07 April 2023

The Zen and Art of Suffering: how being good at being miserable can make you a better founder

Max WalkerCo-Founder @ Piton Labs

Suffering is a learned skill, or at least that’s how people in the Mountaineering / Alpinism / Climbing circles talk about it. Of all the ideas I have been exposed to since the end of my first company, this one is the most intriguing, especially when viewed through the lens of a startup founder. I spent an awful lot of time being vaguely miserable, trying to find product market fit and get my company off the ground. Even though I may have put in 10,000 hours, they weren’t focused practice. I didn’t get any better at suffering.

Why you need to get good at suffering

The reason Mountaineers fixate on suffering is simple: climbing a mountain is a huge amount of work for an often small chance of a payoff. You spend a lot of time trying to get to the top and a lot of time trying to get down. Then, you probably stand on the summit for 5 to 10 minutes, only a few minutes out of days or weeks of toil and months and months of training. This is what we call “Type 2 Fun,” things that are only fun when you're looking back on them.

Startups are similar in many ways. While at times things may move unbearably quickly, most of the time they’re barely moving at all. Long hours of work appear to be pushing you and your company no closer to your goals. Like mountain climbing, startups are a slog and you’re often unsure of your own ability to succeed. It’s important to get good at this sort of suffering as a founder since it’s going to happen a lot.

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Simply quietly being miserable is not productive for your company and it’s really detrimental to your mental health

Before you accuse me of promoting a cut-rate version of stoicism, where everyone should just shut up and quit whining, I’m actually talking about the opposite. Simply quietly being miserable is not productive for your company and it’s really detrimental to your mental health. This is essentially what I did when starting my first company. I tried to just “tough it out” and this is a big part of why I didn’t get any better at suffering, even if I did it a lot.

How can you get better at suffering, and at running your company?

#1 "Why am I doing this?"

This is a question I asked myself many times when starting my first company as well as while trying to climb mountains. The thing I failed to internalize when I was starting my company is that I knew the answer. It’s the same answer when getting snowed on in the middle of summer trying to reach some summit. I was starting a company because I wanted to.

No one made me found a company. It was a path I had set for myself. Reminding yourself that starting a company is something that you want to do can go a long way to building resilience when faced with inevitable challenges. Once you get good at this, it will become a lot easier to bounce back when you hit the things that suck about starting a company.

#2 You can turn back

You have the option to bail. In climbing, knowing when to turn back is a critical, lifesaving skill. In startups it’s more about not needlessly dragging things out when they aren’t working. Before I decided to pursue an acquisition for my first company I spent a long time feeling like there was nothing I could do and I was stuck running the company. While I think you have some obligation to your investors, cofounders, and team there are definitely times where the right choice is to call it and move on. Our investors were surprisingly understanding of our decision to sell the company.

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If you’re at a dead end, there’s no point trying to flail around with a company that’s making you miserable

Even though this tweet was mocked, the core point is solid: If you’re at a dead end, there’s no point trying to flail around with a company that’s making you miserable and definitely not going ever make anyone money. Developing a sense of when it’s the right choice to give up goes a long way. Sometimes it’s not about giving up on a company entirely, it’s about letting go of things that aren’t working or adjusting your expectations. Maybe you aren’t making it to the summit today, but you could make it to that awesome lookout over there.

#3 Suffering is not a competition

Finally I’ve learned not to compare how bad a time I’m having to others, but instead to find people whose support I can rely on. Many times on a trek or a climb I will find myself getting frustrated by how much easier it seems for “that person over there”, which is not only unproductive but just plain silly. It ignores all the times I was the one who was casually walking up something that other people were really struggling with, and without getting too philosophical or preachy, really there is no fairness to what is easy or hard for different people. Them’s just the breaks.

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Find other founders and collectively share your suffering ... it will probably make you feel better.

A real game changer though for both entrepreneurs and climbers is to find someone to build camaraderie in your suffering with. I have been on a lot of outdoor outings where things were going so comically awfully that we had more fun joking about that than we were ever going to have on climb. Find other founders and collectively share your suffering and even if it doesn’t help it will probably make you feel better.

blacksmith
"Literally the best software engineers I’ve ever worked with, and they are really productive. I can’t recommend them enough, especially for the tough stuff."
Haytham Elhawary
CEO, KINETIC
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