Failing sucks, but it doesn’t have to

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Takeaways

  • Don’t attach your self-worth to the outcome of your work.
  • If you set out with a goal, you have a single success state against a multitude of failure states.
  • Don’t think in terms of goals. Think in terms of experiments, little bets, and iterations.
  • You can never fail at running an experiment, because every outcome teaches you something.

Five weeks ago, I set out to publish one post per day, Monday to Friday.

I had in mind a beautiful hand-drawn illustration for my “lessons learned” post. A 5-by-5 grid of green checks.

It went well for the first three weeks. Then during the fourth week, after a sleepless night with my little daughter, I missed a day. In the fifth week, life got in the way again, and I missed two posts.

I had failed.

I had failed and was pretty bummed about it. All sorts of self-doubt and unhelpful self-criticism bubbled up in my mind.

All of which were unnecessary.

No one got hurt, and it’s not like I had quit my job to start a daily blog. I had placed a little bet, and it didn’t play out. No big deal.

I went back and checked the first weekly digest email I sent out. It started with: “Hi friends, I’m running an experiment this month. I aim to write a post every day, Monday to Friday.”

Somewhere along the way, I went from “I’m running an experiment” to “I’m the five posts a week guy.” I made the mistake of attaching my self-worth to the outcome of what was supposed to be an experiment. Ego entered the playing field, and when that happens, things are bound to get messy.

You and I are more than the work we produce. Our posts might fall flat, our business ideas might find no traction, our pull requests might get rejected. But those are discrete events occurring to discrete manifestations of part of ourselves. They don’t speak for the whole of us.

When you obsess on a goal, you set yourself up for unhappiness. “Goal-oriented people,” writes Dilbert creator Scott Adams in How To Fail At Almost Everything And Still Win Big, “exist in a state of continuous presuccess failure at best, and permanent failure at worst if things never work out.”

My true failure was going from experiment to challenge. A challenge has a goal and has a binary state of success or failure. The only way to complete the challenge is to reach the goal; every other state is a failure.

An experiment, on the other hand, is a learning game. You can’t lose at a learning game. Every moment you spend playing, you are learning something.

Goal-oriented me failed at publishing five posts a week for five weeks. It doesn’t matter that he got 88% of the way there, with 22 posts instead of 25.

Learning-oriented me won. The experiment delivered plenty of learnings. First and foremost, it taught me a five posts per week schedule is not sustainable.

Adopting a learning mindset allows us to go beyond the binary success-failure state and obtain insights from every experience.

For example, none of my existing subscribers, to whom I sent only weekly digests, opted in to receive daily posts. Moreover, some of the new subscribers, who received daily emails, asked to switch to digests. Those are strong indicators that my hypothesis that a daily drip of content would be attractive was wrong.

It’s never nice to be told you are wrong. Yet, even if it doesn’t feel good, it is a good thing. Discovering you were wrong is an opportunity to make things right—or at least less wrong. Error correction is the only way towards improvement.

I published on a wide range of topics. Posts like Hybrid Work Doesn’t Work and Three Tips To Get Started With Deep Work touched on workplace productivity. Other posts, such as How To Cut Through The Crypto Noise and You Don’t Have To Have An Opinion, were more about extrapolating lessons from current events. Using page views as a proxy for interest, I learned that my writing is more appealing when it’s about applied productivity advice. I’ll save the philosophizing for my journal.

My failure at shipping twenty-five posts actually won me many insights. It gave me valuable feedback, which I’ll feed into my next iteration. I might “fail” that one, too, but by now, I know failure is in the eye of the beholder.


Failing sucks, but it doesn’t have to.

According to Naval Ravikant, “which games you play is more important than how well you play them.” When you play a goal-oriented game, you have a single win condition and countless failure possibilities. In a learning game, you always win because no matter the objective outcome, you always learn something.

The good news is most goal-oriented games can become learning-oriented games. The trick is to make learning the goal.

Play the game of learning and you’ll never lose.

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