Learn to Fail

When you start a company, failure is anathema. It's also the most important thing to learn to do.

Take Two

Learning to fail is a far more valuable skill than learning to succeed. You can’t truly understand the latter until you’ve mingled with the former.

There was a time I thought Footprint was going to fail. I remember the moment viscerally. Laying in my parents’ bathtub at their apartment. Listlessly. I had sat for so long, the water had gone from hot to lukewarm to cold.

It doesn’t really matter that I was wrong. It doesn’t really matter that, I suppose, I still could have been right – just many years too soon.

What matters is that I had never actually stared at failure. And as a result of that, and a culmination of other unhappy habits, failure was much bigger than the moment. It felt like an invalidation of my life. Milestones were stepping stones to some ultimate goal. Success would beget enough success to find that. Even one disruption to that pre-defined journey would topple the whole tower. I was so afraid of failure because failure was this gigantic obstacle. When you never learn to fail, you overestimate its impact.

Another element to this is changing your definition of dreams. Another way to view failure is the disruption of you accomplishing your dreams. Failure wasn’t just a bad moment, it was a force working against my inertia. But, I think both of these relationships must be evaluated. And the one with failure likely will be a pre-requisite to examine your dance with dreams.

Life feels different now.

I don’t look to our Series B next year as the milestone I need for happiness. Nor the milestone I need for success. I find happiness in the journey. I don’t view the potential to not achieve future milestones as failures which would invalidate the whole journey.

Success in the elements and parts of me which make both today and tomorrow possibilities. I’m also not sure if I would have gotten there if I never had moments where I wasn’t sure about my ability to reach the next milestone. It’s not that the concept of failure makes you accept failure. It changes your relationship to the definition of failure. It’s less nebulous. More tangible. And by being more real, failure can metamorphose from a monster under your bed to a made up phenomenon.

You’ll note that the start to this essay is titled Take Two. You may have wondered why. You may have also not taken stock. Or, you could be wondering why I have switched to second person narration. All would be fair responses!

It’s because this is my second attempt to write about failure.

Take One

There are a lot of bad reasons to start a company. I’ll write about them soon. But before I try to talk you out of those reasons, some people may be past the starting line. And may be wondering what to do next.

I recently saw a friend at a party. He had wanted to start something. A few weeks in, he had been hit with a realization many feel after the initial honeymoon period: building is tough.

“Will it get easier?” he asked, looking to me for comfort.

I paused.

“Probably not.”

“Why do you sound calm in saying that?” He had noticed the dichotomy between my tone and my words. “Because you’ll learn to fail.”

Let’s be honest, most young people who start companies have never failed. They’ve gone to good schools. Gotten a cushy job out of school. Their imposter syndrome in part stems from having never had a chance to respond to failure. Whether aware or not, they have no clue how to actually face adversity.

Not stemming from a midterm. Or a deadline for a client. They’ve been successful. This was the next step. Everyone in their life also assumed it was their next step. In the eyes of others, they’re the one who is to go do something even more ambitious. More difficult to others, but not to them.

They think a lot about others. The folks whom they would like to continue to view them in such light. And the folks whom they think have done whatever they want to do.

Those who hold you in high regard will likely always do so, regardless of the outcome of your B2B SaaS co (so long as you don’t get 30 Under 30 and promptly head to prison, but even in that scenario they’ll still think you’re smart!). The professional mentors know building is hard. That success is based on luck in many ways. That it is equal measures the painter and the supplies they were given at the shop.

Failure is the guaranteed gift of starting a company. Staring it down. Will you make payroll during a bank run? How will you tell the team you couldn’t raise a round? What happens if you miss numbers a second quarter in a row?

Because when you contemplate these answers, you can go two directions.

One: the world is melting. A crescendo of ensuing bad. My company won’t be successful. I’ll never become rich. It spirals. Will never find happiness. Will never find love.

Or, you can view it through a less binary lens. The things you want for vanity likely won’t be changed that much. The chances of you getting them won’t be all that altered by things which seem big in the moment. Those will happen because of you, the person. Not due to one fund raise. Or one hire. Or one sale.

In fact, investors like second time founders who have had to answer these questions. Who encountered failure and came back a second time. They have learned many lessons. One is how to genuinely not be scared of failing. When you’re scared of failing, you get desperate. You think short term. You play to not lose. You flail.

When you play to win, you take risks. I think founders—people in general—all take fewer risks than they should. Because they over-estimate the negative ramifications of the risks and under-estimate the positive expected value.

You don’t need to start a company to learn to fail. In fact, contrary to what I said, founders have “failed” at many things before starting companies, they often just didn’t view it that way in their minds. Failure, like happiness, is a construct.

Reflection on Takes One and Two

As you’ll see, Take One is far less personal. I was afraid of the failure I would face if I couldn’t accurately reflect my emotions. Or feelings. But even if I can’t really describe that moment, I want to publish Takes One and Two. To show you that it’s okay to fail. To show you that when you end up in the bathtub, you’ll trust me more because I shared my experience instead of just giving a pedantic lesson about some anonymous conversation I had at a party.

And when you get there, I hope you smile. Heck, I hope you laugh. Promise me you’ll laugh? Then grin. Take stock of whatever objectively dumb thing drove you to question everything. Then take stock that you’re in a lukewarm bath tub and agree that the first success you owe yourself now is draping yourself in a towel. Once ensconced in Turkish cotton (or Egyptian cotton; I don’t judge your bathroom accessories), you may get back to being sad. And mourning. At this point I won’t ask for a wry smile or even a chuckle. But I ask for gratitude to yourself.

You put yourself in a position to fail. Do you realize how few people actually do that? And do you realize how much more confident you’ll be the next time you do that, regardless of outcome? Because you sat in the tub. You saw everything flash.

And flash I did. I saw a future of no love. Of family and friends no longer believing in me. Every stupid belief I saw. It was dumb but it was my truth and I had to laugh about it and cry about it and reflect on it.

That is why failure is a super power.

Don’t desire to get back there. Don’t let it fuel you. Don’t go for revenge. Just learn from the feeling. Not how it brought you down. How it actually did not impact you half as much as you expected. It didn’t destroy you.

I don’t find failure motivating. I used to be afraid of failure. But I wasn’t motivated by not failing, I was motivated to achieve what I thought I would get if I did not fail. This view was wrong. Both in that failure is not some binary thing. Where a bell is rung and you are paraded through the streets. And at the same time, success is not binary. If you don’t fail, that does not guarantee all of your wildest dreams come true.

However, when you’re able to act without fear of failure. Either because you no longer view those milestones of success as so binary, or because you’ve seen failure isn’t so bad. Or both. Well then you’re going to succeed a lot more.

This obviously applies in far more to life than starting a company. A Substack went viral last week encouraging men to walk up to more women in person. The core thesis? Not enough try, too confident they’ll fail and afraid to take the chance.

This is true in sales. In marketing. Heck, in getting adventurous ordering at restaurants. The best things come with risk of failure. Build a portfolio of things that may fail.

We spend most of life avoiding failure as if it’s a threat to our identity. But the truth is, it’s the only thing that ever teaches us who we are. Once you stop fearing failure, you stop mistaking comfort for safety—and that’s when life actually begins.