking lots" or iceboxes or aging Jira tickets because they're not formal enough to get prioritized in a production pipeline.

At the opposite end of the spectrum, ideas can end up on the product roadmap because someone with enough power was willing to champion the project.

Combined with the list of projects determined through research, customer feedback, and other production channels, this can lead to a sense of both being overwhelmed by the amount of things to do and feeling powerless to influence the roadmap because ideas from team members don't have champions to push them through prioritization.

A validation pipeline acts as a stabilizer: by working on ideas with a "learn fast and don't make a mess" mindset, it's less challenging to get an idea prioritized for validation; by creating a culture of validation before adding a project to the production workstream, it's harder for a pet project to leapfrog the queue and clog up the product roadmap.

What happens if stakeholders don't care if a project is a long-term success?

If someone in leadership or management is trying to ship a project so they can land their next raise or promotion, they don't necessarily care if they're saddling the team with a bunch of tech debt; they just want to ship to production so they can show that they delivered something.

In some companies, the incentives get misaligned and promotions and raises get tied to visible delivery with very little concern for long-term cost or maintainability. (For a solid breakdown of how "doing good work" gets decoupled from "deserves a promotion", read this post from Michael Lynch about why he quit his job at Google.)

If that sounds like your company, and you decide it's worth sticking it out and trying to make positive change, here are a few strategies you can try.

You can ship more and faster by embracing experimentation

Visibly shipping something, as far as I can tell, boils down to having something you can link to or share metrics from. And by that standard, leadership can visibly ship so much more by adopting the parallel workstream process.

Experiments are small, have clear success metrics, and make a big impact on the company's bottom line. While I was at IBM, my team was able to ship multiple experiments faster than other teams delivered a single feature. The validation research from those experiments helped us avoid person-months of effort on ideas that didn't work, which meant we shipped production features faster because we had more information about what success looks like.

Everyone I worked with on that team got promoted. My old manager has been promoted twice. This process made us more visible, and more likely to get a promotion.

This goes back to the idea of finding the win-win. This process truly is better for everyone; we just have to help the whole team see the individual benefits for them.

Shipping responsibly compounds wins until it seems like magic

Managers and leaders who not only ship, but who ship things supported by data that make measurable, positive improvements to the product get promoted further and faster. Investing in learning fast and not making a mess helps teams (and leadership) appear to be superhuman: they have tons of new things shipping with clear metrics on what's working and what's not; they have fewer projects that go over schedule or end up failing after months of effort; they have great team dynamics, trust, and engagement; they rack up meaningful wins reliably.

This isn't magic — working quickly to learn whether or not something is a good idea both racks up the "we shipped!" wins while also quickly identifying which projects will be successful. Only putting validated projects into production lets teams work with confidence and clarity to deliver production-ready wins consistently. Being on a team that ships things is extremely motivating, and the higher communication required for this process builds more trust among team members.

I've seen multiple teams pull this off at companies of wildly varying sizes. The secret isn't in who the team is or how big the company is; it's in creating the right environment and processes that let teams thrive.

The process alone isn't enough — the team needs to be bought in

These questions all point to a larger challenge: to get the benefits of a dual workstream, the whole company (or at least the whole team) needs to be bought in and willing to follow the process. This isn't unique; the work required for any idea to succeed is 20% building the tool and 80% driving awareness and adoption of the tool.

This means that it doesn't matter whether we think this approach is correct. What matters is whether or not we can bring this approach to our team, discuss the trade-offs, and arrive at an approach that we all agree works and — critically — that we're all willing to adhere to.

But if we're willing to do that work, the benefits (to us as individuals, to our team, to the company, and to our customers) are incredible. It's work well worth doing.

Yeet. Delete. Repeat.

Thu, 07 Jan 2021 00:00:00 GMT

To survive, companies need to provide something valuable to their customers. To know what's valuable, companies need to get feedback. To get feedback, companies need to ship. And to do all of this without wasting huge amounts of time, money, and momentum, companies need to do all three of these quickly.

Let's talk about a strategy for moving quickly without breaking things or burning out your team.

Not shipping has high business and emotional costs.

Every company has its list of "we should" and "what if" ideas. In growing companies, this list often ends up collecting dust because there's so much to do that squishy projects like these get pushed back indefinitely in favor of more concrete, immediate needs.

Working on immediate needs puts out fires, but it leaves the company in a reactive pattern. This is high stress and can be demotivating, especially if the teams doing the firefighting wish they had time to experiment.

No one wants this outcome — so how do we avoid it?

Protect time to create dual project streams.

Carving out and protecting time for teams to work on squishy ideas is critical for businesses to keep stay innovative and motivated. This time can be allocated in any number of ways:

quarterly hackathons
every 4th sprint is dedicated squishy projects
one day a week

In a perfect world, teams will have parallel work streams: one dedicated to the well-defined, urgent, load-bearing projects, and one dedicated to exploring and pursuing the "what ifs" and "we shoulds".

To make parallel work streams sustainable, the exploratory work needs to happen within clearly defined boundaries.

And to that end, dear reader, I humbly suggest adopting the YEET DELETE REPEAT pattern.

Yeet experiments to small test groups as quickly as possible.

Teams should aim to complete an experiment as quickly as possible, which means aggressively scoping down to test a single hypothesis. By limiting the size of the project, the team is forced to focus on the core of the idea, which makes it easier to nail down what the ideal outcome looks like and measure whether the project succeeded.

Then, using small test groups through feature flags, closed betas, or whatever channel the company gathers feedback through, the experiments should ship. Immediately. Like, the day they meet the minimum threshold for letting a real person look at them.

Just... please just ship it. Stop thinking about it. Ship. For the love of god. Yeet it and start getting feedback.

Delete experiments after collecting all the research.

One of the major complaints about shipping quickly is that it creates overwhelming technical debt. I've worked in companies where this is the case, and I've felt the pain of digging into an undocumented weekend project that's somehow the only thing keeping a core part of the product functioning.

We do not want to create that problem for ourselves. Instead, we want to optimize for deletion — and delete our experiments by default.

To avoid technical debt, experiments should be deleted as part of collecting research. If possible, ship the experiment as an entirely separate codebase. Barring that, build the entire feature into one squash commit that can be reverted. No matter how you build it, assume that the experiment will be completely erased once it's complete.

Once your team has enough research to make a decision, delete the experiment. Add a production version of the project to your load-bearing workstream and include the research and deleted code for reference. Make sure the production project doesn't start with a mess.

Repeat the process and keep the momentum going!

If this process is set up well, teams can quickly ship experiments, then work on load-bearing projects while data is collected to validate the experiment. This means the critical work to keep the wheels on is getting done as well as the exploratory work that unlocks innovation.

It may seem counterintuitive, but creating space for an experimentation pipeline will increase productivity on the production pipeline:

Rapid experimentation quickly pares down a crowded backlog, creating more clarity on which features are the most valuable to customers and the company
Validated projects are more likely to be correctly scoped because discovery work was already done during experimentation

Even without these benefits, teams that have the autonomy to try things and influence the company's decision-making tend to feel more in control of their careers, which has the wonderful side effect of making your company a place that people enjoy working (for the BossBots™ out there: that means increased engagement, higher productivity, and lower turnover).

Learn fast and try not to make a mess.

No process is perfect, and we'll all need to bring the nuance and context of our own companies into the design of a parallel workflow design. If we take the time to do it, though, building the habits, and processes — as well as the team trust and safety — that make parallel workflows possible will pay dividends across multiple areas of the company.

Plus, it's super fun to say: YEET. DELETE. REPEAT.

Try it.

...did you say it?

See? Super fun.

Squishy vs. Load-Bearing Projects (or: How Not to Flatten Innovation)

Wed, 30 Dec 2020 00:00:00 GMT

A tragic experience at work is to share an idea you're excited about, get a genuinely enthusiastic response from your team, and then look on in horror as folks gather around to bludgeon it to death with The Process™.

The idea never has a chance to gain momentum or make any meaningful progress — it's dead before it starts because it collapsed under the weight of a full team's worth of process.

Establishing vocabulary: the squishy-to-load-bearing project spectrum

Projects happen on a spectrum, with mature, well-established work at one extreme that we'll label "load-bearing" and the Galaxy Brain wouldn't-it-be-cool-if ideas at the other extreme, which we'll label "squishy".

Projects that affect critical areas are load-bearing.

A load-bearing project has tons of context, research, preexisting requirements, and non-negotiable contracts that need to be accounted for and handled properly. They're much less likely to shift drastically as new information comes in.

At Netlify, when we want to roll out a new feature to our build system, we have to be extremely careful not to introduce bugs for existing workflows — we have dozens of coworkers and over a million developers counting on Netlify being stable.

Load-bearing projects need thorough, cross-team processes. Shipping changes to something that lots of people rely on needs to happen safely, and safety is created by adding lots of checks to the process. Each involved team has checklists, and all of those checklists need to be signed off at each stage before the project moves forward.

Exploratory projects are squishy.

At the other extreme are squishy projects that still need a lot of fleshing out. For example: I have a project I want to tackle for Learn With Jason that will allow live viewers to move a tiny submarine with my face on it around the screen. That's the entirety of my progress on this project so far.

Squishy projects don't always have a clear path forward. These are the projects born out of hunches, something we heard a customer say, or a question that we think it would be valuable to answer.

At its squishiest, a project can be an effort to define what we meant when we took a screenshot of a tweet thread and said, "I think there's something important in here". It's necessarily ambiguous because the bulk of the work of a squishy project is to try and desquishify it with definitions and direction.

Squishy ideas are too fluid to survive rigid processes, and that can lead to them being dismissed — but skipping squishy ideas is a huge, costly mistake.

Processes are not one-size-fits-all

As teams and projects grow, the need for process grows as well. More and more projects become load-bearing, more people are working on them, and it becomes extremely important that everyone follows a process to ensure that nothing slips through the cracks.

However, even the largest teams will have squishy projects. And when a squishy project gets hit with a load-bearing process, it tends to get flattened entirely.

Sometimes we need to go slow to go fast.

By putting solid processes in place for load-bearing projects, we gain confidence that the work we're doing will be shipped safely and without creating more work to clean up accidental messes. Despite feeling like the process adds time to a project, the net effect is that projects get completed faster because we're not losing time to mistakes, reworking to handle things we forgot, and other sneaky time thieves that solid processes help avoid.

But sometimes we need to go fast to go fast.

As frustrating as they can be, squishy projects are a necessary part of learning. Chasing down a hunch is an important way for teams to innovate. Asking a question and setting out to find an answer is valuable work that helps identify new opportunities (and, perhaps more importantly, enables us to say no to things because we explored them enough to know they're not a good match).

If we try to apply rigid processes to squishy projects, we end up spending a lot of energy trying to fit ambiguous work into unambiguous boxes. Processes only work when we have a clear path between where we want to go and where we are now. The more question marks that exist in a project, the more likely it becomes that we'll end up changing direction, reimagining part of the plan, or otherwise altering the project in ways that grind processes to a halt.

So, what? Squishy projects are just "no parents no rules"?

My argument to this point makes it sound like I'm advocating for a free-for-all when it comes to squishy projects. That's not the case — I'm arguing for minimal in-flight process to make it easier to explore and adapt, balanced out by much larger guard rails around what a squishy project can affect.

In the broadest possible strokes, squishy projects should make a trade-off: the amount of formal process is limited to allow for exploration and rapid change, and risk is minimized by limiting the audience that will see it. Squishy projects become a research tool to inform load-bearing project planning.

Fewer stakeholders and less process — but also a short leash.

Put another way, a squishy project doesn't end up widely shipping to customers. Instead, a squishy project explores a potential product direction to validate it with a small test group. The research and feedback provided by the small test inform a largely desquishified next project that can be built with more process and the intention of shipping much more widely.

A squishy project is less restricted by in-flight process and (ideally) has significantly fewer stakeholders — in a perfect world, only one or two — to allow for rapid exploration, iteration, and execution. By restricting it to only a small test group, risks are contained and the team doesn't need to worry that a squishy project will create technical debt, pager duty, or other expensive, stressful problems.

Desquishing becomes part of the process.

You may have picked up on this already, but restricting squishy projects to small tests that are used to informed more structured projects is, in fact, a process. But an important distinction is that it's a process that supports squishy ideas instead of flattening them.

And, just as importantly, this process wouldn't be very successful if applied to a load-bearing project.

Does this matter? Why is this valuable?

Shaking up processes to accommodate squishy projects is a significant effort, so why should we bother at all? It can be tricky to draw a direct line between this kind of work and value, profits, growth, or whatever metric drives decisions at the leadership level. However, creating the space to not only allow, but nurture squishy projects has a huge impact on the bottom line.

Squishy projects are where innovation comes from

Having the space to chase down a hunch, implement a long-standing, hard-to-prioritize customer request, or validate a big idea is how companies create value. There's a reason that there's a stigma attached to "design by committee" — it's extremely hard to create new things in large groups. By giving squishy projects to small teams and reducing the amount of process hurdles they have to clear, they're given the space and freedom that helps them shape a new idea into something that can withstand a more formal process.

Without support for squishy projects, your company might be suffocating innovation.

Squishy projects save time and money

Building something is expensive. It costs time, attention, and money. How much does it cost to have a team of 15 people work on something full time for a month? And if that project doesn't work out, how much did it cost to not be working on the thing that was the right idea?

Squishy projects remove a ton of cost by reducing the scope and the team size required to validate an idea. A team of two or three can quickly prototype something that's at least 80% of what the full team could create, and they can likely build it significantly faster.

Rolling that prototype out to a small test group provides actual research data that tells you whether or not this project is going to pay off. If it turns out to be a good idea, the squishy project provided inexpensive validation of a good idea and makes it easier to justify putting the full team on it. If it doesn't work, you're only out a week or two of time from two or three team members vs. a month from the full team.

Squishy projects provide valuable data, avoid expensive mistakes, and lower production costs.

Squishy projects declutter the product roadmap

A huge challenge in every company I've come into contact with has been prioritization. How does something get on the roadmap? How do things get prioritized?

Squishy projects help provide concrete data to inform roadmap design. By quickly launching prototypes to small test groups, the company is able to get actual data from actual customers that shows the impact of a given project. This can simplify the roadmap process, because the projects with the highest impact on the most critical areas of the product can be prioritized easily: there's data to back up those decisions!

Additionally, this helps avoid the problem where every idea gets put on the high-priority list, because all unvalidated ideas can be put on the squishy list to be prototyped and validated.

Use the right process for the current project

Our goal is always to get things done as quickly as possible with as little duplicate work and risk as we can manage. To do that effectively, we need to balance our need to innovate and explore squishy ideas with keeping the load-bearing parts of the company healthy.

This means adapting our processes to support projects at both ends of the spectrum: less process, fewer stakeholders, and smaller test groups for squishy projects, and more stringent processes and stakeholder checkpoints for load-bearing projects that will reach general availability.

By letting squishy projects quickly prototype ideas and gather feedback, we can make better choices about which projects get prioritized for the heavier investment that goes into bringing the full team and process onboard.

Embracing the full spectrum of squishy to load-bearing projects enables the company as a whole to move faster without losing the ability to experiment and innovate.

Creating Great Content Is a Process, Not a Project

Sat, 11 Jul 2020 00:00:00 GMT

When I see incredible content like this beautiful, interactive piece on a car-free New York, I sometimes feel like I’m lagging behind and not creating cool enough experiences. If I’m not careful, I can feel discouraged and start beating myself up for not doing enough.

But an amazing piece like that wasn’t created in a vacuum. It’s built on previous content, like the groundbreaking Snow Fall article from 2012 that introduced experiments around interactive storytelling, and dozens of pieces since then that iterated on that approach.

What may seem like a single project is, in fact, one artifact generated by a long, iterative process at The New York Times. And it won’t be the last one.

Content creation is a continuous process that generates artifacts. It is not a string of standalone projects. This realization has been a critical factor in unblocking my creativity and giving myself permission to ship things that don’t feel perfect. After all, there’s going to be another piece, and the next one will be even better!

Great content is the result of repetition.

Repetition creates expertise. Early on in any process, we have to spend all our mental energy just to do the thing we’re doing. We aren’t able to experiment much, because we’re still trying to figure out how things work.

With repetition, the general process becomes second nature. We don’t have to think about how things work because we’ve developed habits and muscle memory that let us do the thing unconsciously.

That’s when we can start to get ambitious.

Once you get in a groove, experiment.

When the process itself stops requiring all of our attention, we can use that extra mental energy to play. What’s one idea that could make this even better? What could we try to have even more fun? What feedback did we get on the last artifact that we could incorporate to improve the next one?

Each experiment evolves the process. We’re gaining experience, gaining expertise, iterating on ideas for the way things are presented, packaged, and delivered. Over time, every piece we release improves, and eventually we’re shipping incredible content like The New York Times — not because we spent months planning the perfect piece, but because we continuously shipped new ideas with small improvements to each one.

Slow, continuous improvement is like compounding interest: at first, it doesn’t seem like much, but — assuming we stay consistent — it pays enormous dividends.

A real example: livestreaming.

When I first started livestreaming, I was overwhelmed by trying to remember what was on screen, reading the chat, paying attention to my guest, and trying to stream. I was barely able to get through the show — I had no mental energy available for making it look nice or thinking about how to make it more interactive.

As I got more and more episodes under my belt, I built up habits around how I organized my desktop, where I placed the chat so it was in my eye line, and how I structured discussion with guests so things flowed and I didn’t feel like I was actively managing them.

Once the basics of streaming felt more natural, I had the ability to try out experiments on the show: sound effects triggered by chat commands; a counter that keeps track of how many corgi emotes get used in chat and triggers a stampede once a certain number is hit; a boop dropper that lets the chat bury the screen in boops if they work together.

In addition to the sillier things, I also made all sorts of small improvements to the stream: more design effort for scenes, custom transitions, better automation, live captioning, and other iterative projects to make the experience better for everyone involved.

Because I stream frequently, I get the chance to try things out. Some of them work and become part of the format, like the boops and corgis. Others don’t hit and fade into the background. But over time, little improvements have stacked up to create a fairly polished experience.

There are tons of things I still want to improve, and because I know that this show is a process, I feel confident that I’ll be able to try them all . . . eventually.

Everything is a work in progress.

The content experiences we hold up as “the gold standard” are not created whole; they’re a snowball created from experience and small improvements applied over time. In most cases, the people creating these experiences have been iterating on the ideas that led to this particular artifact for a long time, and they’ll continue to iterate on these ideas and processes in future creations.

We can create amazing experiences too, if we trust our own process, continually learn, and experiment. The trick is to keep creating so you have the ability to evolve and adapt over time.

How to Build a Consistent Content Creation Habit

Fri, 10 Jul 2020 00:00:00 GMT

If your goal is to be more consistent with content, your instinct may be to make a plan. But — and I can’t believe I’m about to say this — trying to plan your way to a creative habit is a mistake.

Look: I love to plan. I love it so much that I’ve written about planning, preparation, and yak shaving at length. However, there is such a thing as too much planning. When it comes to building a habit for creating content, doing is so much more important that planning at all can hinder progress.

Don’t let planning get in the way of doing.

Until we’ve built a content creation habit, planning is the enemy of consistency. If we spend too much time trying to create the perfect website for blogging, or to create the perfect scenes for streaming, or brainstorming the perfect format for sharing content, we’ll burn all our energy preparing and never actually get around to doing things.

With content, the goal should be to do the minimum amount of planning required to get something shipped. For writing, the digital garden format (or, really, lack of format) is a great way to lower the barrier to publishing. For streaming, pushing the button to go live on anything we can share publicly — a hobby project, learning a new language, building something for work, whatever — switches the thinking from “I need to be ready to stream” to “I am streaming already; what would I want to change next time?”

Focus on consistency, not correctness.

When trying to build a habit, the most important thing is figuring out how to stay consistent. We should be setting up routines and incentives that help us do the thing, and worry very little (if at all) about whether or not the thing we’re doing is done “correctly”.

When we’re building a new habit, there is no such thing as “correct”; there is only “doing the thing” and “not doing the thing”. We have to be consistent about doing the thing before we can start to think about whether we’re doing it well.

Go wide, then go deep.

Until we try, it’s hard to know whether or not something is enjoyable enough to keep doing it. This is where plans gets us into trouble: we’re forced to hypothesize about how much we would enjoy something, and humans are tragically terrible at predicting that sort of thing.

This means that we can’t really plan our way to consistency; we have to experiment our way there. We have to cast a wide net, try anything and everything that sounds fun, and keep track of what we’re enjoying so we can do more of it.

To start, try everything that sounds interesting. As you learn about what you enjoy, focus on doing more of the stuff that’s fun.

Just make sure not to mix up “hard because I need practice” with “not fun” — don’t give up on something too early just because you’d have to work at it.

Try everything. Keep doing the fun stuff.

We all enjoy different media when we create things. I love to draw on my iPad, but I don’t like the setup or mess involved with painting or charcoal.

Livestreaming and conference talks give me energy and make me happy. I could keep going for hours — I’m having a blast, so why would I stop? For me, a chance to get up on stage, share information, and perform a little is a bright spot that I cherish.

My relationship with writing is more of a pendulum: some days I can write for hours without stopping, and sometimes stringing two sentences together is so hard it drains all my emotional energy and leaves me curled up on the couch whining because I don’t have any melted cheese to eat.

I only know this about myself because I experimented with creating content using all of these approaches. When I was starting out, I decided to just try things. I wrote; I spoke; I went live on Twitch. I learned what I enjoy (and what I don’t) and now I know where to focus my efforts.

It’s easier to stay consistent (and grow an audience) when you’re having fun.

People can tell whether or not we’re having fun, and it’s way more fun when it feels like the creator cares. There’s a sense of joy that shines through, and that joyfulness makes everyone — creator and consumer alike — want to come back for more.

Watch on YouTube

A notable example of this for me is Anderson .Paak. I had heard a song or two and was pretty meh about it. Then I watched his Tiny Desk concert, and the pure happiness you can see in that performance turned me into a fan.

Creating content that’s fun to create makes it feel like play instead of work. That makes a huge difference in our ability to stay consistent.

Draw the Box Smaller

Mon, 27 Apr 2020 00:00:00 GMT

Back when I worked at IBM, my team worked on a project to automate a bunch of busywork that was being manually handled by every team separately.

My back-of-the-napkin math said this would save each team several week's worth of working hours every year, and when that was multiplied out across all teams it added up to thousands of hours and hundreds of thousands of dollars saved — all by doing less work.

I was extremely proud of my team. We'd managed to take something that was a constant source of drudgery for our coworkers and eliminate it while also saving the company money.

But when we started talking to teams about it, no one would use it. I was at a loss — how could teams choose a bunch of manual busywork over a drop-in solution that removed all that hassle?

I was venting about this in a meeting with my manager’s manager, Nic Sauriol, and he said, “I know exactly what you’re going through — I’ve been there before.”

Then he told me about The Box.

What story are you telling?

In his previous career, Nic was working on a similar project: take a bunch of hassle and make it disappear with a drop-in replacement. His project hit the same wall: teams just wouldn't adopt it, despite the benefits it promised.

The meetings consisted of an explanation of the work that was being removed, a discussion of the migration path, and an architectural drawing that showed how the new tech fit in.

That diagram had two parts: a drawing of the old way, and a drawing of the new way that used his team’s system.

The old way was an anxiety-inducing system diagram with lots of interconnected components and arrows.

The new way showed all of that complexity abstracted away into a The Box: a new, improved system that would solve a ton of problems!

Nic and his team took this around to teams throughout the company, explaining the benefits and showing these diagrams, and no one would make the switch.

This was baffling, because why on Earth would anyone want to keep all of the mess from the old way when they could drop in a replacement that made all of that go away?

What’s in The Box?

On digging deeper, Nic discovered that teams were worried that the switch would be a lateral move.

The new system seemed big. Wasn’t this just taking all of the old stuff and putting it in The Box? That would be harder for them to fix problems. They worried it would be more hassle, and they didn’t want to take the risk.

Nic was baffled by this — his team’s presentations went into detail about how this wasn’t the case.

As he was reviewing the presentation materials, he found himself staring at the diagrams and realized something: he was drawing the box for his system at the same size as the other teams’ systems, and that made it look like a big thing.

He was drawing the box too big.

Draw the box smaller

Nic‘s team started presenting a revised diagram in these meetings that made their system look as small as just one of the components in the diagram of the old way.

The teams’ systems were represented as large boxes, but the new system was drawn as a tiny box. After this change, teams were willing to give it a try because it seemed a tiny change that would be easy to back out if it didn’t work.

Pay attention to visual metaphors

As silly as this seems, it’s actually a really important thing to realize about human psychology: we evaluate things as we see them, and when the things we’re evaluating are intangible, like software systems, we “see” them through visual metaphors and evaluate those.

If we’re attempting to convince someone to try something, we should try to empathize with the people we’re presenting to. Are they overwhelmed and dealing with lots of complexity? If our proposal helps them remove some of that work, drawing a small box helps emphasize that we’re trying to reduce or eliminate work; a large box might communicate that it‘s a lateral move or actually creating additional work.

Maggie Appleton is one of the brightest minds in this space, and she explains this much better than I can in a killer talk on visual metaphors.

The right metaphor gets results.

After my conversation with Nic, I changed the way I presented my team‘s tool. We drew the box smaller and talked about all the work that disappeared by using this tool. We stopped talking about all the amazing things our tool could do — the part that was exciting to us — and instead focused on what was exciting to the people we were trying to convince to try it out.

We didn’t change the tool at all; we only changed how we communicated about it. We drew the box smaller.

Our new approach worked, and teams started to adopt it.

What boxes could you redraw?

Are there any challenges you’re facing right now where you’re having trouble convincing someone to try your idea? What kind of boxes are you drawing? How could you draw them differently?

Let’s talk about it on Twitter!

Toolkits Over Checklists

Mon, 27 Apr 2020 00:00:00 GMT

When a process is designed, it’s almost always coming from a good place. A process is introduced to avoid a specific problem, smooth out a tricky job, or otherwise make it more likely that we’ll get the desired outcome from our work.

“We made a mistake, so let’s add a safeguard to make sure we don’t make that mistake again in the future.”

Processes get bundled into checklists, because managers are always on the lookout for quantifiable metrics.

Checklists treat people like robots.

The biggest problem with checklists is that they’re linear: we start with step 1, and there’s a decision tree to be followed based on what happens.

In a lot of checklists, a non-trivial amount of the required work ends up being irrelevant. The team has to check a bunch of boxes that don’t apply to their project just so they can move on to the steps that do matter.

The Official How-To-Eat-Food Checklist™

Imagine you want to eat some soup, and you have to follow a linear “meal consumption guidelines” process to eat it:

Attempt to eat the meal with chopsticks
If unsuccessful, attempt to eat the meal with a fork
If unsuccessful, use both a fork and a knife
If unsuccessful, attempt to eat the meal with a spoon

This process is generic, and that makes it absurd: it creates waste and busywork (unnecessarily dirty utensils that need washing), burns a lot of time, and manages to insult the intelligence of the eater in the process.

A decision tree like this assumes that the person using it has no knowledge or judgment at all. It’s the sort of list that makes a ton of sense for a robot, but is utterly insulting to a human. Even if we’ve never eaten soup before, we can probably think through things and determine that a spoon is the best soup-to-face delivery method.

Checklists can be a good thing, but they shouldn’t be the first thing.

A checklist that helps enforce relevant, necessary behaviors is a good thing, and we should keep them around. However, we should also work hard to keep checklists small and relevant — and we should stop using them when they stop making sense.

As companies evolve, a once-helpful process can turn into an unnecessary chore. Since checklists aren’t revisited often, they don’t adapt quickly (or at all). As a checklist becomes outdated, it often becomes an outdated hindrance instead of the helpful safeguard it started out as.

Checklists feel official, so they tend to evolve only by expanding. They become irrelevant, atrophy, and can often turn into busywork like reports, forms, and other artifacts that start in a good place but end up creating drag on teams that draws out turnaround times, saps energy, and drains motivation.

It’s usually far harder to remove a process than to add a new one, so teams end up with huge process checklists that they must follow before they can ship.

Overused, overgrown checklists are a huge source of bureaucratic outgrowth. To keep our teams moving quickly, we should reach for checklists last, opting instead for flexible toolkits.

Go nonlinear with toolkits.

A better way to think about processes is as a collection of tools.

Going back to the soup analogy, if we consider each utensil to be an individual process, we can trust our team to reason about which process they actually need to follow and choose the ones that make them most effective.

(In this case, that means reaching for a spoon because it’s the right tool for the job. Unless it’s a really chunky soup, in which case you might add in a fork or chopsticks. No, dear god, please don’t add that to the decision tree.)

Reframing our processes as toolkits instead of checklists lets us keep all the benefits of well-designed processes without the drag of jumping through irrelevant hoops to satisfy a checklist.

Processes exist to solve problems; toolkits let us choose only the processes we need.

Solving real-world problems is rarely a predictable process. This means that comprehensive checklists are inherently unsuitable for the task. This is why strategies like the waterfall model have slow, demotivating timelines: you can’t predict the exact process for solving novel problems, and that means any checklist-based approach will either be out of alignment with the end goal or so broad as to be largely irrelevant.

However, if we break a linear checklist into its component subprocesses and treat each of those as a tool, we’re able to use our smart, non-robot, human brains to assess the situation and choose the processes from the toolkit that let us accomplish the task at hand.

Toolkits combine safeguards with autonomy and trust.

One of the major issues with process checklists is that they don’t trust the person following them at all. An exhaustive checklist implicitly says to the reader, “I don’t trust you to get this right, so I need you to prove that you did it properly by checking each of these boxes in order.”

A toolkit inverts that relationship. It says, “You’re the expert here, so we trust you to get this done. Here are all the tools you might need to get there.”

Realistically, the outcome is the same: the useful processes will be followed, and the irrelevant ones will be ignored. The difference is that in a checklist scenario, the person doing the work is forced to prove they tried each irrelevant step before moving on, while a toolkit-based approach allows the worker to use their own deductive reasoning to make the decision.

A checklist can be part of the toolkit.

The wonderful thing about toolkits is that they can include checklists that are useful in certain contexts. “Is this your first time doing a task like this? No problem! Use this handy checklist to see all the questions we recommend asking to decide how to solve it.”

Next time, you may not need the checklist, so you won’t reach for that tool again.

Toolkits enable results-based work.

One of the best ways to improve a team’s sense of autonomy and job satisfaction is to use results-based management strategies. Toolkits give teams the ability to choose their own approach (autonomy) and allow them to be measured on the outcome of their work rather than the specifics of their workflow.

Many checklists can be broken up into toolkits easily.

The main distinction between a checklist and a toolkit isn’t actually what they are; it’s how they’re expected to be used.

If you’re leading a team, you can turn a linear checklist into a toolkit simply by changing expectations: rather than saying, “I need you to prove to me that you did everything on this list”, say, “I expect you to meet our quality standards for shipping. This collection of processes is here for your to use as needed to get there.”

It’s subtle, but it makes a huge difference in outcomes. It makes your team feel like experts instead of worker bees. It allows people to take pride in their work. It treats people like people and not robots.

What toolkits already exist on your team? What will you create?

Are there checklists you can reframe as toolkits today? What toolkits could you create that would empower your team to succeed without removing their autonomy?

Let’s talk about it on Twitter!

The problem with grinding

Sun, 01 Mar 2020 00:00:00 GMT

Early in my career, I swore by “the grind”. I treated concentrated force of will like vegans treat nuts and just substituted that shit for everything.

Lack of experience? Underestimated how long it will take? My original plan hit a dead end and the deadline was looming? No problem — I’d just grind until I figured it out.

For years, I believed I could solve any and every problem by working harder. And it almost ruined my career.

Don’t get me wrong: a willingness to work hard is a great quality to have. After all, just about every project is going to hit a stretch of sloggy, boring work, and having a lower gear to drop into and push through that is really valuable.

What I am saying is that the substitution of grinding in place of careful consideration, planning, and processes is a huge problem that massively contributes to burnout and the glamorization of unhealthy habits.

Hooooold up. Let’s set some context here.

This is an extremely nuanced area of discussion, and I want to make sure what follows doesn’t come off as blanket advice that applies to everyone.

So let’s start by setting expectations: in the context of this article, “grinding” is a reference to my early days as an entrepreneur where I was skipping sleep, social activities, hobbies, relationships, health, and just about everything else in favor of trying to build my business.

There’s a certain corner of startup culture that glorifies this lifestyle. These are the “sleep when you’re dead” types; the “eat ~~sleep~~ work repeat” types; the “100-hour weeks are a rite of passage” types.

Everything that follows is directed toward the voluntary grind.

"Powering through" is rarely the best option.

By one measure, my ability to power through problems is one of my greatest assets: deciding that I'm going to do something, then sticking through it until it's done, has allowed me to finish things even when it‘s a miserable slog, which helped me build my reputation and network, which in turn helped me build my career to where it is today.

However, my stubborn strength of will prevents me from thinking laterally about some problems, and that causes me a nontrivial amount of unnecessary pain and difficulty. It enables me to be bullheaded about seeing my solution through, even if it's not a great solution.

If I see a problem, I have always relied on The Jason Lengstorf Rock-Solid 3-Step Plan to Overcome Any Obstacle:

Identify the wall between you and the thing you want to accomplish
Bash your head against the wall until the wall gives out
Climb through the hole you've just made to victory

In the broadest sense, this approach has delivered repeatable success for me. However, it’s a gross oversimplification that leaves out all the sub-steps, such as:

Step 2, part 9: rage weep because the thing you copy-pasted from Stack Overflow doesn't do what it says it should do and you don't know enough of the underlying concepts to debug it
Step 2, part 27: angrily slam your laptop shut and take 30 minutes to seriously consider homesteading in Montana, or
Step 2, part 28: take a deep, ragged breath, press the heels of your palms into your eyes, and open the laptop again because this is your life now and you'll never not be doing this so you may as well accept it.

While I was busy bashing my head against problems, I failed to realize that maybe — just maybe — alternative options existed that didn't rely on the thickness of my skull.

Long-term success is not sustainable through constant effort.

Force of will is like a rocket booster: it can exert an incredible amount of force for a limited period of time — but once the fuel runs out, you're left with a burned-out husk that needs to be fished out of the ocean and repaired and refueled at extremely high cost.

In addition to the short-burst nature of grinding, there's also the major issue with finding the work interesting (or at least rewarding).

This is a losing game for several reasons:

If we’re not interested in the project, we don't get the rocket boost (until a panic-driven race to the deadline kicks in, that is).
If we develop some other focus outside of the team's project, we’ll apply our force of will to that, leaving the project hanging (until the panic kicks in, of course).
Appreciation for this kind of work has diminishing returns. You can't promote someone who's single-handedly driving a project forward, and teammates will likely be both dependent on this effort and resentful of their dependence — over time the relationship sours, as imbalanced relationships tend to do.

And that's the risk: force of will is capricious. We can only apply force of will if we feel strongly enough about the thing to feel it's worthy of the effort. And a lot of the work that moves the needle isn't that exciting.

What should we rely on instead?

Relying on sheer force of will to finish projects should be treated like a disaster preparedness kit: it's great to know it's there in case of emergencies, but — and this is the important bit — if we need to use it, it means something has gone wrong.

Grinding should be our last resort.

In my grindier days, I already knew I was going to bash my head against a problem before I'd even heard the full project brief. This all but guaranteed I'd stay locked in the cycle. Had I taken some time upfront to ask more questions and consider more options before diving in, I could have saved myself thousands of hours and a beard-killing amount of stress.

Ask more (and better) questions.

Asking better questions guarantees the desired outcome is clear. And often, what someone tells you they want doesn't always line up with their desired outcome.

We need to ask the right questions at the right level to make sure we understand not just the current project, but how that project fits into the overall goals of the business, team, household, or whatever larger unit the project is in service of.

Knowing what we're actually trying to accomplish means we can feel more confident in questioning the how of things, which means we're more likely to make smart decisions instead of obvious ones that rely on force of will to complete.

Think laterally and consider more options.

Instead of committing to bashing through the wall every time, spend some time looking at alternatives.

In a staggering number of projects I've worked on, I started out believing that the only way to get it done was to put my head down and grind it out.

As I've become less willing to make personal sacrifices for professional goals, it’s become clear that just about every project has multiple solutions — and many of those solutions don't require any grinding whatsoever.

It's like I realized that most of these walls could just be walked around. Half the time they had doors I could have used, or at least a window I could wiggle through.

Now that I know this, it feels less like I succeeded because of my willingness to grind, and more like I succeeded despite my tendency to do things the hard way.

Are we succeeding because of the grind? Or in spite of it?

I stubbornly refused to buy a suitcase with wheels on it for years.

I'd carry my suitcase through airports like a tough guy, judging the “lazy” people who were effortlessly rolling their luggage along, shoulder burning, sweating through my shirt like some kind of smug masochist.

Grind culture feels like that to me: people acting smug about their inability to get ahead with reasonable hours, good rest, and healthy social lives.

Sometimes we have to live lessons to learn them.

Maybe a little bit of doing things the hard way is just part of learning. We have to see what the hard way feels like so we can appreciate the ease of alternative approaches.

Maybe the drive that leads us to grind is made of stubborn pride, and we can’t have one without the other. Maybe that’s why we refer to the early hardships as “paying dues”.

Or maybe that’s just how I try to justify my decision to do things poorly for so long.

Work smart. Grind sparingly.

Ultimately, this is a note to my younger self that I am positive he would brush off as “probably true for most people, but I’m different — I can handle this”.

So I’m not here to convince anyone. You’re going to do what you believe is right for you, and I support that: it’s what I’ve been doing my entire career, and I’m doing fine in spite of all my stubborn, terrible decisions along the way.

But I wanted to write this for anyone out there feeling tired — like really tired — who’s starting to feel like maybe this career was a mistake, or maybe this level of sustained superhuman effort might not be sustainable after all, or who’s feeling lonely because the hustle and grind lifestyle has kept you isolated.

For those people, maybe this post can be a reminder that between grind and burnout there are options. We can work hard without working constantly. We can achieve our goals without giving up our relationships, hobbies, and downtime.

We can build a career that supports the lifestyle we want and have the time to actually enjoy that lifestyle.

It’s a balancing act, but we can do it. You can do it.

We just have to do the work to give ourselves permission not to do the work sometimes.

Get the results you want more often by reducing friction

Mon, 17 Feb 2020 00:00:00 GMT

One of the best ways to create a successful product is to find something people need to do, then reduce the friction for them to do it.

If you need food, a grocery store creates less friction than farming. To get to the store, a bike is less friction than walking; food delivery removes the need to leave your house at all; ordering delivery via app removes the need to talk to humans. We’ve removed so much friction from the process of feeding ourselves that we can push a button, hide in our house, and wait for a stranger to shove a burrito through our mail slot.

People are intrinsically lazy; they’ll always end up on the path of least resistance. And what‘s another word for resistance? Friction.

Making things easier helps us get the desired results more often.

If we're trying to get a group of people, such as coworkers or customers, to do things a certain way, we can get much closer to guaranteeing that outcome by making it as easy as possible for people to do that thing.

If we make the right thing the easy thing, we can count on people to take the path of least resistance and know that they're taking the ideal path.

What the "right thing" is here is less of a moral decision and more of a business goal, but the principle holds.

The myriad apps that make our every impulse a button push away want us to buy things from them. They've removed all of the obstacles — all of the friction — so that we don't have to think at all to give them money. If I'm too tired to cook, I can open Postmates and reorder one of my five tried-and-true delivery meals in a few taps.

At IBM, my team took a whole bunch of compliance requirements and foundational code and packaged it up into a module. This transformed a process that used to be copy-pasting 700+ lines of code into a new service (which would go out of date and never ever get prioritized for upgrading) into a one-liner that could be easily upgraded and that guaranteed they were meeting foundational requirements for their services. It was optional to use, but nearly every team made the switch because it was so much easier than the alternative.

In both cases, the path of least resistance becomes the default, and through thoughtful design, the path of least resistance has become the path of best results.

Reduce ALL the friction!

If making the right thing the easy thing means reducing friction to help guarantee desirable outcomes, it might be tempting to make a blanket statement like “reducing friction is always good”.

Once we see the benefits of reducing friction in a few areas, we get the urge to find all the other places where we’ve been enduring unnecessary friction. This leads to life hacks and shortcuts and Killer Apps™.

In my world — the Land of Developers — this urge is strong. We nerds take our productivity optimizations seriously.

This drive toward reducing friction has completely transformed modern life. Amazon is eating the world by allowing us to impulse purchase a waffle maker Friday night and have a waffle party Saturday morning without leaving the house. Subscription services let us automate everything from dressing ourselves to charcuterie boards to getting busy.

Just about everything we can dream up has been turned into an app that will make that thing happen — we still have to lift a finger, but there's no effort required beyond that.

Reduce ALL the friction?

Is removing all of the friction in our lives a good thing?

I guess it depends on what we’re optimizing for. There are always trade-offs.

On one hand, services like MilkRun make it far easier to support local farmers and eat healthier by putting together a box of seasonal produce and delivering it to my front door.

On the other, reducing all friction seems like a great way to end up like the people in WALL-E who float around in hoverchairs and literally never do anything.

With that in mind, we may want to revise our premise to something like “reducing friction is sometimes good.“

That seems reasonable. Drawing the line for when it is and isn’t good is going to be pretty nuanced, but hopefully we can all agree that taking the “always good” premise to its logical conclusion would be too much.

But if we want to make this actionable, we need to decide when reducing friction is good. And if there are times when it’s not good, does that mean that there’s such a thing as “good friction”?

Not all friction is bad.

Sometimes added difficulty is a good thing.

Lessons are stickier when we have to work for them.

Without application or practices, education runs the risk of going in one ear and out the other. If we only read or watch something, we won't retain much — and it certainly won't help us cultivate a new skill.

Doing the work of practicing, taking notes, and other higher-effort learning activities helps the information stick in our brains and helps build actual expertise in new skills and patterns.

Awards feel awardier when we feel like we accomplished something.

Our sense of accomplishment is often directly correlated to the amount of friction we overcame. Beating long odds carries a higher emotional reward than winning a participation trophy. Both have value — it feels good to be included — but there's an extra something special about doing hard work and being recognized for that.

Teams feel teamier when we're empathetic and intentional.

Group dynamics rely on intentionally making some things harder to do.

Want to stress out your teammates and cause a lot of resentment? Change the plan with no notice and no explanation.

Adding friction to changing decisions that affect the whole group means that it's harder for an individual to make changes, but that extra friction also means that it's less likely for the group to be caught off guard or to feel like they've lost their agency.

A team's roadmap is probably a great place to add extra friction to ensure that changes are well understood, fully justified, and generally agreed upon by the group.

Adding friction to one path can reduce it on another.

If we think a little further about the team example, something interesting emerges: by increasing friction for individuals to alter the course of the group, we decrease friction for the group to accomplish its goals.

So maybe it's not so much that we're adding "good friction", but that we're making sure to reduce friction at the right level.

Maybe we shouldn't be asking whether we need to introduce good friction, but instead should ask some qualifying questions:

who benefits if we remove this friction?
does removing this friction introduce new friction somewhere else?

If we apply these questions to the question of whether we should make it really easy to change a team's roadmap, the answers make a pretty clear case:

Who benefits if we remove this friction? Leadership benefits — they'll be able to make changes to the roadmap quickly whenever they feel like it.
Does removing this friction introduce new friction somewhere else? Yes. The team can't be sure that the roadmap is accurate because it can change at any moment, so there will be uncertainty about what to work on. Unexpected changes mean work will likely get thrown away, which is demotivating and frustrating.

