😈 Productive Procrastination

• 4 min read

A few years ago—while trying to get Insomnia off the ground—I took some time to “modernize” the codebase by updating its import statements to the new ES6 syntax. Here’s what it looked like.

// Old way
const http = require('http')

// New way
import http from 'http'

It’s a simple conversion, but there were hundreds of imports and I knew there would be bugs if I edited them by hand. So, I came up with a clever set of find-and-replace macros to reduce the amount of manual edits, then got to work.

After a few hours of keyboard kung fu I was done, and I felt so productive! I started with a difficult problem, came up with a creative solution, and finished in less time than expected. Amazing! ✨😃

Procrastination in Disguise

Don’t get me wrong, sometimes it’s nice to sprinkle an easy task here or there for the sake of enjoyment, but that’s not what was happening; this was a pattern I’d been repeating for months before realizing it. And, once I did, the course-correction quickly backfired.

Instead of replacing the easy tasks with more meaningful ones, I simply switched to a different kind of procrastination—an unproductive kind—distracting myself with Twitter, Google Analytics, and Stripe. I was no longer getting anything done. My subconscious was doing everything in its power to prevent me from moving forward.

So why was it so hard? Why wasn’t I able to stop procrastinating and focus on the big picture items? It was because my fear of failure was more powerful than my motivation to succeed. 🤯

You see, growing a company is about placing the right bets at the right time. Most of them don’t work out, but eventually some do, resulting in positive growth. The problem with placing so many bets, however, is that most of them end in failure. And, while failure is manageable the first few times, it really takes a toll if it keeps happening.

So, after trying many different things to grow the company, it seemed like there was nothing left that I could try. I started believing the problem was with me—that I was the failure—and that maybe I just didn’t have the skills to succeed.

Finding Productivity Again

After a few months of struggling to motivate myself, I decided to take a break. Hoping to gain some new perspective, I started drawing again, developed an exercise routine, and even tried recording a podcast. And you know what? That simple shift changed everything.

I didn’t end up sticking with any of those hobbies in the long run, but they gave me something else to care about. My identity was no longer tied to the company, allowing me to rise above the emotional fog and see the big picture.

After nearly a year of cycling between productivity and procrastination, I was able to get back on my feet. It turns out that the problem wasn’t me, after all. The problem was perspective.

Building a company is just hard and there’s no silver bullet to help get through it—mistakes and failure are guaranteed. However, I have come up with a few tips and tricks along the way.

So, if you’re ever struggling like I was, give some of these a try:

  • Don’t associate your project with your identity or you’ll go down with the ship
  • Break down ideas into smaller parts so you can fail (learn) faster
  • Read business memoirs like Shoe Dog or Chaos Monkeys to realize that it’s just as hard for everyone
  • Realize that it’s okay to feel demotivated, sad, or inadequate sometimes
  • Start going to therapy (there are some good online ones)
  • Keep a journal to reflect on the past and plan for the future
  • Ask for help from your friends and family and be open about your struggles

And my final tip is to try not to care so much. ❤️

At the end of the day we’re just typing keys on a keyboard. Keep learning new things, enjoy the people around you, be grateful for when and where you were born, and keep moving forward. Personal growth is a long journey that has no end, so try to enjoy every step along the way.

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