We love to talk about the times when things go well.

We enjoy showing how our well-laid (or even ill-laid) plans happen to work out just right.

Of course, it’s more fun to write about the good times. It’s easy to lay down a to making that first bold step, especially when that first bold step worked out so well for me; it feels like inspiration to trumpet out Just Do It! calls to action; it’s self-affirming to tell you to say “Yes” to your adventures; it’s gratifying to preach “leap and the net will appear.” After all, the net seems to occasionally appear for me. And so it will with you.

But what if the net doesn’t appear? What about the times when things go horribly wrong? What happens when we say “Yes” to our adventure, and instead of a glorious and romantic jaunt, we’re sent swirling down the shitter?


About a year ago, I wrote an Essay for The Escape School entitled . The Essay was about my decision to quit a job that was no longer serving me and my dreams, and to pursue a life that felt more meaningful. It’s one of our most popular essays to date, and by far the most popular one I’ve personally written for The Escape School. Over the holiday break, I was trying to dissect why it resonated so much.

One obvious thought is that quitting is core to our brand at Escape. While so much of what we do is about StartingThe Startup Tribe, the Startup MBA weekend course, our Do Work You Love career change workshop — Quitting is a logical first step before any sort of Start. It’s not always about quitting a job full stop. But it is always about quitting something, even just the little things that aren’t adding value to the life you want to live so you can welcome in new things that do. At Escape, quitting resonates.

Because if you think about it, isn’t “Escape” just the more positive, proactive and adventurous relative of “Quit?” The cool, fun young uncle who slips you a beer on Christmas Eve when you’re 12; the one with the wildest and funniest stories; the one who grabbed life by the horns and said, let’s ride. Not the one who opted out of life, but who instead opted in. Fully, richly, viciously.

As I wrote the Essay, the audience I had fixated in my mind was Escape the City members I’d met— the bankers, the lawyers, the consultants, any sort of corporate folk like my prior self who woke up one day realizing they’d drifted into their occupation due to…well, we didn’t really know how we ended up here. I was writing to those considering hitting reset, but who were still in the process of mustering up the courage, the excuses, the alibis.

I wrote to those for whom the spark was already lit. I just wanted to stoke the fire.

What I Talk About When I Talk About Mistakes

A major sticking point in that essay is the idea of Regrets vs. Mistakes. I referenced Jeff Bezos’s super nerdy Regret Minimization Framework — essentially, the thought process the man used when considering starting up Amazon.com:

“I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. And I knew that if I failed, I wouldn’t regret that. But I knew the one thing I might regret is not ever having tried. And I knew that that would haunt me everyday. So when I thought about it that way, it was an incredibly easy decision.”

I pressed further with my own thoughts:

Near the end of your days, when you’re 80, will your life be measured in the regrets of the things you didn’t have the courage to do, or of the mistakes you had the courage to make? Will your life be driven by the fear of potential regrets or the fear of potential mistakes?

Stoking the fire.

I managed to retroactively justify my own grand (yet when compared to Bezos’s, admittedly timid) plan to avoid an unlived life littered with regrets, and instead, blaze a trail more vibrant and adventurous. Potentially, a trail that could likely be splattered with more failures and mistakes than I was accustomed to making.

Which highlights to me another reason why this piece may have resonated. Underneath the surface of that piece is a certain rawness that isn’t literally spelled out, but perhaps felt. Maybe I was talking about something more than just our careers and jobs. Something deeper, all-encompassing and grander. Maybe I was writing a cryptic letter to myself.

Because in all stories, there’s the story. And then there’s the story behind the story.


Days after hitting publish, I’d be spending the next month of my life in a beloved Balkan city of mine: Belgrade, Serbia. Like many of life’s stupidest stories, it was because of a girl.

We had first met a couple years earlier while I was traveling around Northern and Eastern Europe on a . A oneway ticket to Iceland and a dozen random events later, I found myself in Belgrade.