Introducing a process that requires fully qualifying proposed changes might be frustrating for the "move fast and break things" types, but putting those additional gates (friction) in place removes a ton of friction for the broader team — and in terms of absolute reduction, that's a larger amount of reduced friction.

Put another way: adding friction to one step to reduce friction in the overall process is still a net reduction in friction.

How you can start reducing friction for yourself, your team, and your customers.

If you're interested in making the right thing the easy thing, start by asking questions to discover opportunities to reduce friction:

When you look at the broad scope, what is the desired outcome? For example: "a website visitor buys our product", "all teams comply with security requirements", "I get to the gym twice a week".
What does the path to achieving that outcome look like right now? Think through each step that has to happen in order to get the desired outcome. User workflows, flowcharts, and checklists can be really helpful for visualizing this.
What are the stumbling blocks on that path? Use whatever data you can get your hands on to understand where friction exists in your existing workflow. Where do people fall out of your sales funnel? What do teams consistently get wrong with security? Where do you feel the most reluctance on your way to the gym?
How can you remove stumbling blocks? Once you've identified stumbling blocks, the real work begins: you know what the friction is — now how do you remove it? Sometimes this is obvious once you're looking at the whole picture ("people can't find the 'buy' button!"). Other times it's really tricky ("I just can't get myself out the front door to go to the gym"). Don't forget to ask yourself who benefits, and how removing this friction might introduce new friction elsewhere!

This is far from a comprehensive framework, but I've used this set of questions as a basis for building new habits in my personal life, helping my company identify root problems, and just about every other situation where I've needed to help improve a process.

How are you making the right thing the easy thing?

Do you have strategies for reducing friction? When have you found it to be a good thing to make something harder? What other questions do you ask when you set out to improve a workflow?

Hit me up on Twitter or join the Party Corgi Discord — I'd love to chat with you!

2019 Personal Retrospective: Measuring progress and setting goals

Wed, 01 Jan 2020 00:00:00 GMT

I've been writing a retrospective every year for a while now, and we've ticked over into the '20s, so it's that time again.

A retrospective is a format for reviewing progress to extract useful information from the past to inform actions going into the future. It's popular as a business practice, but (in my opinion) severely undervalued as a personal tool.

A personal retrospective is a way to measure progress and check in with ourselves: are we improving the baseline? Are we steadily becoming better versions of ourselves?

Taking the time to reflect and record our progress helps us qualify, quantify, and concretely describe the things that made us feel good, the things we want to improve, and the things we want to change as we go into our next year.

First, a recap: where was I at the end of 2018?

In my 2018 retrospective, I laid out several goals for myself:

Be more creative off the computer. I was feeling like I spent way too much time looking at a screen, so I wanted to take on new projects that weren't screen-based.
Write more often. This has been my ongoing struggle. I love writing, but I struggle to make time for it. In 2016 and 2017, I only published three articles each year that weren't retrospectives — this was a huge drop-off from previous years: in 2015 I averaged a post every month, and in 2014 I wrote 33 posts. 😱
Double down on community. I moved to Portland at the beginning of 2018 after a year in Austin and two years before that living out of a suitcase. A large part of our decision to settle down in Portland was because we missed having a close network of friends and family. And I knew that if I wanted to actually have the community I was missing, I needed to work for it.

I also set a goal to write quarterly retrospectives. I managed to get Q1 and Q2 done, but they felt less helpful than I'd expected, so I skipped Q3 and Q4 in favor of going back to the annual check-in.

Using these goals for context, let's get into the retro.

What went well in 2019?

Overall, 2019 was a good year for me. I feel like I'm stepping into 2020 in a good place mentally, professionally, personally, and (somewhat) physically.

I developed hobbies that don't involve computers.

Over the last year I've taken salsa dancing lessons, built a shed, decorated our house, and became regulars at a few local businesses.

we got the lights and a few more plants on the bar shelves and hoooooooly shit I'm in love with this 😍😍😍
pic.twitter.com/Q91cOmwt0g
— Jason Lengstorf (@jlengstorf) November 28, 2019

I'm still more or less an indoor pet, but I feel less like all of my attention goes to screens, which feels nice.

I wrote significantly more content.

In 2019, I was able to get more content published on my blog than 2017 and 2018 combined. I also wrote technical articles for publications like CSS-Tricks and Smashing Magazine — this was fun, because it's been a while since I've written technical content.

A lot of this content happened in later 2019, which was after I left Gatsby and joined Netlify. It felt like I had more time to sit and think after I left Gatsby, and that gave me the headspace to turn some of my thoughts into coherent posts.

Another huge factor was surrounding myself with people who regularly discuss the kinds of topics I love to dive into — several posts I wrote in 2019 started as copy-pasted excerpts of discussions from those chats.

(If you're a content creator and you like discussing both "philosophy of work" and web development, you may want to join the Party Corgi Discord, which is where I've been having these discussions.)

In addition to writing, I also created a bunch of code-related video content on Learn With Jason, egghead, and Frontend Masters.

My community ties felt strong and got stronger.

One of the major reasons to settle in Portland was to build a strong community, and it feels like we're doing that. In 2019, Kyle Shevlin and I turned our impromptu get-togethers into a somewhat organized, usually monthly get-together over food and beverages called Food With Friends, where anyone in the Portland community is welcome to join, with a nice group of regulars.

Today was one of the last few sunny days we’ll see in Portland this year. So we celebrated with smashburgers on homemade potato buns (by
@marisamorby
) and a side of triple-fried Belgian fries by @jhooks . @matthewhoward followed with chocolat malted milkshakes.

Holy. Crap. 😋🤤
pic.twitter.com/FEMjDHr2WC
— Jason Lengstorf (@jlengstorf) November 3, 2019

I also feel like I've built some really strong friendships over the last year. Our friends Joel, Kristina, Matt, and Leslie get together with Marisa and me for The Steadily Escalating Dinner Party, where we cook an elaborate meal together every month or so.

It's nice to have people I call "friends" instead of "acquaintances" or "work buddies" or "people from the internet".

I learned more about what I want in my career.

Finding the right fit professionally is a continuous process of working, evaluating, and adjusting. In 2019 I reflected on what I'm optimizing for and landed at Netlify, where I'm working with people I really look up to and operating as part of a team. The company is also paying a lot of attention to representing the communities we want to serve in our hiring decisions and the ethics of how to be a tech startup. It feels like the right place for me.

I also doubled down on Learn With Jason, which has felt like the right format. It combines all the things I like: learning, teaching, interacting with the community, and talking through approaches with smart people.

What could have gone better in 2019?

Overall, I'm pretty happy with the outcomes of 2019, but there are a few things I would have liked to improve.

I wanted to work more on my physical health.

I managed to get to the gym twice a week in 2019, and I did lose ten pounds, but I haven't paid enough attention to my health. I really struggled in Austin, where every vegetable is deep fried and covered in cheese, so moving back to Portland was a big improvement on its own — and it feels like I was kind of relying on the environment and not actually making an effort of my own.

I wanted to make more music.

I started taking music lessons, but I didn't make time for music as often as I wanted to.

I have no excuses here. I just... didn't do it.

What will I change going into 2020?

All things considered, I feel like I have a pretty good rhythm going right now, so I'm not feeling the urge to make any major changes.

That being said, I have a few ideas for what I'd like to see happen in 2020.

High-level 2020 goals.

I want to make more music. John Lindquist challenged Chris Biscardi and me to make original music for our livestreams by the end of 2020, so I want to use that as an accountability tool.
I want to improve my physical health. I made some progress in 2019, but I'd like to make this more of a priority now that I've got a little more mental energy available.
I want to maintain the improvements I've made in other areas of my life. I want to make sure I don't forget to maintain my current relationships, hobbies, and the other improvements I've made up to this point. I have a tendency to finish something and then immediately forget about it, so keeping myself honest about the work required to keep these aspects of my life healthy is important.

What are your goals for 2020?

Running a retrospective remains one of my favorite methods for measuring my progress and making sure I'm actually moving toward the things I want to move toward. If you've never tried this, I highly recommend it. The format is to ask and answer three questions:

What went well?
What could have gone better?
What will I change going forward?

Sharing it publicly can be a good way to hold yourself accountable if you're comfortable with that. I strongly recommend posting it on your blog, but you can also tweet at me. And if your goals for 2020 include creating stuff and you want a safe, supportive community to bounce ideas off of, please join the Party Corgi Discord!

Here's to making 2020 the best year yet!

Planning vs. Execution: How much planning is too much?

Mon, 30 Dec 2019 00:00:00 GMT

I place a lot of value on planning. Which means I talk about it a lot. Like, a lot.

For all my talk about planning, there comes a point at which we need to stop planning and start, y'know, doing stuff. But where is that line?

How do we know when we're done planning and ready to start executing the plan?

My friend Chris Biscardi gave me some feedback on a post I wrote about the concept of mise en place as it applies to project planning and made excellent points:

In cooking, everything is planned down to the last detail. It's all plan, then execution. It sounds like you're saying, "Plan everything before you begin," and that feels a bit at odds with software development. You can't entirely plan the surprises out of projects.

Possibilities open and close as you do more research. Figuring out the optimal time to stop researching, make a decision, and start working to implement that decision is important — and you'll never get to 100% complete research. You also need the ability to switch from active work on the project to researching potential future roads again. It's more of an ongoing process than a strict plan-then-execute.

Chris makes three extremely good points here:

It's impossible to plan in such a way that surprises can't happen.
The process of working on a project exposes areas that need additional research and planning.
Projects — especially large ones — aren't fixed efforts. They're processes.

Hearing this feedback made it clear that I've been banging the "do more planning!" drum without digging deep enough into handling the messy realities of working on real-world projects.

So let's fix that.

tl;dr

Including stakeholders in planning and limiting project scope will help minimize surprises.
To complete large projects, break them into smaller projects, plan the highest priority small project, execute the plan, check assumptions, then repeat.
Short-term plans should be high-fidelity and we should have high confidence in their success.
Long-term plans will be lower fidelity and more likely to change over time.
If we spend too long planning, we waste time for marginal improvements to the plan.

We can't plan our way out of doing the work...

No amount of planning will deliver a finished product. Plans are the rails that guide the train to its destination, but we still need an engine — that's us, doing the work — to move the train along those rails.

Planning is a critical step, but it's still only one step along the path to success.

...but we also can't work our way out of a bad plan.

There's a reason we regularly say a project that's gone horribly wrong has "gone off the rails".

Without a good plan, we can move the project forward, but exactly where we're moving it isn't clear. Execution without planning is risky and stressful and potentially very expensive and wasteful.

We need both.

Finding a balance between planning and execution — as well as a good rhythm for planning and executing as a continuous cycle — can be the difference between stressed out, unproductive teams and highly efficient, happy teams.

Surprises are inevitable — but they don't need to be destructive.

There are myriad ways we'll be surprised during a project. A chosen tool may prove incapable of handling a critical feature. The project stakeholders may swoop into a meeting and change the entire direction of the project without notice. Another team may have already built this feature and no one told us about it.

Many of these surprises can be eliminated with good planning: for example, we should be confident that our chosen tool can support the required features before we start building with it. Learning that our plan has a fatal flaw mid-way through a project is a signal that we failed to research and plan properly.

Some of these surprises are kind of like the weather when we book flights: there's not much we can do about a severe thunderstorm shutting down our connecting flight in Denver, and there's even less we can do about an executive with a new pet project. We do the best we can, but it is what it is.

One strategy that can help mitigate issues with stakeholders changing their minds is to involve stakeholders in the planning and make sure the outcome is clearly defined with a public sign-off on the scope. It won't matter if they're the type to contradict themselves and ignore their own sign-off, but honestly, if your stakeholders can't sit still long enough for you to get through two weeks of work, it might be worth looking for new stakeholders.

The plan defines the work defines the next plan.

Big projects are impossible to plan in entirety. However, it's critical to have a clear idea of the desired outcome in just enough detail to get the whole team on the same page about what direction we should be rowing in.

Big projects, in my mind, are better described as a related collection of smaller projects. These small projects are temporally bound to each other in many cases, meaning that one project can't start until another is completed.

Planning big projects is an exercise in multi-level thinking. We need to hold in our minds The Project™, while breaking off chunks of The Project™ into small-P sub-projects.

The Project™ is the vision.

The Project™ is a vision: it's a high-level, long-term, low-fidelity plan. It's huge and complex and full of assumptions and educated guesses. It will see dozens, if not hundreds, of small revisions and adjustments as we work toward realizing this vision.

Work backward from the vision to create a roadmap.

But from The Project™, we can work backward from our desired outcome to get a rough sense of the steps that need to be taken to get there. Those steps can be further broken down into a roadmap, and that roadmap gets turned into a prioritized list of smaller projects that are short-term and focused on a single sub-goal.

Prioritize the roadmap, then thoroughly plan the first project.

These smaller projects should be prioritized. The highest priority project can then be planned in high fidelity, with a short time horizon. Then, with high confidence, we're able to execute the plan to complete the first small project.

Repeat until the vision is realized.

When the project is done, we go back to The Project™, check our assumptions against new information learned while executing the last plan, then choose our next small project and start from the top.

By taking a moment at the end of each small project to check assumptions, we can make small adjustments to The Project™ to ensure that our vision lines up with the realities of building it. This avoids the pitfalls of waterfall project management while still providing a lot of structure for teams.

Confidence in a plan should decrease as the time horizon gets further away.

We should be able to plan for short-term, high fidelity plans with fairly high confidence. We're never going to be 100% sure that something will work out, but it shouldn't be unreasonable to expect that we can plan 2–4 weeks of work confidently.

As we look further into the future, however, we should be comfortable working with lower confidence. We can't predict the future, so getting comfortable with uncertainty is a critical competency.

To give a practical example, my plans for tomorrow are more or less finalized. Barring any substantial bad luck (e.g. a sick friend, a burst pipe, the apocalypse) I know exactly what tomorrow holds in terms of where I need to be and who's expecting things from me.

My plans for three months from now are significantly less concrete. I'm talking to a few friends about visiting, and in discussions with some conferences about speaking, but the dates are still unclear and there's a reasonable chance that some of it won't happen at all. I have plans, but I'm less confident about them this far out.

There is a point of diminishing returns with planning and research.

While it's important to do the meta-work and ensure that we're going into our projects with high confidence and a clear plan, there's a point at which we cross over from planning to procrastination.

It's hard to know exactly what the "right amount" of research is, but that number for sure is not 100%. The amount of extra confidence that comes with gathering 100% of the available information isn't going to be large enough to make up for the extra time required to gather that information.

My personal guideline is to plan until I don't have any question marks left. I may not have all the information to be sure my chosen solution is "the best", but I do know that it can deliver everything that I need to execute my plan.

If I find myself looking at a proposed solution and thinking, "I don't know if we can do X with this setup," then I know I need to keep researching and planning.

Let's recap: how do we find balance between planning and execution?

For any project to succeed, both the planning and execution need to go well. For larger projects, we need to do the research and planning up front to avoid the most obvious failures and road blocks, and mitigate as best we can the parts of a project that we can't control, like stakeholder-driven changes mid-project.

We can't plan entire ambitious projects from start to finish, but we can break large projects into smaller projects and thoroughly research and plan those.

After completing small projects, we should check our long-term plans and assumptions against any new knowledge we gained from the project, make any necessary adjustments, and then repeat the process for the next small project.

While our long-term, large project plans will necessarily be a little vague and subject to change as we learn new information, our short-term plans for small projects within the larger project should be thoroughly planned and fairly concrete.

However, we need to keep in mind the balance between planning to improve our chances of success and planning to put off making a decision and doing the work. As a general guideline, plan until there are no question marks left in the short-term plan, then execute.

How do you plan your projects?

I've seen a huge amount of success (and a significant decrease in my stress levels) by implementing the planning guidelines I talk about here, but I by no means think that this is the only way to do it, and I know there's always room for improvement.

I want to hear from you! How do you and/or your team plan projects? What works? What doesn't?

Share your ideas on Twitter, or join a group of content creators and enthusiasts discuss this stuff at length on the Party Corgi Discord. (A lot of my posts — like this one! — start as discussions in that group.)

What Are You Optimizing For?

Sun, 17 Nov 2019 00:00:00 GMT

An easy trap to fall into is believing that decisions have right and wrong answers.

"I have a good job now, but I have an opportunity to get a different job that I'm pretty sure will be better! What's the right thing to do?"

"I have the opportunity to travel for a year, but my significant other doesn't want to do the long-distance thing. Am I wrong for wanting to go?"

What's "right" today may not be "right" tomorrow

One way to frame this is to think about it like choosing what to eat. Do I want a greasy smashburger and fries for dinner? Or do I want to eat something healthier like roast chicken and vegetables?

The "right" decision here very much depends on a lot of personal context. What's my diet been like lately? Have I been eating pretty healthy and this is a reasonable indulgence, or am I three weeks into a binge? Am I trying to lose weight, or am I pretty happy with where I'm at right now? Do I have any upcoming dinner plans where I know I'm eating something particularly healthy or unhealthy?

Depending on my answers to those questions, the "right" decision will change. And — more importantly — if I find myself in this same situation six months from now, the "right" decision may very well be different, but still "right".

If my diet has a cheat day every Saturday, then my answer on Saturday will be different than my answer any other day of the week.

Every decision is partly right and partly wrong

Because we don't make decisions in a vacuum, we don't get to make clean-cut decisions. The best we can hope for is "mostly right, with minimal collateral damage".

My decision to pay a premium price for locally made furniture makes a small contribution to things I think are important: supporting local businesses, reducing the amount of cheap crap that gets mass-produced to break and end up in a landfill in a year or two, and so on. However, when I pay higher prices it drives demand that keeps locally made furniture out of reach for people who earn less money. So did I do a good thing and support local business? Or did I do a bad thing and empower capitalism to worsen wealth disparity?

Unfortunately, it's not an "or" — I did both. I don't get to exist without causing harm somewhere downstream from me.

The best I can hope for is to minimize harm and maximize benefit. But "harm" and "benefit" aren't absolutes, so really, what I'm doing is taking my own worldview, distilling it down into a model of what I consider to be beneficial and harmful, and optimizing my decisions to get the maximum benefit while causing the least amount of harm.

Each decision point is a course correction

Because there are no "right" or "wrong" decisions, we're always optimizing for whatever's most important to us right now.

Each decision will give us new information, and that often means making small adjustments to our worldview. This means each decision is an opportunity to adjust where on the spectrum we're aiming for.

It's like making bread: you start by combining the ingredients, and once you see how they're combining, you might need to add a little more of something to get the consistency right. The dough has to rise, and you might decide to add or remove some time based on how quickly it's rising. During baking, you start with a set amount of time, but you might pull it out early if it's getting too dark or leave it in for an extra few minutes if it's not quite done.

You always know where you're trying to end up — eating a delicious loaf of homemade bread — but as you move through the process and gain more information, you're able to make small adjustments to your decisions that improve the outcome.

On a more macro scale, this is what most of us would call "personal growth": as a teenager, I was so occupied with maximizing benefits for myself that I barely noticed when I caused harm; as an adult, I try my best to consider the trade-offs for myself and others before I make decisions.

I still get this wrong all the time — my goal isn't to be perfect, but to improve my averages so I'm improving the baseline, not just for myself, but for everyone I come in contact with.

What am I optimizing for?

Because it can be difficult to wrap your head around abstract concepts, I wanted to write out my own abridged career history and map the decisions I've made to what I was optimizing for when I made each move.

This isn't intended to be a guide for anyone, but rather an anecdote to illustrate the concept and how it influenced my own decisions.

My optimizations started out broad and had wild shifts

The first thing that I really threw myself into headlong was music. I was optimizing for the success of the band, and everything else was secondary. I slept in vans and on concrete floors, ate instant noodles for weeks on end, and worked endless hours trying to book shows, build and grow a fanbase, and whatever else it took to become a rockstar.

When I saw the level of "rockstar" that was available to me,, my priorities shifted. I didn't want to be broke and struggling and partying all the time. So I started optimizing for something else: I took all the things I'd learned to support my band and started looking for ways to use them more lucratively. I landed on web design and started an agency.

As my agency grew, I was optimizing for control. I wanted to choose who I worked with, when and how I worked, how the projects were tackled, etc.

Once I had a general direction, I had to learn what was valuable to me

As I got further along in my career, total control started to lose its shine; I was exhausted, beaten down, and physically self-destructing.

For my next role, I didn't want more of the same. I changed what I was optimizing for: time.

I didn't mind giving up some of the creative control if it meant I could get back to a reasonable schedule. So my next role was a long-term contract for a client that I knew well, working on a single project that was more research than a real product, which meant the urgency was low. As a result, I found myself working about 35 hours a week — it was glorious.

Toward the end of that contract, we ran out of things to do. I offered to let them out of the contract early, but this was a dream client — they held up the last three months of the contract even though I had no tasks. And then I realized something: I don't want all of my time to be free.

Three months without anything to focus on caused me to drop into a full-blown existential crisis. I didn't have a project to give me direction, so... what was I going to do? I felt rudderless and spent several weeks on the brink of the most privileged depression, I think anyone's ever had.

This wasn't actual, real depression. This was fancy depression. "Woe is me! I get paid to do nothing! Do I serve a purpose? Am I but an expensive pet? Doth my existence merit the tallow in its brief candle to flicker upon this mortal sphere? Woe! Woe! Woooooooeeee!"

But let me also caveat that by saying: look, this is 100% what we should all call "a good problem to have", but good problems can still be problems. Each new phase of our life we enter leaves behind one set of problems and introduces a new set that's challenging and frustrating, albeit less life-threatening. So while we need to acknowledge that we're privileged, it's also okay to see these problems as real problems. We just probably don't want to tweet about how hard our life is because we don't have to work to get paid and we're bored oh em geeeeeeeee.

I'd been optimizing for free time, and I'd over-optimized for it. I learned that it wasn't time that I wanted, but balance. I want plenty of free time to play, relax, socialize — but I also want to do work that felt important and impactful. One without the other leaves me unfulfilled.

I changed what I was optimizing for in my next job search.

Knowing what I valued let me zero in on specific optimizations

When I joined IBM, I knew that it was a big enough company that I could go home and forget about work in the evenings and weekends and nothing would fall apart. I also knew I'd be on a team, where I'd learn from people far smarter than I am and help coach up people who were earlier in their careers.

I was optimizing for growth — with a non-negotiable requirement of balance.,

IBM was incredible for my growth: it gave me the resources and freedom that led to me leading a team that built an open-source framework for GraphQL, which opened the door to speaking about building teams and architecting systems — and that opened the door to a huge number of new opportunities.

Over time, IBM's bureaucracy became too challenging to navigate, and I found myself in months of meetings trying to get approval to do weeks of work, which made me feel like I was no longer in control of my work. That led me to look for a new role that was more in line with my goals.

When I moved from IBM to Gatsby, I was still optimizing for growth, with a redoubled focus on autonomy. I joked that my job title was Human Duct Tape because I ended up going wherever there were new challenges, from designing a hiring process to creating open-source contribution automation to creating a swag store (and the swag to go in it).

The optimizations freed up space for me to see outside my own experience

While I was there, I also started to realize that I didn't feel as motivated by career growth in the "get promoted" or "make more money" sense. I was realizing that what really felt valuable to me was helping other people grow — I wanted to share what I'd learned, so other people could (hopefully) learn from my mistakes and avoid some of the difficulties I'd brought upon myself early in my career.

I started spending a huge amount of my time thinking about what could be done, both personally and at a company level, to help open doors for people and provide as much guidance as support as possible.

Watch on YouTube

My shifted focus showed me some of my blind spots

My transition out of Gatsby was another slight shift in optimization: I wanted to be on a team where more people were working on what I was working on. More than that, I wanted to be surrounded by people who could teach me to be better, at the new things I found myself learning, like how to create space for other people and make them feel welcome enough to contribute.

When I was working on my own growth, it was hard to imagine experiences other than my own. It was also hard to imagine that the things that worked for me might not work for everyone.

When I started focusing on actively helping other people, I quickly realized that I not only had a shitload of personal privilege that I'd never really considered — I'd built my career as a young, healthy, straight, white man with a middle-class family that would take care of me if I took a risk that didn't work out — but that I also only knew how to communicate in the ways that had worked for me — jump in with suggestions; try something and ask for forgiveness later; question authority and put up a fight — which carry a high risk of catastrophically backfiring for others (especially people who weren't backed up by similar amounts of privilege).

I wasn't going to be able to learn how other people experienced the world on my own. I needed to be on a team where people could coach me to frame my advice and add the proper disclaimers and avoid saying "this will work for you" if it will only for sure work for me.

At Gatsby, I was a team of one. That was amazing for all the original optimizations: I had full autonomy, I set my own deadlines and hours, I was able to drive my own roadmap — but I wasn't getting much feedback. And it just didn't make sense to expand my team yet.

We knew whether or not a thing I'd done had worked in the general sense, but there was no one with experience doing the same things to give me feedback about what could have been tweaked or improved.

The worst outcome I could imagine for myself is to reach a point of complacency or feeling like I've "finished" learning. I knew I needed to join a team where people would challenge me to do better and give me feedback and ideas that would help me avoid settling into a comfort zone.

When Sarah Drasner, one of the people I admire most in the community, approached me about joining her team,, I knew I had an opportunity to get feedback and have my ideas challenged by the best in the business.

At Netlify, I'm optimizing for new kinds of growth: I want to continue doing what I can to help people succeed, both through my own efforts and through company initiatives; I also want to grow as much as I can with the support network of Sarah, Phil, Divya, Tara, and Shawn.

What I'm optimizing for will evolve over time

That's what I'm optimizing for right now, but I know that I'll need to adjust as time goes on. My adjustments have been much more subtle as time goes on ("I want to do the same thing but with an experience leader" is very different from "I accept that I will not be a rock star so I guess I want to be a web developer?"), which I take as a very positive sign: I'm not veering wildly from thing to thing, hoping to find something that makes me happy; I'm making small adjustments to keep me pointed in the direction that I know makes me happy.

What are you optimizing for?

We're all optimizing for something, whether or not we've made a conscious decision to do so.

So what are you optimizing for? How are your decisions helping you get there?

First, Get Ready: What Mise En Place Teaches Us About... Everything

Sun, 17 Nov 2019 00:00:00 GMT

The first few times I tried to cook, I stressed myself out and the results were disappointing.

I couldn't understand how it went wrong. "I followed the recipe! What the hell?!"

I'd start cooking by reading step one, which might say, "Add the garlic and onions to the pan and sauté until fragrant." Then I'd jump up to the ingredient list and read that I needed one medium-sized onion (diced) and three cloves of minced garlic. So I'd bust out the cutting board, dice 'em up, and start cooking.

Then step two would come: "Add in the tomatoes, tomato paste, chicken broth, paprika, cumin, salt, and pepper and bring to boil, then let simmer for ten minutes."

Oh. That's a lot.

I'd frantically measure out ingredients while trying not to burn the garlic and onions.

Chaos reigned, and I'd measure wrong, overcook things, or forget ingredients entirely.

Then I learned about mise en place

French culinary education teaches a practice called mise en place, which roughly translates to "everything in its place".

In practice, this means the first step to cooking a meal — before any actual cooking happens at all — is to measure everything and make sure it's prepped and ready to go.

Learning mise en place changed the way I cook.

Every year around the holidays I make a batch of Jeffrey Morgenthaler's egg nog. The first couple of times I did this, I found myself trying to quickly measure all the ingredients while the blender was running, which tended to work out, but was more stressful than I prefer.

After learning about mise en place, I start the recipe by measuring and prepping the ingredients, then putting them into bowls according to the step where they're added — cream and milk in one bowl, sugar in another, etc.

Now the recipe is a breeze: I'm just pouring in Bowl #1, watching the clock, pouring in Bowl #2 slowly, and so on until I end up with a stress-free batch of delicious egg nog.

Mise en place is for more than just cooking

The more I think about it, the more I'm convinced that the concept of mise en place has applications across all aspects of life. Whether I was specifically calling it "mise en place", or thinking about it as efficiently planning projects, or waving my arms about the importance of setting good expectations, the common thread is in preparing up-front to make doing the work more effective and less hectic.

I tend to call this kind of work meta-work.

If we know that we want to achieve a certain outcome — a delicious meal, a successful project — we give ourselves far better odds of achieving that outcome by learning what we need and getting it ready first.

Mise en place at work

At IBM, I ran a couple projects where I just dove in. I had a rough idea of where we needed to go, so my team just started building stuff. This put a lot of strain on us: it always felt like we were just making it up as we went along (we were) — we kept throwing away work when we hit surprises and had to regroup and adjust our plans.

Had we done planning work ahead of time, we would have spotted most of the surprises before we ever wrote a line of code, which would have saved us quite a bit of time and frustration.

At Netlify, I'm adopting a mise en place approach. I'm in charge of building the swag store, and starting by doing the planning. Instead of diving in, we're asking questions:

What are we building?
What work has already been done by other people in the company?
What is our budget?
Who are the stakeholders?
What technologies do we need to integrate with?
What are the non-negotiable features that need to be complete to mark this project as "done"?

Because we took the time to slow down and ask before starting to build, we already have answers to these questions. No time has been spent on design or code yet.

This has a profound effect on the project: rather than a panicked race along a path that we're making up as we go along, we have the whole project mapped out, with a clear understanding of the technical scope, business goals, ownership, and checkpoints.

Instead of relying on assumptions and sheer force of will to complete the project, we have a clear path, with the requirements for each step ready for when we get there.

Sure, it starts out a bit more slowly, but now that we've got the plan things are humming along quickly and I haven't felt stressed about it once.

Less splatter paint; more paint-by-numbers

There's a time to make it up as we go along — experimentation and play are critical parts of learning and improving — but when it comes to projects where we need the closest thing to a guarantee we can manage, we don't want to be wandering around; we want to know exactly what's going on.

Mise en place changes projects from unbounded exploration to paint-by-numbers: we know what to do at every step; we just need to do the work.

How to apply mise en place to your own life

If you want to give this approach a try, choose anything that you want or need to get done and try to separate out all the bits that can be done ahead of time, then do those first.

Are you putting together a bookshelf? Lay out the pieces for each step in order before you start building anything.

Starting a new project? Figure out who the stakeholders are and learn what their desired outcomes are — get those nailed down first. Then map out the project and figure out what questions need to be asked. What are the checkpoints? When do they happen (e.g. at the end of certain phases)? What needs to be true for a given phase to be complete? Who owns final approval?

All of this will need to be answered at some point.

Doing meta-work ahead of time doesn't add extra work — it moves the decision-making to the beginning of the project, which eliminates mid-project surprises and decreases the overall amount of work required.

The added clarity goes a long way toward reducing the team's stress and improving their ability to work quickly and effectively without constant oversight.

We're not choosing whether or not we plan — planning will always happen — we're choosing whether we plan first, or plan after we've done a bunch of work against incorrect assumptions.

What else can be simplified with mise en place?

What other projects or activities get simpler if we prepare ahead of time? How do you use mise en place in your own life?

Share your ideas and stories on Twitter!

The Ugly Other Half of Creativity

Mon, 19 Aug 2019 00:00:00 GMT

My little brother and I used to play cars when we were younger. We grabbed our favorite Hot Wheels and staged death races, limited only by our imaginations.

“Blam! Blam! I’m shooting at you with spikey cannon balls!”

“Nope, you missed me! I activated my car’s wings to fly away.”

Our play battles were an endlessly creative effort. We added any feature, bell, whistle, or concept we could come up with to make ourselves unbeatable. Silly constraints like cost, physics, or reality couldn’t stop us — we were being creative!

“Nuh-uh! These are heat-seeking spikey cannon balls! They followed you into the sky.”

“No, my car has a freeze mode so heat-seeking stuff can’t see it.”

There were no limits. No rules. If you could imagine it, it was allowed.

“Oh yeah? Well my car has a laser cannon that shoots at the speed of light and has motion tracking, radar, satellite targeting, and a human spotter. I blast your stupid ice car out of the sky.”

“NOPE. My car has a laser reflecting shield. You just blasted yourself, idiot!”

These battles usually ended with one of us getting beaned with our stupid ice car.

Without rules, imagination is ridiculous.

For most of us, “being creative” means unlocking the furthest reaches of imagination, plucking new ideas out of the ether, and inventing groundbreaking new ideas, products, or services.

And, sure, a big part of creation is a swan dive into the Land of Imagination. For those of us who enjoy creative pursuits, this is the fun part.

But it’s not the only part. And — if we’re speaking from a strictly “using creativity to pay the bills” standpoint — it’s not the most useful part.

Creativity happens in two stages: first, unbounded imagination; then — more importantly — ruthless editing.

Editing is how we transform imagination into creativity.

The fun part of a new project is scaffolding out into the stratosphere and thinking of all the endless possibilities. This is a decidedly good starting point; we should try to imagine what could be done with endless resources and bottomless support.

However, most businesses and side projects don’t have unlimited resources. So after we’ve done the fun part of imagining what’s possible, we have to sit down and do the much less fun part: deciding what’s practical.

Think of creativity like a Pinkberry: imagination is realizing that we can put kiwi, cookie dough, or gummy bears on frozen yogurt; editing is what keeps us from adding all three at once.

We willingly suffer to avoid decisions.

In an experiment made famous in the book Predictably Irrational, Dr. Dan Ariely and Jiwoong Shin found that people were willing to pay a cost to keep options available — even when the option wasn’t actually a good one.

When we create things, we’re opening every door we can imagine. We’re zooming out to look at all of the options.

To be effective as creators, however, we have to choose the best options — and discard the rest.

In other words, after we imagine, we have to decide.

To decide means killing your darlings

The word “decide” shares its roots with words like “homicide” and “patricide”; it literally means “to cut” or “to kill”.

The imaginative part of creativity is fun. We get to create as many options as we want with no rules or constraints! It’s a party! Each idea is special and precious and dear to us; we love them all.

But the editing part is (almost literally) murder.

“In writing, you must kill all your darlings.” – William Faulkner

After we see all the options spread out in front of us, we have to choose which ideas live — and which ones die.

This makes editing uncomfortable. Each decision can feel like we’re boxing ourselves in, limiting our freedom, and locking ourselves into a course of action.

Not deciding means we suffer for options

If we don’t make decisions, we can’t act. Taking action requires a clearly stated, clearly understood goal. You can’t tell the team, “We have a hundred amazing ideas and we might do any of them; let’s keep our options open.”

In the words of Ron Swanson, “Never half-ass two things. Whole-ass one thing.”

Turning ideas into action requires clarity. This is true whether you’re a solo act or working on a team. Meaningful progress on knowing where you’re headed and why — but just as much (if not more) value comes from knowing where you’re not going.

Editing turns idea soup into action steps. It transitions from searching for new possibilities into focusing on probabilities. Your roadmap shouldn’t be a list of every possible idea; it should be a list of the ideas with the highest probability of success.

The process of editing ideas into a roadmap allows a team to move as a unit. It sets expectations so the people around you know not only that the vision is to accomplish Goal X, but that the next steps are to complete Ideas A, B, and C. More importantly, this process of editing makes it clear to everyone that if Idea D arises, it can be considered at the next checkpoint, but it’s not part of the plan right now.

If your strategy can’t be articulated with clear, concrete action steps, it’s not a strategy; it’s a mood.

What about agile? Move fast and break things? Startups?! Disrupt! PIVOT!

Committing to a course of action is not choosing to never learn or adjust course. Instead, it frees us up to stop reacting to every great idea, and instead to be intentional about which ideas are really worth doing the work of rewriting the plan.

The goal isn’t to stifle imagination, but rather to prevent us from chasing something shiny to the detriment of our progress. This new thing we’ve learned is super exciting! But if we do the thinking and editing, is it a big enough deal to upset the apple cart and change the entire direction of the project/team/company?

A healthy strategy includes regular checkpoints where the team’s results and any new knowledge are held up against the strategy, and — if something sufficiently compelling has happened — the team can choose to update the strategy.

On top of that, a healthy team is intentionally underutilized. This creates free time for chasing shiny things with low risk. A roadmap with this kind of slack built-in supports exploratory tinkering by defining a clear plan with clear boundaries: I know I need to complete these 5 tasks this week to keep us on track; I finish them by lunchtime Thursday; I now have a day and a half to do whatever I find exciting without hurting the overall strategic goals or slowing things down.

Creativity two ways: a dinner party

Let’s imagine ourselves as part of a team that’s going to make a large dinner together. We want to create a memorable evening filled with great food, company, and conversation.

Now let’s imagine two different outcomes: one based on limitless imagination and possibilities, and one that combines imagination and editing.

Failure to decide leads to chaos

If we fail to edit, our dinner may go something like this:

We list off cuisines that sound delicious: Thai, French, Italian, Mexican
Everyone is excited about the potential
Someone says, “What if we had a chocolate fountain?”
There is much rejoicing
We all high five and agree that dinner should happen

Our strategy here is... what? We know that we want to make dinner. We know that we like lots of different cuisines and that a chocolate fountain would be cool — but how do we get there?

When is dinner? Who’s getting the chocolate fountain? Is this a coursed dinner? A potluck? What is everyone cooking?

There are so many great ideas here, but no decisions have been made.

I’ve been in situations like these before, both professionally and as part of a dinner party planning committee, and it tends to shake out like this: eventually someone goes into Superhero Martyr Mode™ and does all the work because no one is making decisions, and dinner is served with a heaping helping of bitter resentment over wilted trust with a delightful citrus-and-suck-it vinaigrette.

Decisions suck at first but lead to strategy and happiness

If we follow through and edit, we might come up with our cuisines, then start making decisions:

We throw out ideas for cuisines
Our mouths water
Someone proposes a chocolate fountain
We fist bump and then blow it up, wiggling our fingers like flowing chocolate to show our excitement
The question, “Okay, so what are our action steps?” is tossed out
We all groan because the fun part is over
There are 3 couples, so we’ll split the dinner into appetizers, a main, and dessert
Jason likes making cocktails, so he’ll handle drinks
We decide on Italian as our cuisine, so the chocolate fountain is out (boo!) but Leslie is making tiramisu (yay!)
We all check our calendars; the Thursday after next works for everyone

Yes, it would be great to eat Thai food. Yes, it sucks not to have a chocolate fountain. But you know what doesn’t suck? We have a date, a strategy, and clearly defined ownership — this means that we have a shared understanding of the desired outcome. We can work toward our part of this dinner independently with confidence the others are headed to the same destination.

And because we’re flexible and ready to respond to new information, if we ruin the main, we can enjoy the appetizers and desserts while we wait for the pizza to arrive.

Our roadmap isn’t permanent, but it needs to be stable.

Get comfortable closing doors.

The most effective people and teams I know are incredibly good at saying no to things. They pass on opportunities. They let good ideas wither on the vine.

In Essentialism, Greg McKeown makes the argument that we only have so much energy in a given day, and we have to choose where we spend it. We can put a little bit of energy into a lot of different things — chasing down every good idea we come across — or we can put all our energy into just a few really important things.

The difference in impact is huge.

Effective people don’t turn things down because they don’t want to succeed; they turn things down specifically because they know they need to focus if they want to succeed.

One of my favorite examples of this in practice is Jeff Hawkins’s approach to designing the Palm Pilot: he created a wooden prototype that he carried around and pretended to use to check his calendar or take notes. When his team proposed new feature ideas, he’d reach into his pocket and ask where the new idea would fit on the wooden block.

Hawkins wasn’t letting great ideas slip through his fingers by resisting feature creep on the Palm Pilot; he was intentionally focusing on a small, ruthlessly edited set of strategic ideas to ensure the success of his project.

Are you creating something? Or just imagining things?

The next time you start brainstorming, planning, strategizing, plotting, scheming, or trying to take over the world, here are a few things to keep in mind:

Imagining all the incredible possibilities is critically important, but it‘s only half the work of creating something. After we imagine all of the opportunities, we have to edit our focus down to the right opportunities.
Editing is a painful process that requires us to kill our darlings. An idea can be great, but still be the wrong thing to focus on.
No matter how good your ideas are, they’re worthless without action steps. Once you’ve dreamed big, you must turn the ideas into a clearly defined roadmap; otherwise, you’re just dreaming.
Don’t get distracted. Assess your progress regularly — try a retrospective! — to see if adjustments need to be made, but don’t change the whole strategy every time you see something shiny. Chasing exciting ideas is easy; consistently executing a well-defined strategy takes hard, disciplined work.

The ability to take Big Ideas™ and translate them into clear, actionable strategies is what turns a dreamer into a leader. It‘s what translates the vision into progress. It‘s what keeps teams motivated and making progress.

And if we get this wrong, the consequences are... well, I’ll just let you use your imagination.

Personal Retrospective: Q1 2019

Wed, 24 Apr 2019 00:00:00 GMT

I’m a firm believer in borrowing business ideas for personal life. At the beginning of 2019, I held a personal retrospective and set goals for the year, and decided to do quarterly check-ins to see how I’m progressing against my goals.

What are my goals for the 2019?

I set goals at multiple levels in an effort to have a long-term vision of where I’d like to go as well as short-term tactical goals that I could work toward to make measurable progress.

High-level goals

Be more creative off the computer.
Write more often.
Double down on community.

90-day tactical goals

Sign up for one class to learn a creative hobby. (Status: ✅)

I had originally planned to take a woodworking or music class, but I ended up signing up for salsa dancing lessons instead. This happened for a few reasons — it’s something I can do with Marisa, it’s extra exercise, it’s something that I’m definitely not comfortable with or good at — and wasn’t something I would have predicted I’d ever do, but it turns out that it’s a whole lot of fun to learn to dance.
Publish two articles per month. (Status: 😕)

I wrote two blogs on my main blog, one on my code blog, and a few on the Gatsby blog. This doesn’t quite average out to two per month. However, I did end up starting a weekly livestream that I’ve been really consistent with, so I feel pretty good about the amount of content I’ve been creating.

Really, though, I’m still not quite satisfied with the amount of non-work writing I’ve done. So I want to do better here.
Do at least two community events per month. (Status: ✅)

I had no problem hitting this goal because I absolutely love doing these community events. Between local meetups and hosting a rotating dinner party series with friends, I’ve had no problem keeping my calendar full of great community events.

What do I want to change for the next 90 days?

For the most part, I’m pretty happy with how 2019 has gone so far.

However, there are a few things I’ve noticed that I haven’t loved.

I get too many notifications from my phone

When I started at Gatsby, I installed Slack on my phone again. I left the notifications on, despite knowing better, because Gatsby is an early stage startup and things are volatile.

None of the notifications have been an emergency. So, really, I’m just looking at my phone instead of paying attention to the world around me.

I want to ride my bike more often

I bought a bike when we moved to Portland, but I’ve used it far less than I’d like to. Part of this is because I like to walk, even if the walk would take an hour, but far more often it’s because I get lazy and decide I’d rather deal with parking a car than carrying a bike helmet around.

And — as silly as this sounds — my bike is downstairs in the basement, and carrying it up and down the stairs is usually enough of a deterrent that I end up driving instead.

What are my goals for Q2 2019?

Based on what’s happened so far and what I’d like to change going forward, here’s my next set of tactical goals for the next 90 days.

