Writing on bootstrapping, product, and web development

Quit Doing Stupid Shit

At one point in my time at CareerPlug, the company adopted a phrase that I said in passing a few times - “Quit doing stupid shit” - as a company-wide mantra.

Was that a great phrase for the company to rally around? Probably not.

Most office workers do some amount of pointless busy work in their day (some more than others, perhaps), but saying that out loud can rub people the wrong way. No one wants to hear that their bosses think they’re doing stupid shit!

In spite of the insulting phrasing, there’s a lesson to learn from the mantra.

After leaving CareerPlug, I’ve been reflecting on the events that led me to the end of my time there. Chief amongst those reasons was intense burnout. After ten years of grinding to build the business, my brain and body needed a break, and they told me that by breaking down.

By the end of 2020, I was constantly sick, my cholesterol was through the roof, I was exhausted, and incapable of focusing on anything for more than a few minutes. I got diagnosed with two separate autoimmune disease in Q4. Both diseases are genetic and weren’t caused by the burnout; however, I believe the timing of the emergence of symptoms is directly related to the burnout I experienced.

What caused the burnout? Doing stupid shit, repeatedly.

I didn’t follow my own advice, even as I pushed for my team and the company to focus on what mattered most. I did all kinds of things that didn’t need to be done and put pressure on myself to do more and more, even when I knew that I was doing things that were unimportant.

Why didn’t I follow my own advice?

  • Focusing is hard. Especially in a bootstrapped business when resources are extremely tight. There’s always something else to do, and only so many people to delegate to. I took on tasks to avoid burning my team out, and paid the price.
  • Pushing back doesn’t come naturally to me. I like to help people. Other people realized that, and got into the habit of coming to me to solve things for them. I didn’t do a good enough job protecting my time, especially in the early years, leading to me inheriting many low value tasks that couldn’t be delegated.
  • I was too optimistic. I committed to things that were not realistic because I believed we would find a way to get them done. I set outrageous deadlines, missed them, and then tried to push harder to make up for the missed deadlines.
  • I was unhappy. The work the I love doing is building. CareerPlug was no longer primarily interested in building. The company got bigger, teams began competing for resources, new product work became harder and more fraught. Every change was mentally taxing. The joy in the work went away and I tried to grind harder in response, despite the bad feelings.

What did I learn from burnout land?

  • Focus is a company-wide effort. If you preach focus at an individual level, but everyone has a different focus, no one will focus on anything.
  • Work towards clear, measurable outcomes. If you don’t, you will end up doing all kinds of work that has no impact on the business without having any idea what work matters and what work is worthless. If you don’t know where you’re trying to go, you won’t get there.
  • Being a short-term pessimist has advantages. Optimism is necessary to succeed in the long term - big wins come from big bets. In the short term, when it comes to delivery, being a pessimist gives you space to deal with unseen problems without blowing a deadline. Stay positive about the future, be pessimistic about what you will deliver in the short term.
  • Loving your work can carry you through hard times, but you’re on thin ice. I worked long hours for years without feeling the pain, largely because the work was energizing. Once the work was no longer energizing, I was in an unhealthy place with a rapidly depleting gas tank.

Moving on to the next phase in my career, I’m hopeful I will be able to identify burnout-producing busy work more effectively, for myself and, more importantly, for my company. Tune out the noise, focus on what matters, and measure the outcomes your work produces. Easy.