Become the kind of person who fails

Become the kind of person who fails

Or, how I became an expert at sucking


In April, I stepped down from a job I’d held for just shy of two years.

Out of respect for the many good people who work there, I’m not publicly discussing the reasons I left. That’s not the point of this post.

Instead, today will be about how we talk—and don’t talk—about failure.

What we communicate when we don’t talk about failure.

Some backstory:


I’d been hired into that job to accomplish a few things—exciting things, hard things, things I couldn’t wait to sink my teeth into. I took the post believing I could engage in consequential work, in a field I love, with people who themselves were up to their elbows in world-changing activities.

Twenty-two months later, I boarded a westbound plane and left the job behind.

When I talk about these last two years to my friends, I often use the word failure. “I failed to accomplish things I wanted. Heck, I couldn’t even work out the entire length of my contract,” I’ll say.

Invariably, they bristle. “Wait, wait, wait,” they’ll retort, “the whole thing was an unwinnable situation from Day 1.”

Or they’ll try a softer tack: “Sometimes things just don’t work out, and that’s ok”

Or they’ll point the finger at Covid: “Going to a new country, for a new job, in the middle of a pandemic is an insanely difficult task.”

No one has yet to agree with me. No one says, “Yup, you’re right. You failed.”

And that—that aversion to, that dread for the word failure—that says a lot.

How I became an expert at sucking

If you’ve read my book, you know that I’ve spent a few years competing on American Ninja Warrior. (Side note: the nerdy, shy, sixth-grader that still lives inside me remains shocked at that).


My decision to try out for ninja warrior came in the way that all bad decisions do—after midnight, while watching YouTube videos.

A rock climber for six years by that point, I watched as climber after climber made a meal of the obstacle course. And I thought, “Clearly, it can’t be that hard.”

I promptly googled “How to apply for American Ninja Warrior,” answered eight pages of invasive questions, made a three-minute video, and—three weeks after the producers called to officially invite me to the show—I stood at the starting block.

Turns out, it was that hard. And an obsession was born.

Until I completely destroyed my right knee falling off an obstacle in 2021, I thought of little else. I worked during the day—and I ninjaed at night.

I became obsessed with the feeling of flying through the air, with the challenge of balancing on things designed to trip you up (even if they do destroy your knee in the end), with the crazy things I asked my body to do—and with the way it eventually complied.

Most of all, I became obsessed with the incessant mental fight that ninja requires, the Jacobean struggle against chattering mental voices telling me I can’t do it.

These voices would point to mountains of evidence. As a solidly mediocre ninja athlete, I’ve fallen off every obstacle and onto every part of my body. I’ve sprained, strained, and now broken things for how hard I’ve failed at this sport. Like this:

And, through it all, I’ve fallen in love with failing. I also believe you should too.

We fear failure, because of the implication

By any objective accounting, that job was a failure. I didn’t accomplish the things I’d wanted to do, the things that I’d been asked by my bosses to do. I left early, having achieved some things, for sure, but far less than I’d hoped.


By any objective accounting, I also fail at ninja all the freaking time.

To ignore these incontrovertible facts, to ignore the fact that, sometimes, we just fail, does us a tremendous disservice.

That doesn’t stop us from trying to ignore it, though. We hate the word failure. We avoid it like (some) people avoid plagues.

I suspect we do so because we conflate failing with being a failure—and we’ve decided that being a failure is a bad thing. But is it? Is it truly bad to be the kind of person who fails at things?

It is—only if we believe that failure, in and of itself, is fundamentally bad. Being a failure only becomes morally suspect if we assign a normative value to the act of failing.

Become the kind of person who fails at things

Why should we? Calling failure “bad” ignores the fact that, no matter how hard failure hurts, no matter how deeply it sucks, it does two absolutely spectacular things for us.

First, failure points us to our values. We can only fail at things we want to succeed at.

Take, for example, somebody with social anxiety. Those of you who, like me, are familiar with the creeping panic of large groups (especially—dear lord!—if we’re expected to participate) will often critically assess how we performed after social gatherings. More times than I’d like to admit, that assessment is negative. I am, after all, not an extroverted man.

But why does that even matter? Why would I even give a passing thought to performance at social gatherings?

Because I can only fail at things I value. Think about it: if I didn’t care connecting with people, care about friendships, care about developing a community, then I wouldn’t even have social anxiety in the first place!

I get anxious about social gatherings because I value human connection.

Second, failure pushes us up against the edges of what we know. Take, as another example, our daily routines. There’s nothing wrong with routine, per se, but if we peek under the hoods of our routines, we might find that we stick to them not because we’re truly passionate. Rather, we stick to them because they’re safe.

We know how to do our routines. We know we can meet their demands.

We may not particularly enjoy our day-to-day, may not have a passion for it. But we live with it because we’re sure we can do the things it asks of us.

In other words, we can’t fail at it.

Which means that if we’re failing, we’re upending our routine. If we’re failing, it means we’re trying to do something we don’t—yet—know how to do. Failure is a green flag of sorts: in this thing, in this part of our lives, we’re a beginner again.

Failure means we’re trying something we care about, something we don’t yet know how to do, and, as a result, something that can’t but expand our lives.

Instead of fearing it, fall in love with failure.

And that’s why failure is something to fall in love with.


I’m using that phrase — fall in love — absolutely intentionally. I’m not saying we should just start calling a spade a spade, just naming failure when it happens. We should do that, sure, but we can’t stop at simply admitting that we failed.

I also don’t mean that we should endure failure, grit our teeth through failure, meditate our way through failure, remind ourselves that the road to success is paved with failures, pretend away failure, disregard failure, hope that if we don’t acknowledge it then failure will go away.

No. I mean that we need to fall in actual, honest-to-god love with failure.To fall in love with the joy of growth, the wonder of exploration, and the satisfaction (and even the exhilaration) of being a beginner again.

Because of everything that failure gives us, become the kind of person who fails.

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