Keep going to salsa lessons. I’ve enjoyed these, so I want to keep them going. It’s a fun hobby that doesn’t involve the computer, so it seems like something I should continue.
Carve out two hours a week for writing personal posts. I feel better when I spend time writing out things that aren’t work-related, so I need to actively make space for it. However, I need to let go of my old routine where I had huge, uninterrupted chunks of time in the morning — that’s probably not going to happen for me anytime soon. Instead, I need to put dedicated writing time on the calendar and actually buckle down to do it.
Keep Slack notifications turned off on my phone. I don’t need them, and everyone at work has my phone number if there’s an emergency. I’ll be happier without the distraction.
Find a way to store my bike upstairs. I need to make the right thing the easy thing here — if I pretend that I’m going to suddenly develop the self-discipline to haul a bike up and down stairs, I’m lying to myself. Instead, I need to make it just as easy to get on my bike as it is to get in the car.

How’s your 2019 going?

Did you set goals for 2019? How are they going? Hit me up on Twitter and share!

The Importance of Setting Good Expectations

Sun, 24 Mar 2019 00:00:00 GMT

Every negative emotion I can remember feeling (or causing) can be traced back to violated expectations.

Realizing this may have been the single most valuable thing I’ve learned about human relationships.

What do expectations have to do with anger, hurt, or outrage?

The last time that I got mad — like, really mad — I was trying to contact the Internal Revenue Service about some tax stuff.

IRS: Call this person.
Person: *doesn’t answer phone or return calls*
IRS: You can contact this person’s manager.
Also IRS: We have no way for you to figure out who their manager is and also we don’t answer our phone or return calls.
Me: pic.twitter.com/Fkn3jXvHIh
— Jason Lengstorf (@jlengstorf) June 6, 2019

I got a letter from the IRS telling me I needed to provide additional information about my tax return. The letter gave me an agent’s name and phone number, which I called. And called again. And again.

After a week of no responses, I tried to call the main office. It hung up on me automatically.

The letter listed one of my options as, “talk to the agent’s manager,” but failed to tell me who their manager is or how to get in touch with them. So I called the IRS hotline and waited on hold to talk to a human, hoping to figure out how to contact the manager.

I was told they can’t share that information. Instead, they have to put my information into a queue that will get me a call back “within the next 30 days between 7 am and 7 pm”.

By the time I got off the phone with the IRS hotline, I was fuming.

What expectations were set?

When I got the letter from the IRS, two expectations were set:

I had a direct line to an agent who would help me understand what they needed from me.
I could escalate to the agent’s supervisor if I had any trouble.

These are both great things: I can get help, and I have a fallback.

How were the expectations violated?

My expectations were repeatedly violated throughout this process:

The agent has not answered their phone at any time of day.
The agent has not returned any of my multiple messages.
I have no way of figuring out who the agent’s supervisor is (meaning I can’t escalate).
I was unable to get any actual help after calling the general help line.

At each step, I was told something would be true, only to hit a wall and learn that what I was expecting to happen wasn’t actually happening.

My frustration got worse and worse until I was so mad that it actually ruined my day a little bit.

The worst part of this experience is that this was all completely avoidable.

Setting better expectations changes everything.

When I look back on interactions that went poorly in my past, something becomes apparent: it’s not what happened, but how it happened in relation to what was expected that determined how people felt about the outcome.

If the IRS letter had just said, “You need to call this number and put yourself in a queue for a callback within 30 days,” I probably wouldn’t have been thrilled, but I also wouldn’t have ended up so mad it wrecked part of my day.

Setting expectations properly doesn’t eliminate bad news, but it can significantly reduce the fallout from bad news.

How to set good expectations.

Be honest with yourself.

You can’t set good expectations if you’re fooling yourself.

Can you actually hit that deadline, or are you saying what you think people want to hear?

Do you actually want to commit to this opportunity, or are you just afraid of losing it?

People are masters of self-deception, so it’s hard to get this right, but in a lot of cases just asking the question makes a difference.

Focus on clarity.

The biggest risk for violated expectations is ambiguity. For example, I might say something to a coworker along the lines of, “Take all the time you need!”

But that’s not actually what I mean. What I mean is, “This is important, but not urgent. Please finish it as soon as you can, but not at the expense of working extra hours.”

If I don’t communicate that, however, there’s a risk that my expectation won’t be communicated properly. My coworker might hear it and set their own expectation: “This isn’t urgent, so I’ll put it at the bottom of my todo list and get to it someday.”

Both of these expectations are valid interpretations of what I said. Later, when the project isn’t done, I’ll be angry because my coworker ignored my request, but my coworker will feel confused and frustrated because I’m coming after them for work I said wasn’t important.

Unclear expectations are the single biggest factor in violated expectations.

Communicate changes as quickly as possible.

Expectations aren’t permanent after they’re set, but all changes need to be communicated clearly and — this is the important bit — before the changes catch people off-guard.

If you and I agree to meet for dinner at 5 pm and you’re going to be late, there are two ways the evening can go:

you can call or text me as soon as you know you’ll be late — definitely before 5 pm — to let me know you’ll be late and set an updated arrival time, or
you can let our meeting time pass without an update, at which point you’re dead to me.

If something changes, share the updated expectations as soon as possible with everyone who will be affected by it. Getting good at this is a superpower in both life and business, because it takes situations that were previously terrible and turns them into no big deal.

Are you going to miss the deadline on a project? Bring it up a couple weeks in advance and it’s usually pretty easy to adjust the timeline to accommodate it.

Deal with discomfort now — or hurt feelings later.

Setting clear expectations can be hard to do in the moment — it can feel like letting someone down or being pushy — but I promise you it feels way worse to have that conversation after someone’s expectations have been violated.

Setting clear expectations ahead of time is the difference between someone calling you in the morning to let you know that they aren’t going to be able to make your evening plans vs. standing you up and not saying anything until you text them asking where the hell they are.

No one likes to get stood up. Set good expectations!

Automation + Control: Progressive Disclosure of Complexity

Sun, 13 Jan 2019 00:00:00 GMT

In user experience, there’s a concept from the Nielsen Norman Group called “progressive disclosure”, which is an approach to designing better user interfaces (UIs).

From their summary:

Progressive disclosure defers advanced or rarely used features to a secondary screen, making applications easier to learn and less error-prone.

A common use of this pattern today is on user profiles. If you’ve ever seen a page that has a link to “advanced settings”, that’s progressive disclosure: most people don’t care about or need to touch the advanced settings, so those are moved to a secondary screen where only power users will bother to go. This simplifies the experience for most people without limiting the abilities of more advanced users.

What’s powerful about this approach is that it gives the UI the ability to “react” to feedback. An advanced learner can ask for more, and the “teacher” (the UI) can turn up the complexity to meet the learner’s needs.

Progressive disclosure of complexity in systems

Outside of user interfaces, is progressive disclosure possible? How can we apply this approach to other areas?

Provide abstractions for most decisions

The most important concept of progressive disclosure is abstraction.

Put simply, abstractions are a set of default decisions that allow someone to accomplish something while remaining blissfully unaware that any decisions were made at all. When done well, good abstractions are how we make the right thing the easy thing.

If someone wants to change the defaults, they opt out of the abstraction and make those decisions on their own — and this is where things get tricky. To make sure we have progressive disclosure of complexity, we need to avoid a scenario where the abstraction becomes all-or-nothing.

In a lot of cases, we’re faced with the all-or-nothing dilemma: either I can accept the default options and make none of the decisions, or I can opt out of the abstraction and make all of the decisions.

Layer abstractions: keep it “need to know”

To avoid this, we need to think about the defaults and make some decisions about them:

What kinds of decisions are being made?
Do those decisions fall into subgroups or themes?
Which defaults rely on each other?

By thinking through this, we can start to arrange the defaults in to layers of abstraction, which gives the person using the system far more control. With well-designed layers, people only opt out of the default decisions that need to be changed. This gives them full control while still keeping as much of the complexity as possible abstracted away.

Progressive disclosure, layered abstraction, and dinner

Let’s keep going on this cooking metaphor to see if we can design a progressive disclosure of complexity around dinner. We’ll start with very little abstraction and add layers until we’ve created a fully abstracted version of dinner.

No abstraction: home cooking

We finally decided to get a grill and I’m regretting not doing this a long time ago. These burgers are unreal. The charcoal makes a big difference. 🤤🤤🤤 pic.twitter.com/GsTXUNLRFq
— Jason Lengstorf (@jlengstorf) February 25, 2019

With no abstraction, dinner requires a lot of decisions and actions:

Grocery shopping for ingredients
Food prep: chopping, slicing, measuring, and so on
Cooking
Serving: setting the table, plating the meal

Abstraction for shopping: meal kits/CSAs

Our first layer of abstraction might be to sign up for a CSA or a meal kit service like Blue Apron that send over ingredients directly to our house. This abstracts away grocery shopping and leaves us with only the prep, cooking, and serving of the meal.

Abstraction for food prep: frozen dinners and take-and-bake

If we don’t feel like prepping dinner, we might get a frozen meal or a take-and-bake pizza. This abstracts away the prep — we just need to put it in the oven and serve it.

It’s worth noting that this layer of abstraction doesn’t necessarily include the previous abstraction. We might go grocery shopping for our take-and-bake pizza, or we might get one delivered by a service like Instacart. Since we’re layering abstractions, we aren’t stuck with all-or-nothing.

Abstraction for cooking: drive-throughs, deli section, restaurants, delivery

On those nights where we don’t have time or energy to cook, we can abstract away the cooking process, too.

This layer of abstraction is a little harder to separate entirely from the prep layer — though I guess if you go to a Mongolian barbecue you prep your own meal but don’t cook it? — but it’s still independent of the shopping layer. We can choose to abstract away all the steps and order delivery, or we can go shopping in the hot foods section of the grocery store and bring home a ready-to-serve meal.

Full abstraction: chef’s tasting menu

To abstract away the entire process, we can go to a fancy restaurant and choose the tasting menu or omakase. We don’t have to shop, prep, cook, or serve — we don’t even have to choose what we’re going to eat. Food will arrive, and we just have to eat it.

At a good restaurant, the chef’s tasting menu is a perfect example of making the right thing the easy thing: you make zero decisions, you don’t need to learn or do anything, and leave with a full belly and good memories.

How to introduce progressive disclosure of complexity to systems

To roll out our own layered abstractions and introduce progressive disclosure of complexity to our systems, we need to:

1. Identify the decisions that have reasonable defaults

In any system, there will be decision points. If you’re creating a business system, you probably have a set of decisions that lead to the “happy path” (best-case scenario) for people using it.

Before any abstractions can be introduced, at least the happy path needs to be mapped. One great way to do this is with a flowchart, but how you map it doesn’t matter as long as you know:

all of the decisions that need to be made, and
which decisions have sensible defaults.

For example, it doesn’t really make sense to set a default for someone’s email address, but it might be useful to set defaults to opt out of paper statements.

2. Group the defaults into layers

Once we have a set of decisions with sensible defaults, we can group them into layers. Each layer should consist of logically related decisions. For example, color preferences might be one layer and flavor preferences might be another.

The goal is to find the balance between creating as few layers as possible while still allowing people to opt out of one set of defaults without being forced to make a bunch of decisions where the defaults were perfectly acceptable.

We need to design abstractions that avoid overwhelming people while still giving them total control of their decisions.

3. Introduce the layers to the people using the system

Once we’ve defined our layers, we need a way to expose them to the people using the system. In software, this might be an “advanced options” link or a section of the documentation describing advanced use cases. At In-n-Out Burger they have their not-so-secret secret menu. Online retailers like Bose have the floor models and the ability to fully customize the product.

The approach will vary from system to system — there’s no One True Way™ to share information, so our approach needs to be tailored to what we’re trying to accomplish and who the people are using the system.

4. Enable opting out of abstractions

Allow people to opt out of one layer of abstraction at a time while still keeping the rest of the defaults. In an ideal system, each default can be opted out individually, but that needs to be balanced against overwhelming people. This might be easier in software (the options pages can load with defaults, so only things that need to change require interaction), but definitely requires specific tailoring for each system.

However we get it done, once we’ve created the abstractions, people need to be able to opt out of them individually.

Yak Shaving: On Doing the Work Before the Work

Sun, 13 Jan 2019 00:00:00 GMT

One of my favorite phrases in the tech world is “yak shaving”.

It’s commonly used to reference the tedious chores that need to be performed before the Real Work™ can be done.[^etymology] Most of us have run into this before: we want to make coffee, then realize we’re out of beans and need to make a run to the store, so we jump in the car — only to realize that we’re almost out of gas and need to make a pit stop if we want to make it back home again.

Is yak shaving always a bad thing?

“Yak shaving” gets tossed around as a pejorative in meetings to imply inefficiency or wasteful work: “This is a bad idea because it’s going to introduce a shitload of yak shaving we don’t have time for.”

But sometimes we describe “any work that I don’t personally find enjoyable” as yak shaving — things like planning and measurement, for example. This decreases the perceived value of really important work, and sometimes leads to skipping it altogether.

Not all meaningful work is fun. Not all boring work is meaningless. This is a lesson that’s dangerously easy to forget, because the modern attitude toward work makes it extremely easy to confuse “motion” with “progress”, and “busy” with “productive”.

To put that another way, nothing is ever all fun, all the time. We have to pay bills, run errands, clean up after ourselves, and dozens of other mundane tasks that are just part of being a grown-up.

By devaluing important-but-not-fun tasks as useless yak shaving and skipping them, we might create the illusion of progress — but we also might miss the dirt floors, potentially burning countless hours on meaningless-but-fun Real Work™.

There’s more than one way to shave a yak.

Some chores are just that: chores. We have to do the dishes sometimes; bills need to be paid if we want the lights to stay on; we probably ought to shower every once in a while.

But other chores fall into a different category, which I like to call “meta-work”.

Meta-work is the work we do before the Real Work™ to make it more efficient and productive.

This is something like installing a dishwasher or putting the bills on auto-pay.

On the surface, “set up auto-pay” seems like just another chore on a list of yak-shavey bullshit work, but there’s a key difference: when executed well, meta-work requires an up-front investment, then little (or no) additional effort afterward.

Paying bills isn’t hard, but it takes time an attention every month. By contrast, setting up auto-pay takes a bit more work to set up, but afterward requires zero additional work to ensure bills get paid on time.

Put another way, putting in the meta-work means the yak stays shaved.

Are you grinding? Or getting things done?

It’s common to hear successful people credit their success to things like hard work, ambition, grit, and hustle.

More and more, I’ve started to think of these qualities like sunlight: they’re warm and bright and powerful and hold incredible potential, but they don’t accomplish much on their own.

Meta-work is the solar panel that harnesses the power of sunshine to make it productive. It directs the solar energy toward a goal, which ensures the energy actually means something.

Potential means nothing on its own. Without direction, we run an extremely high risk of working really hard and not getting much done. And while we tend to hold up high-potential people as “the best of us”, someone with high potential who grinds themselves to dust on low-impact work will lose against someone who thinks hard about what needs to be done and makes perfectly average progress toward the most important goals.

In order to be truly effective and make meaningful progress, we need to do the meta-work and the Real Work™.

Skipping the meta-work means frustration, inefficiency, and wasted time.

Throughout my career, just about every team I’ve worked on handled new projects something like this:

An idea comes up that gets everyone excited
The team immediately gets to work on the MVP

We jumped straight into Real Work™, riding high on our excitement and trusting our brilliance to push us through to victory.

And in nearly every case, we ended up stalled, discouraged, not making much progress, feeling like maybe this wasn’t such a great idea after all.

These projects often resulted in dead ends, ripping out features that turned out to be a waste of time, and sometimes giving up altogether.

In every case, we failed to do the meta-work and paid the price.

Getting meta-work right makes all the difference.

On a few glorious occasions, I’ve been on a team that followed a different process:

An idea comes up that gets everyone excited
We do research to validate the idea
Several meetings are dedicated to understanding (and limiting) the scope at every level and thinking through edge cases
Time is spent creating a solid plan
Once we’re confident we know what we’re getting into, we start doing the Real Work™

In every situation where this happened, we were dying to jump ahead and start building things. The research and planning meetings felt like yak shaving, and we had to fight the urge to skip them.

And in every situation where we kept our discipline, the project was finished on timelines that seemed bureaucratically impossible.

Doing the meta-work is the most important part of making meaningful progress. Instead of forging ahead on doomed tasks, we were able to carefully prune the idea down to just the meaninful pieces, which meant that — despite taking a little extra time up front — we were able to move fast with high confidence, and rarely found ourselves throwing away work or hitting dead ends.

Are you willing to do the (meta-)work?

The most important question we face in our working lives is this: am I working on the right things?

And unless we take the time to do the meta-work and understand what progress actually looks like, we’re unable to answer that question confidently. Without handling the yak shaving that ensures we’re pointed in the right direction, we have no way of knowing if we’re going in the right direction or merely grinding ourselves down with hard work that isn’t getting us anywhere.

We’re faced with a choice: we can create the illusion of progress by “staying busy”, or we can do the meta-work — boring though it may be — and guarantee progress toward our goals.

So what’ll it be?

2018 in Review: How I’m Structuring Goals to Make 2019 My Best Year Yet

Fri, 28 Dec 2018 00:00:00 GMT

For the last few years, I’ve stolen Nate Green’s tradition and written a personal retrospective for the previous year.

In both 2016 and 2017, my life was in flux: I ended my two-year streak of living in different Airbnbs around the world in 2016, then made the switch from contracting to a full-time job at IBM in 2017.

2018 was another year of major changes for me. I’m reasonably confident, however, that this was the last “huge life changes” year for a while.

What is a retrospective?

A retrospective is a review process most commonly used in businesses to review the outcomes of a given project. The general format is to answer each of the three following questions:

What went well?
What didn’t go well?
What will we change going forward?

The exact format varies between teams, but this is the format I’m most familiar with, and the format we’ll use today.

I’ve been missing a key part of the process.

In reading last year’s retrospective, I realized that I started with more or less a clean slate. I looked at 2017 as a whole, and completely ignored the fact that I’d set goals for 2017.

This was a mistake. Why set goals at all if I’m not going to hold myself accountable?

What were my previous goals?

In 2016, my goals were:

Dedicate more time to keeping up with the people I care about.
Speak at one conference per quarter minimum.
Stay consistent in the gym.
Work on code videos and tutorials.
Replace my morning phone habit with writing.

In 2017:

Walk more often.
Reduce my commute to two or fewer days per week.
Rededicate a couple mornings a week writing.

This year, I’m going to frame the retrospective not just around “how did 2018 go?” but “how did 2018 go in relation to the goals I’ve set for myself?”

What went well?

2018 held a few huge changes for me, both professional and personal:

1. I bought a house.

I’m probably on record in multiple places saying something to the effect of, “I will never buy a house. Buying houses is a terrible idea. Why would anyone ever buy a house?”

This year I bought a house.

Marisa and I moved back to Portland this year, and when we sat down to list out what mattered to us, a few key themes emerged:

We didn’t want to keep moving every year when our lease was up. It was stressful and made it really hard to build a strong community.
We were sick of being stuck with our landlord’s shitty choices to install cheap things that break and/or don’t work properly.
Marisa read Happy City and learned that both green spaces and ground-floor living have positive correlations with happiness.

Those factors pointed toward buying vs. renting. And Marisa likes gardening, so I was informed that we were getting a house with a yard.

We’re both very privileged to work in tech at high-paying companies, and we saved a shitload of money by traveling full-time for a couple years, so we pulled the trigger and bought a house in Portland, walking distance from many of our favorite places in the city.

This relates to several goals from 2016 and 2017: it helps me get more involved with the community, makes it easier to stay consistent with the gym, and lets me walk far more than I ever did in Texas.

2. I started a new job.

In February, I left IBM. I lasted about 18 months there, which is longer than most of my friends thought I would. I loved my team at IBM, but I didn’t love the complete lack of autonomy and accountability that meant it tooks months of meetings to get approvals for weeks of work.

I left to join Gatsby, an open source website-building startup, where I’ve been working to connect with the amazing community, help teach people the technology, and help build an amazing team of incredibly talented people.

This had several really positive effects on my life:

Gatsby is a fully remote company, which means I no longer have a commute.
The team is small, so we’re able to make decisions quickly and execute on ideas rather than spending months chasing “decision makers”.
I get to work directly with the community as both an advocate and a teacher, which helps me connect with more people.
I was able to join several podcasts as a guest, including the React Podcast, The Changelog, and Toolsday.

Goals-wise, this ticks several boxes: no more commute, teaching code, writing more, and speaking at conferences.

3. I wrote a few pieces I’m really proud of.

I didn’t publish much this year, but the I’m proud of the few things I did publish. Most notably, I wrote an article for A List Apart, which was really meaningful to me; ALA has been an important part of my career development, so being able to contribute back was a milestone for me.

I was also able to put a couple of my core philosophies into words with posts on finding the “why” and looking for the dirt floors.

4. I got to the gym (almost) every week.

There’s not much to this one. We’re back in Portland now, so we’re working out at Elemental Fitness Lab with our friend Blaine, who keeps us accountable. We show up at least twice a week unless we’re traveling, and my joints are extremely grateful.

5. I walked far more this year than in Texas.

It’s probably safe to say I walk more in a given week than I used to walk in the average month in Texas. Portland — especially the area we moved into — is extremely walkable. We’re less than 30 minutes walking from almost everything we need in our day-to-day lives, and that’s contributed to a huge shift in how we get around.

In Austin, it was fairly common for my only walking during the day to be between my apartment and the parking garage. In Portland, I typically walk at least a mile every day — which I realize isn’t that much walking, but if that’s my minimum I’m happy.

6. I spoke at quite a few conferences.

I set a goal of one conference per quarter in 2017. At the end of 2017, I needed to set a new goal: only speak at one event per month. My speaking calendar filled up fast, and I’m now in the extremely fortunate position of having more opportunities to speak than I can reasonably manage.

I was invited as a keynote speaker a few times in 2018, which was a wonderful new development. I’m hoping to do a lot more of that going forward.

What didn’t go well?

Not everything went the way I’d hoped, though.

1. I didn’t write much at all.

For the third straight year, I set a goal to write more and then... didn’t.

I keep setting goals like, “I’m going to write every morning!” and then let things get in the way: I’d be stuck with a commute; I’d have morning meetings scheduled; I’d play on Twitter in bed instead of getting up to write.

This is frustrating to me for several reasons:

I’m usually very good at setting goals and delivering on them.
Writing is one of the things I like most, but somehow I’m managing to deprioritize it consistently. (And I’ve literally written about exactly this and my “solution” hasn’t solved shit.)
I talk a big game about creating effective plans and being super productive and pushing out a shitty first draft, and yet here I am, relatively blogless.

This is something that I want to pay more attention to in 2019, and it’s clear that I need a new strategy here. I have ideas, but I’ll wait and say more on that in the next section.

2. I didn’t pursue any hobbies off the computer.

I’m one of those people whose hobbies tend to be mostly tied to the computer: I like to create software, write, design things, and other things that mostly involve staring at a screen.

While I’m okay at keeping other hobbies — for example, I cook often, have board game nights with friends, and regularly explore new restaurants — none of them are primarily creative.

Overnight sous vide for one of two turkeys we're cooking for tomorrow. I have high hopes for this. 🦃😋🤤 pic.twitter.com/5DViLNzNew
— Jason Lengstorf (@jlengstorf) November 22, 2018

That hasn’t always been the case: once upon a time I was in a band; I would screw around in my dad’s shop and build things; I would design and make my own shoulder bags because why not?

As my career evolved, these creative hobbies all fell away. I still pick up my guitar and clumsily strum through some of the songs I remember sometimes, but I haven’t been a practicing musician for close to ten years now.

I’d like to change that going forward. I like learning new things, and I like being away from my computer. So I need to be better about creating opportunities to do it.

What will I change going forward?

Using the good and the bad from 2018, I need to make an action plan for 2019.

But first, I want to change up the format a bit. A year is a really long time, and it’s very hard for me to know what my life will look like in 12 months. I mean, in general I think I’ll be relatively stable this year in terms of living and working, but who knows if I’d actually be able to stick to a year of guitar lessons or if I can write 25 blog posts for the year?

Instead, I’m going to do 90-day check-ins. A business practice I really love is the idea of short, targeted projects that aim toward a larger goal. This approach makes great progress toward long-term goals, but provides a shorter feedback loop and the opportunity to reassess things periodically to make sure the long-term goal still makes sense.

What this means in practice is that I'll set a high-level goal for the year, then create low-level, tactical goals 90-days at a time.

High-level 2019 goals.

In 2019, I have a few high-level goals:

I want to be more creative off the computer. I don’t really care how, but I’d like to develop new hobbies that don’t involve looking at a screen.
I want to write more often. This is a goal I’ve set and missed two years running now — this year I’m trying a new approach to overcome the various blockers that I’ve allowed to keep me from publishing more content.
I want to double down on community. I feel best when the work I do makes the people around me more successful, happier, more empowered, or otherwise a little bit better off than they were before I met them. I want this theme to inform all of my decisions in 2019.

90-day goals for Q1 2019.

My strategy for this year is to set short-term goals that push toward the high-level goals, but that require less commitment and are easy to adjust if, after three months, I feel like they’re not actually the right goals.

This means that I’ll have to check in at the end of March to run another retrospective, assess how things are going, and set my goals for Q2.

In the next 90 days, I want to:

Sign up for one class to learn a creative hobby. I’m thinking I’ll either take music lessons (guitar or piano) or woodworking classes. I haven’t done any research on these, so my decision is going to depend on the timing, availability, and cost of each option.
I’m going to publish two articles per month. I’d prefer to do two posts on this blog in addition to any external content I create, but I’m setting the success criteria at “two written pieces published on any site” to make sure I don’t set myself up to fail.
I will do at least two community events per month. Last year, I held “office hours” at a local coffee shop to help anyone who wanted to drop by with their projects, and that was a blast. Kyle Shevlin and I organize impromptu drinks the Portland developer community every couple weeks. I’ve been part of a rotating dinner party series with Joel Hooks and other friends.

Hey Portland folks!
@kyleshevlin

and I are going to be at Beer tonight at 6:30pm. If you want to come down and have a drink, meet some fellow nerds, and generally be social, come join us. Everyone is welcome! 🍻 https://t.co/ntkf4LBRON
— Jason Lengstorf (@jlengstorf) October 29, 2018

All of these things were great, and I want to do more of them. If I can, I’d like to make these things even more accessible to people who are earlier in their careers or would benefit from having a stronger community.

What are your goals for 2019?

Running your own retrospective is a really powerful way to ensure your baseline is improving, so I’d strongly encourage you to do it. If you can, share it publicly to give yourself some accountability. And if you do share it, please let me know you did — tweet at me!

Here’s to a great 2019!

Level Setting: Solve the Right Problem at the Right Time

Tue, 20 Nov 2018 00:00:00 GMT

It’s easy to think of problem solving as something that happens in a single sequence: I have a problem, and now I will sit down, think it through, and come up with a solution.

In reality, many problems are too complex to be solved in one pass. This means we have to go through any given problem multiple times, starting with a broad, undetailed pass to get a general understanding of what a solution looks like, and systematically progressing toward a detailed, nuanced set of action steps to solve the problem.

For the skimmers in the audience, problems need to be solved at multiple levels:

High Level, Low Fidelity — no details, no concrete ideas; not even necessarily a plan. This is what you might hear referred to as “vision”.
Mid Level, Medium Fidelity — this is where the high-level vision gets chopped up into goals. You may hear this called “strategy” or “roadmapping”.
Low Level, High Fidelity — during this stage, things get tactical. Strategic goals get turned into time-bound projects with specific deliverables and metrics.

In general, problems need to be solved at all three levels, and things go a little smoother if you only try to solve at one level at a time. And on sufficiently complex problems, this sequence might happen multiple times at different levels of focus.

The rest of this post will add context through an example, as well as provide some guidelines for keeping discussions at the right level.

The three levels of problem solving, as embodied by a meal.

Marisa and I bought a house in Portland this year, which is a huge shift from our previous lifestyle. A decent chunk of our extended family on both sides is within about an hour of us, which meant we were now part of the discussion around Thanksgiving.

Thanksgiving is complex to say the least. There are subtle family dynamics in play, a dozen or so dishes to plan, extra seating and utensils, and the relativity of Relative Time. Dozens of decisions need to be made to ensure the meal goes well.

Low-fidelity: “What are we doing for Thanksgiving this year?”

Before we could actually plan anything, we needed to make some low-fidelity decisions:

Where are we having Thanksgiving?
Are we going to try and pull our families together for a single meal, or have two different stops?

This is low-fidelity problem solving. The answers we come up with aren’t complete, and they’re not particularly actionable. This is the “vision” for what should be done.

And vision is important. If we don’t know where Thanksgiving dinner will be or whether or not it’s a one- or two-family affair, other plans are made without critical information:

If we order a turkey, we might find out that someone else is hosting Thanksgiving and already ordered one.
If we plan a long, slow meal, we might find out that we have to drive an hour to Silverton for a second Thanksgiving meal.

Without a vision, it’s extremely hard to know if the decisions and actions we’re carrying out are sending us in the right direction.

Mid-fidelity: “Who’s coming?”

Our vision is now in place: Marisa and I are hosting a two-family Thanksgiving this year.

In order to make the meal a success, we need to come up with a strategy. Mid-fidelity problem solving is where the vision turns into specific goals.

Some of the questions we needed to answer at this stage included:

How many people will be there?
Should we do just turkey, or another main?
What dishes do we definitely want to include?

From this, we learned that we’d have 12–14 people, turkey two ways, and a few family favorite sides.

We were then able to create goals using the information:

We need to have enough seating and place settings for 14 people.
We need enough food to feed 14 people.

By setting goals, we get a clear idea of what “success” looks like.

High-fidelity: “Let’s make a Gantt chart.”

Marisa doesn’t take hosting lightly. Her first step was to create a spreadsheet for Thanksgiving, complete with all the dishes, who was responsible, and links to recipes.

Hosting Thanksgiving when you work in tech means spreadsheets, pajama party whiteboarding sessions, Gantt charts, and — of course — hand turkeys. 🦃 pic.twitter.com/vfH1XpRTIf
— Jason Lengstorf (@jlengstorf) November 18, 2018

Using the spreadsheet, we were able to turn each dish into a list of requirements: cooking equipment, serving dishes and utensils, oven time, and so on.

From there — stealing a trick from our friends, Ryan and Chelsea — we turned Thanksgiving into a Gantt chart: each dish, its oven time and equipment accounted for, is on a timeline so we know exactly what to do and when to ensure that Thanksgiving is as stress-free as something like Thanksgiving can be.

High-fidelity planning turns goals into actionable todo items.

The Pitfalls of Problem Solving

The challenge with problem solving is that it’s extremely tempting to start solving problems at the wrong level: a meeting intended to brainstorm about tasks for a new contractor becomes a detailed discussion about how to solve one of the proposed tasks; a progress check-in becomes a redesign; a goal-setting session falls down a rabbit hole on the first goal and everything else isn’t planned at all.

This typically gets ignored, because planning is planning, right? But — remember Thanksgiving? — we’re going to waste a lot of time if we move to a tactical discussion before we’ve defined a vision and goals, and we’re never going to get anywhere if we rewrite the vision every time we start creating actual todo items.

Historically, I’m utterly terrible at choosing the appropriate level for discussion, because I’m what Mona Patel would describe as a “scaffolder”. At IBM, people would drop by my desk with a question like, “Where do you think this label should be aligned?” and — fast-forward to three hours later — I’ve cornered the architects for the project and I’m demanding an explanation of why labels were added to this design in the first place.

However, if we’re going to effectively solve problems, we need to be more intentional about what level we’re currently solving for.

How to Use Level Setting for Better Problem Solving

While far from a Complete Guide to Solving All Your Problems™, over time I’ve learned a few tricks that — when I actually follow them — go a long way toward keeping my problem solving efforts on track and effective.

1. Make sure you know what you don’t know.

On any problem, start by doing an assessment of what you know, and what you still need to learn.

If you ask me to cook dinner, I already know how to cook. But I don’t know how many people are coming over, or whether any of them has dietary requirements. If I go to high-fidelity planning before I have that information, I’m probably going to end up backtracking and wasting time.

2. Start with “Why?”

The vision needs to be in place before anything else can be done with confidence. I’ve talked about this before: we need to Find the Why to make sure we actually understand what we’re trying to accomplish.

3. Be clear about what you’re here to discuss — and what you’re not.

The biggest mistake I make — and the most common mistake I’ve seen in all the teams I’ve observed — is that meetings are held without agendas. There’s probably a whole post to write on this, but for context, there should never be a meeting that doesn’t have an agenda with, at minimum:

What the purpose of the meeting is
What deliverables the meeting will produce (e.g. answers, a design document, an unblocked project)

An additional feature of the agendas we send out on my team is this: “What are we not going to talk about?”

This helps us level set the meeting. For example, the agenda might look something like this:

Topic: project roadmapping for Q1 2019
Deliverables: a prioritized list of the projects we plan to complete in Q1 2019
What we are going to discuss: projects at a high level, their impact, and their importance
What we are not going to discuss: how to complete the projects, technical details, or ownership/staffing

4. Don’t revisit the vision or goals to avoid doing the work.

On an embarrassing number of occasions, I’ve hit a hard problem (or just gotten into The Slog), gotten frustrated, and decided it would be easier to redesign the entire project rather than push through it.

Don’t be like me. Be better than that.

If you’ve already thought through the vision and strategy, don’t try to convince yourself to start over when things get hard. Instead, CTFD and JFDI.

Multi-Level Problem Solving: A Recap

To solve problems properly, we need to solve them at three levels:

Vision — understand the problem at a high level to understand why it’s worth solving in the first place
Strategy — create concrete goals that will help us achieve our vision
Implementation — turn the goals into actionable todo items so you can do the work

How do you solve problems? Let’s talk about it on Twitter.

Dirt Floors: How to Stop Putting Out Fires and Solve the Real Problem

Sun, 09 Sep 2018 00:00:00 GMT

In every company I’ve ever worked with, there’s a paradox: everyone seems to want to do things that make the product (or service) better, yet the work to actually do that never seems to get done.

This isn’t because everyone in the company is incompetent.

In my experience, the problem is rarely incompetence. Instead, the problem stems from leadership missing the Big Problems and burning all available time and energy chasing little problems — which are really just the visible symptoms of the Big Problems.

What do dirt floors have to do with skipping school?

Let me veer off into a seemingly unrelated story to illustrate a point: imagine you’re tasked with getting kids to show up to school. If we approach this from a standard business angle, we might start by looking at the education system: is the curriculum engaging? Are the kids being supported? Can we incentivize attendance somehow? Maybe we should look at the buses and other transportation?

And if those efforts failed to improve attendance, we might throw up our hands and call the kids unreachable, or blame their parents and community: “Look, we tried! These kids just don’t want to learn! These people don’t value education!”

The schools, though, are only one part of a much more complex system. The kids going to school are part of a community, and that community is impacted by countless other variables that aren’t visible within the context of the schools themselves.

However, if we take a step back and look at the system as a whole we might start asking different questions:

Do these kids want to be in school? (They do.)

Why are they missing school? (They’re sick.)

If we slow down to ask questions before trying to fix the problem, we can see that the problem we actually need to solve is different than what we assumed at the start. This starts a deeper line of questioning.

Why are these kids sick? (They have parasitic worms and other infections.)

Why do they have worms? (They live in houses with dirt floors.)

Through this line of questioning, we’ve discovered a deeper problem. And it leads to a solution that might seem nonsensical at first: “if we want more kids to attend school, we need to address the dirt floors in their houses.”

But the data supports this: deworming children reduces absenteeism at school by about 25%, and replacing dirt floors with cement reduces parasitic infestations by 78%.

Where are the dirt floors in our projects?

In my experience, every organization has at least one “dirt floor” problem.

When I was a front-end architect at IBM, my team was supposed to be improving the performance of several problematic UIs. As we started our research, we realized that there was more than just front-end development involved: our teams were burning a huge amount of time and energy struggling with seemingly unrelated tasks — by the time they got to performance tuning, they were already stressed out, exhausted, and up against looming deadlines.

We couldn’t just say, “Hey, team, focus on performance!” They would agree with that — we all knew performance was what we’d agreed to prioritize. However, after spending multiple days fighting with all the unrelated-but-unavoidable work, there just wasn’t enough time or energy left to do the job properly.

Before we could fix our performance problems, we needed to fix our dirt floors. We built a few small, internal utilities to remove that frustration: a one-click configuration tool for development environments, a helper library that eliminated a bunch of busywork, an improved data layer to make it easier to understand what was going on.

Once we fixed the dirt floors, we started making incredible progress on timelines that seemed bureaucratically impossible.

By dedicating time to correcting the underlying problems, we went from every developer in the organization wasting multiple days setting up their development environment, to a couple developers spending a week building helper tools.

We slowed down, fixed the root problem, and as a result saw sweeping improvements across our entire organization. Our developers were able to actually focus on the performance of their project, and other teams were able to work on their actual goals instead of yak shaving for days to get there.

Where are your dirt floors?

What problems might be at the root of other problems in your career? In your life? What are you ignoring that might be at the root of your other problems?

Take a few minutes to Find the Why behind some of your biggest frustrations, and see if you’ve got some dirt floors to get rid of.

Find the Why

Fri, 19 Jan 2018 00:00:00 GMT

In some of my previous posts, I use the phrase “Find the Why” as a kind of shorthand for the process of digging deeper into our behaviors, feelings, and ideas to figure out what’s really going on: how we react to events, the way we behave at work and with friends, our fears and habits and vices — all of them have an underlying Why.

In this post, I want to unpack what I mean by that, and offer up a framework for Finding the Why on your own. This is a framework we can use to build a deeper understanding of why we are the way we are. (And, hopefully, a process by which we can be more certain that problems are solved for realsies.)

When we Find the Why, we take back control of our behavior.

Why Is Finding the Why Important?

Not too long ago, I was in a retrospective for a project, and there were a few things that had just plain failed to work. After collecting everyone’s opinion on what went wrong, I started asking why things went wrong.

Someone interrupted me and said, “It doesn’t matter why it went wrong; we need to focus on how we’re going to fix it.”

In certain circumstances, I can see the point: if your pants are on fire, you should focus on putting them out, not asking whether they started burning because you are, in fact, a liar liar.

The problem with only solving the problem, though, is that problems are often just a symptom of something deeper. If I put out the fire, but don’t ask why it started afterward, what’s to stop me from hanging my pants over a scented candle to “freshen them up” again?

If we don’t understand why the problem occurred, we have no way of knowing if our fix has actually solved the problem, or just temporarily covered it up.

How Will Finding the Why Make Life Easier?

By taking the time to examine the underlying causes of problems, we gain subtle but extremely powerful advantages.

We become proactive instead of reactive.

There are a few people I work with on a daily basis who stress me out just to be around. Their entire existence, as far as I can tell, is spent careening from one fire to the next, desparately trying to stay on top of an endless stream of fire drills.

This is a reactive approach, and it’s basically a waking nightmare: the world is constantly happening to you. Chaos reigns, and every problem is a surprise.

Living reactively is like an endless game of whack-a-mole where you’re the one taking all the lumps.

If, however, you take a proactive approach, life starts to look a little different: because you’re making the effort to understand why problems are occurring, you start to see patterns. Problems that previously felt novel start to resemble each other, and you can apply your previous experience to help solve new problems more effectively.

The biggest advantage to a proactive approach is that your deeper understanding allows you to see problems before they happen: because you’ve worked out the underlying cause of previous issues, you can spot potential problems early — and correct them before anything breaks.

We can find patterns that make problems easier to solve.

By thinking through to the deeper causes of our problems, we can start to see that a whole lot of problems share similar root causes.

Part of my job is building processes and tools to make teams more effective. When I first started looking at the bottlenecks and time drains our teams were up against, they seemed like unrelated challenges — this made it feel like the effort was doomed.

After taking time to Find the Why, however, we found a few common culprits:

There was a lack of clarity about goals, so teams were being forced to make educated guesses about what was expected of them.
People were being asked to do things that fell way outside of their job descriptions and/or comfort zones.
Many core pieces of information were completely undocumented, meaning teams had to wait for the one or two people who understood it to have time to help them.

These three problems were causing the vast majority of the bottlenecks, performance problems, interpersonal conflicts, and other issues we were trying to solve. By realizing this, we were able to focus our efforts in a way that actually made an impact.

Had we instead looked at these as unique technical, tooling, and interpersonal problems, we would have wasted a huge amount of effort treating the symptoms — and wouldn’t have made much progress.

Sometimes noticing is all it takes.

When people start working with nutritionists or dieticians, a really common first step is to ask them to write down everything they eat throughout the day. And in many cases, this simple act causes people to make improvements in their diet.

I ask something similar of myself and the people I coach: take note of where your time goes during the day.

When we’re paying attention, we tend to make better choices.

If we take the time to Find the Why behind our problems, we’re able to notice when something has the potential to become problematic.

If you’ve ever burned out an electric motor, you probably now know that there are certain sounds and smells that mean something’s about to go horribly wrong. By recognizing that, you’re able to turn off the machine before an expensive failure happens.

Sometimes paying attention is all it takes to eliminate problems.

How Do You Find the Why?

As with most things, there’s no foolproof formula or ironclad process; every situation will vary in subtle ways, so coming up with a universal solution is impractical. However, there are some general guidelines that will make it easier to Find the Why in most situations.

1. When you notice a problem, pause and assess the situation.

At arm’s length, this may seem like an obvious statement, but it’s important to keep in mind that we exist in a culture of self-destructive work ethic and unhealthy commitment to our own ideas: when we’re in the middle of a project, our instinct may be to just power through.

Before you put your head down and try to smash it through whatever the problem is, take a beat and try to get a sense of what you’re up against.

2. Try to see the whole picture.

While assessing the problem, try to spot all of the symptoms: is there just a puddle on the floor? Or is there a leak in the ceiling, too?

A broad understanding of everthing that’s going wrong provides a more complete context for problem solving. Making decisions with incomplete information will likely lead to incomplete solutions.

3. Think about why it happened.

It’s tempting to stop at the symptoms: “Why did I snap at my friend today? Because I was having a bad day.”

Having a bad day is a symptom of something. Why was it a bad day? Did something happen? Am I frustrated? Is there something common in all of my bad days?

Digging beyond the symptom can help us recognize the cause, which is what we need to address if we hope to fix the symptom permanently.

4. Ask “Why” again.

If you asked Taiichi Ohno how to Find the Why, he’d tell you to ask “Why?” five times to make sure you’ve reached the root of the problem:

Why was the project late? The team couldn’t deliver on time.
Why couldn’t they deliver on time? There were last-minute changes to the deliverables.
Why were there changes to the deliverables? Management was undecided about what to prioritize.
Why was management undecided? There was a lack of clarity about what should be built.
Why was there a lack of clarity? The team wasn’t included in the planning process.

In this example, what initially looks like a performance problem (missed deadlines) may actually be caused by poor communication and planning.

5. Keep asking until you’ve reached the deepest reason you can control.

Going back to the example where I’m having a bad day, maybe I find a chain of causes like this:

I’m having a bad day.
Why? I feel like I wasted the whole day.
Why? I didn’t accomplish any of my tasks.
Why? I spent the whole day in meetings.
Why? People keep inviting me to meetings.

In this chain, the cause of my grumpiness is that I feel like I lost the whole day to meetings. The final cause — that people keep inviting me to meetings — appears to be the root cause, but it’s beyond my control: I don’t control other people, so how can I stop them from inviting me to meetings?