It was a storybook romance inasmuch as I’ve experienced one. Eyes locked from across the room. A window of opportunity opened and was delivered to me on a silver platter. Of course, I’m an idiot, so I denied it. I was too shy to approach. The window shut. She disappeared, never to be seen again.

The universe gave me a second shot in a different hour, among different company, in a different end of the city. Again, the window was brief, but this time I seized it. We spoke briefly. Exchanged information. We made plans to see each other again. And then again, and again, every day for the next week until I had to leave Belgrade.

Eventually I went home. My sabbatical ended. Two weeks later, I quit my job. I started working on other things. Life went on.

But I couldn’t seem to shake her from my mind. I couldn’t deny the magnitude of which I felt something for her, with her. It was something I hadn’t felt in years. I’d hopelessly fallen for some girl I hardly knew. I had to go back.

As I considered booking a ticket back to Belgrade, I realized something else was driving me, a thing that felt an awful lot like that thing that drove me to book a oneway ticket to Iceland and experience the very adventure that let me to Belgrade, and her, in the first place.

If I was going to preach the importance of saying Yes to our adventures, I’d better keep walking the talk.

Belgrade was calling.


As I mentally prepared for a month-long trip back to Belgrade, I had a sobering thought:

I have no idea if this is going to work out.

We’d only seen each other a handful of times, and had spent less than two weeks in the same physical place together. We’d “known” each other for just over a year. On paper, the odds of this thing working out were terrible. My family and my friends knew it. Anyone I mentioned it to knew it. I guess deep down I knew it too.

A few days before my flight back to Belgrade, I pressed Publish on the Quitting essay. In editing it, I scraped away a section of the essay that didn’t quite seem to fit within the scope of quitting jobs and changing careers. But the fact that it came out while writing about those things is telling:

“What if I land in Belgrade and massively regret it? What if we crash and burn, everything ends horribly, and one (or both) of us end up heartbroken?

A scary thought. But to be honest, that doesn’t quite scare me as much as the potential regret of not trying this. While going to Belgrade may be a massive mistake, not going will be a massive regret, one that will likely compound over time as I wonder for the rest of my life: What if I had gone back to Belgrade?

This would-be relationship won’t die because I was too scared to try. It may die. And I may get burned in the process. But it won’t be because I didn’t have the balls to go after the girl. I refuse to give that regret the time of day. That son of a bitch won’t haunt me.”

Others would though.

Without going too deep into the weeds, that month in Belgrade turned out to be a haunting experience.

In short, things didn’t go well.

The Benefit of a Broken Heart

While in Belgrade that month, I signed up for Brazilian Jiu Jitsu lessons at the recommendation of a friend who’s becoming an Olympian in the sport. I’d never done a martial art before and always wanted to try one. I thought a new challenging experience might mitigate the risk of my time in Belgrade being a massive mistake.

I signed up for a series of 1-on-1 lessons with Danijel, the owner and head instructor of Gracie Barra Srbija. Short, muscular, fair-skinned, Danijel looked less Serbian and more like a guy I could have grown up playing football with in Ohio.

Looking back, our weekly lessons together seemed to mirror my overall experience in Belgrade. It was tough, I was challenged, and every week I learned something new — but not without immense pain. It culminated on our final session with us grappling together for thirty minutes straight.

Thirty minutes doesn’t sound like a lot of time, but if you’ve ever grappled or wrestled or been in a fight, thirty minutes of grappling feels a bit like running a half-marathon. A half-marathon where people are punching you the whole time.

At some point while grappling, Danijel asked me if I wanted to stop. My light red t-shirt had turned dark with sweat and my right ear felt like it was about to fall off.

“No, let’s keep going,” I panted.

“Good man. Do you know why we do this?”

I didn’t know what “this” he was referring to and didn’t have the energy to engage in dialogue.

“Why?” I breathed out.

“We put ourselves into difficult situations to get stronger. We practice now so we’re tough later.”

“The world breaks everyone and afterward many are strong at the broken places.”
—Ernest Hemingway

Maybe a broken heart was something I needed in my toolkit of life. It helped me understand that sometimes when we go out on a limb, the outcome doesn’t always come with rainbows trailing. Sometimes it does end up being a massive mistake.