If I take one step back, however, I showed up to those meetings. This is within my control, so I can ask a new set of questions:

I spent the whole day in meetings.
Why? Because I had a buttload of meetings on my schedule.
Why? Because I accepted every meeting invite, even if they were irrelevant to my work.
Why? Because I didn’t want to seem rude by declining.

Beware the rabbit hole here. You can always go deeper, but there’s a point of diminishing returns.

Why don’t I want to seem rude? Because I’m worried it’ll get me fired. Why? Because I have self-worth issues. Why? Because I feel like a phony sometimes. Why? Because...

After a certain point, the “deeper cause” becomes so general — e.g. “I don’t value myself” — that it’s almost a symptom in itself. This is a problem with asking subjective questions: they allow you to talk yourself in a circle if you don’t choose a logical stopping point.

Because — get ready for this — why don’t I value myself? Because I let people abuse my time, which they often do by scheduling too many fucking meetings.

If you chase any strand of logic far enough, you’ll eventually end up staring at the back of your own head.

Now that I’ve explored this new line of questioning, there’s a new potential root cause: I’m accepting meetings even when I shouldn’t be.

This means I’m no longer helpless; I can control the way I respond to irrelevant meeting requests.

If we dig too deep, we end up with problems that are either so broad they’re not solvable in a reasonable time frame, or that extend beyond what we’re able to control, which removes our ability to solve them entirely.

We need to Find the Why at the deepest level we can control. This way, we can come up with a solution and actually implement it. Because — remember — no one is coming to save us.

Life Is Easier When We Know Why

Even though it can be frustrating, stressful, or even frightening to Find the Why, there have been few things that improved my life more dramatically than adopting this as a core strategy for being alive.

If something makes me angry or sad, digging deeper helps me find a healthy and/or productive way to process that emotion. If I’m stressed and irritable, I can dig deeper and figure out where that stress is coming from and how to address it. If something goes wrong at work, I look for deeper patterns that will prevent it from ever happening again, rather than just putting out the fire and pointing fingers at someone else.

After I learned to Find the Why, I became a happier, healthier, less volatile person. (Or, as many of my friends would put it: “He’s less of a dick now.”)

If you put this into practice, maybe your friends will think you’re less of a dick, too.

And that’s a worthy goal if ever I’ve heard one.

2017 Retrospective

Thu, 18 Jan 2018 00:00:00 GMT

2017 was... weird.

I don’t know that the world actually went to hell — in fact, there are a lot of reasons to argue that the world in 2017 was the best it’s ever been — but holy shit if my Twitter feed didn’t make me feel like I needed to move to New Zealand and stockpile non-perishable food.

But what was 2017 actually like? If I step back from the chaos in the media, what did 2017 mean for me and the people I care most about?

As we roll into a new year, I want to continue a tradition I’ve stolen from Nate and write up a retrospective on 2017.

If you’re not familiar with the concept of a retrospective, the core idea is this: whenever you’ve come to the end of something — a project, a sprint, or, in this case, a year — you sit down and review it by asking three questions:

What went well?
What could have gone better?
What will I change next time?

This is an incredibly effective tool for teams because it allows you to regroup, call out the good stuff, notice potential problems, and make adjustments to correct them before they fester into full-on crises.

However, it turns out that it’s an excellent tool for individual development as well. I run a retrospective for pretty much everything I do: projects, contracts, relationships — hell, I’ve even run retrospectives on recipes.

The point is: they’re useful. You should use them.

Over time, I hope these retrospectives help me form a story arc of who I’ve been, where I wanted to go, and where I actually ended up. For example, my 2016 retrospective shows me rekindling an interest in teaching people to code and starting to cook again — both things that I did a lot of in 2017.

It also reminded me that I started a project called Small Adventures and then never finished it. So I should get on that.

So with that in mind, let’s jump in and break down how my 2017 went, and how I’ll use that information to make 2018 a great year.

What went well in 2017?

Overall, I’d call 2017 a pretty good year from a personal development standpoint.

I played well with others.

One of the biggest changes I made in 2017 was switching to full-time employment for IBM. My long-time friend Robin is a development manager there, and — despite my initial skepticism — he convinced me that there was a lot of opportunity for large-scale change at IBM.

So I moved to Austin, started working from an office a few days a week, and joined a team of 12 developers.

Planning software with a team is like juggling 15 balls except some of the balls need to be cubes for backward compatibility and other balls are on vacation until after Thanksgiving and due to a strange edge case one of the balls is an octopus.
— Jason Lengstorf (@jlengstorf) November 21, 2017

Prior to this, I’ve always worked on small teams, and my projects have always been pretty much just mine. Learning to work on a team was a struggle, but I’m probably a much more pleasant person to be around these days.

I learned a ton about convincing others to adopt new ideas.

When I first joined IBM, I saw a problem, did some research, came up with a solution I knew would work, and then ran face-first into a brick wall. Another team technically owned the thing I wanted to fix, and they weren’t super excited about some brand-new hotshot coming in and touching all their buttons.

Something I thought would take a couple weeks to fix ended up taking a couple months just to convince all the necessary people that we should try to fix it.

This was a new and uncomfortable experience for me; in all of my previous roles I’ve either been working alone or the highest-ranked person in the room. I’d only ever had to sell ideas to clients, who generally couldn’t care less how I solved a given problem, so long as it ceased to be a problem at the end of the project.

I spent a lot of time this year learning how to present, how to package ideas, how to frame things to get the best response, and how not to set the building on fire when I didn’t immediately get my way.

As much as this felt like pulling teeth, one of my long-term goals is to start consulting for large companies to help institute broad technical changes, so this experience is going to be absolutely critical as I work toward that goal.

I rekindled my speaking career.

In 2016, I didn’t do much speaking. Partially because I was gallivanting around the world, but also because I just didn’t feel like I was working on anything exciting enough to speak about.

In 2017 I made an effort to get back on the speaking circuit, and made ten conference appearances between March and November, either speaking or teaching a workshop (or both, in some cases).

I didn’t notice it until I got back on stage, but I really missed it during 2016. Sharing knowledge, talking with highly intelligent, highly motivated people, and watching the lights come on in someone’s eyes when a new idea clicks for them — that means quite a bit to me. It felt great to get back out there and do it again.

I released an open source project I'm really excited about.

In line with sharing knowledge, I was able to release some software I built at IBM as open source software, which is pretty exciting.

I’ll spare you all the nerdy details, but it’s called GrAMPS, which deeply satisfies my love of punny names. Since releasing it, I’ve had developers from companies like Target, the New York Times, and the NHL look into it as a solution for their large-scale projects.

I have no idea if it’ll make it into production anywhere (other than IBM, that is), but dammit it felt good to know that my work was helping other people with big problems to solve to do so a little faster.

Marisa and I got pretty good at cooking.

From 2010–2014, it’s safe to assume that I probably cooked fewer than ten meals. It’s just not something I was ever really into.

I mean, I like cooking. But I don’t like grocery shopping. Or cleaning kitchens. Or leftovers. Plus there are dozens of apps that will just bring food directly to my mouth.

But in Texas, it’s not easy to eat healthy. Everything is fried, soaking in butter, covered in cheese, or — in many cases — all three.

Things you don't notice until you leave and come back: the Portland food scene is really good at vegetables.

Corollary: Austin is... not so good at vegetables.
— Jason Lengstorf (@jlengstorf) December 20, 2017

This meant that we could either see how long it takes for me to regain all the weight I lost back in 2014, or we could start cooking healthy meals at home.

It turns out that we really enjoy cooking. And we’re not half bad at it. In fact, if I can toot my own horn for a minute, we’ve got a few meals that we make better than most restaurants.

We started inviting friends over for dinner and taking turns cooking, which helped push us to perfect new and different recipes, and expanded our knowledge of cooking.

And, of course, we leaned on smart people to help us along. We’ve just about worn out our copy of Six Seasons, which I’d highly recommend you pick up a copy of — I’ve sent at least three people copies of this book as a gift because I like it so much.

What could have gone better?

A retrospective is a lot like a compliment sandwich: you start with something good, then launch into what was terrible, then loop back around to positive things.

This is the part where I dig into what I didn’t like about my 2017.

I introduced a commute.

There were a lot of good things that came with taking a job at IBM: I met more people in the industry, landed better speaking gigs, increased my income, and grew my skills in new and challenging areas.

But there were a few downsides; most notably, I have a fucking commute now.

Not every day, but at least two days a week I have to drive 45 minutes each way to my office.[^car] This isn’t the worst commute I’ve heard of by a long shot, but my previous commute was a thirty-second walk to my couch — I really felt the pain of losing 90 minutes a day to sitting in a car.

That time cut into my mornings and had a domino effect that I really dislike: I had to start setting an alarm, had to make a choice between writing and hitting the gym, and had to choose between coffee and breakfast.

I sucked at writing. Like, really sucked at it.

In 2017, I published four posts. Four.

I could make excuses, but what it really comes down to is that my commute screwed up my morning ritual and I never recovered. And while I can say that I don’t regret choosing my health over my writing, I am definitely unhappy about my lack of output in 2017.

My day-to-day walking dropped off hugely.

Texas is not a walking-friendly state: everything is built with giant parking lots; sidewalks were more of an afterthought; Austin isn’t geographically constrained, so it spreads out like a dude on the subway; and even if all of that wasn’t the case, it’s too goddamn hot to be outside for about six months every year.

Because of this, my daily walking took a nosedive. If it wasn’t for the gym, I might have spent the entire year in a seated position.

I paid for it, too. We visited Portland over the holidays and stopped by Elemental Fitness Lab, where Chris and Blaine spent a few hours undoing some of the damage I did to myself.

What will I change in 2018?

The true value of a retrospective is in using the information to improve the next iteration.

To that end, the final step is to look at the problems of 2017 and come up with a plan to make improvements in 2018.

Here are mine.

I will walk a lot more often.

It’s currently cool in Austin, so Marisa and I have been taking advantage and walking everywhere while we can. Whenever it’s not dangerously hot, we plan to walk whenever the destination is 30 minutes away or less.

When it gets too hot for that, I’ll spend 30–45 minutes walking on a treadmill and reading a book. Not necessarily my favorite thing to do, but better than nothing.

I will reduce my commute to two or fewer days per week.

I just can’t handle my commute anymore, so I’m only going to do it a couple days a week to minimize the impact.

I really like my team, and enjoy doing things like team lunches or getting into a room and brainstorming or pairing up with someone to work on a problem, so I don’t want to stop going into the office altogether. However, at least one day a week my team and I can meet somewhere off-site — preferably walking distance for me — and work in a coffee shop. And the other days I can work from home.

I worked from home a couple days a week in 2017, so my plan is to bump that number up from 2–3 days to 3–4 days — the majority of my time will be spent out of the office so I can use the time I’d otherwise lose to my commute on more productive things.

I will rededicate a couple mornings a week to writing.

One of the things I plan to dedicate the time I’ll take back by not commuting is to start writing more regularly.

On days I don’t commute, I can put at least 45 minutes toward writing with no net change in my ability to work and hit the gym. Ideally I can push that closer to the 90 minutes I prefer, but I’ll be happy as long as I can get back to a more regular publishing schedule.

What Does Your 2017 Retrospective Look Like?

If you’ve never tried it before, I would strongly encourage you to do a retrospective for your 2017. Feel free to share it publicly on a site like Medium or your own blog, or to share it privately with people you trust (or someone like me, if you’re not sure who else to share it with). Or just write it, think about it, and burn it.

The value is in doing the thing, not having the thing.

If you do decide to share yours, I’d love to hear about it: hit me up on Twitter.

Here’s to a great 2018!

Make the Right Thing the Easy Thing: Better Choices by Default

Fri, 10 Feb 2017 00:00:00 GMT

For a year or so, I lived on the top floor of a fancy building in Portland's Pearl District.

This place was dope: giant balcony, concrete floors and walls for soundproofing, a 24-hour concierge — this was the kind of place where I signed the lease and thought, "Clearly I've now arrived, and Jay-Z will be calling any minute to discuss how our lives are very different but equally awesome."

But there was a catch. I was scared to take out my recycling.

It wasn't scared-for-my-safety scared. Or scared-because-it's-dark-and-there-might-be-a-monster scared.

No, nothing like that.

I was scared someone might see me.

Because here's the thing: across the hall from my front door was a closet, and that closet had a trash chute. This was extremely convenient.

The recycling, on the other hand, was a sixteen-floor elevator ride down, and then you had to carry the recyclables, like, a hundred feet to the dumpster. This was extremely inconvenient.

Now, look: I don't hate the planet. I like the planet. I would very much like for it to continue to be habitable for human beings.

But also, who’s going to change out of pajama pants and put on shoes just to get rid of a couple cardboard boxes, amirite?

I did make an effort — at least at first. But after a while, I rationalized it: There's probably someone who sorts the trash anyways, right? I'm creating jobs! I'm a goddamned American hero!

Eventually I just started taking out the boxes late at night in hopes I wouldn't see anyone in the hallway. I'd be safe from judging eyes. Eyes that would see me stuffing recyclables into the trash chute like one of those people — you know the type — who drives a Hummer with vanity plates that say ERTHFKR and tosses styrofoam cups out the window like confetti in a parade.

I'm not a dick — I'm lazy

Why would I consciously accept guilt and shame just to save myself a couple minutes of inconvenience?

I could — and did — blame the building for its lack of forethought in designing the trash rooms.

I could — and did — come up with numerous other excuses: this was a failure of the management! the system! humanity in general!

But, despite my rationalization, this was my failure. I could have done the right thing, but I did the wrong thing anyways. Because the wrong thing was easier, and I'm lazy.

Less obviously, though, is something more interesting: this was a completely predictable failure.

In the long run, convenience always wins.

The frustrating trend in my life is that I will nearly always end up doing the most convenient thing.

Despite all the shit I talk about great coffee, given a choice between instant coffee at home and walking 35 minutes in oppressive heat for a really good cup of coffee, most mornings I'd end up making the instant coffee.
Even though I've seen the documentaries and read the studies, after a particularly stressful day I'd go to a McDonald's in Japan instead of a local restaurant because I didn't have to think about the menu.

This list could go on for days — I have dozens of examples of me making poor-but-convenient decisions, and I don't expect that this is a trend that will stop any time soon.

After all, I'm writing this early in the morning, and my willpower is high, so right now I'm up on my high horse and judging my past self. But check in with me at 8pm most days and I'll do just about anything to avoid having to make an effort.

So we're just hosed, then?

Of course not. But we have to start looking at the problem differently.

In each of these situations where I did the wrong thing:

I was completely aware of what the right thing was
I logically understood that I wanted to do the right thing, and that the right thing would make me happier
I also knew that I'd feel shame and/or guilt about doing the wrong thing

And yet I did the wrong thing anyways.

I could chalk this up to me being a weak person with shitty willpower, but that's not particularly productive. But if we look a little deeper and Find The Why another, more useful thread shows up: these decisions are born out of convenience, not ignorance or malice.

So I'm not choosing to throw recyclables in the trash because I don't want to recycle; I'm doing it because I don't want to deal with the hassle of going to the recycling room when there's a hole I can toss it down right here.

I'm not choosing McDonald's over a local izakaya because I prefer fake cheese and extra preservatives; I'm eating there because the izakaya would require me to translate a menu and decide between unfamiliar preparations of ingredients, whereas McDonald's will serve me a 100% predictable meal with zero mental effort.

Make the right thing the easy thing

The fact that people default to convenience over doing the right thing might sound discouraging at first, but it's actually great news.

It means people aren't stupid or cruel; they're just lazy.

So if we're aiming to change behavior — whether it's our own behavior or the behavior of other people — we don't need to convince them that something is The Right Thing To Do.

Instead, we just need to make it easier to do the thing we want done than to do anything else.

We need to Make The Right Thing The Easy Thing™.

Okay, but how does that actually work?

Theoretically, this all sounds great. But can this really work in practice? How do we make it easier to study math than to not study math?

And let me be the first to admit that this is not a miracle cure for all the world's problems. But I do think that this is a powerful tool that can change an unproductive, negative feeling — "I'm shitty and I have shitty willpower" — into a productive, positive solution: "I need to make it easier to do this the right way."

And I think this works on and individual basis and at global scale.

Another way to think about this is that we’re “smoothing the path”, or creating our mise en place to give ourselves the best chance at success.

An anecdotal example: smoking.

You could argue that cigarette use is decreasing because more people know how bad it is for them, but I don't know if I believe that.

I'd argue that cigarette use in the U.S. has declined for two reasons:

People will openly scold you for smoking now.
It's really fucking hard to find a place to smoke.

In the past, everyone smoked and smoking was allowed everywhere — it was easy to become a smoker. These days, it's so inconvenient to develop the habit that it’s far easier to just not bother at all.

A real example: electric cars in Costa Rica.

Monica Araya is working to get Costa Rica off fossil fuels entirely. But she's not doing it by running a smear campaign against oil. She's also not focusing all her efforts on educating people about the environmental "rightness" of eliminating fossil fuels.

Instead, she's working to make electric cars cheaper than gas-powered cars.

If she succeeds, Costa Rica will become the first country to completely eliminate fossil fuels. Not because it's the right thing to do (it is), but because Monica Araya realizes that most people will do the easy thing by default. If electric cars are the easiest and cheapest option, electric cars win.

Ideas and strategies for making the right thing the easy thing

Here are a few ways I'm trying to Make The Right Thing The Easy Thing in my own life:

Create social pressure to do the right thing. I pay a personal trainer because it means someone is waiting for me at the gym. I’ll inconvenience them if I don’t show up — and I'd rather haul my ass out of bed and get to the gym than explain how I'm a lazy sack of shit who didn't feel like working out.
Make it more work to skip it. If I have something I want to take care of, like folding laundry, I'll dump the pile on the bed. Sure, I can now make the effort to pick up the pile and move it somewhere else so I can go to bed, but the part of my brain that harps on boosting efficiency shorts out — so instead, I just fold the clothes so that I can go to bed.
Remove the temptation altogether. I don't keep snack food in my house. I know that if I have access to a bag of chips, I will eat that bag of chips. Not because I want it, but because it's there.
Make it hard to procrastinate. To keep myself from going off-task, I kill all notifications and turn on FocusTime so that I can't even load Twitter, let alone use it to put off doing work.

How will you make the right thing the easy thing?

What choices are you making right now that you know are bad, but you make them anyways because it's more convenient?

How could you tweak things so the right choice becomes more convenient?

Let’s talk about it on Twitter.

I spent 2 years living abroad in Airbnbs. Here’s what I learned.

Tue, 07 Feb 2017 00:00:00 GMT

For the last two years, Marisa and I have been living outside the United States, staying exclusively in Airbnbs. In strangers' homes.

When we first set off on our grand travel and remote work experiment, we had several hypotheses about how things would go. Here's a quick recap of what we expected:

We don't have to wait until we retire to start traveling.
It's possible to be productive during sustained periods of travel.
It's just as cheap (or cheaper) to live abroad.
It's healthier to live abroad than it is to live in the United States.
Living abroad for extended periods of time means huge tax breaks.

Two Years In: Were My Hypotheses Correct?

When I boarded a one-way flight to Milan at the end of 2014, I had no idea whether or not I was right about any of these hypotheses. Sure, I had my gut feelings and I'd done my research, but without putting it into practice, I was still making educated guesses at best.

Now it's been two years, and I've been testing these hypotheses the whole time. So... was I right?

1. Is it possible to travel extensively before retirement?

tl;dr: Abso-fucking-lutely.

There are only two prerequisites for long-term travel:

a willingness to spend an extended period of time exploring the world, and
a stable source of income that never (or rarely) requires physical presence

If you don't have a location-independent source of income, it's easy to throw your hands up and say, "Well, that works for programmers, but not for [INSERT PROFESSION HERE] like me."

Bullshit.[^probably]

[^probably]: Hold your fucking horses before you jump down my throat here — I'm getting to the fine print. Don't begrudge a guy his flair for the dramatic, okay?

While there are obvious exceptions — hard skills like carpentry and transmission repair don't travel well — a huge number of jobs in the western world have moved online.

In my travels I've met trademark lawyers, stock brokers, accountants, journalists, customer service reps, marriage counselors, and real estate consultants; if your job is performed on a computer, it's extremely plausible that you can become a remote worker.

However, there is a caveat to all this: you need to have your network in place first.

When I left, I had already been in my industry for a decade, and I have an amazing group of previous clients who have always sent interesting opportunities my way. I've also put a fair amount of time into meeting other people in my industry and building a professional network.

My network meant I could rely on my sales pipeline staying full when my existing contracts wrapped up. It meant I had people who could send me leads if I needed work. Most of all, it meant my income was stable.

Freelancers: you need a network first.

Marisa, however, had just switched industries when we left. She realized that most of what she'd been doing in her role as a human resources director crossed over with user experience, and she was way more interested in working in user experience.

When we started traveling, she was trying to build her network. It's not impossible to create a network while traveling — she pulled it off — but it is way more difficult. There were a few tough months where she didn't have anything in her pipeline and wasn't sure where her next contract would come from. There were times she felt hopeless because no one was responding to her cold emails. There were a crying jags in the bathtub. And since we were in Vietnam or wherever, she couldn't just roll down the street to a business meetup and use her trademark combination of giant sexy brain + irresistible curly cuteness to win clients over in person.

So if you aren't already established with a network, spend time building your network first: go to meetups, attend conferences, meet people, and create a solid pipeline. It may take a year, but when you're in Thailand and your current contract ends, a network means the difference between dropping a few lines to let people convince you why you should work with them, and trying to decide exactly how close you're willing to get to broke before you pull the rip-cord and head home.

2. Is it hard to stay productive while traveling constantly?

I closed my eyes and let the déjà vu wash over me. I was having this conversation. Again.

"I'd never get anything done," she said with a self-deprecating chuckle. "I'd be too distracted by the sand and the ocean."

In an alternate reality where my filter is all the way broken,[^filter] I clunk my beer down and turn to face her. "Listen," I snap, "if all it takes to keep you from getting your shit taken care of is a beach, then I'd say the beach is the least of your fucking problems."

[^filter]: In this reality, my filter is only mostly broken.

But I'm a coward, so instead I just nod and smile and look for a way to politely exit the conversation.

Here's the thing: staying productive on the road is easy. Once you get your productivity habits sorted, hitting "office-standard" productivity goals for an eight-hour day takes at most six hours. Probably four.[^time]

[^time]: The industry's dirty little secret is that working longer hours makes us less productive, and the constant distractions in an office add up to huge amounts of wasted time while working.

For the last two years I've averaged roughly 37 hours a week on a computer — that's including Netflix time – and my productivity sits at 75%[^email] overall.

[^email]: I categorize email, chat, and all meetings as unproductive time. That accounts for an additional 10% of my screen time in 2016.

However, productivity goes to hell if you travel too fast.

A few times over the last couple years we decided to make "quick trips". A long weekend in Berlin; a couple days in Budapest; five days in Istanbul. Had we looked at these trips as vacations, things would have been fine. But we didn't — we thought we'd be able to get things done on these short trips.

Fast travel makes productivity hard. If you're in a place for a few months, there's time for both work and seeing the city. But when your time is restricted, you have to start making choices between a thing you want to do in the city and a thing you need to do for work — and work typically loses.

Everyone will have a different Goldilocks Zone for balancing experience, productivity, and exploration,[^goldilocks-zone] but it's important not to get antsy and try to see everything in a hurry. Working and traveling is a way to avoid high-stress, high-speed vacations; don't forget to take advantage of that freedom to maximize both your productivity and your level of satisfaction about traveling.

[^goldilocks-zone]: For me, the Goldilocks Zone is about two months. If I stay longer, I start to feel listless and catch myself settling into the kinds of routines that spurred me to leave in the first place.

A month can work, but I usually feel like I've just started to make friends and know the neighborhood at that point. For the last year Marisa and I have aimed for about 6–8 weeks in a location, and we've been happy with that result.

3. How much does it actually cost to travel the world for two years?

When I left the United States in 2014, my only experience of traveling abroad was a short trip with Nate to Belgium, the Netherlands, and the UK.

That trip nearly bankrupted me.

Over the course of ten days or so, I managed to spend every penny I had (and quite a few that I didn't). After Nate left a couple days early for a work thing[^borrow] I was forced to ration food for the last 36 hours because I'd maxed out all my credit cards and only had about €8 or so to my name.

[^borrow]: Which meant I couldn't borrow any additional money from him.

My experience isn't uncommon. My dad always grumbles about travel because it costs too much. Friends are always putting off vacations because they can't afford them.

So naturally, most of us — myself included until mid-2015 or so — immediately assume that long-term travel will be expensive. Prohibitively so.

But that's simply not the case. For most people living in the United States, long-term travel is significantly cheaper than our current living costs.

My cost-of-living for 2016–2017: $54.80/day

For the last two years, I've averaged $1,666.88 per month to live. And that's not just rent; that's rent plus utilities plus cable and internet plus electric plus property taxes or hotel taxes or whatever taxes.

In that time, I've lived in a dozen or so different countries, ranging from oceanside resorts in Koh Samui (~$22/day) to a courtyard apartment in Rome (~$79/day) to a kitschy apartment in the heart of Zagreb (~$34/day).

For reference, my cost of living in Portland was ~$88/day.[^portland]

[^portland]: My rent was on the higher side in Portland at $1,950/month — I was happy to pay a little more for a nice place in a great location. However, it's worth noting that most of the Airbnbs we were renting for less were just as nice (and in some cases nicer) than my Belmont loft in Portland.

It's also cheaper to eat (and do other stuff, too).

Beyond just the cost of rent and utilities and other living expenses, we also saved a ton on food. Most of my disposable income goes toward eating well, so this was not an insignificant savings.

For example, in Vietnam we regularly ate banh mi sandwiches that would cost about $10 in the United States for less than VND 25,000 — which is roughly a U.S. dollar. A fancy meal — a multi-course affair for two — would cost maybe $20. Most of the time Marisa and I both ate for less than $5 total.

Thailand was astonishingly cheap as well.[^thai-food] Ditto Croatia.[^split]

[^thai-food]: One of our favorite meals was marinated pork grilled in the back of a truck. It cost 50 baht (USD $1.41). When we felt like eating a Western breakfast, we went to the "expensive" brunch place — a restaurant that could have been plucked off any hipster street in a U.S. city called Rustic & Blue — and paid 200 baht (USD $5.65) for eggs Benedict or a breakfast sandwich that held up to many restaurants at home.

[^split]: In Split, Croatia, Marisa and I sat down to a five-course meal at one of the most expensive restaurants in the city. We ordered two drinks each. Including a fairly large tip — especially considering the European standard is 10% — the whole meal cost USD $125. (That's not exactly cheap, but for comparison, a meal of this quality in the U.S. would easily run $400+.)

Most meals in Croatia were closer to 25 kuna (USD $3.58).

The food wasn't an anomaly, either. Our gym memberships, mobile phone service, and other day-to-day expenses all went down. The United States is expensive, y’all.

Plus you can't buy new shit.

Probably the biggest impact on my spending was the fact that I couldn't store anything. If I bought something, I either had to pack it every couple months or leave it behind when we moved.

So my impulse purchasing dropped to near-zero.

4. Is it actually healthier to live outside the United States?

This is going to be a loaded question, I guess; it depends on who you are and where you go.[^france]

[^france]: If you go to France and don't walk at all and eat croissants and cheese all day, you probably aren't doing your body any favors. There's a reason no one in California has started a fad diet based on the French way of eating.

Then again, if you go to France and don't eat croissants and cheese all day, I'm not sure you and I have much to talk about.

But for Marisa and me? Yes. Marisa is in the best shape of her life. I lost a lot of weight without doing anything that would be considered a diet.

A few things happened once Marisa and I left:

We started walking way more. In 2016 I averaged 7,500 steps a day — which isn't all that much, honestly, but it's a hell of a lot more walking than I did before I left.
The amount of processed food we ate dropped significantly. This wasn't a conscious effort; there's just less processed food in a lot of the places we visited. We tried to eat local food, which meant there was a lot less bread and cheese, and a whole lot more veggies and fruit.
We made it to the gym regularly. This was much easier to do when there was no commute or early meetings to worry about; we weren't able to claim that we were "too busy" to make it to the gym.[^habit]

[^habit]: Now that we've built the habit, it's much easier to keep it now that we're on more of a schedule. But it still takes effort; that's why staying consistent in the gym is part of my 2017 action plan.

It's also worth noting that portion sizes were notably smaller. Our typical approach to a restaurant was to order three entrees: Marisa would eat all of one and a few bites of the second, and I'd eat the rest.[^vegas]

[^vegas]: Portion sizes in the United States are insane. I spoke at a conference in Las Vegas in 2015, after we'd picked up the three-entree habit, and ordered three entrees in a diner — an egg dish each, with pancakes to share — and the waitress couldn't fit our order on the table.

I'd never really thought about portion sizes in the U.S. being all that big, but y’all they're fucking huge.

In Japan, both Marisa and I noticed that we just plain felt better eating Japanese food. Western diets have a lot of bread and cheese, which — despite being delicious[^food-group] — tends to make me feel gross and bloaty. Which I didn't realize until I wasn't eating bread and cheese all the time. Which never would have happened if I hadn't left the U.S., because there's so much bread and cheese available.[^back]

[^food-group]: I truly believe that, were it possible, I'd be perfectly happy eating nothing but cheese for the rest of my life.

[^back]: And let me be clear: I am by no means advocating a diet that doesn't include bread and cheese. Hell, I ate a sandwich an hour ago. I'm just saying that I'm now aware of the consequences of my high-cheese diet, and I'm choosing to accept them.

5. Are the tax breaks for long-term travelers real? And how much is actually saved?

This was the big one: my research and the advice from a couple accountants seemed to imply that anyone living outside the U.S. for 330 days or more wouldn't pay federal income taxes because of something called the Foreign Earned Income Exclusion. And since I wouldn't be working in the countries I was living in, I used tourist visas — which means I don't pay taxes to the country (except sales taxes).

This means roughly 25% of my gross income that usually goes to taxes goes straight to my savings instead.[^tax-note]

[^tax-note]: Keep in mind that you still have to pay Social Security and Medicare, which is roughly 15%. And each state has different rules about what you do and don't owe, so do your research — or move to one of the states without income tax before leaving.

Is this legal?

As far as I can tell, yes.

How visas work for people in my situation is a legislative grey area. The laws about working in foreign countries are in place to protect the local economies: if I come in, take a job locally (which takes money out of the local economy), and don't pay taxes, I'm creating a leak that could become a big problem. However, if my job is in the United States, I'm not taking any money out of the local economy — I'm only putting money into it. This is what tourists do, and in many countries tourism is a large portion of the economy.

There are a few ways to interpret what a tourist visa allows, but in the case of remote work, the rules are poorly defined: if I sit down in a coffee shop in Thailand and working on a U.S.-based website that pays my U.S.-based company, am I working in Thailand? And if so, does that mean that everyone who goes on vacation and checks their work email is also violating their tourist visa?

My feeling here is that remote work while traveling is still falling through the cracks because a very small number of people take advantage of it. I'm willing to bet that there will someday be laws passed to cover this edge case, but for now — especially considering the lower cost of living — world travel is easily the world's greatest savings plan.

Okay, fine, but did it work?

It sure did. For 2015, I kept 25% of my gross income. The IRS still has time to audit me, but my returns were all accepted without complaint, and I was able to hold onto a significant portion of my income.

I'll be filing for the FEIE again on my 2016 taxes, and I expect similar savings.

What I Know About World Travel From Two Years Living & Working Remotely

I had five hypotheses about travel, and all five held up to real-world testing.

It's absolutely possible to travel extensively before retirement. In fact, it's a really smart move to help save for your future if you've got a steady source of remote income.
Staying productive is just as easy — probably easier — while traveling. Being halfway around the world is a great way to limit your meetings and focus.
The cost of living in Airbnbs around the world is significantly cheaper than paying a lease or mortgage in the United States. You'll pay less in rent, utilities, and insurance. (And food, and entertainment, and...)
Staying healthy is easier outside the United States. Especially in Asia.
There are enormous tax savings for long-term travelers. 25% of your gross income stays in your pocket if you travel for 330 days a year.

There are a lot of reasons not to travel. Some of them are valid. Some of them are excuses. Ultimately, whether or not travel is a good idea for you is going to come down to you.

But if I can make a suggestion: if you fantasize about traveling, buy the fucking ticket.

I promise you this: you'll never regret taking the trip; you might regret not taking it.

How I’m Looking at My Past to Improve My Future

Wed, 25 Jan 2017 00:00:00 GMT

I didn't make any New Year's resolutions for 2017.

Honestly, I wasn't really planning to say anything at all about 2016.[^momma-says] Then Nate wrote a retrospective, and I decided that was a good idea.

[^momma-says]: If you can't say something nice and all.

A good idea that I intend to steal outright in this post.[^timeline]

[^timeline]: "Wait," you might be thinking, "isn't it almost February? Aren't you a little late to the 2017 party?"

Indeed I am, dear reader. Indeed I am. I'll talk more about this later in the post.

Why a Retrospective? (Also, What Is a Retrospective?)

One of the more valuable strategies I picked up from my time as a contractor for Precision Nutrition is the idea of holding a retrospective[^post-mortem] after each project (or phase of a project).

[^post-mortem]: I first heard the concept described as a post-mortem, which tickled the dormant emo kid lurking in my subconscious. I pictured black veils and sullen silences set to AFI's Sing the Sorrow.

A project retrospective follows a simple-but-effective format that aims to answer three questions about the given project:

What went well?
What could have gone better?
What will we change to improve our next attempt?

As a business strategy, this is huge. It frames things positively and calls out the good parts in addition to the bad. It gives the team a platform to share negative feedback in a structured, expected way. And — this is the most important part — it creates a plan for getting better.

How does this apply to our personal lives?

Nate said this well, so I'm just copy-pasting his words here:

If we don’t learn from our past, we we won’t be able to identify our biggest opportunities to make life better. Which means we’ll likely suffer through the same situations and thought-patterns again and again.

Nate Green, My 2016 Personal Retrospective (And 2017 Action Plan)

People say things like "learn from your past" all the time. But this is one of those vaguely idea-shaped truisms: it's cute and inspirational and all, but it isn't really useful without a plan.

A retrospective creates a plan for learning from the past.

My 2016 Retrospective

Overall, 2016 was a great year for me. My personal and professional lives grew in ways I'm proud of, I made choices I'm happy to defend, and I can't think of anything I regret.

However, everything I just said is fluffy, and not particularly useful. So let's dig into specifics and see if I can come up with a plan to make 2017 a great year — even if that plan ends up being, "Just keep doing what you're doing."

What went well in 2016?

I had a lot of things to be happy about in 2016:

Marisa and I continued our traveling adventures for the second year.
Nate and I released an online workshop/course for gaining better focus and productivity. We also recorded a half-dozen episodes of our podcast.
I launched a code blog to share (far geekier) content about building better software.
With help from great people like Mackenzie Child, I learned a bit about making videos and launched a YouTube channel for nerds.
I started cooking again after years of almost exclusively eating out (or buying pre-made meals).
With help from the incredible people on my newsletter list, I went on dozens of Small Adventures.[^small-adventures]
I was more consistent in the gym than I've ever been in my life.

[^small-adventures]: If you're not on my newsletter list, I ran a series of emails where I talked about Small Adventures: quick, inexpensive things we can all do to switch things up and add a little adventure back into our lives. (Also, consider getting on my newsletter list so you don't miss fun stuff like this. You'll get a free guide with three tips for being happier, too.)

If you are on my newsletter list, I'm still working on something cool that combines my ideas with the dozens of incredible ideas you sent me — stay tuned.

What could have gone better in 2016?

Even though I don't have regrets about last year, I do see some room for improvement. So let's run through a quick list of my shortcomings, shall we?

I did a bad job of keeping up with friends.

If something's not at the front of my mind, I tend to forget about it entirely. And while this is great for productivity, it's terrible for keeping up with people I don't get to see very often.

Left unattended, I can go months without calling my parents. Years without talking to people I consider close friends.

And while part of that results from a (typically mutual) disinterest in forcing a catch-up call "just because", a good deal of the blame falls on me for straight-up never thinking about things that aren't in front of my face — whether it's a project I forgot I was working on, or a person I really like but haven't thought about in a while.

Whether or not anyone but me has noticed, I don't like this.

I wasn't proactive about public speaking.

In the years before I started traveling, I was constantly speaking at conferences. For a couple years I was averaging a talk every month or so.

After leaving, though, that number plummeted: I gave maybe three talks in 2015, and only one or two in 2016.

That bums me out, because I enjoy challenging myself to learn something well enough to teach it. And I really enjoy watching the light come on in someone's eyes when they comprehend a new idea for the first time.

There were events everywhere, so I could have made it work. I just... didn't.

I fell out of my writing habit.

In 2015 I wrote a whole post about creating a writing routine. The short version is that I was keeping myself consistent with writing by doing it first thing in the morning, before the gym. Part of that included leaving my phone away from the bed to avoid the temptation to waste time on social media or games.

Sometime last year, I broke this routine. The phone has been showing up in bed in the mornings, and my 90 minutes of writing time has degraded to 45 minutes of wasted phone time.

As a result, my publishing frequency has gone way down. And since I'm not writing every day, a lot of posts die as drafts because I either argue myself out of the point I was trying to make[^arguing] or lose the thread of the post and end up scrapping it.

[^arguing]: I like to play Devil's Advocate with everyone. Including myself. This means that, given sufficient time, I will successfully overthink any point I'm trying to make until I've taken the opposite stance.

This is bullshit, and I know it.

What will I work to improve in 2017?

After going through the process of complaining about 2016, there's a critical step left to make this productive: I need to make a plan to keep the good things good, and improve on the things I wasn't so happy with.

I will dedicate time to keeping up with the people I care about.

Last month I was in Toronto, where I watched Sol Orwell network like a fucking magician.[^cookielife] He showed me his spreadsheet for organizing an upcoming charity event, and I realized how much effort goes into keeping up a strong network.

[^cookielife]: I hung out with Sol three times while we were in Toronto. On two of those occasions, he had received a shipment of cookies from a stranger (or at least someone he only knew from the internet) — all because he does a really good job of talking to people, learning what they're about, and connecting them with other people.

I should know this already; I used to watch Nate go way out of his way to send a small-but-thoughtful gift to someone he'd just met, or dedicate his time to bringing together a few people for lunch who stood to benefit from knowing each other.

Both Sol and Nate have built incredible networks. Nate's entire livelihood is built on the back of his outstanding networking skills.[^me-too]

[^me-too]: And, if we're being totally honest here, a pretty decent portion of my livelihood has roots in Nate being roughly 1,000,000x better at networking than I am.

So in 2017, I'm actually going to schedule time for keeping up with people. And not just for professional networking; I'm going to make sure I've set aside time to call my mom, or send a card to my grandparents, or follow up with my friend who just got a new job.

I don't need to be a networking genius like Nate or Sol, but I definitely need to stop being an out-of-sight-out-of-mind jerk like I have been.

I will submit proposals so I'm speaking at one conference per quarter minimum.

It's important to me on both a professional and personal level to continue speaking.

Professionally, speaking gigs help me increase my value to the companies that want to work with me, and it establishes me as an expert on a variety of subjects. This gives me more freedom to negotiate on rates and specifics — such as working remotely.

Personally, it feels really good to know that someone is going to have a better career — and hopefully, a better life — because of something I helped them understand. I may not be changing to world, but for a small handful of people, I have the chance to spark an idea or offer a little insight that can help them get where they want to go.

It's why I write, and it's why I speak. Or at least, it's why I want to speak.

Most conferences open up a request for proposals, where people can submit talk ideas.[^rfps] I need to be more proactive about looking for these and submitting ideas if I want to continue speaking regularly.

[^rfps]: If you're interested in getting into speaking, Lanyrd has a round-up of open calls for proposals, and PaperCall is a tool used by conferences looking for speakers. You can also check out We Are All Awesome for resources to help you build confidence and get your proposals accepted.

I will stay consistent in the gym, even though things are going to be a little different now.

For the last two years I've been really consistent in the gym. At least twice and usually three times a week, Marisa and I have been in the gym. We worked with great coaches to build a remote program, including remote programs from Chris Bathke, Precision Nutrition and Craig Weller. I'm in better shape now than I've probably ever been in before — I can do pull-ups now.[^pullups]

[^pullups]: This is a new development for me. I was always the kid in gym class who just hung on the bar and looked hurt that I was expected to do anything.

However, we had an advantage: we were halfway around the world, so if we felt like sleeping in and working out at 10:30 am, that was okay.

Now we're in Austin, working regular business hours. We have to be at the gym by six most mornings or we won't have time to work out.

This is where I've struggled in the past: when things get busy, my health slips first.

So I'm not going to do that. This year, I'm going to make sure I continue with my good habit of hitting the gym three or more times a week.[^so-far]

[^so-far]: A month in, this has worked out well. Early mornings suck, but I've found I tend to sleep better, have more energy, and just generally feel less like a damp sack of shit when I make it to the gym early.

I will make time to continue working on videos and tutorials for my code blog.

Writing a blog post like this one is therapeutic; I have a thought, wrestle with it, and flesh it out in a few words.[^few-words] The process is simple: write until something that makes sense is on the page.

[^few-words]: Ha. I say "few words" as if I've ever written anything shorter than 2,000 words.

Code posts, by contrast, are fucking difficult. There's research, testing, demo applications, and rounds of feedback — and then you write the post. And after that, you record the video, edit it, and post it on YouTube.

A blog post for this site might take me two hours if I'm fucking around, or having a hard time articulating myself; a code post will easily take days.

So I can't just sit down and throw one together. I need to ~~make~~ find time to work on these if I plan to release more than two or three a year.

And that's exactly what I plan to do: I want to spend a few hours every week working on a code tutorial.[^nerds]

[^nerds]: Fellow nerds: I'm looking for ideas, so open issues for topics that interest you.

I will replace my morning phone habit with writing (again).

I don't really remember how this happened — I was kicking ass with waking up phoneless and writing and then... I don't know. We moved somewhere that changed my schedule? I was hungover one day?

Whatever it was, I fucked up and started bringing my phone into the bed after I woke up. So my Boom Beach ranking went up, but my writing output tanked.

(For example, I started this post on January 4. Three weeks later and I'm just now getting back to it. Like a slacker.)

I didn't notice at first. That's how bad habits tend to work: we don't notice the slide; we just wake up one day and realize, Holy shit, I've made a huge mistake.

But noticing the problem is the first step toward fixing it. So as long as I take this as an opportunity to get a little better,[^again] I can feel confident that I'm making progress.

[^again]: Even if I'm getting a little better again.

To that end, I'm going to leave my phone outside the bedroom at all times, and put my computer next to my coffee stuff. If I Make the Right Thing the Easy Thing™, I'll have a much better chance of succeeding.

Making it real: how I'll turn these thoughts into action steps.

Based on the ideas I've just listed, I need to make a list of todo items that I can follow every day. I'll call it Jason's List of Habits for 2017:

I will schedule two hours every week to connect with friends, family, and my professional network.
I will submit at least one talk idea for every conference that fits my calendar.
I will stay consistent with my existing gym routine of 3–4 mornings per week.
I will schedule 2–3 hours each week to make progress on writing and/or recording a code tutorial.
I will resume my habit of writing for 30 minutes minimum before looking at my phone in the morning.

Your Turn: Do a 2016 (+ January) Retrospective

Even if you've already made your New Year's resolutions,[^broken] take 15 minutes to do your own retrospective. Remember: you're asking and answering three questions about the last year of your life.

[^broken]: And even if you've already broken those resolutions.

What went well?
What could have gone better?
What will I work to improve in 2017?

Share one or two of your answers in the comments. Here's to continuous improvement — and our best year yet!

Only Keep Score Against Yourself

Sun, 11 Dec 2016 00:00:00 GMT

How do we know when we're successful?

There's no formal award ceremony denoting success. There's no set quantity of stuff we can acquire that guarantees success. We can't inherit our parents' success — only the results of it. We can't buy or steal success, either.

Worse, what feels like success now can slide out from under us and feel like stagnation or failure, like a kid who feels so proud of her B+ on the math test until her parents ask, "Why didn't you get an A?"

The fluidity of success — or, more precisely, of feeling successful — has been on my mind recently, due mostly to some big changes I'm navigating.

The feeling of success is a maddening subject: everyone wants to feel successful, but how we define and measure what success feels like is infinitely varied.

So let's try to pin it down, yeah?

Objectively, It's Hard to Argue Against Our Success.

At first blush, success doesn't seem hard to nail down. After all, don't we have perfectly valid, objective definitions of success?

Let's do a quick run-down of all that ways I'm really successful, shall we?

Nothing tries to eat me. Ever. The likelihood that I'll be knocked out of my spot at the top of the food chain is so low that it would be a legitimate reason to doubt my grasp on reality if I started to worry about it.
It's below freezing and snowing outside, but I live in a heated box with a hot beverage and access to an army of delivery drivers.
Thanks to the internet and the growing ability to do almost everything remotely, I have virtually unlimited options for what I do to earn a living. When I wanted to make money building websites while living on an island in Thailand, that was a perfectly realistic option.
I make more than USD $32,000 per year, so I'm in the top 1% of global wealth distribution.
I had the freedom to "find my passion" — and to learn (the hard way) why that's a bad idea.[^passion]

Of course, this isn't true for everyone — but since you've landed on a post about feeling successful, I'll make an educated guess that most of this list applies to you as well. All of which makes a pretty compelling case that we were born objectively successful, and will likely stay that way unless something goes horribly wrong.

The Problem With Objective Success

But despite being — y'know — true, measuring success objectively is met with eye rolling and near-instant dismissal. When someone interrupts us mid-complaint-turned-angry-rant to remind us how lucky we are, it feels less like a confirmation of our success and more like a lecture from our parents about "starving kids in Africa" when we don't want to eat our spinach.

A conversation about why this happens inevitably spirals outward and downward until eventually we land on the greatest conundrum in the human tragedy: people don't like facts; they like feelings.

All the objective truth around us proves that — simply by being born in the first world — we've already won life by any reasonable measures. But since everyone we know has also won life, it doesn't feel very good.

What feels good is being a winner among losers. And since the reasonable criteria for success are "too easy", we had to make up unreasonable criteria.

Success by ownership: there's a pile of shit in my house to prove I'm not a piece of shit.

Five or six years ago I found myself in a fancypants kitchen store looking at pots and pans. At this point in my life, I cooked meals maybe three times a year.

Logically, I knew this. Hey, self, I thought with my smart brain, you don't need much, here. Grab a decent frying pan and get out of here.

Now wait a damn minute, here, chimed in my Idiot Lizard Brain, if you don't have the best pans money can buy, who will ever love you?

I felt the damp sheen of fear sweat. Felt my lungs shrink and my heart thump and my mouth go dry. I set down the perfectly-fine frying pan I was holding and reached for one with a special copper core that was guaranteed to distribute heat more evenly or something. I imagined perfectly-cooked meals, the booming success of my imaginary dinner parties, the awed respect in my imaginary guests' voices as they gasped, "My god — is that the skillet with the special copper core?"

When the dust settled, I'd spent over a thousand dollars on a complete set of pots and pans. I didn't have a thousand dollars to spend; I spread the purchase across two credit cards.

I probably used the stock pot once. The skillet less than a dozen times. A year and a half later I sold it all for maybe 20% of what I paid for it. It was another year before I'd finish paying off my credit cards.

What happened? To be perfectly honest, I have no fucking idea. I just felt that I needed the nicest set. Or at least the nicest set out of all of my friends.

How else would everyone who came to my apartment know how successful I was?

Success by comparison: you have a thing, so obviously I need the nicer version of that thing.

Once, I was in an upscale bar in Vancouver, BC, drinking a $12 cocktail. It's 4pm. Marisa and I are both out of todo items, so we've packed up and left the coffee shop we'd been working in to kill time until our dinner reservation.

In short: we’re living easy.

To my left, a couple guys walk in, fresh from the office. One is rocking a perfectly tailored three-piece suit, a fantastic trench, and a hat that belonged on a film noir detective. The other is dressed even better.

For the briefest of moments, I am utterly convinced that unless I have a nice suit, I'll never be as successful as these guys, and all the men like them who show up in Esquire and James Bond and Mad Men.

It feels bad.

Which is ridiculous, because I know how good I have it. The smart part of my brain has no doubt that I'm happiest where I am right now, but I still sit there feeling jealous of this bro with a power tie and a haircut like he's Harvey fucking Specter.

Later, I spent some time reflecting on exactly how much I like my life. But this is pretty new for me; historically I wouldn't have realized I didn't actually want a suit until after I'd bought it, worn it once, and left it in my closet for a year.

How to Feel Successful: Stop Keeping Score

There's this scene burned into my memory, and whenever I replay it I can feel the blood rushing to my face: I'm at dinner with the Precision Nutrition team, where the topic of conversation wanders onto the idea of success. As the scene opens, I am haranguing the group.

I'm feeling slighted because strangers dismiss me as an "average human". This is obviously an unforgivable offense.

In the course of my rant, I use the phrase, "...and I could buy and sell that guy, and he doesn't even know it!" I mean this in the same douchebag sense that one might screech, "Don't you know who I am?"

Someone at the table remarks, "You're awfully concerned with how you stack up to other people."

I'm humiliated. I sulk about it. I probably push my food around my plate like a sullen teenager.

It was much later when I realized that my constant worry over comparison was a disturbing insight into my contentment — or lack thereof.

Who are you measuring against?

If our self-worth is tied to what other people are capable of, we'll always be miserable.

If we're looking to beat ourselves up, someone is always more impressive. Natalie Portman graduated from Harvard at the same time she was making Garden State, for chrissakes; we're not going to top that.

Or, if we're looking to comfort ourselves, we can always find someone doing worse. If all we're looking for is someone to make us look good by comparison, a quick scroll through social media is all we need.

Someone will always be better, and someone will always be worse.

There are too many variables.

If I were to spend the rest of my life practicing my breakfast sandwich technique, I could maybe get to the point where someone called my breakfast sandwiches the best breakfast sandwich in the world. That's success, right? I'd be the best!

Except someone else is vegetarian, and someone else doesn't eat gluten, and someone else doesn't like mayonnaise. So to them, I'm not the best. And of course, if I'm asked to make Eggs Benedict, I'm going to be mediocre at best.

We all have strengths and weaknesses. We all started at different times, with different levels of background knowledge. Comparing our success to someone else's is apples and oranges; it all boils down to opinions and rhetoric in the end.

Instead, the only way we can realistically measure our success is to measure against ourselves — and only ourselves. Am I better than I was yesterday? Than I was last year?

That is progress. That is success.

Success Is Cumulative

If we're only measuring against ourselves, the conversation becomes very different. We're no longer looking at other people and panicking because they have things we don't have, or know things we don't know. We're already sure of it — and that's okay.

Instead, we're looking at what we're working toward, and answering a single question each day: Did I do something today to take me closer to where I want to be?

Success means answering "yes" more often than we answer "no". And that's all it means.

Success is not the stuff we own, or our bank balances, or any of the other crap we get fed by advertising or social norms or The American Dream™. Success is having a target and knowing that you're putting most of your effort toward hitting that target. And then setting a new target once you've hit the first one. Because the target is always moving.

Because if we can stop evaluating success as a subjective measure of us vs. them, we can leave the panic of "keeping up with the Joneses" behind.

And that leaves us free to define success by what makes us happy, instead of what keeps us competitive.

Why you should never feel guilty about “wasting time”.

Wed, 28 Sep 2016 00:00:00 GMT

In high school I wanted to be a rockstar.

In the pursuit of that goal, I eventually managed to drop out of college, become more or less unemployable, ruin most of my relationships, and — most notably — utterly fail to become a rockstar.

It might be tempting to consider 2004–2007 "wasted time".

After all, I set out with a goal to make a living as a musician. And despite hundreds of days touring the country, living in a van, and making ramen in styrofoam cups, after a few years the band broke up — and I was nowhere near a professional musician.

And yet, I would never call that time wasted. In fact, those "wasted" years were a critically important step in my early journey toward building a successful career.

What did you learn?

Trying to make it as a musician threw me into the deep end of several new skill sets.

I wasn't just a musician; I was a promoter, a manager, a designer, an accountant, and a dozen other jobs we couldn't afford to pay someone else to do for us. We needed shows booked, and t-shirts made, and payments negotiated (and collected). Equipment needed repairs and replacement. Concert posters needed to be designed and printed and mailed to people — and those people needed to be convinced to hang them up around town.

Even though I was failing to make it big as a musician, I was gaining a lot of valuable information: I liked the business part of the experience; I really enjoyed designing posters and building websites; I wasn't terrible at promotion and sales.

I also learned to rely on myself; each day on the road was sink or swim. And despite the frustration and near-hopelessness of it, I found that I deeply enjoyed the attempt at taking an unknown, generally unimpressive entity (my emo band) and trying to get people to support us with downloads and dollars.

The skills we learn cross over to other areas

Every single skill I learned during my rockstar days has proven useful in other areas of my life.

Convincing someone to buy an album or a t-shirt is awfully similar to selling web design or consulting services.

Collecting payment from a broke promoter when my options were A) I get $100 for gas money, or B) I live in Tucson now — that was a stellar crash-course on chasing down overdue invoices.

Learning to customize my band's MySpace page started me down the path toward what I do for a living today.

In light of that, it's hard to call my musical pipe dreams "wasted time". Instead, that so-called "wasted" time was more of a roundabout discovery process, during which I learned about things I liked and/or was good at (e.g. business, design, travel, challenging environments), and things I didn't like so much and/or was terrible at (e.g. singing and playing an instrument, living in a van, wearing eyeliner).

If you're learning, no time is wasted

From all this, I've realized that looking at anything ambitious as "wasted time" is a serious error.

Life is a process of discovery. We start with a tiny spark of consciousness and absolutely no idea what is going on elsewhere. Over years of experience, we chip away at the mysteries of life, learning what things make us happy, what things make us sad; what things we care about, and what things don't matter.

Every new project — foolish, doomed, or otherwise — furthers that discovery process. Every time we follow through on a new venture, we can add to the pro/con lists that inform our decision-making processes, and our lives become a little (or a lot) better for the experience.

Remember Minesweeper?

When I was in high school and trying to avoid homework, I used to play a lot of Minesweeper.

The game starts with a blank board: we have zero information; our world is 100% mystery and chance.

But then we try something: we click a square. We get new information.

Sometimes it's not much. We reveal a 5 and learn very little other than, "Don't click near that square."

Other times it feels like half the board is revealed, and suddenly we have tons of new information and ideas about where to go.

Life is a lot like Minesweeper...

Every single action we take in our lives gives us more information about what we do and don't want — what we do and don't enjoy. Each decision and action clears a square in a life-spanning game of Minesweeper.

Often we try dumb shit, like sticking our fingers into electrical sockets. Aside from learning not to do that again, we don't get too much insight into our own version of happiness.

Every once in a while we do something new and the whole board seems to open up. That was me and booking my first tour as a musician. That was Marisa and leaving a comfortable corporate job to go freelance.

Most of the time, though, we clear a few squares and at get a little more clarity about what we want to try next. We try out a new skill or hobby. We take on a new responsibility. We try food we've never tasted before. And with each of those squares cleared, we learn more about what will make us happy going forward.

...but mistakes don't end the game.

Where the Minesweeper analogy breaks down is with the mines. When we hit a mine — when we screw up; when we fail; when we do something stupid and humiliate ourselves; when we try something and hate it — it's not game over. We don't have to start all over with a blank board.

Instead, we get to keep everything we've learned, dust ourselves off, and pick another square.

Game on

We only get one life. One shot. One round of Minesweeper.

While we can't hope to clear the board entirely, we can make an effort to always be learning. To always be curious. To keep choosing squares and using that information to make better decisions. And — most importantly — to see setbacks not as Game Over, but as one more piece of information to help us make better decisions moving forward.

If we worry about wasting time — if we freeze up and wait for the perfect moment, idea, or opportunity to come along — we're leaving the board blank. We're not learning. We're not gathering more information to help us steer toward happiness — and away from the stuff we don't like.

As far as I'm concerned, the only way to really waste time is to leave the board blank.

How to Have Great Ideas: Write Everything Down

Fri, 16 Sep 2016 00:00:00 GMT

If I've had one Big Idea™ in my life so far, it's this: careers and income are tools, not goals.

Currently, my goals are:

to live a life where I'm not obligated to do anything I haven't chosen to do;
to have the personal and financial freedom to do the things that sound interesting to me;
to live a life where every day I'm saying, "I can't imagine any way I'd rather be living right now."

That idea wasn't born whole. For anyone who's been reading along, I've slowly built this idea, starting in late 2013 when I realized how unhealthy my working situation was, gaining steam in early 2014 when I wrote about my workaholism, and evolving ever since as I've shifted into a new lifestyle of permanent travel and far more balance.

I can't point to an exact moment where I suddenly "got it" with work. If you asked me to pinpoint a date when I realized I was killing myself, I can't.

Some of the Best Ideas Have Nothing to Do With Inspiration

Since I grew up watching American television, I'd always imagined the discovery of evolution as a kind of action movie plot:

It's 1857. Charles “Willis” Darwin is just trying to get home to his wife and daughter for Christmas, but he unwittingly stumbles into a secret lab on a remote archipelago in the eastern Pacific — and there's trouble brewing.

Only Darwin stands between the terrorists and global destruction, so he grudgingly accepts the call to adventure. For 85 action-packed minutes, Darwin banters, beats, and blasts through unspeakable odds.

In the climax, the terrorist leader dangles a hundred feet above a rocky shoreline. His eyes are wide with terror as he screams, “This is murder!”

“No,” grumbles Darwin, lifting his boot from the rope and letting the terrorist plunge to his death. “This is natural selection.”

The world is saved. And also he developed the underlying theory behind On the Origin of Species.

Of course, the reality was nothing like that.

The only remarkable thing about Charles Darwin developing the theory of evolution is how utterly uninteresting it is.

Darwin never had a eureka! moment. No chance encounter or happy accident. He just... kept scratching an itch. And after several years, the pieces finally fit together in a coherent way — and he had a theory.

Steven Johnson calls this a "slow hunch", and attributes several great breakthroughs in history to it. His argument, really, is that very few ideas happen suddenly and without warning; rather, "they fade into view."

The Tragically Short Half-Life of Ideas

For a month in early 2016, I lived in Hanoi, Vietnam.

The sidewalks in Vietnam are used for everything except walking; the corners are packed with people sitting on tiny stools, enjoying street food and bia hơi; scooters weave through the pedestrian press, blasting horns, carrying everything from families of four to refrigerator-sized boxes, somehow staying upright and avoiding the thousand other quick-weaving, horn-blasting scooters.

On a walk through this chaos one evening, I had an idea. It was a good idea. I know this because I remember the giddy-silly excitement I felt after it hit me.

And then? I fucking forgot it.

When I got home, I could remember being excited, but I could not remember what I had thought of.

Had I taken a few seconds to put a note into my phone, I'd still have it. But I couldn't be bothered, and now I'm sans-idea.

Trends from a Long Time Ago That Can Power Slow Hunches

Losing that idea wasn't the first time this has happened to me. And apparently I'm not the only one who does this.

Keeping a slow hunch alive poses challenges on multiple scales. [...] Most slow hunches never last long enough to turn into something useful, because they pass in and out of our memory too quickly[...]. So part of the secret of hunch cultivation is simple: write everything down.
Steven Johnson, Where Good Ideas Come From

Darwin was very good at taking notes. He had notebook after notebook filled with ideas, quotes, sketches, and whatever else came to mind as he wrote.

He reread those notes, which allowed his new ideas to mix with his old ideas, and that led to new lines of inquiry and thought. Most importantly, the ideas were able to marinate without being forgotten, because there was a record of them.

Eighteenth-century aristocrats had Tumblrs. No, for real.

Darwin's note-taking was similar to a trendy seventeenth- and eighteenth-century practice called "commonplacing", which was essentially the act of writing down things that were interesting or inspiring, along with the commonplacer's independent commentary and thought.

The goal was to keep a written record of the transient thoughts that we catch and release each day, in hopes of preserving them beyond the limits of our own memories — giving us a better chance to find connections between our current ideas and those we've had before.

Most of my ideas have been slow hunches.

Most of what I write about is the product of slow hunches. I've only had a few moments of blinding clarity — like this one — where I believed one thing one moment, and another things the next.

Instead, most of my ideas slowly emerged as bits and pieces that I'm still working to fit together properly.

A few examples:

I was still advocating 12-hour days in early 2014 — which is exactly the wrong idea.
I was in the nascent stages of the ideas that currently inform my style of working back in early 2014.
I wrote several posts like this one on magic, in which I've almost articulated a thought, but I'm still not able to fully explain what I was getting at.

Every month or so I scan through my older writing and take a pulse on where I was versus where I am. Sometimes I get an idea for a new post. Other times I cringe at an awkward phrase.

But revisiting previous ideas always helps me refine my current thinking — and in a lot of cases it leads me to solutions that I most likely would have missed otherwise.

The Revolution Will Mostly Go Unnoticed

Taking notes is not a new idea. It's not a revolutionary idea. I'm not arguing that I've stumbled upon some deep secret of the universe.

However, taking notes will improve your ability to track multiple ideas over longer periods of time.

And that just might change everything.

Why do I always feel disappointed after I get something I want?

Fri, 09 Sep 2016 00:00:00 GMT

You know how we always want what we can't have?

And how once we can have it, we lose interest?

Have you ever wondered why that happens? Logically, it doesn't make any sense: if I want a thing, and that thing becomes available to me, I should be happy that I now have that thing.

But that's not how it works.

The Thrill of the Chase

Before my adult morals had grown in, I was addicted to the problem-solving challenge of convincing someone to date me. I loved the chase, the dance, the puzzles — when should I call? should I be sincere or playful right now? am I striking the right balance between interested and independent? — and the rush of knowing that I was successfully convincing another person that I was worth their time.

And in the cases where I was successful, I found myself with a shiny new relationship as a prize.

And that relationship was doomed.

Am I even interested in this?

I bring this up because my decision-making during this phase was suspect at best. I'm better now. I swear.

Here's how things happened in my brain back then:

I stumble into a conversation with a girl.
She does not run away or start crying.
This is encouraging; she likes me!
My campaign to make out with her begins.

Thinking through what happens next.

Two considerations were conspicuously absent in my decision-making process:

What will happen after we make out?
Would I enjoy being in a relationship with this person?

I was after the thrill of wooing — I had zero interest in the post-woo responsibilities.

And because of that, I painted myself into a lot of corners, and made huge messes that I could have easily avoided if my head hadn't been up my ass.

This Is More Than a Dating Problem

Short-term thinking is obvious in dating: we've all had the experience of one person in a relationship only being invested in the short-term, leaving the other feeling slighted.

Where it was less obvious for me was in literally every other aspect of my adult life.

I chased business opportunities I never wanted.

Building a business is — for me, at least — the ultimate thrill of the chase. We don't have coming-of-age rituals anymore, so the closest I could get to discovering what I'm made of was to pin my survival to my ability to grow and maintain a business.

Growing a business gave me a sense of self-confidence and self-reliance that I wouldn't trade for anything. But for all the good, I made many mistakes — and almost all of them because I wanted the thrill of a good chase.

I sold projects even when I hated the work.

"More is better."

It's an American mantra. We don't have time for your weak-ass "moderation" here — we see a hint of progress and it's GO GO GO until we win or we crash and burn.

Thanks to that mentality, I didn't think very hard about prospective projects. I wanted the sale. Full stop.

I ignored red flags and explained away my get-the-fuck-out-of-here gut feelings. I saw another rung on my ladder to success, and I wasn't going to pass it up.

As a result, I ended up with more than a few projects where I was miserable, doing boring work for companies I wasn't particularly fond of.[^companies] I was going for the sale with no consideration of what came afterward.

[^companies]: You know the trolley problem? "Would you kill one person to save five? Or let those five people die?"

There's a freelancers' edition of this problem: "If [huge corporation] offered you a shitload of money to work on a project for them, would you take it — despite a mountain of information detailing their obvious evil?"

In the theoretical models, I steadfastly refuse. I launch a scathing attack on Corporate America and its erosion of the human spirit. Triumphant music swells in the background. I exit to a slow clap, astride a grizzly bear. The corporate sleazeballs cry, then explode.

But in reality, I just cashed the fucking check and felt dirty.

I worked hard to get responsibility I didn't want.

I went after power in the same way: I angled for management roles, trying to amass as much authority as possible. Because — again — I saw a new achievement. A next step toward advancement.

Except I hate working in management. I like to do stuff; telling a team of people to do stuff and keeping them on task does not make me happy. The politics and scheduling and meetings and reporting makes me miserable, and — most importantly — I'm not actually very good at it.[^leader]

[^leader]: Marisa says that I'm "a good leader, but a terrible manager." I think this is her way of diplomatically telling me that my human interactions should be limited to speeches that have been prepared — edited — in advance.

Let me state that again, because I still can't believe the cognitive dissonance that was happening:

I worked very hard to convince people to give me more authority on projects — which put me in a management role — because I liked the challenge of convincing people to trust me with high-dollar, high-risk projects.
I fucking hate working in management.

I went after status indiscriminately.

My personal life is just as littered with the wreckage of my shitty decision-making as my professional and romantic lives.

I bought "heirloom-quality" shit for my house.

In Portland, I spent way too much money on a Dordoni Worktop Table, because I needed the right desk; Demeyere stainless steel pots and pans, because "I'd have them forever"; a Herman-Miller Embody office chair; a custom-made platform bed.

I thought having all this stuff made me a successful grown-up.

In retrospect, I sounded an awful lot like the narrator in Fight Club:

It's just, when you buy furniture, you tell yourself, that's it. That's the last sofa I'm gonna need. Whatever else happens, I've got that sofa problem handled. — Narrator, Fight Club

But none of that crap actually made me happy.[^chair] And I don't have any of it anymore — I got rid of everything I owned when I was preparing to travel.

[^chair]: Except the chair. I loved that chair.

I was caught up in the chase: I wanted nice stuff to prove I was a successful guy. But I didn't actually want the stuff I was accumulating.

I went to college with no plan.

Both of my parents went to college. My mom dropped out with just a few credits to go before graduation so she could go with my dad to California for his new job. She never ended up finishing; partly because she wasn't ever really sure what she wanted to be — she changed majors several times — and partly because of me.[^its-not-a-tumor]

[^its-not-a-tumor]: My mother was so sure she wasn't pregnant that she didn't bother with pregnancy tests; she jumped straight to "oh my god I have a tumor" and started looking for oncologists.

This overreaction predates WebMD by over a decade, by the way.

Between that and my dad's degree landing him a great job right out of college, it was just a foregone conclusion that I'd go to college, too.

So I did.

But when I got there, I realized that I had no plan. No end game. I'd just shown up because college was the next item on my todo list. I was there because I was supposed to be there, but beyond that? I had no idea.

When I dropped out, it felt like a betrayal. My parents had paid a good chunk of money, I had taken out loans, and I'd made zero progress toward being an adult.

What's Going on Here?

Am I just an idiot?[^rhetorical] Why the hell do I continually chase after things that I don't actually want?

[^rhetorical]: That was a rhetorical question. Jerk.

I don't have an answer. But I have a theory:

The effort to achieve something and the results of having achieved something are entirely separate things. And we often only weigh the value of the first part in our decisions.

An oversimplified example: puppies!

Say we're walking into the grocery store, and there's a box of puppies out front with a sign that says, "FREE PUPPYS".[^save-you]

[^save-you]: I know. We've already made the decision to adopt all of them so they won't suffer another minute of the owner's terrible spelling.

We weigh the decision:

Holy crap, how cute are these puppies? And it would be really fun to have a dog, you know?

We'd get to train her, and she'd keep us company, and at Halloween we could dress her up as a dinosaur and see if it goes viral.

Yes. This is happening.

Gimme that puppy, grocery store parking lot person.

All of these considerations are valid. But they're all part of the first half of the decision: the initial effort to become a dog owner.

What didn't get factored in at all was being a dog owner: early morning walks, restrictions on our ability to travel, the extra hassle of finding a place to live if we move, and a dozen other little complications that are part of pet ownership.

So even though the first part sounds like a lot of fun, and it would probably be pretty rewarding, the second part might actually cause resentment toward the dog in the long run.[^after-dog]

[^after-dog]: I've been part of several conversations where people have said, "...and we're really excited about it, but we have to wait for Kim Dog Un to die first."

Damn, Dog Mama. That shit is cold.

Of course, for many people, dog ownership is really rewarding. But that's not something we want to be figuring out after we've brought the dog home.

How to Reconcile the Chase With the Outcome

Every problem I've described so far has been a situation where I chose to shoot first and ask questions later.

I still do that sometimes. But I'm getting better.

Here's how.

1. Start with the end in mind.

We're always making choices that are at least nominally aimed toward creating a better life for ourselves and the people we care about.

The tricky part is realizing when a fun chase might actually do damage in the long run — especially if we never consider what "the long run" actually looks like.

I've found it helpful to think about what my "better life" looks like. What am I doing every day?

This is kind of like the guidance counselor, what-would-you-do-if-you-had-a-million-dollars question, but think past the first few days. Sure, on day one we'd all fill up a pool with champagne and play lawn darts with taxidermied swordfish, but that'll get old fast.

What will outlive the novelty? What will you still want to do when it's old news? That's the stuff we want to work toward.

That's what the end goal looks like.

With the end in mind, we can look at our decisions differently:

Should I try to get this promotion?

Yeah! A challenge!

But wait: if I got that role, I'd spend most of my time in meetings, and the rest managing people. I wouldn't be able to build stuff.

That's not really what I enjoy doing, so I'm going to pass.

Do you want this dog?

That is a cute dog. Give it!

Well, hold on. If I get a dog, I'd need to be fairly stable, so that probably means cutting down on travel. It also means the stress of housebreaking, the interruptions of playing and walks and feeding, the hassle of vets and buying pet food and dealing with chewed up furniture while we're training.

But... it also means having a totally dedicated friend, and a reason to get up and go outside often. So... yeah. I'll take that dog.

2. Know the difference between achievement and fulfillment.

Kevin Heffernan, the actor who played Farva in Super Troopers, was chasing an achievement when he fell into an escalation of dares which ultimately led to a full-frontal nude scene in the movie.

The thrill of the achievement — in this case, showing his friends that he had the balls[^dad-joke] to get naked on camera — lured him in. There was excitement, and a short-term gain of out-badassing his castmates.

[^dad-joke]: Literally! Ha! Okay, fine. I'll head back to r/dadjokes where I'm appreciated.

But the long-term effects — the immortalization of Farva's sugar-coated schlong on the big screen — may not be all that fulfilling. In the wake of this movie, the nude scene is a staple in any interview with Heffernan — he has to talk about it all the time, whether or not he wants to.

This example is ridiculous, of course, but it's something to think about:

Will the outcome of what I'm about to do feel rewarding to me? Or am I just chasing a rush right now?

The Goal Needs to Be Fulfillment

Achievements fade. If we're not careful, we can get trapped under the idea that happiness lies in our next achievement.

Fulfillment, however, is like the tide. If we can increase our overall fulfillment, we're always feeling a little bit better.

And when we know we're working toward fulfillment, it gets easy to spot the achievements that won't make us happy — and to turn them down.

Stop Glossing Over the Good Stuff: How to Be More Positive

Thu, 01 Sep 2016 00:00:00 GMT

As simple as it seems, taking the time to recognize the good stuff can have a huge positive impact on your relationships with colleagues, significant others, friends, and clients.

It’s easy to take a good thing for granted

As much as I hate to admit it, I’m kind of a shitty person by default.

With very few exceptions, nearly every part of my day goes off perfectly.

I wake up every morning without an alarm, next to a woman who makes me deeply happy. We playfully argue about whose turn it is to make coffee, cook breakfast and listen to Radiolab, and head to a local gym to get our day started.

My work schedule is flexible. The projects I work on are of my own choosing; I have the freedom to only take on tasks that are both extremely interesting and intensely satisfying.

Evenings are free to meet friends for drinks, or to have a slow dinner at some fantastic restaurant I read about somewhere.

Every so often I’m asked to speak at a conference, which means I get paid to travel to a cool city like Austin or San Francisco and share my ideas with people who love web design as much as I do.

I’m not telling you this to brag about how great my life is.

I’m trying to paint a picture of what an entitled asshole I can be.

Ask me how my day was

With all the great things I’m lucky enough to do on a regular basis, you might expect that I wear a permanent grin on my face and pour out gratitude at Niagara-esque volumes.

But if you asked me how my day was back in 2013, you’d probably hear something like:

“It’s okay, I guess.”
“Super busy. I’m so tired.”
“It’d be better if ________ would finally ________.”

What an ungrateful dick, right?

“Are you actually complaining right now?”

One of my long-term clients is a company called Precision Nutrition. It’s run by Dr. John Berardi and Phil Caravaggio, and employs a good number of truly brilliant people, including my long-time friend Nate Green.

During a trip to Toronto for an all-hands PN meeting, JB, Phil, Nate, and I went out for dinner at a very cool Italian restaurant. We had an incredible family-style meal, and afterward we started talking about whatever was on our minds.

During the course of conversation, I made a couple negative comments about my life; essentially, I started complaining about my situation.

Phil looked me in the eye and asked, point blank, “Are you actually complaining right now?”

The question caught me off guard, because I was used to commiserating with other entrepreneurs about how “hard” our lives were and all the things we wished we could change.

Yet here was a fellow business owner staring at me like I just set the restaurant on fire.

“How many good things happened today?”

I started feeling foolish and fought the urge to start rambling in an attempt to backpedal. I decided the best thing I could do was try to steer into the skid.

“I guess I was, yeah.”

JB leaned in. “How many good things have happened to you today?”

My four-star hotel room and the day’s extremely successful meeting with PN flashed through my mind. I felt blood rushing to my cheeks.

“And how many bad things?”

I had to think pretty hard. I forgot toothpaste and had to call the front desk to get some. They sent peppermint, but I prefer spearmint. I had to wait in line for a taxi for, like, ten whole minutes.

I was acting like a colossal tool.

It's easy to only focus on the negative things.

“We tend to forget all the good things that happen to us. I mean, why make a note of something that goes well?” Nate joined the conversation, and continued, “But if something goes wrong, that sticks out in our minds. So when we think about our days, just the negative stuff jumps out at us and we complain.”

JB smiled and said, “It’s a psychological default. We all do it.” He looked at Phil.

“Until we decide to stop doing it,” Phil continued.

JB swirled his wine and said, “This is going to feel silly, but list three good things about today. Out loud. Doesn’t matter what they are.”

I felt like a kid getting a lecture, but I knew they had all done this previously, so I played along.

“My hotel has a great shower, our meeting today has really good implications for my business, and this is one of the best Italian meals I’ve ever had.”

Phil beamed; he had picked the restaurant.

“It feels silly,” said JB, “but every time I find myself complaining, I immediately stop and list off three good things about my day.

“Over time I stopped complaining, partly because I felt silly having to stop mid-conversation to derail a complaint,” JB paused to make eye contact, “but mostly because I just don’t think of the negative stuff as often.”

Reprogramming my brain

In the weeks that followed, that conversation stuck with me. I was acutely aware of my negativity, and admonished myself publicly by stopping mid-complaint to apologize and list the day’s high points.

Most of our lives are full of creeping, incremental changes that we can't really pinpoint; we start in one mindset, and over weeks or years we find that we've shifted, and now we have a different mindset, even though we didn't notice the change.

This conversation was a hard, serious, overnight change. I can distinctly remember how I used to feel before taking this advice, and how I felt immediately after — it was like flipping a light switch that made me less of an ungrateful asshole, and more of a happy, fun-to-be-around person.

It didn’t take long for me to notice a significant drop in complaints. But that wasn’t the only thing that happened; I started to pay more attention to the positive things as well.

Don’t let the good go unnoticed

In my new effort to curb negativity, I started making “anti-complaints”.

“I really like Dave. He’s such a happy guy.”
“Our waitress was really excellent tonight.”
“This project is going really smoothly.”
“I’m so happy someone invented toast.”

These anti-complaints did more than realign my perception of the world, though; I started to see the people around me becoming more positive as well, which made for better experiences in both my professional and personal life.

Putting positivity into practice

Being positive doesn’t stop at making you sound less whiny at dinner: a positive outlook can be the catalyst for huge improvements in all areas of your life.

How to stay positive at work.

In a healthy workplace, you’ll be asked for feedback on projects — it’s inevitable that some of that feedback will be negative.

By taking the time to point out the good things your colleagues are doing, the negative feedback is less jarring.

Imagine a situation where you turn in projects to your boss, and she never says anything. Every project is accepted silently without any feedback.

Then a project gets rejected: your boss tells you all the things that are wrong with the project and sends you on your way to try again.

It doesn’t matter that every project before this one was accepted; the only feedback you’ve received from her has been negative.

However, in the exact same situation, if every accepted project had been accompanied with positive feedback — “great job on the layout”; “I love this sentence here”; “I really appreciate you getting this in on time” — the negative feedback wouldn’t have felt so jarring.

It would have been feedback as usual, working with you toward a better final product.

It’s not weak or overly emotional to tell someone you appreciate them. In fact, sharing positive feedback makes both people feel great, and creates a strong foundation that helps weather any rough patches.

How to stay positive at home.

I tell Marisa how much I like her probably a half-dozen times a day.

I try to remember to call out all the things I like about her, whether it's her constant drive to improve herself, her unwillingness to accept that other people can do things she can't, her ability to match my giant-bearded-toddler playfulness, or the fact that she can handle my so-coldly-logical-it's-often-hurtful tendencies.

Relevant example: as I was updating this article, some of the edits involved an ex-girlfriend, and — like a robot — in one section I merely replaced my ex's name with Marisa's.

When I did this, I thought to myself, "Well, what I said about my ex then is now true about Marisa, so this is acceptable."

When Marisa read that draft, she was (understandably) pissed. I didn't understand. So she patiently explained that normal people — including her — have feelings, and that a find-and-replace to swap out one name for another was a good way to hurt those feelings.

So we argued, I apologized, she was grumpy with me for half a day, and I (hopefully) learned something. There was no yelling. No crying. No sulking silences or blistering attacks on each other's character. We knew we were only fighting about this mistake I made, and not about anything else.

As a result, we can share frustrations with each other without worrying that the relationship is falling apart. When we argue, it's not about whether or not we like each other; it's just that one of us was supposed to get ready to leave, and was still sans-pants three minutes before we're supposed to be out the door.

Even when it’s bad, it’s not that bad

If your partner makes a decision you disagree with, or a colleague shows you a project that you think needs work, it’s extremely important to remember that very few things are a total failure.

Try to start by acknowledging the effort that was put in, and listing any positive aspects. Remember whose team you’re on, and that everything can be fixed if you’re working together.

Next time in you’re in this position, try this experiment: don’t look at the project as a failure with salvageable parts; see it as a solid effort with room for improvement.

It's a subtle difference, but it reframes the situation from a botched outcome to an obstacle in an otherwise pleasant journey.

Make sure to share the love

Positivity works best when it’s shared. The people around you can’t read minds, so even if you’re noticing all the things they do that you appreciate and admire, they’ll never know it unless you tell them.

If you make a habit of sharing all the good things, you become someone that makes the people around you more positive. You become a bright spot in people's days. You create a vacuum where negativity cannot survive, because you don't give it the chance to feed and grow.

My efforts to become more positive were immediately met with more positivity from the people around me: I talked about what I liked, and that encouraged others to talk about what they liked, and that made all of us feel better — a welcome break from the cycle of commiseration that I'd grown accustomed to.

Life is exactly as good (or as bad) as we choose to experience it

In the years since I’ve forced my brain to focus on — and share — the positive things in my life, I’ve seen a marked improvement in my relationships across the board. This has led to a better home life, a better workplace, and happier clientele.

All of these things have improved my happiness, made me more successful, and (I hope) made me more pleasant to spend time with.

I think it’s important to note that nothing else changed while these improvements were happening. I was living the same life, working the same job, spending my time with the same people.

The only thing that changed was the lens through which I chose to view my world.

Your turn: list 3 good things that happened today

You can change your life too, starting today. Share your experiences in the comments and tell me 3 good things that happened today.

The Baseline: How to Create Long-Term Happiness

Thu, 25 Aug 2016 00:00:00 GMT

The first time I left the United States, I was 100% sure I was about to have the best experience of my life.

This was a trip Nate and I had been talking about since high school — it was supposed to be the big trip after high school graduation — and after years of "saving up", delays, and excuses, I finally had my ticket.

My mood improved steadily as the trip grew closer, dipping slightly a week out when the "why am I not leaving neeaaooooowwwww" fit of whinery kicked in, spiking up drastically when my feet touched non-American soil for the first time.

I was able to keep the good times rolling until a few days after coming home, feeding on the envy of my family and friends as I flipped through photos and told stories.

But then came the drop. And it was no small thing; this was the precipitous, stomach-jumps-to-the-throat variety of emotional free-fall.

I sank low. For years I'd been looking forward to this trip.

But now? It was all over.

I had nothing to look forward to. I started to worry I may never feel that kind of happiness again.

My incredible high was matched by an equally crushing low.

Finding happiness the hard way

It's tempting to measure only by extremes.

Happiness, especially, tends to be noticed only at its heights, or in its utter absence.

A "happy person" is a walking highlight reel: a dream wedding with a romantic destination honeymoon chaser; a new puppy to round out graduation and the start of a promising career; a bucket list vacation photo series with a first-class-upgrade cherry on top.

Our high points are often the only metric used to determine how happy we are. And thanks to the latent one-upsmanship we all tend to suffer from, in order to "stay happy" we need to reach for higher and higher highs.

More exotic vacations. Bigger adventures. Go further, go harder, do more, or else you'll be sad.

If we only chase higher highs, we're opening ourselves up for lower lows.

The catch with focusing only on the ups, though, is that it ignores a fundamental truth: life happens in swings.

If the highs are getting increasingly higher, we stand to experience even lower lows.

My big trip, for example, was the highest high I'd reached at that point in my life. So on the downswing — when the trip was over, and all my anticipation, planning, and experiencing were behind me — I was crushed.

Here's a simpler example: say you've got a cupcake

This cupcake looks amazing. It's still warm from the oven. It's the perfect mix of moist and springy. The icing is buttercream, made from scratch. It's filled with freakin’ salted caramel.

As you look at it on your plate, you think about how great it will taste. Your Pavlovian cupcake response kicks in and you drool and lick your lips and your palms sweat and you close all the curtains so you can be alone for this.

And then — oh god — you take a bite. Holy dammit Christmas this is a good cupcake. The world fades away, and it's just you and this cupcake and "Endless Love" playing in the background.

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But then, just as quickly as it started, it's all over. Even as you desperately lick your fingers, the crushing weight of reality settles on you: the cupcake is gone.

Where once you soared on the sugary wings of eagles, you now wallow in the bitter depths of sadness. Never again will you have this cupcake. Never again will this heavenly confection pass your lips.

The cupcake is gone. The plate is empty.

You are alone.

Minutes pass, feeling like years. The world is cold and flavorless. All color has bled from this miserable world without cupcakes.

But no! This is not the end. You are strong. You've lived without cupcakes before, and goddammit you can live without them now.

You don't know how, but life will continue, step after merciless, unsprinkled step, until — somehow, someday — hope returns.

How to create long-term happiness: focus on the baseline

For most of my teens and twenties, I chased happiness as a sort of destination. I'd see something shiny, struggle toward it, achieve it, feel amazing for the briefest of moments, and then plunge into the existential quagmire of existing without goals — until I saw something shiny.

It was a strange sort of holding pattern, where I'd oscillate between euphoria and angst, always at about the same frequency. My average happiness, if we look at the highs and lows on a graph, stayed about the same.

I was pretty happy sometimes, and pretty sad sometimes, and mostly nothing changed.

Don't live in a world where the best cupcakes are behind you.

Since we generally acclimate to circumstances pretty quickly, staying the same often feels like things are getting worse.

And that is where things get ugly, because when we make predictions about how we're going to feel, they tend to be self-fulfilling prophecies.

If I believe that things are in decline, and all the good stuff happened in the past, it's a short jump to resigning myself to a life where the best years are behind me.

This is where bitterness comes from, and the suspicion that there's only so much happiness (or love, or money, or whatever) in the world, and that someone else is getting your share.

And if we look at happiness as a zero-sum game, we all lose.

How to have higher (crash-free) highs

So if you'll humor me, let's all agree that the following assumptions hold true:

Chasing happiness as destinations leads to seeking higher highs, with the accompanying lower lows.
This leads to a baseline happiness that more or less stays flat.
A flat baseline happiness can start to feel like things are stagnating and/or getting worse.
This can lead to believing things are actually getting worse.
If we start to believe our best years are behind us, we become bitter and unhappy.

With all of that laid out, we'd be hard-pressed to find many benefits to this approach.

So what are our alternatives?

Are you ready for me to stop talking about cupcakes?

Going back to our cupcake example, what if we made one simple adjustment?

What if, instead of seeing the cupcake as the reason for our happiness, we look at it as a starting point?

Maybe our thought process goes something like this:

This cupcake looks amazing. How do you make a cupcake look this good?

And holy shit — it tastes as good as it looks. How do you make a cupcake taste this good?!

I should try and make cupcakes. I bet I can make pretty good ones.

Instead of a deep crash when the cupcake is gone, we come out of the experience with a new goal: we're going to learn how to make cupcakes that taste this good.

This means we have something else to look forward to — we're not left without a goal once the cupcake is gone — and we get to chase our curiosity.

Each new experience brings us happiness and gives us new ideas to pursue.

By looking at each new experience as a step instead of a destination, we're reducing the full depths of the crash. And that's really important.

If our post-high crashes are less extreme than our highs, our baseline happiness will increase over time.

It's a subtle shift: instead of thinking, "I'll be happy when...", we think, "This will be fun to try."

Removing the focus on the destination makes the whole process a reward, instead of just the outcome. On top of that, learning something almost always exposes new things to learn, and — if you give yourself permission to keep learning — that means you'll always have some interesting thread to tug at.

What's your baseline?

Which way is your baseline trending? And what could you do today to get it trending upward? Share your action step.

Balance in Your First Year of Business

Tue, 09 Aug 2016 00:00:00 GMT

Last week I sent out a newsletter about balance.

The email centered around finding your own perfect balance, rather than the idea that there's a perfect, externally-defined balance out there somewhere.