Now that I’m on the other side of it, I can say with conviction: I don’t regret going to Belgrade. I don’t regret trying. I don’t regret that I was willing to give myself so freely to someone I cared about. I don’t regret that I had the courage to go after something that was important to me.

I don’t despair because I felt the pain. Although I certainly wasn’t rejoicing at the time, in a way, I can now rejoice because I’ve felt it. And maybe this feeling — the pain and the joy of being truly alive — is really what we’re after.

“I don't believe people are looking for the meaning of life as much as they are looking for the experience of being alive.”
—Joseph Campbell

We hear from plenty of startup founders, career changers, and , and at some point, most have said a flavor of a similar thing: it ain’t easy. Sometimes the journey toward potential mistakes stings and it breaks our hearts. Sometimes it hurts. It really fucking hurts.

When we march toward potential mistakes and fail gloriously upon meeting them, hopefully we learn something along the way. Even better if we can reflect those lessons back for others to learn as well.

“Use It As Fuel.”

After returning from Serbia, I spent some time with my parents in Ohio. My dad, in classic dad fashion, tried to dispense dad-like wisdom upon me when dealing with my hurt:

“Don’t lose that feeling. I know it hurts. But you can’t forget it. Take it and hold it right in front of your face.”

To really hit upon the point, he literally stuck his hand just in front of his face. He stared through his hand and punctuated the following four words that convinced me he was speaking from a place of experience:

“Use it as fuel.”

It’s often preached as wisdom to follow your heart (or your gut or your intuition or whatever you want to call it). We sometimes preach it here. If only you follow your heart, you won’t be led astray.

I often touch on the idea that by proceeding toward possibilities (rather than sticking with probabilities), you give Faith and Trust a chance to show their faces. And sometimes, they do show their faces.

But you know what? Sometimes those bastards don’t show up at all.

They certainly didn’t show up for me in Belgrade.

But maybe Faith and Trust don’t always show their faces in a way we can recognize them. Or at least not at first they don’t. I do believe that at some point, whenever it’s ready to, the veil comes off; the silver lining is revealed. It wasn’t all for naught. We learned something in the process. We got tougher. We tasted defeat. We felt something. And God damnit, we lived.

A Case for Glorious Mistakes

When something breaks us badly, when it shatters us to pieces, and when it seems like our entire existence is ablaze and burning brighter than the sun, we have two choices:

We can either stand among the flames, let them swallow us and wallow in the despair of our loss.

Or we can size up the fiery mess before us and take that rocket ship that’s strapped to our backs (surprise! it’s been there the whole time), slowly back it into the fire, light it up and let it burn.

We can use it as fuel. To grow. To do something great. To turn our pain into a business or a movement or a piece of art.

We can use it as fuel to get the hell out of there. And maybe even enjoy the ride.

So whether we’re talking jobs or startups or love, I like to think we’re talking about similar things here. If we’re staying on paths because we’re afraid to do something potentially stupid, then maybe we’re doing it wrong. Following your heart isn’t often the most rational play. The probability of “success” is low. On paper, it often doesn’t make sense.

But here’s the thing: maybe instead of the hermetically sealed life we think we should be building for ourselves, it’s wounds we should be seeking. Not fatal wounds, but strengthening wounds. Wounds that make us tougher, help us learn, and remind us that we’re still alive.

I told myself two and a half years ago that I’d rather live a life stacked upon interesting stories — grand ones, sad ones, euphoric and dark ones — than a life void of interesting stories altogether. I’d rather feel something than be numb to both the joys and pains of life.

I guess it’s inevitable, really. Whether we invite life to grapple with us or not, grapple it will.

So we might as well continue to make the mistakes. Glorious, stupid and heartbreaking mistakes. And share our stories of them as to encourage the next generation of foolhardy women and men to do the same.

Mistakes quote Neil Gaiman
Image via Escape the City

This post originally appeared at .

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