I got quite a few responses back, but one in particular stuck out to me. It came from a guy named Alex Mullan, who recently started a new fitness company called MASSthetics. He's still in his first year, and that's keeping him in a dead sprint:

On a day-to-day basis, I have very little balance.

At this stage of growing my biz, I spend 8-14 [hours a day] working (for the most part), take 1.5–2 hours to train, eat, [...] and fill in any remaining time with my girlfriend.

— Alex Mullan

That's a pretty brutal schedule, and Alex knows it.

He tries to offset this rough day-to-day schedule with the occasional day off, weekend trip, or computer-free day, but that doesn't always work out.

"In reality", he says, "I’m not as adept at doing so as I’d like to be."

There's some cognitive dissonance at play. On the one hand, Alex knows he should be taking more time to relax, spend time with the people he cares about, and give himself room to recharge.

But on the other hand, he's made this huge bet on himself as a business owner, and, as he says:

When you rely on yourself to generate income and a living, it’s tough to shut off. Especially in the early stages when there’s not as much stability as there will be down the road.

If you could, what would you tell yourself about balance during your first year of full-fledged entrepreneurship?

— Alex Mullan

This is a good question — and a hard question — and I liked it so much I asked Alex if he'd mind me answering on the blog rather than in email.[^spoiler]

[^spoiler]: SPOILER: He was into it.

What Would You Tell Yourself About Balance During Your First Year of Entrepreneurship?

In my life, I've had multiple "first years": I got my first taste of entrepreneurship as a touring musician; after I realized I probably wouldn't make it as a rockstar, I started over as a freelance web designer; later, I took a shot and started my own web agency.

One thing that was consistent across all three experiences was my total obsession with what I was working on. I didn't just have a new project; I was my new project.

I had a schedule that was similar to the brutal hours Alex is putting in now, and if you'd told me there was another way, I'd have scoffed and written you off as "not hungry enough".

So the rest of this post is written with two caveats:

The Jason writing this post is not the same Jason who was married to his projects during each one's first year, and
If I actually could go back and give myself this advice, I'm almost certain I'd tell myself to fuck off.

But, with the benefit of hindsight, I do have some ideas that I wish I could have internalized sooner.

1. Not all motion is progress.

I have a guilty conscience when I sit still. This still happens today.

The idea of sitting down, doing nothing, when there's "something productive" I could be doing instead, makes me itchy.

But there are two huge problems with that idea, so let me deconstruct what I just said and point out the flaws.

I'm almost never "doing nothing".

These days I harp on the importance of downtime and not creating problems where none exist.

At the core of that line of reasoning is a shift in perspective:

Time spent on hobbies, friends, and rest is NOT wasted time.

Younger me made an extremely dangerous leap: I had decided that any time not spent on work meant I was "doing nothing", and was therefore wasted time.

This is an extremely corrosive view of the world. It implies that the only thing in my life worth effort or attention is work — and even my 23-year-old workaholic self would have called that view unhealthy.

However, until I dug down to Find the Why behind my view that non-working time was as good as wasted, I would have defended that belief — and all the appalling consequences — as a virtue that made me good at being an entrepreneur.

Which, of course, it wasn't.

There's not always "something productive" to be done.

Another problem with my guilt over not being productive 100% of the time is the simple fact that there's not always something productive to do.

If you're any good at business, you'll end up with days where you've emptied your inbox, caught up on your projects, and sent out all your sales material.

And once you hit that point, there's not really anything else to be done.

Sure, you can find ways to "stay busy", but are they moving the needle? Or are they just preventing you from catching your breath?

Sometimes the most productive thing you can do is shut your goddamn computer and stop thinking about work; your subconscious needs room to roll ideas around if you're going to actually grow the business, after all.

2. Your business is not different or special.

We all think we're special. Especially those of us who were raised to believe that we're unique snowflakes with unlimited potential and the mandate of heaven to really do something great with our lives.

And that leads us to believe that the advice we give to other people doesn't apply to us, or to our situation.

Sure, most people need time off to recover, but I'm different.

Yeah, most businesses grow best by building a great team and making sure there are no bottlenecks, but my business is different and only I understand how it really works.

I spent years telling people — especially myself — that my agency needed me in order to function properly. But I sold it in 2014. It's been a couple years now, and the company's revenue is still going up — so clearly I wasn't as much of a lynchpin as I thought.[^opposite]

[^opposite]: In fact, I was kind of the opposite. My insistence that my way was the only way actually worked to demotivate my team. They all assumed I was going to make major revisions to any work they did — a sort of pointless tinkering I told myself was a "quality check", but was really just a way to make sure that everything was mine mine MINE — and that meant that their work was ultimately meaningless. So why would they be interested in putting in their best effort?

In fact, if I would have realized this and let my team help me back in the early days of the agency, maybe I never would have been so stressed out that I got sick and felt the need to sell the agency in the first place.

3. Try not to learn everything the hard way.

I am surrounded by smart people.

As a musician, a freelancer, and an agency owner, I met people who had made more progress toward the same goals — record label folks, musicians with deals, more successful freelancers, agency owners, business consultants, and more — who were all happy to share their stories about where they'd been, what they'd learned, and what they wished they'd known when they were in my position.

These folks had mountains of information that was applicable and helpful to me as I grew my business.

All of these people were extremely bright, incredibly generous with their time and knowledge, and kind enough to offer me a helping hand as I was learning a new set of skills.

And — in keeping with my identity as a special little snowflake who knew my circumstances were "different" — I ignored them all.

I spent an embarrassing amount of time bashing my head against the wall, mere inches from a door that multiple people were trying to point out to me, and I'd condescendingly wave them off and say, "Yeah, yeah" — bash — "I hear what you're saying" — bash — "but I need to do it this way" — bash — "and besides I've pretty much got this handled right now."

The Checklist: What I Wish First-Year-of-Business Me Would Have Known

Not all motion is progress. "Keeping busy" doesn't mean you're more successful, and taking time to recover is not a sign of weakness.
Your business is not different or special. The way you would do it is not the only way. The sooner you learn that "my way" and "the right way" aren't the same thing, the happier you'll be.
Try not to learn everything the hard way. When someone who's further along down the path you're on offers you their personal experience, don't dismiss it out-of-hand. You just might save yourself some heartache.

What would you tell yourself about balance during your first year of business?

Or, if you don't own a business, what do you wish you'd known during your first year of a job that took all of your time and energy?

Are you working in your “Goldilocks Zone”?

Tue, 12 Jul 2016 00:00:00 GMT

There's this idea in American culture[^worldwide] that's so pervasive we tend to accept it as fact:

[^worldwide]: As I've traveled the world, I've realized this isn't just an American problem: everywhere I go, I see signs of the Overkill Cult at work.

In order to get ahead, you've got to be willing to hustle harder than everyone else, and grind it out through long hours and late nights.

We see it everywhere, celebrated as the highest virtue: t-shirts and posters that just say HUSTLE in a cool, hand-lettered font.

Hustle & Grind can be poisonous if it's not balanced.

I hustled hard for over a decade: I started multiple businesses, grew my client network, and built a reputation for myself.

I powered through when I felt exhaustion creeping in. What's a few hours of sleep now, I chided myself, compared to becoming wildly successful in the future?

I stayed on my grizzly through weekends and holidays and late nights.

And while I was ostensibly successful — I had a little money, I'd earned a little recognition — I was also seeing real consequences: I gained a lot of weight, I rarely saw my friends or family, and then there was the curious matter of my fucking beard turning white and falling out in patches.

To hustle without clear goals and defined downtime is just as dangerous as unchecked sloth.

To grind without limits — without sanity checks in place — will bring us as many setbacks as it will advantages.

The Truth: We Should Hustle Enough and Grind a Little

If I'd never hustled, I wouldn't have my current skill set or network. If I hadn't been willing to grind through tough problems, I might have given up a long time ago.

So I'm not in any way advocating the abandonment of hustling to get ahead, or grinding to finish the hard things.

But without limits, Hustle & Grind hits a point of diminishing returns.

Hustle & Grind is a critical part of "making it" — especially as an entrepreneur or freelancer. However — and this is a huge however — there comes a point where you've hustled enough; any additional hustling will do very little to move the needle, but will do a lot to harm your mental and/or physical wellbeing.

Consider this: when you're cooking a steak, you need to apply heat to make it delicious. But if you continue to apply the heat past a certain point, you're only damaging the meal; the additional heat doesn't make the steak more edible, but it does start to decrease how delicious that steak will taste.

The secret to a delicious steak is finding the sweet spot between "not cooked" and "overcooked" — the point where it's not too much, and not too little, but juuuuuuuuuuust right. The Goldilocks Zone.[^gz]

[^gz]: This is also the term used by scientists to describe the required planetary conditions for sustaining life, and by the Mythbusters to describe the amount of explosives that's not too underwhelming, but not so overboard that it blows everything to hell.

That Goldilocks Zone varies from person to person. I like my steaks just a hint shy of medium-rare; my dad would happily take a bite out of a live cow; my mom prefers her beef served a la brick of charcoal.

How to feel productive and avoid burnout: aim for the maximum results possible without decreasing your overall happiness.

The same applies for Hustle & Grind. There's a Goldilocks Zone where the effort being made yields great results, and the reward and enjoyment for making that effort is high.

With too little effort, we might feel restless or lazy.

Too much, and we start to burn out — without much extra output to show for it. And while "too much" is going to mean something different for everyone,[^limits] that limit exists for all of us.

[^limits]: For example, I know I'm good for about 6 hours in 90-minute bursts, with actual breaks in between. If I try to power through in a dead sprint, I've got maybe 4 hours before I start to collapse in on myself.

If we want to be truly happy — to really get that life we all set out to make for ourselves through our work — we have to find our Goldilocks Zone: where we make enough progress to feel that our efforts are paying off, and where we get a huge amount of satisfaction from the work.

How to Find Your Goldilocks Zone at Work

Avoiding burnout at work is one of the best ways to keep your morale, productivity, and energy levels high.

If we overdo it, we end up grumpy, unenthusiastic, and generally unpleasant — but on the other hand, if we don't feel challenged enough, we can feel useless, bored, and underutilized, which is just as toxic in a work environment.

This is why finding the Goldilocks Zone is critically important to the wellbeing of companies and workers alike. And since everyone has a different ideal range, finding your Goldilocks Zone is not a simple "do this, not that" answer.

There are, however, some ideas you can keep in mind to make things easier.

Make the maximum possible impact in the minimum possible time frame.

The secret of the Goldilocks Zone is feeling like you did good, meaningful work, and that you still have time and energy left to dedicate to other parts of your life.

If you work too long or too hard, you end up in zombie mode. The stress creeps in that there are other parts of your life that are being ignored.

If you don't work long or hard enough, you feel like you're not contributing. That creates stress because a key factor in how meaninful our lives feel is a sense of contributing something.

A good way to find the Goldilocks Zone is to create a clear plan for what should be done, then schedule your day to maximize productivity so you can get through the plan quickly.

Creating a plan and executing it efficiently is a three-way win: you have a clear idea of what should be done, the sense of accomplishment that comes from doing it, and extra free time to spend in any way you choose because you worked efficiently.

Follow through with non-lucrative hobbies.

Practice guitar. Cook. Go camping. Learn to ride a unicycle. Join an ultimate frisbee team. Take up hand-lettering. Build furniture. Plant a garden. Play pickup games of basketball. Learn to throw a pot. Draw something.

There's an incredible joy in doing something that exists strictly for its own sake.

Our jobs have stakes: if we do them, we eat and pay our bills and have money to go out; if not, we struggle and scrape and stress out.

But there are no stakes for me drawing a kid dressed up like a dinosaur. So if I do it, it's being done purely for the smile it'll put on my face.

Having a hobby with no reward beyond the thing itself gives us something to look forward to after work. It's a stress-free activity to give us the chance to unwind and disconnect from the worries and burdens of our jobs.[^science]

[^science]: Ironically, getting enough leisure time makes us better at our jobs. So when we say that we're too busy to take a break, we're actually working against our goals and decreasing our effectiveness.

Remember: hobbies are not wasted time.

One of my biggest challenges with avoiding overwork is the fear of wasting time.

I think to myself, If I'm not working, what the hell else will I do?

And when my only hobby was what I did for work, that was a fair question. I'd end up sitting restlessly, watching Netflix, feeling guilty that I wasn't working because this felt like a colossal waste of time.

But with a hobby, I've got something to look forward to. My time out of work has purpose.

And that makes it far easier to stop working when it's time to stop working.

Why Can’t I Stay Consistent?

Thu, 19 Nov 2015 00:00:00 GMT

I've had trouble writing over the last few months. It's not writer's block, though; I haven't even been trying to write.

It's been bumming me out, because writing makes me happy.

I realized recently that I hadn't written anything in weeks. I knew I was screwing up. I was ignoring my own advice: I needed to find time to do the things I care about.

Why can't I stick to the things I want to do?

What I was curious about, though, was why I'd fallen off track. I didn't suddenly forget that I liked writing. I hadn't shifted focus away from writing. And I certainly hadn't forgotten the advice I was giving to other people: if it's important, do it every day.

The plan seemed simple enough: do a couple working blocks on my critical projects, then dedicate the last block to writing.

So what was going wrong? Why was I failing to do something I both enjoy doing and consider valuable to my happiness?

I don't have any magical answers, but I do have a theory:

I had too many active demands on my time.
I was running into context problems.

What are active demands?

I consider myself to be pretty motivated. I like creating things. So to the logical part of my brain, taking some time to write each day seems like it should be a foregone conclusion.

However, taking time to write is its own activity. I have to make an active decision to stop what I'm doing and start writing.

That makes writing an "active demand": a task requiring conscious effort — however small the effort seems.

During the day, I deal with lots of small active demands, such as forcing myself to put on gym clothes when I'd rather stay in bed, or closing down the software project I'm working on to write.

These demands are almost all trivial. They're not hard or important decisions; they're just things that require conscious choice and willpower.

Researchers have found that willpower is an exhaustible resource. If I have to make a lot of active decisions throughout the first part of my day, by the afternoon I'm fried. And when I'm fried, I struggle to make any decisions, let alone the tough-but-good-for-me variety.

As my day goes on, active demands pile up — no matter how small they are — and my willpower drains. By the time I've fought off my inner fatshit and dragged myself to the gym, stepped through the rest of my morning activities, settled in to work on my current project, and put in a solid few hours of programming, I just don't have enough willpower left to force myself to switch contexts and start writing.

My creative brain gets tired faster than my programmer brain, so after a couple programming blocks I'm too mentally tired for creative writing, but I still have plenty left in the tank for coding — I was inadvertently sabotaging myself by trying to write later in the day.

How does context fit into this?

I'm a firm believer that the key to high productivity is context-based scheduling.

In order to keep myself productive, I group all of my tasks by the kind of work they require: email and social media and catching up with family in one group; software, accounting, and complex problem solving in another; creative efforts like design and writing in a third.

Under my initial plan — work on software for a couple blocks, then do a block on writing — I was able to break up the contexts the way I prefer. In theory, this should have been easy for me.

In practice, however, it wasn't happening. I'd usually end up doing a third block on the software projects and defer the writing to "later".

The failure point, I think, is that I wasn't taking a long enough break between contexts.

Ten or fifteen minutes is plenty when I'm planning to go back to a similar context in my next block, but it can take me as long as an hour to truly shift contexts.

So while I was coming into my third block with the right intentions, I was still thinking with my programmer brain, and that meant writing sounded worse than continuing to solve whatever problems I'd been working on in code for the last couple hours.

Solving the problem

If my theory is true, I'm failing to write consistently because I'm running out of willpower. I've been requiring myself to make a conscious decision to sit down and write, and I've been placing that decision in a context that made the decision more difficult.

The solution, then, is something that addresses both challenges:

The decision to write should be a passive demand.
The act of writing should avoid overlapping with other contexts.

Make decisions passive by creating a routine.

I have a bedtime routine: I set my phone to charge in a place away from the bed, floss and brush my teeth, and bring water to my bedside.

If I try to change the order — say brushing my teeth and flossing, then sitting in bed with my phone for a while — I almost always end up wasting an extra hour scrolling through social media or playing a game.

However, I've never settled in, then gotten out of bed to go get my phone. The routine makes the right thing the easy thing.

This is because the routine takes away the active demands: on the way to brush my teeth, I put my phone away for the night.

I don't have to decide to put it away. It's an established step in a larger process: I do it "on the way" to something else.

This is what James Clear calls a habit trigger: a thing or event in our environment or our behavior that cues us to do something else. Think "socks and shoes" — those are actually two distinct acts, but we've combined them as a cultural routine: putting on socks triggers putting on shoes.

So if I want to be consistent as a writer, I don't need to decide to write every day. I need to make sure that writing is part of what I do every day.

This is my first objective: I need a writing trigger.

Do the more demanding thing first.

The two things I struggle most to stay consistent with are writing and going to the gym.

These are both things that I like, and that make me feel good when I stay consistent with them. But they're also things that cause me discomfort. So if I give myself an out, it's very easy for me to take it — even though I know blowing off a workout or writing session will make me feel worse.

I also know that there's a strong correlation between the number of hours I've been awake and the number of excuses I'll make to avoid things that aren't comfortable and easy for me. This is due to willpower fatigue.

Since both writing and working out present a challenge for my willpower, and my willpower is strongest in the morning, I can increase my chances of actually following through by scheduling them for the morning.

This is my second objective: I need to work with willpower — rather than against it — by front-loading the tasks that challenge my willpower most.

How a morning routine might solve all my problems

I set out a couple weeks ago to address my writing lapse. My plan was to come up with a way to meet my two objectives:

Create a trigger habit for writing.
Front-load writing to leverage my willpower.

I've seen dozens of articles posted about "successful people" and their "morning rituals" — and promptly blew them off as fetishizing an Early Bird Gets the Worm mentality.

But between the inevitable Steve Jobs quote and 4:30am wake-up recommendation, there's a pattern in these rituals:

Most of these rituals involve doing things that most people struggle to do consistently first thing in the morning.

This is exciting, because it's anecdotal evidence that my theory is correct, and that I'll be able to meet my two objectives using a morning routine.

Building the routine

With my objectives in mind, I went to work creating my own morning ritual. Here's what I'm currently doing each morning:

Wake up without an alarm
Spend a few minutes doing my blink-and-stare thing, then grab a coffee
Read a few articles to get my brain engaged
Open my laptop and write for about 90 minutes
Walk to the gym and work out
Head to breakfast with Marisa
Go home, shower, and start work on whatever is on my list for the day

It's important to note that the only thing that changed in my ritual was to add reading and writing before the gym. Before, I'd wake up, have coffee, work out, and head to breakfast. Now I have coffee and write, then work out and head to breakfast.

A small change, and one that — so far at least — has resulted in better consistency.

Why this routine works for me

After a couple weeks of following this new routine, I've been amazed by the results. On reflection, there are several small factors that add up to this big difference.

1. I've removed the active demand.

I don't have to decide to write. I just know that once I have coffee, I'm going to open my laptop and put some words down. The routine states that writing is a thing that will happen. It's no longer a thing that I will try to make happen if I have the time and also don't get too hungry first.

2. I have a habit trigger.

I grab my laptop on the way back from grabbing coffee. I'm reminded every morning by the act of getting coffee — a thing I do every day — to get my laptop. The trigger makes the first step toward writing almost automatic. Coffee and laptop. Like socks and shoes.

3. I have more willpower (and creativity) in the morning.

Saying no to cheesecake is very, very easy to do first thing in the morning because my willpower tank is full. When I write first thing in the morning, I can leverage my brain chemistry to make it easier to do the stuff I want to do. This removes the need to rely on willpower later in the day, when I'm running on empty.

4. I'm creating an "extra" work day with a really long break between contexts.

A surprise benefit of my new morning routine was feeling like I have two "work days" each day. Before, I'd sit down after breakfast to work and complete three or four working blocks with short breaks in between. The working blocks could span multiple contexts, but it was harder to shift into some contexts than others.

By adding a huge break of two or three hours between my first working block (writing) and my later working blocks (development or communication, typically), I noticed a big difference: after a long break between context shifts, I felt like I was starting completely fresh.

My second working block felt like my first — a workout and breakfast is a full reset button that leaves me so refreshed it's like I never did the first working block at all, from a fatigue or context lock-in standpoint.

I spend the same amount of time working as before, but I break it apart differently — with incredible results.

5. The new routine is so easy to follow that it doesn't feel like work.

In the past, I've tried to implement new standards for myself, fought hard to keep them up with varying levels of success, and ultimately found myself sliding back toward the baseline where I started.

In contrast, my most successful lifestyle changes never feel like work because they're so effortless. I barely notice the change, and that's the secret sauce in making big changes.

This routine falls in the latter category, because I don't feel a strain implementing this new routine. I didn't have to start waking up earlier, or "grinding out" a little extra for my own good.

Instead, I rearranged the things I was already doing in a way that effortlessly and painlessly created space for something rewarding. By moving my writing from the afternoon, where I struggled with it, to the morning, where writing came easily, I made my life easier and saw more success. I didn't create a struggle for the sake of progress; I removed a struggle and progress followed.

Things that have nothing to do with why the routine works

I think it's worth mentioning that I didn't claim my routine is working because of the exact things I'm doing, or the order in which I'm doing them.

It doesn't matter what I'm doing. What matters is that I've organized the things I consider important into an order that works for me in a way that leverages my own daily rhythms.

I'm more creative in the mornings, and writing is harder for me than coding. A workout gives me energy that carries me through the day. A slow breakfast with my partner keeps me relaxed and lets us spend time together before we start working.

But this works for me because it is specifically built for me. If I tried to adopt some millionaire CEO's morning routine, I'd be miserable.

The trick to a successful routine isn't mimicking someone else; it's looking at their approach, understanding the reasons they did it that way, and using those reasons to build your own strategy — one that fits your unique situation.

Is this forever?

I sincerely doubt that I'll follow this routine until I die. Later, when I have new information, or a new situation, or a different priority, I will inevitably change my approach.

But for now, I've been able to get in an hour and a half of writing every day following this routine, without getting less done elsewhere. For now, I don't feel guilty about ignoring something I care about.

So while I'm sure I'll need to create a new routine in the future to address some other area of my life that I'm neglecting, for now this routine is good enough — and compared to where I was before, it feels like magic.

Navigating the Tourist Trap

Mon, 22 Jun 2015 00:00:00 GMT

In my worst nightmare it goes something like this:

I'm standing somewhere significant. Maybe historical, or cultural, or just totally fucking majestic. The sort of place your well-traveled friends tell you no but seriously you have to see it.

It's the sort of moment camera companies have trademarked. Before now the thing I'm looking at was only an understanding of a place in my head, but now it's becoming an experience; a memory: the image from Wikipedia grows a Z axis and I can touch it and there's a smell and now I can give you directions to here complete with landmarks and everything.

I inhale deeply through my nose. This is exactly the kind of shit that makes travel worth—

My reverie is shattered by a tiny old woman in a sleeveless floral blouse and a white visor who elbows past me to take a photo of the "Sortie / Exit, Toilettes / Washroom" sign.

A British tour group forces me forward, each of them labeled with a neon Post-It™ note signifying which bus brought them here. A middle-aged woman is digging in her purse in the middle of the path, preventing anyone from going around her, which has infuriated her husband up ahead to the point he's now standing in the middle of the path with his hands cupped around his mouth screaming get out of the damn path, Emily, no one can get around you as a queue builds on either side of him.

A Japanese kid is switching out absurdly expensive optics on his DSLR and taking macro shots of a fencepost, which doesn't bother me except that I know his photos of nothing are better than any photo I will take in my lifetime.

Behind me, a meaty shoulder or belly or breast presses into the back of my arm, and in front of me a child who is far too young to have any hope of remembering this family outing is melting the fuck down because he's the only one of us sane enough to realize that being here, on this path, in this place, is the worst kind of hell.

This gorgeous outdoor space starts to feel small, and the press of tourists is taking all of my oxygen. I suppress the urge to Barry Sanders my way to the nearest exit.

Fear and Self-Loathing in Claude Monet's Garden

Last Tuesday I lived my nightmare.

In the early afternoon, I climb out the back of a van and into an enormous parking lot[^village] to join a queue of art- and/or flower-enthused travelers who've made the trip to get a glimpse of Monet's botanical muses.

We enter through a small gate at the southwestern corner of the property. Inside the gate, there's a ticket booth and high hedges all around — no peeking, I guess. Marisa's mom bought some package online that lets us skip the line and duck through the hedge.

As weather for standing in a garden goes, this afternoon in Giverny is just about perfect. It's about 20°C under a bright blue sky with what Bob Ross would certainly describe as "happy little clouds" hovering over the Seine in the western sky.

The garden is huge. Maybe a little bigger than a football field[^pitch] and crosshatched with paths that lead through intensely colorful landscaping that overflows with flowers I can't identify[^flowers] in colors I didn't know flowers could be.

Monet's garden is a special place. And not just because it was the inspiration for a large number of his paintings — this is a place where it just feels good to be for a while.

And the Locusts Descend...

Yet, for all the beauty that the garden has to offer, there will be no peace or reflection here.

By my estimation, roughly 30% of the global population is stuffed inside the walls of Monet's garden, all jockeying for selfie-space along the garden paths.

Dozens of old women[^oldwomen] from every corner of the globe totter along the path, asking each other how their cameras work and (loudly) discussing the scene:

Aren't these gorgeous?

What?

The flowers!

The flowers?

Yes!

What about the flowers?

Aren't they gorgeous?

What's gorgeous?

And so on.

Teenage girls who've slipped away from their parents make doe-eyes and duck-faces for strangers on Instagram.

A young couple detains me and holds up foot traffic so I can take their picture in front of the main path. Four times.

...Sayeth the Locust

I fucking hate tourists, I think to myself as I crouch down in front of a flower that sort of looks like a popcorn ball to take a close-up with a shallow depth of field. Those tend to get more likes, I've found.

I smile apologetically at the people waiting behind me as I usher Marisa and Jil into position for a mother-daughter photo. Marisa keeps talking, so I have to try three or four times before she's not pulling a goofy face in the photo.

When a baby bird I think is a black swan starts jumping from lily pad to lily pad, I take a video and point it out to Jil and we discuss what type of bird it is. The ladies next to us start trying to take a video — what button do I push again? — and point it out to each other and start calling it a baby duck, which I decide is wrong and hold against them as ignorant Americans.[^bird]

Marisa and I decide to skip Monet's house[^house] and duck outside the walls to buy ice cream. We find a spot in the shade to sit down and I silently judge all the other fatties on tour buses eating ice cream.

The Trouble with Tourist Traps

I cringe at the thought of waiting three hours to ride the London Eye. At Sacre-Cœur, I came as close as I've ever been in adult life to starting a physical altercation with some overly-touchy peddler.[^touching]

By default, I recoil from anything that would be called an "attraction" when I visit a new city.

The way I see it, these are the places that — once, long ago — had significance, but have now been roped off and sanitized and crammed full of souvenir shops to the point that, really, they're not anything like what they were when they became significant.[^edinburgh]

Anything with any value to a city's tourism board quickly becomes the Attraction of Theseus: if an historically significant site, incrementally, has all its parts replaced by informational plaques and concession stands, is it still the same historically significant site?

And Yet...

Despite the issues with tourist traps, there's no denying that some of this stuff really does have historical significance. And really — significance aside — some of it is just really fucking cool to see up close.

The Eiffel Tower is probably one of the top 5 most recognizable structures in the world. Almost everyone can sketch a rough approximation of what it looks like.

But, goddammit, standing on Passerelle Debilly facing SSE at 23:00 is still breathtaking, no matter how many times I've seen the photos online before.

So for all the venom and vitriol I spit at tourist attractions, I'm still susceptible to the sense of wonder and awe that made these places attractions in the first place.

Building a Better Mouse Trap

On Tuesday, back in Monet's garden, I started solving problems in my head.

These paths should be made one-way to avoid this clusterfuck.

Why are half the paths closed?

They should let us pay more for a ticket where only 25 people get to go in at a time.

My claustrophobia and impatience grew in intensity, and my solutions became more extreme.

You should have to pass a basic camera competence exam to get into this place.

Everyone should be allowed three photos before moving further down the path.

By the end I was more or less a Marvel supervillain:

Humanity has failed to make tourism work. To fix tourism, we must kill all tourists.[^exceptions] This is the only way.

Coming to Terms with Tourism

So I'm here, standing on a bridge over the world's most famous waterlilies, fuming over the crowds and the chaos and the commercialization of history. I feel cheated because I can't truly enjoy this experience with all these other jerks pushing their way past me.

The hypocrisy of it all sneaks up on me. I feel a little sick.

I'm one of them.

I came here to look at this place. To take iPhone photos and tell my Facebook friends I'm here.

Honestly, I'm probably less qualified than many of these people: they might be able to name a few Monet paintings — maybe they know more about this painter and his garden than just his name. Really I only came because Jil wanted to go and I wanted to make an effort and keep an open mind.

But really, at the core, I'm only one Tommy Bahama button-down removed from the guy next to me. We're both foreigners. We both speak no French and have bad American habits and probably offend[^offense] nearly half the locals we meet. We wanted to see the best things the world has to offer, and this particular piece of the globe has been deemed noteworthy — so here we are.

We're Not So Different, You and I...

My self-consciousness about being an outsider makes me quick to put some distance between myself and tourists. I don't want French people to look at me and immediately peg me as an American[^american] and assume I'm just some tourist.

More importantly, I don't want to be just some tourist.

So, sure, maybe the people in this garden with me will spend their vacations eating burgers because coq au vin sounds too exotic, and maybe they'll never leave Champs-Élysées unless it's in the back of a tour van. Maybe they won't even bother trying to speak French.

None of that makes me better than they are.

When I sit next to an American couple and pretend not to speak English so I don't have to talk to them, that's not making me more worldly; it's further isolating me.

In Search of Authenticity

I want to "live like a local" — it's been this location independence experiment's raison d'être[^french] from the start — but my eagerness to have an "authentic" experience built a wall between me and other travelers.

I want to be seen as The Right Kind of Traveler™: when I meet someone from another country, I want to become the example they offer up as an exception to the rule during a discussion of how awful American tourists are.

But if I let my desire to live as locally as someone can for a month become a default avoidance of anything that could be called "tourist activities", I'll miss out on a huge percentage of the world's beauty and history.

Just because it's popular doesn't mean it's not worth doing.

Authentic Tourism

Outside Monet's garden, Jil asks me, "Did you have a good time?"

Our ride home is pulling into the parking lot, near the bench where we were all told to meet at 14:30. We hurry to polish off our ice cream cones and buy a bottled water for the drive. The older couple we rode up with looks exhausted — "...can't wait to get to Provence so we can finally slow down and relax," the man is saying to his wife, who is flipping through the photos she's taken today.

Jil lives for this stuff: tomorrow she'll be waiting outside a comfortable hotel at 05:30 for a bus tour to Normandie in the morning, back in the late afternoon to haul ass to Musée d'Orsay before closing, off to the Eiffel Tower to see it sparkle at 23:00 on the dot, and in bed right away so she can get up at 04:00 to do it all again the next day.

I get exhausted just reading her itinerary.

But I can see on her face that this — standing on the bridge Claude Monet painted in 1899 — this is a moment for her. Walking through Monet's house, she could feel Monet in those rooms; she was sharing space with one of her favorite artists.

The meaning — the emotion — that this trip held for her was beyond anything I could ever hope to feel about a house or a garden.

I can't hold that against her. I can't hold that against any one of these people here to see something significant from human history.

"This was great, Jil."

She smiles and thanks me for putting up with the crowds. Then she asks if I want to go to Normandy tomorrow at 05:30. (I don't.)

But I'll go to Versailles[^versailles] the day after. And then we'll go to a local bar I like where we're the only people who don't speak French. Because I don't have to choose: I can be a tourist sometimes without ruining my chances at experiencing local hangouts.

So, quick: take my picture in front of this moment. I want all my friends to know I had a like life-changing epiphany in Paris.

That shit gets retweeted like crazy.

[^village]: Under which I assume used to stand a very charming village.

[^pitch]: And just a tad smaller than a football pitch.

[^flowers]: Though — let's be honest — I can only identify maybe a half-dozen flowers without help from Google.

[^oldwomen]: The relationship between septua- and octogenarian human females and botany has a distinctly moth:flame character to it. This was something I had always considered a kind of good-natured stereotype. At least until I entered the garden to find a field of blue and silver hair, about 1.5m tall, swaying slightly in the breeze.

[^bird]: It was actually a baby rail (I think). Which I didn't know was a type of bird.

[^house]: Presumably, it was filled with doors, tables, chairs, and a fucking gift shop.

[^touching]: Can we all agree that you just don't touch strangers? NO TOUCHING!

[^edinburgh]: The castle in the center of Edinburgh, Scotland is a great (?) example of this. All the cannons are covered in high-gloss paint. The dungeons are gift shops now. There's a concession stand. It feels about as authentic as an Olive Garden.

[^exceptions]: Except me, of course.

[^offense]: Mostly because we're ignorant and — despite our best efforts — just clueless about the proper approach to certain situations. Sometimes because we're painfully, obviously American and bulling through the world's china shop. And every once in a while because I can just be a dick when I'm hungry.

[^american]: They do. Every time. Usually before I even open my mouth. Serious question: do I look that American?

[^french]: Something I hadn't realized when I first arrived in Paris was the astonishing number of French words and phrases that have been ported directly to English. I knew raison d'être was French; I didn't know that (just in the As and Bs of the American lexicon) we'd borrowed "aperitif", "armoire", "belle", "boulevard", "bourgeois", "bouquet", and "brunette".

[^versailles]: The grounds at Versailles were incredible, but the palace itself was awful because holy shit the crowds. If there was anything worth seeing there, I couldn't make it out over the sea of phone screens and miscellaneous objects waved by tour guides to keep their groups from disappearing into the mêlée. 0/10 would not return.

Get More Done Faster: Scheduling for Maximum Productivity

Thu, 07 May 2015 00:00:00 GMT

If you write down everything you have to get done for you to do your job well, what does the list look like?

If you're like most of us, your list of duties will have a wide variety of tasks that require different kinds of attention and focus. We have to play multiple roles: communicator, planner, creator, administrator.

Each of these roles requires different skills, and different parts of our brains.

For example, when we check email, jump into the work chat, or scan social media, we're working in the context of communication. Research and learning are in the context of information gathering. Design, development, and writing are in the context of creation.

If we spend a little time looking at our list of duties, we'll start to see that our jobs expect us to work across multiple contexts to get things done.

The variety of jobs we're expected to do adds a new challenge for us: we have to shift gears in order to get our work done. And while we all know that constantly shifting gears slows us down in our work — in the same way we know that we should exercise more, and we know seeing the movie based on a book we love will let us down — we don't do much to fix the problem.

And it turns out, trying to do all the different jobs at the same time is a big problem.

I Used to Be Terrible at Working

When I first started freelancing — and worse, when I started hiring subcontractors and employees — I was awful at getting things done effectively. I felt tremendous pressure to be everything to everyone: if I wasn't available on Slack, I was holding up my team; if I didn't respond to an email within an hour, my clients would hire someone else; if I didn't finish a project by the deadline, I'd lose the project.

This led to a horribly unsustainable working style.

Before my eyes are even open I'm reaching for my phone. The lock screen is loaded with notifications, and a knot starts to form in my stomach. Oh Christ. Here we go again. Scan the email for emergencies. Check Twitter. Only 1 new follower. Note to self: suck less as a person. More email. Mash out typo-riddled responses with my thumbs as I walk to get coffee and scan calendar invites on the walk back. Open a code editor. Chat beeps. Forget what I was working on. Remember. Email beeps. Forget again. Start working on the issue in the email. Chat beeps. Remember what I was supposed to be working on. Email beeps. Forget. Look at the clock. Goddammit, I forgot to eat again. Order delivery. Move to the couch. Put on Fringe. Remember today's deadline. Panic. It's after nine so chat's quiet; finally, I'll get some work done. Close the computer with four half-finished emails and two of three projects incomplete. Fall asleep checking email.

Most days, I did a lot — I just didn't get much done.

Most of my time was spent on things that weren't very important, and very little of my effort was spent on what I was supposed to be doing.

If I had to guess, about 75% of my working hours were lost to fumbling between tasks and trying to ward off the onslaught of realtime communication with all the sad determination of a cartoon character plugging holes in a sinking boat with his fingers.

My target for each week is to spend fewer than 40 hours on the computer total,[^computertime] so I needed to be way better at this if I wasn't going to end up jobless.

The Productivity Supercharger: Separate Tasks by Context

My friend Phil Caravaggio is one of those people who optimizes everything. It's necessary for his job — he's the CEO of Precision Nutrition, a multi-million dollar company — if he's going to live a life outside the requirements of the company.

Phil introduced me to Dan Sullivan's time management ideas, which center around context. He has a trademarked approach to time management called The Entrepreneurial Time System™ that's worth looking into.

Phil has implemented this system into his working style with massive success. Encouraged by Phil's experience, I decided to try out the broad strokes of the system in my own planning.

In simple terms: the best way to maximize your productivity is to separate tasks by context.

We have three kinds of tasks as entrepreneurs: high-impact tasks that require all of our attention and produce big results; regenerative tasks that allow us to recharge and let our subconscious work on new solutions and ideas; and low-impact tasks that just have to be done in order to allow us to perform the high-impact tasks.

If we group these tasks into three kinds of days, we get Meaningful Work Days, Off Days, and Bullshit[^bullshit] Days. (For fun and brevity, we'll call this the MOB System.)[^sullivan]

Meaningful Work Days: Focus Exclusively on Big Tasks

Meaningful work days are reserved for high-impact work only. The act of actually writing, developing, or designing something after all the preparatory work is done. If working is an episode of MTV Cribs, Meaningful Work Days are the bedroom, because, "This is where the magic happens."

Off Days: Relax, Recharge, Let Your Mind Wander

Off days are technology-free. Or at least work-free. I aim to have at least one day a week where my computer isn't opened at all, and I use that day to do something adventurous, like heading out to a water fight or taking Thai cooking lessons.

Bullshit Days: Prep Work, Busywork, Chores

Bullshit days are for all the things that are required for us to do our important tasks, but that aren't necessarily the flashy parts of the job that we look forward to. This can include email, accounting, research, outlining, setting up development environments, or collecting inspiration for a new design.

All Three Days Are Necessary for Maximum Productivity

It may be tempting to think, "Since all the best results come from Meaningful Work Days, why don't I only have Meaningful Work Days?"

There are two problems with this kind of thinking.

1. All Work and No Play Makes You Suck at Work

It turns out that human brains just aren't all that good at sustained periods of focus. We can cram for a while, but it's a game of diminishing returns.

If we try to force focus days every day, we'll eventually end up hurting ourselves. Too much time on the job results in less output at lower quality than if we'd kept a more balanced schedule.

Off Days create mental space where our subconscious can form new ideas.[^walking] They create distance from the job, which allows us to remember what's important to us. They keeps us from burning out.

2. Hard Work Without Preparation Is Wasted

Very few meaningful tasks can happen in a vacuum.

To write a good article, there's prior reading to be done, research to be collected, interviews to be conducted, and various other prep tasks that need to be completed.

Similarly, to design something for a client, resources need to be collected, the requirements need to be gathered from the client, and marketing content needs to be approved.

Without doing the prep beforehand, you'll have to do it while trying to complete the task. And there's no better way to end up down a Wikipedia Hole and accomplish nothing than to try to do research for an article as you write it.

If we want to be effective on our Meaningful Work Days, we need to have all the bullshit out of the way first. Without proper prep work, a Meaningful Work Day becomes a Bullshit Day instead.

How to Split Up Your Todo List

To start MOB-bing,[^ha] you need to go through two critical steps. Schedule these for your first Bullshit Day.

Write down everything you do for your job. If it happens while you're at work, write it down.
Separate your tasks into "Meaningful" and "Bullshit" categories. What makes a big impact in your job? What just needs to be done to get you to the next big task?

Meaningful Tasks

Meaningful tasks are the things that make the biggest impact, and that take the most concentration. If we're in a job we love — or even a job we just like-like — these are probably the things we enjoy doing the most.

For me, meaningful tasks are writing, development, and design. I get a big emotional payoff from these jobs, and they make the biggest impact on my career.

Bullshit Tasks

Bullshit tasks are the tasks that have to be taken care of for the meaningful work to have meaning. Tasks like these aren't necessarily exciting, but they lay the groundwork for the fun stuff.

For me, bullshit tasks are research, editing, email, billing, and code maintenance. I don't feel particularly enamored with this stuff, but I know that it needs to be done so I can keep the lights on and create more opportunities for my more enjoyable tasks.

How to Give Yourself Permission and Space to Improve Your Scheduling

The idea of taking full days away from email and chat to focus on the most meaningful work may seem impossible. "Sure, you can do that," you may be thinking, "but I have [clients/coworkers/managers/customers] to consider. I can't just not check email for a full day."[^meaningfulmorning]

I felt the same way before I started.

At the time, my agency was growing: I had over a hundred clients, a half-dozen employees and contractors, editors, and conference producers, and all of them had questions, problems, and needs that required my attention.

I was absolutely positive that if I wasn't 100% available, everything would fall apart around me.

Thankfully, my concerns were absolutely wrong.

Here's how I was able to make the switch, and how you can, too.

1. Start with a Plan

Meaningful work days can only happen after you get the bullshit — planning, gathering resources, asking questions — out of the way first. Otherwise, you're dead in the water.

Use a Bullshit Day to write out all the tasks on your plate. Then break them down into smaller steps and figure out what needs to be done before you can focus on the meat of the task: if you're on the hook for an article, you'll need to research other articles on the topic, find studies that back up your points, and write an outline before you can start writing.

If you try to start without doing the initial prep work, trying to do meaningful work becomes more challenging and — most likely — less productive.

2. Let Everyone Know What's Happening

The week before I started using the MOB System, I told my team that I was going to start spending three days a week on Meaningful Work Days. This meant on Monday, Wednesday, and Friday, everyone would be entirely unable to reach me.

To prepare my team, I set clear expectations that "needing my input" was not a valid excuse for missed deadlines. If they needed me, they needed to get in touch before my Meaningful Work Days.[^empowered]

To prepare my clients, I created an autoresponder saying I only checked email on Tuesdays and Thursdays, and that they could route their requests to our general email if the request was urgent.[^bottleneck]

By being upfront and very clear with both my team and my clients, no one was blindsided by my changed schedule. As a result, no one seemed to be particularly bothered or slowed down. I honestly don't think anyone noticed most of the time.

I hadn't realized it before, but by making myself fully available at all times, I had actually made my team and clients worse at things. I was a crutch. A shortcut. As soon as I made myself less available, they stopped looking to me for approval or help.

They remembered their own power and competence, and as a result they got things done.

3. Remove All Distractions

Getting work done means giving yourself a period of uninterrupted time during which you can focus exclusively on the task at hand.

If your phone is vibrating every few seconds, or the work chat is chiming non-stop, you're not working uninterrupted.

Use "Do Not Disturb" mode, or turn off your network connection entirely. Turn your phone face down and silence the ringer and vibration.

If you have trouble avoiding distracting sites, use something like RescueTime to block sites temporarily.[^blockers]

If you work in an office, find a space where you can avoid coworker interruptions. If all else fails, put on headphones and hang a sign off your back that says, "Unless the building is on fire, please don't interrupt me."

(Or, even better, convince your boss to let you work remotely.)

However you do it, find a way to buy yourself two blocks of 2–3 hours, at least twice a week.

If your boss has any interest in results, your extra productivity will be noticed quickly, and you'll find yourself being protected from distractions.

4. Use a Timer

Using a timer is critical, because without one we're bound to run over our allotted time slots. I use a simple app called Pocket Cup Noodle Timer to keep track of my work blocks.

I like 90-minute cycles because it's supported by research into our bodies' natural rhythms.

Another popular approach with shorter working bursts is the Pomodoro Technique.

5. Follow a Simple Schedule

Scheduling is a touchy subject for me. I hate it when people tell me how to spend my own time. So let me be very clear that this section is just a suggestion, based on my own experience.

There's nothing particularly groundbreaking about the way I schedule my days. The difference, really, is in the types of work being scheduled.

The secret for me has been concentrated bursts of work, punctuated with full disconnection for short breaks.

Here's the general scheduling template I follow:

90-minute timed work block
15-minute technology- and work-free break
90-minute timed work block
60-minute lunch
90-minute timed work block
75-minute technology- and work-free break
90-minute timed work block

This is 7.5 total hours of work, with 6 hours of screen time.

6. Take Real Breaks

Short breaks are vital for staying productive because, according to science, taking breaks keeps us focused.

And if you use your break to take a walk, you can boost your creativity and lower your stress levels.

Just make sure to leave your technology behind. No phone checks, and leave your laptop closed. Take your breaks like it's 1991 and phones are only used for talking to people far away.

7. When You're Done, Be Done

Each day starts with your todo list. Let's say your goals for the day are to clear your inbox, edit a blog post, and fix a bug in the website; when you've finished the list, write your todo list for tomorrow, then stop working for the day.

If you only need three of the four 90-minute working blocks, be okay with stopping early. Productivity is measured in results, not how many hours your butt is in a chair.

(More on this: How Time-Based Management Kills Motivation)

Better Productivity Means a Little Discipline Now and a Lot of Freedom Later

Understanding the role context plays in our work — and its extreme effects on our productivity — is helpful, but it won't make much of a difference if the knowledge isn't applied.

All the knowledge in the world means jack if we don't change after we know better.

The initial challenge of guarding our time can seem daunting. Our coworkers have grown used to the way we work now — changing that seems like it could cause tension.

In all fairness, it might. But only at first.

In a healthy workplace, both management and the workers value results. By giving yourself the freedom to work optimally in a flow state, you stand the best chance of producing truly outstanding results.

This is a win for everyone: the company sees better results, your coworkers have clear guidelines for getting in touch for help and information, and you get more done in fewer hours — which gives you the opportunity to keep your life in balance.

You're going to do the work either way, so why not find a way that keeps your stress low and your overtime at a minimum?

[^computertime]: After my brush with stress-induced beardlessness, it became critically important to me — a literal matter of life and death, in my mind — to spend the majority of my time disconnected from a screen.

[^bullshit]: I say bullshit lovingly: "I have to deal with this billing bullshit or I won't have any money." It's the kind of thing that I someday (soon) plan to delegate entirely — once I've written out the process in a manner that's bulletproof.

[^sullivan]: This is very similar to Dan Sullivan's Focus/Buffer/Free day approach. He has a whole system built around this which is far more comprehensive than mine — my general approach is to do the least amount of structure required to get good results. If you're better when there's a stricter set of guidelines to follow, I highly recommend looking into Dan Sullivan's Strategic Coach programs. He's extremely good at what he does.

[^walking]: The referenced study is centered around walking, but the idea is the same: you're away from the task at hand, and your mind doesn't have the immediate distraction in place. As a result, your subconscious can roll the idea around and make connections that may not have happened if you were still actively focused on the task.

[^ha]: Holy shit, that was terrible.

[^meaningfulmorning]: If a full day is absolutely out of the question, you can switch it to a half day. If your day starts at 9am, set the expectation that your first email check is after lunch. (Or, if you're more effective in the afternoon, don't check email after 2pm.) A three-hour dedicated window for your most important work won't ruffle too many feathers, and it will have a big effect on your productivity.

[^empowered]: Once I was unavailable, my team was suddenly more empowered. I was, in effect, trusting them to make decisions without my approval or oversight. This made them significantly more efficient.

[^bottleneck]: This had an unexpected benefit: clients stopped seeing me as the solution to their problems; instead, they saw the company as the solution, which removed a bottleneck. When I was 100% available, clients might demand to work with me — "the boss" — instead of another member of the team; when working with me meant waiting, they were happy to work with whomever could solve the problem.

[^blockers]: Other options exist to do the same thing, like the Chrome extensions Morphine and StayFocusd.

Do More with Less: Drop Dead Physical & Psychological Weight

Sat, 04 Apr 2015 00:00:00 GMT

"You're serious? I can just. . .take whatever I want?"

I nodded.

The pile of stuff in the corner of my apartment was huge. A drill I'd only used once sat on top of a box full of cables I didn't realize I still had. An empty TV stand was littered with basically-new kitchen utensils and three different wifi routers. A full set of throw pillows I found in a closet sat on top of a toolbox full of art supplies I hadn't opened since I dropped out of college.

My neighbor had responded to a message I sent out to the building announcing a giveaway. I've never met this woman before. I'm assuming we live in the same building, but I can't recall having seen her before — but then again, I'm not usually one to notice people passing by unless they're holding food.

She picks out some kitchen utensils, a whiteboard, and a package of AA batteries.

"You're sure? Anything?"

"Absolutely," I reassure her. "You're doing me a favor by taking this. Honest."

She leaves with her armload of booty, looking over her shoulder at me as if I'm going to change my mind and tackle her.

Later, Marisa arrives with her own pile of stuff. A few hours later our friends arrive at the going-away-slash-holiday party we've arranged so we can see everyone before we leave the country the following Tuesday.

Our friends all have the same bewildered look my neighbor wore when we start shoving our possessions into their arms.

The next day, Nicole from the cleaning service arrives to do the move-out clean. I tell her to take anything she wants, and I'm delighted to see that she wants pretty much everything. She borrows the hand truck from the building to take a few loads out to her car.

We take everything that's left and load it into Marisa's trunk. At the donation drop, a man opens the door for Marisa.

"What a lovely day it is! What a lovely day to be alive! And how are you?"

Marisa loves this guy. He's a bit disheveled and wild-looking, like James Brown's mugshot, and has the best attitude I've ever seen.

"Wow! Look at all this great stuff! Miss, you have excellent taste in movies — see this one right here? I love this one right here!"

He runs a cheerful commentary the whole time he helps us unload the trunk. ("This is a fantastic coat! I may have to buy this coat! You think it'll fit me?") His attitude is contagious. ("My oh my this blanket is lovely! If I had this blanket and a mugful of hot cocoa I'd be the happiest man on Earth.") As we pull out of the lot, waving, Marisa and I are wearing wide grins.

Our next stop is a used car dealer, who buys Marisa's car. He surprises her by offering more than she had expected for it.

Later, lying on the floor of my now-empty apartment, staring at the entirety of my worldly possessions in two small bags against the wall, I didn't feel the way I'd expected to feel. I thought giving away all my things — possessions I'd carefully curated over the last few years — would feel like losing a limb. There was the art I'd collected from local cafés that showed my aesthetic preferences. The couch I'd had custom-built that was wide enough for four people to sit on and deep enough for two people to spoon. The bar full of all my favorite spirits and the proper glasses to serve drinks that announced to the world I was a whiskey kind of guy.

I thought I'd feel empty. I thought the absence of my things — this stuff that turned my insides out — would leave me hollowed out, back at Square One.

But I felt exactly the opposite.

I looked down on the sum total of everything I owned with an incredible feeling of lightness.

This tiny pile of clothes and electronics was all I had to worry about. The internal pressure I felt to make sure my actions matched up with the material presentation I'd constructed — "is my attitude right now the attitude of a person who owns Herman Miller furniture?" — dissolved. My external pressure was gone; I only needed to make sure my actions matched up with the way I believed a person like me should act.

Minimalism, Without the Bullshit

I try pretty hard to avoid labeling myself — I don't want the actions of a group I don't control to affect how people perceive me — so I don't call myself a minimalist. But the core idea of the minimalist lifestyle does align with how I see the world:

Minimalism is a lifestyle that helps people question what things add value to their lives. By clearing the clutter from life’s path, we can all make room for the most important aspects of life: health, relationships, passion, growth, and contribution.

— The Minimalists

Dropping Dead Weight

The way I see it, every single thing we add to our lives, both physical and psychological, adds a tiny bit of extra weight that we have to carry around.

My operating view of the world is that my actual self — the part that makes me a free-thinking, individual entity — is very small and virtually weightless.

As I experience the world, the things I do form memories, associations, and predictive models that help me navigate the world. These are the building blocks of my identity. I once threw up after eating cooked spinach from a can, and now I don't like cooked spinach at all. I learned from my dad to always try to understand why things work, so I'm a shitty employee because I second-guess my bosses at every step of the way.

These experiences make me into the person I am today, informing my personality and worldview, but each one adds a little weight to my identity.

To express my identity, I build a model of the kind of person I want to be seen as. I want to be seen as successful, so I only want to buy nice things. I want to be seen as discerning and stylish, so I only buy clothes and furniture with designs that have stood the test of time.

These possessions echo my experiences and reinforce them. If I thought I was a whiskey guy before I put a bunch of effort into finding a bottle of Black Maple Hill, I was really a whiskey guy once I had that bottle in my bar.

The added weight of the material possessions and emotional biases on my decisions made it hard to be objective. Instead of asking, "What's best in this situation?" I'd find myself asking, "What would a guy like me do here?"

Cutting the Crap

When I pushed all of the possessions out of my life that weren't essential for my daily life, it became easier for me to make objective decisions.

Before, my plans to travel the world came with caveats: I'll have to find a place to keep my Dordoni Worktop Table — I love that table — and my art collection will need a storage unit with climate control.

I could do what I wanted, but only after I'd made sure to take care of all my crap.

Once those things were gone, I could weigh my options objectively and make quick, agile decisions.

Do I want to go to Madrid? Well. . .sure. Let's do it.

No conditions or caveats — I can just pick up my two small bags and go with no guilt, no worries, and no hassles.

People Like Me

Of course, I haven't reduced my essential self back down to its weightless state. I've only changed my view of what "people like me" do; instead of thinking of myself as the kind of person who owns nice things and drinks good whiskey, I've written a new description for myself.

I'm the kind of person who values experience over things and doesn't worry about material possessions because they add stress instead of happiness.

I'm not enlightened, superior, or even better off; I've simply traded one guiding philosophy for another.

However, this transition has allowed me to pursue the things I find meaningful. My old guiding philosophy was holding me back, but I couldn't see it — the threat to my view of "people like me" was blocking me from seeing that I could be happier by trying a different outlook.

Are People Like You Holding You Back?

Separating ourselves from our experiences is hard — there's no denying it. There's a reason people dedicate their whole lives to meditation.

But we don't need to reach enlightenment to try and spot our own biases.

One of the easiest ways to catch ourselves being owned by our emotional and physical crap is to ask what we'd advise our friends to do if they were facing the same decisions.

Imagine a friend came to you and asked, "I've got this opportunity to travel the world while still making a living, but I'd have to sell all of my stuff in order to do it — what should I do?"

You've known your friend has wanted to travel as long as you've been friends. What would you tell your friend to do?

You're facing the same opportunity to travel right now. What would you tell yourself?

If your answers are different, you're probably letting your physical and psychological dead weight get in the way of making objective decisions.

It's hard. You have to be really honest with yourself. You'll need to face some uncomfortable personal demons. But think of everything you stand to gain by freeing yourself from the useless burdens you carry around — both in the closets you haven't opened since you jammed your box full of "just in case" shit inside, and in the biased corners of your mind that hinder your ability to act objectively.

Why We Work: Are We Just Working for Work’s Sake?

Thu, 02 Apr 2015 00:00:00 GMT

It can be hard to remember that we don't live to work.

Cultural pressure is high to have a good job, and to work hard in that job to get a better job. To make more money so we can buy more stuff. To work the hardest and sacrifice the most.

We stigmatize leisure as the mark of someone who won't get far in life. We furrow our brows disapprovingly at the high school graduate who wants to take a year or two off before deciding what to study in college (or whether they should go at all). We look down on the smart kid who works a part-time job because he's "not living up to his potential."

But what does all that really mean? Do leisure time, taking a break to find yourself, and working just hard enough to get by really signify a problem? Or are we uncomfortable with the idea of valuing something else over work?

It can feel a lot like the latter in most cases.

But here's the thing:

We don't live to work.

We work to live.

We Work to Have Freedom

When I was eleven, I wanted a Nintendo 64 in the worst way.

But at $200, my chances were slim. I got a weekly allowance of $10, so by my estimation it would be a thousand years before I'd saved up enough to buy one.

I had to beg my parents and promise that they'd never have to buy me anything ever again[^begging] in order to get one.

[^begging]: "You never have to buy me anything, ever again!" was recently ranked #14 on the Top 100 Phrases Children Don't Fully Understand.

When I was 14 I got my first job washing dishes at a local restaurant. My first paycheck blew me away: I'd made over $160[^suckit] in just two weeks!

[^suckit]: Suck it, allowance!

When the next gaming console rolled out, I didn't have to beg anyone for it — I could buy it with my own money.

The freedom that I felt when I made my first big purchase with money I'd earned at my job was intoxicating. I knew I never wanted to have to ask someone else for the things I wanted again.

Work Shouldn't Rob Us of Freedom

We work to remove the limitations that exist when we can't afford to do the things we want and need. Income gives us the ability to choose what's best for ourselves, rather than being beholden to someone in a position of power over us.

If we let work become the dominant force in our lives, we start to give away that same freedom we've worked to gain. Only this time it's not a shortage of income that shackles us, but a shortage of time.

If we're trading our freedom for higher wages, or for career advancement, or for anything at all, really, we're actively undermining one of the core principles of work: we work so we have the freedom to choose.

We Work to Have Purpose

I recently visited the Elephant Nature Park, run by Lek Chailert, a woman from a rural part of Thailand with deep reverence for elephants.

As an adult, she works hard to rescue abused, disabled, and unwanted domesticated elephants and raise awareness about the rapidly disappearing elephant population and mistreatment of elephants as livestock.

She's found purpose in her work — or maybe it's better to say she found work in her purpose. It's clear that she finds her work incredibly important and fulfilling.

But even if our work isn't our main purpose, it can provide a means to pursue that purpose. Earning a living that enables us to pursue something we find meaningful but doesn't pay well is a viable path forward.

Work Shouldn't Rob Us of Purpose

By working, we create the opportunity for ourselves to apply time, money, and effort on the things that we think are most important in life.

When we let work spill over into our personal lives, the means to pursue our passions begins to diminish. We don't have the energy to go after the things that we used to consider most important — we're too exhausted from working, too preoccupied with meaningless metrics, or too worried about moving up the corporate ladder.

When we let our work displace our purpose, we start to lose steam, and the results can be disastrous: midlife crises, depression, a sense of purposelessness.

Work Is a Tool, Not a Burden

We work because we want to live better lives, and to do that we need to have a way to make an income. For most of us, that means a job.

Work is a tool that gives us access to meet our needs and fulfill our various wants. And when it's treated like a tool, we're able to control our efforts in a way that creates a better life for ourselves and our loved ones.

But if we lose sight of what's important to us, work can become the sole focus in our lives — it's no longer a tool, it's a burden that prevents us from doing what we want to do.

We have to remember that we weren't put on this planet to punch a clock and die on a pile of money; we were put here to live.

So repeat after me:

We don't live to work.

We work to live.

Measure on Results, Not Time Spent

Sun, 29 Mar 2015 00:00:00 GMT

Imagine that you're given a task at your salaried job: you have to write a year-end summary of your department's most valuable projects, which will be used to guide next year's project selection.

You get right to work and knock out the whole report in two days. Your boss is pleasantly surprised at your speed, but nothing can happen until a coworker finishes the report for his department.

In the meantime, there's a box of invoices that need to be audited, and since you're ahead of schedule can you take care of it?

Meanwhile, your coworker takes a week and a half to finish the report. It's mentioned that you finished faster, but that's about the closest thing to a reprimand he'll hear.

You're clearly more productive, but your coworker is rewarded: he made way more money for doing far less work.

You were both paid for time, not output.

The Danger of Butts In Chairs

Because it's hard to measure output, many companies have reverted to a much simpler, horribly inefficient approach to tracking an employee's worth: butts in chairs.

Rather than asking what someone produced, they ask how many hours he worked.

Is it effective at telling who's a good employee? No.

Is it helpful in determining who the company's stars are? Nope.

Does it help motivated employees stay motivated? Exactly the opposite, in fact.

But it does remove the need to do a little extra legwork for management, so — despite the fact that it's arguably one of the absolute worst management metrics available — it still gets used.

Time-Based Management Means Rewarding Poor Performance

In a culture where the only deliverable is time spent at the office, the business is actively encouraging employees to do less.

A project that should only take a day gets stretched out to two, because who cares? There's nothing to be gained by working quickly.

The Frightening Economics of Time-Based Management

For an employee, the economics look like this: that hypothetical report from the beginning of this post took you two days to finish, or 16 hours.

Let's say your salary is $50,000/year. That means that you get paid roughly $24/hour. So for finishing that report, you made about $385.

Your coworker, who spent a week and a half (say 56 hours) doing the same project at the same salary was paid about $1,345 for the same job.

You, by working quickly, were punished for your efficiency. The message being sent is, "Don't worry about how long it takes; you get paid the same salary whether it's done today or done in a month."

How to Stop Rewarding Failure

To solve the problem where your less-efficient coworker gets rewarded, imagine a results-based office instead.

Your boss assigns a project to you and your coworker and sets a due date of the following Monday, giving you six business days (48 hours) to complete the task.

Based on your salary, your boss has just valued this project at about $1,150.

Now let's assume that you still get it done in 16 hours.

Because the business is results-based, you are now free to do whatever you want until the following Monday, and you just made $71.88/hour for creating that report — your efficiency was just rewarded with a higher hourly rate.

Your coworker, on the other hand, manages to spend all of the allotted time plus a couple late nights working on the report, and still somehow manages to take 56 hours to create the report. He's just lowered his hourly rate to $20.54.

This is far more rewarding to efficient employees.

How Rewarding the Right Employees Helps Businesses

For a business that implements a results-based environment, the rewards are also huge.

Easily Spot Star Employees

A results-based company needs to spot stars in the company — the people who seem to always get done ahead of schedule — and move them to more important, higher-value projects. When employees are measured by their results, this is extremely easy.

Spotting and rewarding star employees creates an incentive for employees to work more efficiently, which is good for morale, deadlines, and pretty much everything else businesses want to improve.

Spot Problem Employees Quickly

Measuring results instead of time helps the company identify, coach, and — if necessary — weed out problem employees.

It's very difficult to just coast along in a company where you're measured by results, so employees who don't get much done are quickly identified by their low output.

How to Make the Change

If you're caught in a business that values time over results, or if you're a manager or employer that's fallen into the butts-in-chairs trap, there's still hope.

It will take an effort, but if industry giants can implement and benefit from it, so can you.

Start Figuring Out What Needs to Be Done

If you find that you're unable to clearly state what needs to be done in an organization, drop everything and start by defining what the result needs to be.

Managers can't expect anyone to be effective if there's not a clear plan in place for what needs to be done.

Employees can't do good work if they're not 100% clear on what "good work" means in the context of the company.

Before you can measure results, you need to define the results to be measured.

Make a Case to the Boss

If you're not at the top of your organization, you're at the mercy of higher-ups. That doesn't mean you're helpless, however.

Bring up the detriments of butts-in-chairs to your boss. Talk about the benefits to everyone of results-based work.

If the people at the top are actually interested in making the company better, they'll take what you have to say into consideration.

Be smart about it, though, because your boss won't likely change everything just because you waved this article in her face.

Instead, make a small suggestion: as an experiment, your team could try a results-based arrangement and report back after 3–6 months with findings. Figure out a way to measure results that will get management excited, and put a plan in place.

Once your team has demonstrated that results-based management gets results, your boss will take ownership of the idea and run it up the ladder, hopefully creating a ripple effect that helps move the whole company to a better arrangement.

And even if it doesn't, your team will likely be allowed to keep up the same arrangement — after all, you were more productive.

Vote with Your Feet

If your organization doesn't respond and insists that your only value to the company is your butt in a chair for 8+ hours a day, then it may be time to look at other options.

There are results-based employment options ranging from the obvious (software and copywriting) to the entry-level (customer support) to the unbelievable (accounting firms).

It's stressful to hunt for a new job, but there are lots of options for finding remote work.

If you can't change your culture, don't let yourself be the one who's punished for someone else's incompetence.

Remote Work Is a Win for Everyone

Sun, 29 Mar 2015 00:00:00 GMT

The traditional office setting has its perks: community, an environment set up for productivity, common meeting spaces for face-to-face interaction.

But with global access to reliable video meeting services and a host of other cloud-based team management tools, remote workers have access to the same perks, plus a host of other bonuses: fewer distractions, less micromanagement, little or no commute, and — most importantly — location independence.

This isn't a one-sided victory, either: businesses hiring remote workers also see lower costs, lower turnover, happier employees, and a worldwide talent pool.

When Your Team Can Work from Anywhere, You Can Hire from Anywhere

If your team works remotely, they don't have to be in the city where your company is based. You can hire the right person for the job, no matter where they are in the world.

This means a developer living in Iowa doesn't have to drop everything and move to San Francisco or Brooklyn to have a shot at getting a cool startup job.

This means an entrepreneur in Mississippi can hire top talent from anywhere in the world without having to convince anyone to move to Mississippi.

On a remote team, the workforce expands from whatever the population of your home town is to approximately 4.8 billion working-age people who may be able to meet a need for your company.

Remote Workers Are Results-Based by Default

One of the best ways to make sure employees and contractors feel empowered is to switch to a results-based approach where employees are rewarded for efficiency instead of just showing up.

Moving to a results-based environment is a huge win for any company (and its employees), and adopting a telecommuting culture is a great way to kickstart the process.

Remote Workers Are More Productive

In a study performed at a call center, employees allowed to work from home were 13.5% more productive than those working in the call center.

There's a psychological benefit to this as well: reciprocity.

When we grant an employee the freedom to work on their own schedule, it's a display of trust.

Humans are hard-wired to reciprocate: put your trust in someone and their default response will be to reciprocate by doing good work — repaying your trust, so to speak.

Remote Work Lowers Turnover

After introducing a Results-Only Work Environment (ROWE), Best Buy saw an astonishing 45% reduction in turnover: nearly half the people who would have quit stayed with the company because they were happier with the job.

This is important, because the cost of turnover adds up fast:

It costs upwards of twice an employee’s salary to find and train a replacement. And churn can damage morale among remaining employees.

The Wall Street Journal

Remote Work Empowers Employees

When we're not being micromanaged, we're able to self-direct and take ownership of tasks.

This shouldn't be understated, because employee ownership likely plays a huge role in the reduced turnover ROWE reported.

As an employer, the Holy Grail of creating a healthy culture is employee engagement — this is a buzzword that, at its core, describes employees who feel personally responsible for the success or failure of the company.

Letting employees go remote forces them to own their tasks in order to perform well. This gives them a sense of autonomy and reduced pressure.

Personal responsibility leads to an emotional investment in the success or failure of projects — and like magic, your company has better employee engagement.

Instead of just keeping butts in chairs, you build a family of employees who care about the company's future.

Remote Work Lowers Costs

For a startup in San Francisco, getting office space for 10 employees will cost about $6,000/month.

Imagine putting that money back into the operating fund. Even if you buy all 10 remote workers a Herman Miller office chair, you'd still save about $57K over the course of a year by letting them work remotely and push that chair up to their desk at home.

In addition, remote workers are far less likely to call in sick: there are 63% fewer unscheduled absences for telecommuters over in-office workers.

And that's just the tip of the iceberg. There are quite a few arguments that suggest remote working saves money.

Remote Working Just Makes Sense

According to the research, remote workers are healthier, more productive, less likely to quit, less expensive, and even less likely to get divorced.

Why the hell isn't everyone already doing this?

Overtime: How to Lose Your Employees and Kill Your Business

Sat, 28 Mar 2015 00:00:00 GMT

The way many businesses approach pressing deadlines is terrifying.

It's also, ironically, one of the least effective ways to meet deadlines.

The current mandatory hours are 9am to 10pm -- seven days a week -- with the occasional Saturday evening off for good behavior (at 6:30pm). – easpouse: _The Human Story

This post from ea_spouse caused a huge stir in 2004, citing the slow creep of mandatory overtime into company culture at EA Sports.

EA's reasoning, according to the post, was that engineering needed to go into "crunch mode" to boost output and meet looming deadlines. After all, an engineer working damn-near 90 hours a week should be at least twice as productive as the same engineer working 40 hours a week.

Right?

Productivity Is Not Linear

The thinking behind why managers believe twice the hours results in twice the output is short-sighted and toxic. Companies who regularly enter "crunch mode" forget to consider that their employees are humans — susceptible to fatigue, burnout, resentment, unhappiness — and not robots.

As a programmer starts working, her output will follow a pattern along these lines:

If she's asked to work extra hours, she will produce extra output. But since she's already pretty beat after 8 hours, the extra output will be pretty low, and at a high cost.

Working More Produces Less

After an alarmingly short period of time — just a month in some cases — "crunch mode" productivity will drop.

And not just a little drop. Output drops so much that it would have been more productive to work a standard 40 hours.

Let me repeat that, because this is huge: an employee working 60 hours a week for two months will produce less overall than the same employee working 40 hours a week for the same time period.

But how? How can doing 150% of the work result in less than 100% of the output?

Why Does Productivity Tank During Crunch Mode?

Imagine you work a standard 40-hour week, broken into five 8-hour shifts. And, since it's hard to imagine our minds as a muscle, let's pretend that your job is to unload heavy shit from a truck and move it into a warehouse all day.

A 40-Hour Week Is Sustainable

On an average day, you start out fresh, hit your stride an hour or two in, and start to feel fatigue set in after about six hours. At the end of eight hours, you're beat, but not exhausted.

It's hard work, but after you go home for the day you have time to eat a nice dinner, relax with your friends and family, watch an episode of Orange Is the New Black, and read a chapter of your book before sleeping a solid eight hours.

On the weekends you take care of errands, spend time with friends and family, and sleep in a bit to make up for when you didn't stop at just one chapter of your book.

By the time your workweek starts again, you're fully refreshed — mentally and physically — and ready to get back to work. You could happily keep up this pace for years.

Crunch Mode Starts Strong...

In contrast, when mandatory overtime is assigned, you work a 60-hour week, broken into 6 10-hour shifts.

On day one, you start fresh, but by the end of 10 hours you're feeling really worn out — two extra hours of carrying heavy objects takes a toll — but you did unload an extra truck.

...but It Takes a Huge Toll...

You've also lost two hours of free time to the longer shift, so you have to skip meeting up with friends — and even with the cancellation, you only get seven hours of sleep.

On your only day off, you can't sleep in because you have to rush through your errands early — you're supposed to meet your friends for a barbecue at 4pm, and it's your only chance to see them this week.

Your next shift starts with you still feeling fatigued from last week. No matter how hard you try, you're just too tired to keep up the same pace from last week.

...and It Gets Worse Over Time

As the weeks drag on, your lack of sleep is combining with the stress of your increasingly-hurried personal life and you're feeling ragged. The fatigue is showing in your output: each week is a little less productive than the one before it.

Despite starting strong — during week one of crunch mode your output was noticeably higher than a standard week — over the following weeks your output dipped a little at a time, until you ended up doing less work over ten hours than you would over eight hours.

For 150% of the effort, you're now getting less than 100% of the results.

If Overtime Is Less Productive, Why Do So Many Businesses Rely on It?

Why — despite 100 years' worth of solid research, stating definitively that the 5-day, 8-hour workweek is the most sustainably productive arrangement — are so many businesses still implementing extended, mandatory overtime?

Lack of Effective Measurement

The most likely culprit is a lack of measured results. If you don't measure output, then your only tool for gauging productivity is time and perceived effort: the team has been putting in lots of extra time, and it sure looks like they're working hard!

Misunderstanding of Time vs. Output

In high school, if you finished your assignments early, you weren't let out of class to do whatever you wanted with the extra time. In fact, you were often given extra assignments — things like extra credit — which were, in effect, a punishment for being efficient.

Some businesses operate with the same mindset and pay for time instead of output — you may have heard this called "butts in chairs" management.

By valuing time over output, businesses unwittingly punish their most productive employees and reward the slackers.

Poor Project Management

If a project isn't properly planned, companies can find themselves trying to fit a six-week project into a four-week timeline. If managers aren't actively working on controlling timelines, overtime may seem like the only viable option to meet unrealistic deadlines.

The problem is usually made worse by the fact that the manager doesn't pay for poor management nearly as much as the employees stuck working overtime will.

How Can Companies Fix the Problem of Overtime?

Unfortunately, there's no easy answer to this question. Each company will have its own blend of dogmatic faith in overtime, cultural dependence on long hours, managerial incompetence/inexperience, and buy-in to the Overkill Cult.

There are a few things that are worth auditing, however, that can at least help point out if there are some major, easily-fixable problems at work.

Output Should Be Measured

Every company needs to be measuring output. Where knowledge work is concerned, employee output is the most important factor in determining whether or not the company is doing better or worse.

For some companies, employee output is easy ("how many trucks did Terry unload?") whereas others face more challenging metrics ("how much managing did Pat do this week?").

Before a company can see the detrimental effects on productivity, it needs to be able to define what "productive" means with hard data — otherwise they're just guessing.

Reward the Behavior You'd Like to Encourage

On any project, each team member should be given their fair share of goals to complete.

After that, set 'em loose. If someone finished her tasks today and they're not due until next Friday, she can leave and not show up again until the review meeting — as long as what she's turned in is quality, it doesn't matter how long she took to build it.

Don't punish the stars on your team. Make sure they're challenged, but be okay with results-oriented management — incentivizing your team ("finish ahead of schedule and you can do whatever you want until the meeting next week!") instead of punishing them ("finish ahead of schedule and we'll load you up with busywork!") goes a long way toward encouraging the behavior you want to see in employees.

Plan Projects Effectively

When a new project is in its planning stages, make sure to include people in the decision-making process who will be able to provide reliable time estimates.

A system of checks and balances should be put in place before a client ever receives a timeline to make sure the proposed deadlines are achievable without the need to go into crunch mode.

Businesses shouldn't underestimate the value of properly planned projects; with a solid plan, projects get done faster and with fewer unpleasant surprises — like overtime.

Be Part of the Solution

It's tempting to pretend that we're the exception to this kind of data. Don't fool yourself.

Working effectively — and in a way that makes us happy with all aspects of our lives — is a marathon, not a sprint. We'll feel like we have gas left in the tank. Like we're not giving 100%.

That's exactly the point.

Leaving a little in the tank is vital for sustained performance. When there's a little gas left in the tank, we're still excited to work. We're not too exhausted to spend time with our family and friends. We still have time to pick up hobbies and relax.

And none of that should be undervalued — it's the secret to truly being successful and productive in the long run.

How to Know If You’ve Joined a Cult

Fri, 27 Mar 2015 00:00:00 GMT

You didn't mean to end up here. You didn't even see it coming.

It all started with a chance to earn a living doing something you loved. Your dream job. Creating things instead of rotting in a cubicle. You weren't just going to make a living — you were going to leave your mark on the world.

At first, you loved the work; it was challenging and fast-paced. Everyone around you was crazy smart.

You brainstormed in your off time. Took projects home with you. Put in extra hours on weekends. It never felt like overworking because it never felt like work.

You put in way more than 40 hours a week, but who was counting? This was fun.

But weeks passed into months and somehow you ended up here: Working 60 hours a week minimum, usually more. You greet your coworkers, bleary-eyed, half-joking about needing coffee to survive.

The work is still fun, but you don't feel the same passion anymore. Whole days slip by sometimes and you have no idea what happened; you certainly don't have much to show for it.

Your goals outside of work are on hold. You'd love to find out if the Belgians have anything to be cocky about waffle-wise, but you don't have time for a big trip right now. You know you need to get into an exercise routine, but something always comes up and you skip the gym.

"Later," you promise yourself, "I'll get around to it soon."

You're not exactly unhappy, but something's off. You can't put your finger on it. You've just always felt that there would be . . . more.

You've Been Absorbed

You're no longer a free member of society. You've been lured into the Overkill Cult.

The Overkill Cult is a cultural delusion that working 60+ hour weeks at the expense of everything else in our lives is not only a necessary part of success, but that doing so is somehow honorable.

The insidious thing about the Overkill Cult is that it masquerades as all the things we like most about ourselves: dedication, ambition, follow-through, responsibility.

It tells us to push harder, stay later, sleep when we're dead. It tells us we're never going to get ahead if we don't show up first and go home last.

Cleverly, wickedly, the Overkill Cult persuades us to hang ourselves with our own strengths.

And if we don't break free, we're all going to die.

The Overkill Cult Will Kill You (Like It Tried to Kill Me)

Balance is the first thing to go once the Overkill Cult has us in its grasp.

For me, it started with my health. I skipped the gym — too busy, I thought. I didn't have time to cook — too busy — so I ordered delivery.

My hobbies went next. Everything that wasn't work fell away — too busy, too busy — until I was on the computer constantly, working. In 2012, I was working 70–90 hours a week.

After that, I lost my social life. Friends knew I wouldn't show up — can't; too busy — so they stopped calling. Some days my only human interaction was ordering coffee.

Then — and this, sadly, is where I finally realized there was a problem — I lost my beard.

The Canary in the Coal Mine, or How I Killed My Beard

At the end of 2012, I landed the biggest project of my career at that point: a Black Friday sales site for a Fortune 100 company.

I was thrilled and terrified. A project like this had the potential to move my company to the next level, and I decided to do whatever it took to make this project the best I'd ever built.

The designers had great ideas, and I sat with them to make sure they were possible on our timeline. We came up with a slick, modern idea built on cutting-edge technology. The client loved it.

Then bureaucracy came into play. The legal department made changes. Brand adherence contradicted legal. Design went over schedule. Way over schedule.

By the time the design was approved, I had a third of the time we'd scheduled. And — since this was a Black Friday site — we couldn't push back the release date. It either launched on time or I was a failure. Period.

Not to be defeated, I powered through four straight days leading up to Black Friday, sleeping maybe six hours total. On Thanksgiving Day I skipped family get-togethers in favor of making the final push.

I was exhausted. Delirious. But, goddammit, I finished the project.

The client was thrilled. The site won a couple Addy Awards. I assume they made a metric fuckton in holiday sales.

Over the next few months, patches of my beard started to turn white. The whiskers became ultra-fine. Then they fell out altogether.

Shortly afterward, I lost my ability to grow a beard entirely — I was left with the unsavory choice between a clean-shaven "giant fat baby" look and a creepy mustache.[^mustache]

I had stressed myself out so badly that my body had forgotten how to grow a beard. And for what? So I could work 19-hour days and skip family holidays to meet crazy deadlines?

I was exhausted. My body was failing. I was overwhelmed and unhappy and isolated. I had a mustache, for chrissakes.

I had been guzzling the Overkill Cult's Kool-Aid.

Something had to change.

How to Tell If You're in a Cult

The telltale signs we've fallen prey to the Overkill Cult's influence are subtle:

Frequently working more than 40 hours a week
Frequently sleeping less than 6 hours a night
Feeling guilty about any time away from work— even if that time is with family and friends

We don't join overnight — this is death by a thousand cuts — and once we've joined, we'll probably deny it.[^denial]

But we've joined. By the thousands, we've joined.

The Lies of the Overkill Cult

The Overkill Cult's siren song seems like a healthy sense of ambition. "We have to work hard to get ahead." It's something we've been told our entire lives.

We're doing what we think is best for the future.

But the Overkill Cult doesn't plan for survivors.

Though the symptoms of the Overkill Cult grow from good intentions, they're short-sighted habits that ultimately do more harm than good.

Let's look at each of the Overkill Cult's telltale signs, and how each of them is a long-term detriment disguised as a healthy work ethic.

Frequently Working More than 40 Hours a Week

Long hours often feel mandatory — it's just part of the culture. We think, "My boss/coworkers/cat will judge me if I'm not working the same long hours as everyone else. I'll never get ahead if I don't go above and beyond."

This is just what it takes to make it, right?

Wrong. Incredibly, terribly, spectacularly wrong.

Research has proven over and over again that it's not possible to be productive for more than 40 hours a week. At least not for sustained periods of time. Henry Ford introduced the 40-hour work week in 1914 because he saw — through research — that workers on five eight-hour shifts kept up the highest sustained levels of productivity.

Despite over 100 years of research supporting shorter work weeks, many companies still push for long hours, under the claims of a "sprint" or "crunch time" period.

The irony comes in when we look at productivity over time. After just two months of 60-hour weeks, productivity goes negative compared to what a 40 hour week would have produced.

Did you catch that? By working 150% of the hours, you accomplish less in the long run.

Frequently Sleeping Less than 6 Hours a Night

Somehow, sleeplessness has become a strange badge of honor. We swap "war stories" of sleeping two hours a night with an odd, martyred pride shining dimly in our bloodshot eyes.

I never sleep because sleep is the cousin of death, we murmur drowsily. So many projects, so little time.

But this belief that burning the midnight oil somehow gets us ahead is utterly, tragically wrong.

You're the cognitive equivalent of a drunk driver after being awake about 18 hours. But the problem compounds: if you don't get enough sleep, that level of impairment comes faster the next day. After a few days of too little sleep, you're a drunken zombie.

We wouldn't go to work drunk, so why the hell do we go to work on four hours' sleep, when we're more impaired than if we were hammered?

To make matters worse, sleeping less than six hours a night may lead to an early death. The Overkill Cult is literally killing you.

Feeling Guilty About Any Time Away from Work — Even Time with Family and Friends

When we're in the clutches of the Overkill Cult, we feel a stab of guilt when we're not working.

"I'd love to go to this holiday party, but I really shouldn't; this project won't finish itself."

We fear that any time not spent working is wasted.

The irony is — yet again — science tells us exactly the opposite is true.

Overworking leads to higher stress levels and burnout, which have been linked to increased health risks.

Conversely, time away from work is proven to relieve stress and boost creativity, among numerous other benefits.[^walking]

Besides, if we accept that the ideal is to sleep 8 hours a night and work 8 hours a day, that leaves us with 8 hours[^nonworktime] for non-work activities.

Taking time away from work gives us time to recharge. It puts distance between us and our projects, giving us time to remember why we like doing what we do.

Making Our Escape

While we may have been duped into joining the Overkill Cult, it's not too late to escape.

We've been conned using our own best qualities to develop habits that — even though it seems like they'd make us better — make us worse at our jobs, less satisfied with our work, and less happy in our day-to-day lives.

Leveraging the same strengths the Overkill Cult exploits, we can break free of its clutches and take back our happiness and passion.

After my beard died, I felt the full weight of burnout. I was burnt to a fucking crisp. I realized I could either leave my career altogether, or make some fundamental changes to my lifestyle.

For what it's worth, here are the promises I made to myself that helped me break away from the Overkill Cult.

I Work as Much as I Can — But Not More

Before anything else, I had to accept that it's only possible to do 6–8 hours of quality work each day.

Trying to work longer hours will not make me more productive. In fact, working longer hours actually results in me getting less done as time drags on.

I chose the latter, and implemented some radical (to me) strategies for controlling my time. I cut from an average of 70–90 hours a week in 2013 to an average 38 hours per week over the last year.

I expected to see less professional success in favor of better overall balance in my life — a sacrifice I was willing to make — instead I saw better productivity at work: my turn-around times went down[^turnaround] and I was more consistently hitting my deadlines.

I was floored at the time, but in retrospect I'm not surprised at all.

I Make Sleep a Top Priority

Getting enough sleep is beneficial on every level. Yet it's always the first thing I would sacrifice when life got busy.

Too little sleep wreaks havoc on my ability to think clearly, and that hurts me at work in a big, bad way.

After I cut my hours down, I started sleeping without an alarm.[^noalarm] Since I'm not working crazy hours, I close my computer by six or seven in the evening, and by eleven I'm usually in bed, where I read for a bit before falling asleep. I wake up naturally between seven and eight-thirty.

This has changed my life. No bullshit.

Waking up to an alarm before I'm fully rested starts the day in a groggy, stressful way. Waking up naturally after getting as much sleep as my body needs leaves me much happier to be awake, and far more ready to start my day.

I Dedicate a Reasonable Amount of Time to NOT Working

This was — and still is — the biggest challenge I faced in breaking away from the Overkill Cult. I love what I do, and I want to get my projects finished. It's easy to rationalize working more hours and skipping activities that keep me from working.

But now I know that taking breaks makes me more productive: time away from work lets my passion and excitement for the work renew itself; taking my mind off of a project allows my subconscious to roll around abstract ideas that result in better solutions; breaks from the job lower my stress levels and boost my creativity.

So I make sure to do it, even if my gut (incorrectly) tells me it's a bad idea.

I take walks. I leave my phone in my pocket when I'm out with friends or eating my meals. I spend a fair amount of time on my hobbies, like writing and hunting for the world's best cheeseburger.

I'm happier today than I can ever remember being in my life. I feel excited to work on my projects, to pursue my hobbies, and to spend time with people I love.

I'm excited to be alive.

Leaving the Overkill Cult Saved My Life

When my beard died in 2013, I feared it was only the first sign of an impending decline in my health that would ultimately kill me. It was a glimpse into my future, and I was terrified that if I didn't change, I was in for a life of isolation, ulcers, alopecia, and an eventual heart attack or stress-induced brain tumor.

By changing my lifestyle, I was able to turn things around. After just a year of balancing my work with the rest of my life, my beard grew back. I lost 30 pounds because I was actually going outside and making it to the gym. I felt more awake, and I became more positive.

When I left the Overkill Cult, everything in my life improved. Not one single thing got worse.

Are You Ready to Make Your Escape?

If you've been sucked into the Overkill Cult, know that you're not alone.

You may be facing cultural pressure to keep this crazy pace. You may be struggling with your identity as "a hard worker" and feeling that scaling back somehow makes you lazy or useless.

But I promise you — despite the doubts the Overkill Cult will force into your mind — there's a better way. Better for your career. Better for your health. Better for your relationships. Better for your happiness.

You ended up in the Overkill Cult because you're smart, ambitious, and dedicated. But you were misled by your good qualities and turned them into bad habits.

There's a better way, and you're smart enough to pull it off.

Dump your Kool-Aid in the sink. Take back your freedom. Find the happiness and success you were looking for when you started this career.

Close your computer. Go outside. And call your friends; they miss you.

[^mustache]: "You'll look like Magnum," I tried to tell myself. But I knew — even then, I knew — it was all a horrible, creepy lie.

[^denial]: If you're currently rationalizing how you're not in the Overkill Cult even though you meet all the criteria, you're definitely a member.

[^walking]: These studies focus on walking a few minutes a day. Not even an actual hobby or dedicated non-work activity. The negative effects of "all work and no play" are staggering, if you think about it.

[^nonworktime]: Or, if you want to exclude meals and such, at least four hours. That's enough time to go to the gym and pick up a hobby. Or even, you know, hang out with other humans or something.

[^turnaround]: I also made other changes that helped with turn-around times, such as planning more effectively.

[^noalarm]: Waking up without an alarm is, by far, my favorite thing about the digital nomad lifestyle I'm so grateful to lead.

Shitty First Draft

Mon, 23 Feb 2015 00:00:00 GMT

At Precision Nutrition, the first iteration of any project is called a Shitty First Draft.[^lamott]

This isn't done to make the people producing the work feel bad about themselves; exactly the opposite, in fact: the goal of the Shitty First Draft is to remove the need for polish in favor of making progress.

The Power of Getting Started

A blank canvas is intimidating. You have a vague idea of what you need to create. You have a deadline. You know you have the skill to pull it off.

But there's hesitation.

What if it's not exactly right? What if people judge your work too harshly? What if this idea isn't as good as you thought?

Small worries like these can lead to procrastination and unnecessary stress.

A Shitty First Draft is specifically designed to remove these barriers, making it much easier to just get started:

A Shitty First Draft is not intended to be perfect. It's intentionally imperfect and unpolished.
A Shitty First Draft isn't reviewed for launch-readiness. It's intended to give everyone a starting point to provide real, concrete feedback.
A Shitty First Draft gets the ideas on paper and out of your head. This makes it much easier to see the value of the idea before spending too much time on it.

The Shitty First Draft is fast, and intended only to move the project from a vague, project-shaped idea to a tangible, tweakable, actual thing.

Moving a project from "an idea we need to start working on" to "a project that's started but needs to be finished" has a huge psychological benefit: forward progress generates momentum, and there's no question that projects with momentum get finished faster.

Create Something Simple to Get a "Real" Working Concept

Having something tangible to look at allows the whole team to see a real-world application of the idea. This is far easier to tweak than a collectively assembled mental model and/or flowchart.

With a Shitty First Draft, the time it takes to get something tangible is much lower. The project spends far less time as a concept in the minds of the "idea people", and far more time being shaped into a final product by the team.

For example, I'm currently building a new application that's trying to take certain in-person interactions and — as best as possible — scale those globally. We spent hours talking about how this could work and how to measure success, but because nothing like this app currently exists, we couldn't really wrap our heads around how it worked, because it was only a concept.

We needed something real — something bound by the limits of reality — so that we could start to find and fix issues with our approach.

Instead of trying to code anything, I started by building a Shitty First Draft: low-quality wireframes of different screens in the app, plugged together in a Google Presentation that we used to storyboard what a real session would look like using the app.

This lo-fi storyboard only took a few days to put together, and having "real" screens to look at while walking through a real use case allowed us to find issues that we wouldn't have caught otherwise — issues that would have required a good deal of work done over again had we jumped straight to building a "production-ready"[^productionready] version.

Remove Guesswork from New Projects

The Shitty First Draft also takes a lot of the guesswork out of the subsequent efforts: my first crack at coding up the app felt more like a paint-by-numbers than a blank canvas, and that allowed me to get into a flow state quickly.

The Shitty First Draft paved the way for the real product by smoothing out all the usual bumps that would take me out of building the app to work on its strategy.

The Shitty First Draft has been used effectively at Precision Nutrition for everything from web apps to coaching programs to full-length books. It doesn't matter what kind of work you're doing: start with a Shitty First Draft, you'll end up with a higher-quality product sooner.

Give Yourself Permission to Start Shitty

I shudder to think of now many hours I've wasted trying to write something perfect on the first try.[^highschool] How many lines of code I've deleted after I built out a fully-functional feature that it turned out wasn't necessary at all. How many designs I've scrapped because I started with the aesthetic before I had all the details of how something would be used.

I felt pressure to be perfect. Most of it was internal pressure.

I didn't want to admit I couldn't get things perfect on the first try.

I wasted days of my life. Probably months. All because I was worried that if every word, every line of code, every pixel of a design — if everything I produced wasn't my absolute best work, I was failing myself, my clients, my business, my fucking ancestors.

When I came to accept that Hemingway was right, and that the first draft is always shitty, I started working more quickly, and the work I put out into the world was better quality.

This article started as a list of productivity tips, which was expanded to a series of articles including a piece on planning, which was then simplified into just this concept. From there, it went through several rounds of edits from myself and people I trust before it came out as the post you're reading now.[^anxiety]

Everything about my creative process improved when I started implementing the Shitty First Draft.

What will you create when you give yourself permission to start shitty?

[^lamott]: I did a search for "shitty first draft" after I started writing this article and came across an excerpt from Anne Lamott's Bird by Bird on shitty first drafts. It's worth a read — especially if you're a writer.

[^productionready]: I quote this because it still would have been a Shitty First Draft; it just would have cost far more to produce.

[^highschool]: In high school, I was so hellbent on this I wouldn't edit my writing assignments at all. Hell, I wouldn't even read them after I finished writing. I'd sit down, write the whole thing in one sitting — it doesn't take long to fill two pages, double-spaced, after all — print it, and never look at it again. I remember saying something impossibly pretentious, like, "My writing is born whole. If I have to edit it, it wasn't worth writing in the first place."

[^anxiety]: The anxious part of my brain just started screaming, "No! Delete that! What if this isn't an amazing article and people say, 'This is your edited stuff?'" Yes. This is my edited stuff.[^validation] That little anxious voice can suck it.

[^validation]: Please validate me. My sense of self-worth is bound to my Klout score.

Leaving

Wed, 31 Dec 2014 00:00:00 GMT

I was eating leftovers over the sink with plastic silverware.

The previous morning, Marisa, her mother, and I had braved the line at Screen Door for one last Portland brunch. I finished the remnants of my chicken and waffles, doing my best to not to make a mess on the freshly-scrubbed counter and floor in the kitchen.

The apartment was completely empty. The cleaning service had left it sparkling. There was so much reverb when I spoke that it felt closer to an echo.

The giant living room I'd loved so much was bare. I'd taken the blanket and pillows we'd slept on the night before out to the trash.[^donations] Nicole from the cleaning service had taken nearly everything else — "I didn't bill you for the hour I spent loading your stuff into my car," she texted me later.

Only two small suitcases, two backpacks, a box of last-minute chores, and a couple small trash cans remained.

This is everything I own, I thought to myself.

Marisa showed up around five thirty. We threw away the final few items from the fridge and tossed the trash — cans and all — into the compactor on the building's first floor.

We wheeled our luggage out of the apartment and I locked the door. I stopped by the manager's office. My heart was hurling itself against the walls of my ribcage, and I ran through the checklist for the hundred-thousandth time.

It's all done. The apartment is empty. There's nothing left to forget.

I felt a little dizzy as I dropped the keys in the mail slot. They hit the bottom of the container on the other side with a nauseating finality.

"That's it," I said.

Ever since I started talking about my experiment in permanent travel I've been met with some variation on the question, "Are you excited?"

Reactions from my friends and family have ranged from excitement and good-natured jealousy to near-panic and quiet disapproval,[^disapproval] but — regardless of their view — everyone wants to know how I'm feeling about the trip.

It's a question that feels like small talk. But as I went through the motions of responding — "Yeah, it's going to be a great adventure!" "I know, I've heard amazing things about Italy!" "There won't be any pizza left by the time I leave!" — pointed out something disconcerting to me as the kick-off date drew nearer: I wasn't feeling excited.

I wasn't nervous. I wasn't afraid. I wasn't second-guessing my decision.

I wasn't... anything.

Flight DAL418 to Milan was to me — as far as I was emotionally processing things — just another flight. My 59th of the year. Another 3,982 miles added to my SkyMiles balance.

The realization that I wasn't emotionally addressing this trip concerned me a little. Was I compartmentalizing too much? Was I bottling up my excitement and fear, wiring up an emotional booby trap that could detonate at at any moment? Was I in for a truly spectacular breakdown in JFK, collapsed in on myself in the Terminal 4 Starbucks, sobbing uncontrollably, feeling a year's worth of repressed feelings all at once?

The night before the flight, I was restless.

All of the work was done. The tickets were purchased. All we had left to do was show up at the airport on time in the morning.

We ate our last meal in Portland at Robo Taco around nine. We ordered burritos and settled into a dimly lit corner. To my left, a muted television played PBS reruns.

"Are you okay?" Marisa asked me between bites.

I was giddy. Nervous. Excited. Relieved that the work of severing my ties to Oregon was finally done. Happy that I'd found a traveling partner. Scared that I was jumping with both feet into a world I don't fully understand.

"This feels like the first day of school," I said. I was eating my burrito with a fork and knife because I'd squeezed too hard and broken the tortilla, spilling the contents out the back. "I'm happy and sad and excited and scared. It's that feeling of 'into the unknown', you know?"

She did.

The conversation lulled as we finished eating, and we watched Bob Ross paint some happy little trees. Then we headed for the airport hotel.

At four this morning, Marisa's alarm went off. She got up to shower, and I went back to sleep.

At ten to six we were in the security line. Six fifteen we were at the gate with coffee in hand. On the plane by seven.

As I write this, I'm somewhere over the Atlantic Ocean, getting further and further away from a home I no longer have. All of my former possessions are settling into new homes with the friends and strangers on Craigslist who bought them. The apartment I locked up last night has already been rented to new tenants; I imagine they'll start moving in this weekend.

Everything I own in the world is in two bags: one at my feet, and one above my head. I didn't leave behind a storage unit, or an attic-load of furniture for my parents to hold onto. This is it. These bags. The clothes I'm wearing.

In a few hours I'll be in Milan, Italy, hauling my two bags into a stranger's home.

I should be sleeping to ward off the imminent jet lag, but I'm still restless. I can feel the weight of my eyelids, but I can't stop thinking about the adventures that lie ahead — pizza! gelato! and I guess some old buildings and stuff^food — and the problems I haven't solved yet.[^problems]

I still don't feel as excited as is maybe appropriate. And I certainly don't feel as worried as my mom probably is.

But I feel a pressure building in my chest and throat that makes me want to either burst into laughter or tears. I feel proud that I have built a career that allows me to take this trip. I feel lucky to live in an age where technology allows a lifestyle like this to exist. I feel hopeful that my research and preparation will prove to be at least mostly correct.

I'm not exactly sure how I should feel about all of this. But I'm absolutely sure that I'm ready for it.

[^donations]: I sold, donated, or gave away nearly everything I owned that was suitable for reuse. However, bedding is gross to share with a stranger, and my sheets had worn to the point where — a couple weeks prior to throwing them away — a hole had opened up near my (apparently) razor-sharp toenails.

[^disapproval]: Not disapproval in the sense of, "You shouldn't do this, it's a bad idea," but more in the sense of, "I don't understand how you're going to make this work and therefore cannot condone your actions." No one has told me I shouldn't take this trip; I've just had a few people find the whole concept too big and daunting, and from them I've been met with a lot of uncomfortable silences and worried groans. ("Mom, I'm going to live in Europe for a year." Mom emits a sound similar to Tina in Bob's Burgers.)

Me: "Well, we are only going to be eating while we're there." Marisa: "We're going to see museums and architecture and stuff, too." Me: "I mean, sure — on the way to our next meal."

[^problems]: I still don't know for sure how this whole "unlocked phone with a SIM card" thing will work. I forgot to save the directions to the first Airbnb, so I need to find wifi access before we can get there. I don't speak Italian. I just learned that people in Barcelona speak Catalan, which I didn't even know was a language until a few days ago.

Wizards and Assholes

Sat, 08 Nov 2014 00:00:00 GMT

One of my early jobs was at a local publishing house, where I did typesetting and rudimentary layout work for field guides. There was a guy there — we'll call him Carl — who handled the still-new digital aspect of the business.

I had built a website or two at this point. My work was total amateur hour, but I could tell that this kind of work was something I enjoyed.

Carl was the first person I'd met who worked on websites for a living.[^montana] At the time, he represented all of the things I wanted in my career. So I looked up to him as a mentor.

Hey, Carl, can I ask you a question? How can I get to where you are? What should I do?

Carl looked at me, sizing me up. He had a smirk on his face. His condescending gaze was amused, like, "Who the fuck does this kid think he is?"

I felt ashamed. I wanted to take my question back. I wanted to hide under the desk until Carl left for the day so I could slink home.

He looked at me for a long time. I shriveled under his stare, questioning everything about myself.

"Can you tell me the difference between cell padding and cell spacing?"[^perspective]

I was pretty sure I knew the answer. I thought maybe it was a trick question. I second-guessed myself. I hesitated.

He chuckled and shook his head, disappointed.

"You're not ready to handle the kinds of work I do."

Carl Was an Asshole

Carl was forty-something years old, working a job that — in retrospect — was entry-level at best. His skill level was nothing to brag about; he could get the job done, but no one was going to knock any doors down to hire him.

But Carl was a big fish in a small pond. There was no competition for his job, because no one in Montana at the time was taking digital media very seriously.

This made Carl a lot like the Wizard of Oz: he was mysterious and powerful, dealing in forces that few people really understood.

And I was Dorothy, lost on this brand new career path, looking for someone to guide me.

I was an eager student. Carl was in a position to help me out.

Instead, he chose to be an elitist asshole and made me feel stupid for not knowing the things I'd just asked him for help with.

Fear of Becoming Irrelevant

I used to think that Carl just didn't like me. He thought I was some dumb kid who wouldn't amount to much. Why waste time on the likes of me?

But I think something else may have been at play: Carl might have seen me as a threat.

Not directly. Carl wasn't thinking, "Oh no! This kid's about to take my job!"

On some level, though, I think Carl may have seen my questions as a threat to his job security. After all, if enough people learned this stuff, it'd be a lot more difficult for him to remain the big fish.

Carl wanted to be indispensable. He wanted to be the lynchpin in the organization, without which everything would go off the rails.

That meant treating his knowledge like a trade secret, and boxing out anyone who might weaken his grip on this job.

But it didn't excuse humiliating a teenager for showing interest in his field of expertise.

"Don't Be Like Carl"

Last week I was in Boston speaking at an event.

On one of the evenings there was a cocktail mixer at a bar called Lucky's, a basement bar in South Boston. It was the sort of dimly lit, brick-walled dive where you imagine finding disreputable people discussing unsavory acts, but actually find disinterested twenty-somethings discussing undiscovered bands.

As the night wound down, the group I was standing with was approached by this kid, Jake. He was 20, in college.

For a moment, I was dismissive. He's probably out of his depth, I thought. I hope he doesn't start asking a bunch of dumb questions.

And then I was angry with myself for letting thoughts like that into my head. I remembered how it felt when I asked Carl for advice, and how humiliated I was when he talked down to me and made me feel like I was too dumb to play on his level.

Don't be like Carl, I reminded myself.

Jake was outgoing, curious, personable. He asked a ton of questions, and the whole group joined in to answer them as best we could.

At one point I started giving him shit because he kept pulling his phone out.

"I'm taking notes on what you're saying," he told me.

This was both flattering and terrifying. This kid is listening to me? Is that... Should he be doing that?

But it felt good. Here was this kid: excited to learn, passionate about building a career, and looking to me for a little guidance.

Jake was an eager student. I was in a position to help him out.

I could have been an elitist asshole. I could have done my best to assert my superiority and make him feel dumb.

But it felt way better to help him out.

And Jake felt good about things, too; later that evening, I got a note from him:

Really great chatting with you, Jason. Super great life tips, I hope to be like you when I grow up!

There's Room for All of Us

Jake will end up being pretty successful. He's smart, ambitious, and he's got a head start on his career. He's years ahead of where I was at his age.

So should I worry about Jake replacing me?

Maybe. But at least now I can remind him that I was a helping hand on his way up, and hope that he'll give me a job when he's in charge.

[^montana]: During the early 2000s in Montana, there were approximately seven people who knew what the internet was.

[^perspective]: For the non-nerds in the room, let me try to put this question into perspective. Imagine you're curious to know more about engines, and you ask a mechanic how what you should do to learn more about cars. In response, he says to you, "What's the difference between using a horse to pull your carriage, or using a donkey?"

The Stories We Tell Ourselves

Fri, 12 Sep 2014 00:00:00 GMT

I don't regret anything I've ever done that I saw through to the end. I only regret things I left unfinished, or never started at all.

The Journey Is the Story

If I tell you that a guy named Billy Ray Valentine was a successful investor and made a killing in the commodities market, you probably won't bat an eye.

Whatever, right? Lots of people are good at their jobs.

But if I tell you that he came from the gutter and got his job on a bet, things get a little more interesting.[^trading-places]

[^trading-places]: If you want to know Billy Ray's full story, watch the documentary.

A Good Story Isn't About the Ending

We all love a good story. But it's too easy to mistake the ending for the whole story.

The journey is what makes a story good. It's the details. The twists.

Because of this, stories don't have to end well. Heroes can lose. Main characters can die.

We'll allow any ending, as long as the story is good.

Our Lives Are a Collection of Short Stories

Even if we don't sit around at dinner telling tales, our lives exist as a series of stories. We tell these stories to ourselves, to our friends, to potential employers.

We spin our stories and use them to create little vignettes of who we are and what we value.

Strangers use them to make us real.

Our stories are the only part of us that anyone else really touches.

Every Good Story Has a Follow-Through

But, even though the guts of a story lie in the journey, every story still needs to end.

And it needs to really end.

If the plot of Cool Runnings was the story of that time Derice Bannock was accidentally tripped by an opponent in the 1988 Summer Olympics qualifier before giving up on his Olympic dreams, the story would have felt incomplete.

Instead, Derice took his failure and pushed onward — and ultimately failed again, sort of — and it makes for a great story.

It's Up to Us to Make Our Stories Good

We have a choice with every story we begin: "Am I going to see this through to the end, or am I going to give up and leave the story unfinished?"

When things get difficult, we can always bail and walk away. And sometimes that's how a story needs to end.

But for every story we leave unfinished, we're building a narrative around ourselves. Are we leaving more stories unfinished than we're seeing through to the end?

What Do Your Stories Say About You?

When you play back your stories in your head, do you feel good about them? Or do they feel like a collection of half-finished anecdotes?

The good news is that — regardless of how your stories read so far — you're in the middle of a few stories right now. And you'll start new stories in the future.

Try to make them good ones.

Do Men Have Best Friends?

Wed, 27 Aug 2014 00:00:00 GMT

I have a best friend.

To say that feels weird. I'm almost thirty; thirty-year-old men don't have "best friends".

They have drinking/golfing/hunting buddies.

They have their wives' friends' husbands.

But they certainly don't have a Bee Eff Eff.

Yesterday I read Stephen Marche's article for Esquire about the abuse of the word "bro". I thought it was going to be a silly piece about pop culture, but then I ran into this line:

To mature as a female person is to mature into female friendships. To mature as a male person is to mature out of male friendships.

There's a sort of shyness I've felt about telling anyone that I have a best friend. It feels roughly equivalent to admitting I still sleep with a nightlight or that my mom still packs a lunch for me every day.

Having a best friend feels like kid stuff. It feels like something I should have grown out of.

Nate and Jason, the Best of Friends

I've been friends with Nate since we were eleven or twelve, when his family moved in down the street and our moms set us up on a play date.

We did all the stuff boys do: played Mortal Kombat[^fatalities], shot our little brothers with BB guns, pretended we were the Harlem Globetrotters.

[^fatalities]: What I mean by "played" is that I would mash buttons while Nate and his little brother would expertly and brutally murder my character because they knew all the special moves and fatalities. All of them.

Nate and I were opposites in a lot of ways, but we both felt like outsiders — Nate because he didn't quite meet the criteria of any clique, and me because I was in the midst of several simultaneous identity crises — and that held us together.

Our opposite tendencies were complementary: I did Nate's homework; Nate convinced the cute girls at the beach to hang out with us.

As adults, Nate and I are still opposites. We still complement each other well personally, and now we're able to help each other professionally.[^symbiosis]

[^symbiosis]: I work with Nate to help him implement a lot of his projects that have a design or tech component, and Nate helps me with marketing and networking.

We All Need a Sounding Board

Complementary skill sets aside, Nate and I have helped each other in another, less tangible way: over the course of nearly twenty years of friendship, we've had hundreds of very frank, very honest conversations. The kind that most people have to pay a psychiatrist for.

Being able to discuss the things that scared us — being able to be 100% vulnerable, in other words — has allowed us to work through the source of many of our fears and troubles, which has ultimately led to both of us becoming more aware of our internal motivations and the things that trip us up. We're both better people because of it.

I'm Going to Get So Much Shit for This

Yesterday Nate and I were discussing our most recent challenge to each other: write for at least thirty minutes a day and post whatever comes out on our blogs.

I shared one of Nate's posts yesterday. He mentioned that he was planning to share one as well.

We both got uncomfortable.

Was it weird that we were publicly giving each other so much attention? Would people make fun of us?

Why did we both feel that way? Everyone who knows us knows that we're close, and neither of us is ashamed of being friends with the other. So where does this apprehension over talking about our friendship on the Internet come from?

Hollywood Hates Dude Friends

Stephen Marche argues that pop culture is poisoning the idea of male friendship:

The splendid isolation of masculinity has emerged from so much iconography—the cowboy, the astronaut, the gangster—that almost every hero in the past fifty years has been a figure of loneliness. Current pop culture is even more extreme: It doesn't just celebrate the lonely man; it also despises men in groups.

Marche claims most movies and TV shows show groups of men being idiots. The Hangover, Dumb and Dumber, How I Met Your Mother all paint the idea of male friendship as a way to bring out the least intelligent parts of men.

It's hard to disagree.

And it explains why I feel apprehensive talking about having a best friend.

Do You Have a Best Friend?

I wish I had a solution, or even a suggestion for a solution to the problem. I don't.

I do know that — despite being uneasy saying it out loud — having a close male friend has been one of the most beneficial things in my life, both growing up and as an adult.

Do you have a best friend? Does it feel weird to talk about?

If you don't have a best friend, does it bother you?[^honest]

[^honest]: I'm genuinely curious, not baiting.

Take Away Its Power

Mon, 25 Aug 2014 00:00:00 GMT

At a sleepover in second grade, my friends put on The Blob — a horror film about space jelly that kills anyone it touches. I was so scared I started crying and my mom had to pick me up to take me home.

Another night I snuck out of my bedroom while my parents watched TV, and I saw the sewer scene from It. My dad had to remove everything that even sort of resembled a clown from the house.

I Wasn't Scared of the Story

In both cases, I actually barely saw any of the movie that frightened me. I saw that the movie was a scary movie, I knew that scary movies terrified me, and I knew that watching a scary movie would scare me too badly to be able to sleep.

What I didn't realize, however, was my fear of horror films — and the fear I felt when I imagined what terrors those films might contain — was all it took to ruin my day.

I was scared of the movies themselves. The idea of the movies.

It was so bad that I only had to see the cover of Child's Play in a video store to end up petrified and sleepless for a few nights.

Find Out How It Ends

As an adult, I still don't care for horror films. But if I start watching one, I now force myself to finish the movie.

When I see a scene from a horror film — just like I did when I was a kid — I build a vague, terrifying beast out of my fear of the movie, and this unknowable shape is more monstrous than anything I'll see in a movie. I don't care how good the CGI is.

I have to see the end. I need to know what happens. What really goes on in this movie?

There is no way the actual outcome will be scarier than what I can dream up in my ignorance.

By seeing the full movie, I learn the reality of the story, and that takes away the paralyzing power of my ignorance and fear.[^the-ring]

[^the-ring]: Sure, The Ring still scared the shit out of me, but I didn't lose any sleep afterward. I can guarantee the things my brain will dream up out of a storyline involving a dead girl who haunts your TV are far worse than what happens in the movie.

Take Away Its Power

Most of our fears are imaginary.

We don't know what comes next, so we make projections about the future. And in our imaginations, the potential for catastrophe is alarmingly high.

But we're not actually scared of the experience. We're scared of the unknown: the vague, monster-shaped outline in our imagination.

By facing that fear, we replace the monster with a memory. And even if the memory is uncomfortable or humiliating, it's very unlikely that it will be as horrifying as the make-believe nightmare scenario we dreamed up before.

Shining a Light into Monster-Shaped Shadows

To take power away from your fear, give it a name.

In an effort to limit the number of monsters occupying my headspace, I try to push my fears into reality and name them.

Am I feeling anxious about a client who seems unhappy with my work? Call them and clear the air.

Is there an unresolved tension between me and a family member? Let's sit down and get to the bottom of things.

Is my laundry room haunted? Let's go stand in there and find out.

Whenever I notice a situation that scares me, I try to jump in earlier rather than later, because the end result is always the same: I face the fear and realize the difference between what I thought was wrong, and what was actually wrong is staggering.

What I thought may have been a relationship-ending issue with the client turned out to be a few small adjustments and ten minutes of screensharing to show them how to use a tool.

After a beer with the family member, we realized we were both working toward the same goal even though our methods were clashing.

My laundry room is creepy as shit. But it's not haunted.

Once a fear is dragged into reality and exposed to a little daylight, the giant monster-shaped shadow in my imagination shrivels to a small, silly bit of information.

Name Your Fears

What monsters are lurking in your imagination right now? How many of them can you drag into reality?

Take a Break

Sat, 23 Aug 2014 00:00:00 GMT

On Thursday I took a break. A real break.

I met a few of my friends for brunch at 10:45am in Toronto. When the meal ended, we weren't ready to call it, so we relocated to coffee shop and kept our conversation rolling. Then we were hungry again, so we grabbed lunch, then beers at a brewery. After the brewery, dinner. And an ice cream sandwich to wrap up the evening at 10:30pm.

Twelve hours spent with friends. No electronics. No work. Just conversation.

This may sound like a waste of a day — especially if you consider that it was a Thursday — but would you believe me if I told you that I was more productive than usual this week?

If I Look Away, This All Falls Apart

Disconnecting is hard. When I'm not staying on top of email and checking in with my team at work, I feel like I'm cheating. Like I'm somehow letting myself and my coworkers down.

"If I look away, this all falls apart," I tell myself.

This makes the idea of leaving my phone at home terrifying. My chest tightens the way it would if I forgot my wallet or left the stove on — something terrible is about to happen.

My fear of the chaos that could happen if I wasn't constantly present led me to work an average of 10 hours every day in 2013.

Not Monday through Friday. Every. Damn. Day.

Setting Myself on Fire

My health and happiness suffered — mostly due to the high stress levels of never turning off — and I realized something needed to change. I suspected my work habits were the source, so I decided to experiment.

Since I'm not one for dipping a toe in, I decided to do it on hard mode. I went to Alaska for eight days without a phone or a computer.

No safety net. No escape hatch. I was there until my return flight, with no option to change my mind. Like it or not, I was disconnected and I was going to see the experiment through.

Here's what I thought would happen when I disconnected:

All of my clients would fire me
All of my projects would descend into chaos
I'd come home to the wreckage of my career
After sweeping up the shattered bits of my former life, I would move into my parents' basement
I would die poor, alone, and ashamed

Here's what actually happened when I disconnected:

None of that

I hiked, and relaxed, and had some time to reflect on how things were being done (rather than just focusing on what needed to be done next). My unconscious mind spun up and rolled ideas around, and I found the solutions to several lingering problems on both work and personal projects.

Everything was okay.

All of my fears were ridiculous and unfounded.

Doing Less Is More Productive

Turning off isn't slacking off. I'm giving the other parts of my brain time to work. This is actually better for productivity.

Additionally, when I work non-stop, I find myself moving slowly and wasting a lot of time idly checking email. I'm not getting more done in more hours; I'm just there, and it's likely I'm actually accomplishing less.

What should take three hours takes six because I don't feel any urgency.

With breaks, your work days become shorter. It becomes easier to focus. "I know I have to shut down by 3pm, so I'd better crank on this for the next four hours to make sure it's finished before then."

Since I've adopted actual breaks into my days, I have actually been getting more done in fewer total hours worked. It seems counterintuitive, but there's actually a mountain of research supporting this.

A Dare for You: Take a Personal Day

If you're feeling overwhelmed at work, or if you feel like your productivity is starting to flag, try an experiment: take a day off.

Plan a full day without your computer. Leave your phone at home. Shut off. Work less.

Is a full day too scary? Start small: take just two hours to leave your phone at home and spend time alone or with a friend without any electronic distractions.

You might be surprised at what you're able to accomplish.

Your Taste Doesn’t Matter

Mon, 31 Mar 2014 00:00:00 GMT

Anyone who knows me knows that I love a good cup of coffee, and that my first order of business upon arriving in a new city is to locate the best barista in the area.

Good coffee is important to me.[^marco-arment]

[^marco-arment]: I spun off on a tangent and wrote this article after reading Marco Arment's article, Throwing K-Cups In Glass Houses.

My dad, however, doesn't give a shit about coffee.

He loves a good cup every now and then, but most of the time he drinks K-cup coffee or — gasp! — instant Folgers.

This used to bother me.

Fighting the Urge to "Fix" My Dad's Taste in Coffee

But here's the thing: my preference in coffee only matters to me. His preference in coffee only matters to him. And the little bit of overlap when he drinks my kind of coffee, or when I drink his, just isn't worth the emotional effort of caring.

When I call my dad's preferences into question, it puts strain on both of us. He's defensive because I'm attacking something he's doing; I'm frustrated because he can't see how unbelievably, unflinchingly right I am; both of us start thinking of excuses to leave the room.

How Could You Possibly Like That?

It's easy to lose sight of what's really important in relationships. We all have a tendency to get caught up in a little cloud of "my way" that makes opposing viewpoints seem scary, stupid, irresponsible, ignorant, or any combination thereof.

But the majority of the decisions I make have zero impact on the people closest to me. If I'm not into Parks & Recreation, it doesn't make any difference[^mustache] for my friends who love that show; if I don't see the appeal of running a marathon, it doesn't mean anything at all for the people who embrace the challenge.

[^mustache]: Except that I don't understand half the Ron Swanson jokes they make about my mustache.

More importantly, the opposite is true: my friends' decisions don't actually impact me. Yes, I would love it if all of my friends loved whiskey and talking about business development. That some of them don't means nothing within the scope of my experience; I can still enjoy whiskey, even if Chelle prefers tequila.

Getting worked up because things that don't affect me aren't done my way is a shortcut to an extremely frustrating and deeply dissatisfying existence.

You want to know how to solve all your problems? Just be a little less like you, and a lot more like me.

I used to start a lot of monologues with the phrase, "You know what you should do?"

I'd listen — for a few seconds, at least — to someone's experience, apply my own tastes to it, then harangue them about all the ways they were doing it wrong. In effect, all I was saying was, "Do you even know how much easier your life would be if you were just more like me?"

This is something I always hated in other people: they'd just start telling me how to solve problems that didn't exist.

What I was ignoring, though, is that I'm just as annoying when I force my taste onto others.

My taste doesn't matter. At least not to anyone but me. (And neither does yours.)

Just Shut Up and Drink the Shitty Coffee

I could get offended by my dad's ambivalence toward a thing I care about. I could try to convince him that he's wrong, and that his decision to drink awful coffee is somehow linked to his happiness and overall wellbeing.

And when I visit my parents and my dad serves me K-cup coffee, I could throw a fit and refuse to drink it. Or I could bring coffee with me and supplant his morning coffee ritual with my own.

But I don't.

Instead, I drink coffee with my dad. Because as long as I’m spending time with people I love, it doesn't matter if the coffee is terrible.

A Guide to Drinking for Adults

Fri, 17 Jan 2014 00:00:00 GMT

In my younger days, I had mixed feelings about going out for drinks. Lately, though, I love bellying up to the bar. Just not the way you might think.

"Let's hit the bars."

My younger, single self did bars differently.

We start at the trendy bar: we lean against the bar, Putting Out The Vibe so the cute girls in the bar will notice us, drinking Jameson and PBR to give us the courage to approach them. (We never actually approach them.)

Later, we grudgingly accept that drinking does not make us attractive. We move to the "cool bar". One of us starts buying shots for the others that nobody wants. The smoke is thick. We choose songs on the jukebox ironically; Lionel Richie asks the room if he's the one we're looking for. (He's not.)

At closing time, we're at the bar we swore we'd never drink in again, where sorority girls wobble like baby gazelle on their six-inch heels and frat boys circle like hyenas, ready to pick off the ones who get separated from the group.

The next day, we come to surrounded by fast food wrappers, nursing seventh-level hangovers, feeling greasy inside and out, promising ourselves we'll never do this again. (We will. Sooner rather than later.)

I'm Not Drinking Alone

These days, I love drinking. But I wouldn't call what I do drinking.

I know what you’re about to say, but stay with me.

I like to meet friends at bars and have a couple drinks. I do not like "going drinking".

(My friend Nate once argued, "Look, I'm not drinking alone — I'm having a cocktail by myself!" — this feels like an important distinction to me.)

So while I may be heading to a bar with the intention of having a cocktail, I'm never going out with the goal of getting drunk.

It's important we establish this early on.

It's Not Drinking, It's Research

I like learning about the things I'm into. Experiences mean more when we fully grasp the complexity of what's happening.

Cocktails caught my attention because they're a lost art that's been rediscovered in recent years. It wasn't all that long ago that bartenders enjoyed a similar level of respect as doctors and lawyers. Like any trade, a bartender who takes it seriously is on the level of an artist or chef.

Half the fun for me is learning how the Old Fashioned morphed over time to include club soda and muddled fruit[^prohibition], or that the daiquiri wasn't always a fruity Spring Break booze smoothie.

[^prohibition]: During the Prohibition they were introduced to cover the flavor of low-quality alcohol.

I could certainly learn most of this by doing online research, but half the fun in cocktails is learning about them from smart people.

How to Drink

When I go to a bar, I sit at the bar.

I want to see the drinks being made, and ask questions. I want to get the bartender talking so I can hear about the history of the cocktail I'm about to drink.

When I drink now, I go to Clyde Common at 4pm on a Monday and ask Junior endless questions.

I don't go during happy hour or on Friday night when the bar is packed and the bartenders are too busy to talk.

My best experience at a bar was in Rum Club after I was stood up for a 5:30 meeting. Bartenders from Expatriate and Broder Nord were there; otherwise, the bar was nearly empty.

I sat with a few of Portland's biggest cocktail nerds for an hour, learned about Aquavit and Angostura bitters, and even did a shotski[^shotski] with them.

[^shotski]: "Didn't you just spend 200 words talking about how drinking for the sake of drinking is bad?" Hey. Shut up. We were bonding.

I didn't just have a great cocktail or two; I had an awesome experience learning something new.

Let's All Have a Drink

The best part about learning all this is testing my knowledge by trying to make drinks at home.

One of the first things I really learned (from Daniel at Teardrop) was the proper way to make an Old Fashioned.

The Old Fashioned is a simple drink that dates back to before Prohibition. It follows a simple formula: spirit, sugar, water, and bitters.

You should find a great bartender near you and learn about this drink. If you don't have access to a great bartender, here's a video of Jeffrey Morgenthaler showing you how it's done.

Here's a variation I've been making at home recently:

2 oz Old Overholt Rye
1/4 oz honey simple syrup
2 dashes Fee Brothers black walnut bitters
Orange twist

This is basically an Old Fashioned, but each varied ingredient makes the drink just a little different.

You can make it with rum instead of whisky. Maple syrup instead of honey simple. Orange bitters instead of walnut bitters.

And these are all variations on just one style of cocktail. The depth of information here is incredible.

I Need a Drink

Drinking is something I regularly look forward to now. Just not the way I did when I was younger.

Gone are the days of pounding Irish whiskey and bar hopping to see if something exciting will happen. I’ve reached the age where a hangover lasts multiple days, so there’s not a whole lot of upside to getting drunk.

Instead, I look at cocktails the same way I look at code, business, art, and philosophy: it's a fascinating world to study, with a rich history.

And it's delicious. Also, making a good cocktail makes me feel like a cool chemist.

Tonight, I'll be making a drink. But remember: I'm not drinking alone; I'm having a cocktail by myself.

It’s All Jazz

Fri, 10 Jan 2014 00:00:00 GMT

I have a mantra. It's the metronome that keeps me from going into a tailspin when things go wrong.

It's my reminder to keep perspective.

It's all jazz.

It's simple. Almost silly. And it probably doesn't make any sense unless you're me.[^lecture]

[^lecture]: Or one of the people close enough to me that you've heard the lecture.

So, Wait. Jazz?

When you listen to jazz improv, the musicians are all working within the general framework of the song, but they each take turns making shit up as they play.

A good jazz musician will play something he's never played before — something he's literally making up on as he goes — with the kind of skill and ease that makes everyone watching feel as though it's a standard that's been thoroughly rehearsed.

And while it's incredible to watch, this kind of improvisation also has huge implications outside of music.

Plans, and How They Never Work Out

Every time I make a plan, it's virtually guaranteed that something will go wrong.

This used to drive me crazy. I'd develop a vision of the way things ought to go, and when they failed to go exactly right, I'd be angry, disappointed, and resentful of the outcome.

U Mad Bro?

It bothered me that I let myself get beat by a changed plan, so I started thinking about what it was that bothered me so much when a plan went off-track.

Most of the time, my plans went well. The outcome was really close to what I wanted. So what was the big deal?

I had set my expectations in such a way that only perfection would be considered a success.

Anger, fear, and disappointment happen when our expectations are violated. [^expectations] This meant that even when things went my way, I'd still be upset because they didn't go exactly the way I'd imagined.

[^expectations]: There's so much to be said about this — it really does explain almost every negative human interaction. Think about it next time you get mad: "What was I expecting here, and how does the reality differ from my expectations?" You're in for a serious moment of zen, mon frere.

The Art of Improvisation

Knowing this, I had two choices: I could A) accept that I'd never be happy and resign myself to a life full of disappointing, mostly-successful plans, or B) figure out a better way to plan that allowed for some wiggle room.

Of the two, the latter seemed more palatable.

After a large amount of trial and error, I finally came up with the jazz analogy, and built a new planning approach on two tenets:

Skip the Details
Expect Everything to Change

Skip the Details

Every plan is an effort to obtain a desirable outcome (e.g. "improve my client's online marketing," or "have a nice dinner with my friends").

My plans, however, didn't stop at the outcome; I'd work out which sides I would make to pair with the entrée, what games we'd play after dinner, and what cocktail I'd make to complement the meal.

Inevitably, one or two details would change — no one would want to play a game, or I'd forget to grab an ingredient for the cocktails — and I'd be upset that it didn't go according to plan, even though the dinner was a success overall.

By not worrying about the details, I'm free to focus on the outcome.

Something will go wrong. So what?

When it does, I adjust within the framework of the plan and make something up. We'll still get where we need to go.

Forget about managing the details. Just focus on getting the desired outcome.

Expect Everything to Change

This is another case of framing, which I've touched on before. If I enter a situation expecting only one outcome, I'm doomed to fail.

But if I expect that things will change and trust myself to adjust accordingly, my expectations are very hard to violate.

It's easy to get sucked into believing that if anything goes wrong, all is lost. But in most cases, the only person who knows anything is amiss is the person who made the plan.

Where plans actually get ruined is when the planner sinks into a funk and everyone else gets uncomfortable.

If the musician misses a note, but powers through and just keeps playing, almost no one will notice. But if he stops mid-song to apologize about the mistake, it becomes a big deal.

Just Keep Playing

Nothing I do ever turns out exactly the way I expect. But it usually goes pretty well.

All I can do is keep playing, and, with enough practice, maybe everyone will believe that — for me at least — it's all going according to plan.

See the Tree Coming

Mon, 06 Jan 2014 00:00:00 GMT

When I fail, I'm presented with a choice: do I learn nothing, learn one thing, or learn a life lesson?

Maybe that sounds ridiculous. Of course I should learn a life lesson, right?

Unfortunately for me, at least, learning something valuable from failure hasn't always been easy.

The Treadmill Treadmill

Let me try to explain with a story:

I struggled for years to stay consistent with my trips to the gym. I would get inspired, find a workout program, pick a diet plan, write a detailed daily fitness agenda, and start planning how I'd handle the attention once I became The Hottest Person On The Planet.

But, despite my initial optimism, I'd find myself feeling discouraged, making excuses, and eventually abandoning the whole idea.

I was failing. And I was being presented with a choice.

The First Five Times I Failed In Exactly the Same Way

At first, I made the choice to learn nothing.

I made excuses. I blamed external circumstances. I tried to convince myself that I was just better off ignoring my health.

I'd brush it off, the memory would fade, and eventually I'd start the cycle over again -- only to fail in exactly the same way.

I was learning nothing, and it showed in my embarrassing lack of progress.

The Next Five Times I Failed Creatively

After I recognized that I was stuck in a loop, I started choosing to learn one thing.

First, I learned that I wasn't very good at working out first thing in the morning. Then I learned I couldn't always make the afternoons work. After that I discovered that I couldn't sustain a chicken-and-steamed-broccoli diet like my bodybuilder friends.

Each time I failed again, I was learning one thing -- one precise set of circumstances -- that led to my failure.

The Last Time I Failed, I Learned

After repeating this cycle maybe a dozen times, I finally took a step back and thought about my situation.

Here I was, trying to stay consistent with a plan to make myself healthier -- what better motivation is there? -- and somehow I was failing every time.

I'd learned lots of "one thing" lessons, but I'd never taken the time to examine the root of the issue.

I was treating the symptoms instead of the disease.

So I analyzed, and I ultimately came to the conclusion that the common thread in all my failures was that I gave up after I made any mistake at all. If I missed a workout or had some ice cream, I felt like I'd ruined everything and just gave up.

I'm an "all or nothing" type. So when I made a plan, I had to execute it flawlessly or I was wasting my time.

So I learned a life lesson: I need to set my bar low enough that I can always hit my goal.

My plans started out as, "I'm going to do this huge workout and eat exactly these things." The simple lowering of that bar to, "I'm going to do something active every day and make sure I eat vegetables with every meal," has made it possible for me to always hit my goal, and as a result I've stayed consistent for nearly a year now.

To clarify, this doesn't mean that I set low expectations that allow me to skate by. I'm just adjusting the definition of "success" so that I can sustainably hit my goals. If my goal is "just get to the gym, even if you show up, turn around, and go back home," I've set the bar really low. However, while I've been to the gym and done a less-than-stellar workout, I've never showed up to the gym and done nothing.[^starting]

[^starting]: The big difference here is framing. Before, when I was failing, doing a quick workout because I wasn't feeling 100% would constitute a failure; now, I look at any workout being better than no workout. Get it?

I'm no picture of perfect human health or anything, but I can climb stairs without wheezing and I don't have any aches or pains -- that's all I really need to feel like I'm taking care of myself.

Finding the Source

Aside from the obvious benefit to my physical well-being, dealing with my failures taught me one of the most useful life skills I've come across yet:

When you fail, try to understand why you failed instead of just learning how to avoid repeating this one mistake.

If I run into a tree, I shouldn't just glare at the tree and then go about my day.

I shouldn't just make a note of where the tree is so I can avoid it next time I pass this way.

Instead, I should try to understand why I didn't see the tree coming in the first place.

In Practice

Beyond my fitness goals, this approach to failure has helped me in every area of my life.

It's helped me understand that when I lose clients, it's not because that client is beyond help or because I worded something incorrectly; it's because I violated their expectations, which put them on edge and started a downward spiral.

It's helped me understand that when I end up fighting with my girlfriend, it's not because she's irrational or because I'm too detached; it's because I made her feel attacked, or unimportant, or a similarly unsavory emotion.

This applies to dozens of other examples that I could have brushed past as one-off incidents (or worse, forgotten entirely). Each failure gives me a little window into how I'm perceived by others, or how I'm wired, and it allows me to "hack" my personality -- I can see certain trees coming and avoid them.

I'll hit hundreds more trees -- thousands even -- as I continue to grow and learn and fail, but if I'm doing this right, they won't be the same trees all that often.