Failure is inevitable. Not in a doomsday “everything sucks” kind of way. More like … failing is just what we do. It’s how we stumble around figuring things out. Babies fail at walking before they figure it out. We fail at talking, reading, relationships, business.
And honestly? It’s kind of fun.
Well, fun in hindsight. Fun because it gives us stories to tell.
The Almosts Are Better
Let me tell you something I’ve noticed: nobody cares about your success stories. They don’t.
“Oh, you launched a product, made a bunch of money, and everything went exactly to plan?” Cool story, bro.
But failure? The big, messy, gut-punch kind of failure? That gets people leaning in.
Like, how many times have I started a conversation with: “You want to know how I could’ve been Facebook?” And immediately, people are hooked. Nobody wants to hear about my successes. But a billion-dollar screw-up? Tell me more.
Here’s the thing: your “almosts” are way more interesting than your wins. They’re full of drama, risk, bad decisions, and lessons. They’re human.
Why It’s Fun to Fail
It’s not fun at the moment. At least not always. But somewhere along the way, I started smiling when I failed because I knew—this is going to make a great story.
Like the time I spent two years coding in my parents’ basement, trying to build the next big thing. Back then, “the next big thing” was about connecting people online. This was before Facebook. Before MySpace. It was just me and a bunch of ideas about how the internet could bring people together.
It worked. Kind of.
I built a platform, got 750,000 members, and felt like a king. But then I got greedy. I focused on squeezing every ad dollar I could instead of improving the product. I didn’t care about the users; I cared about the money.
Spoiler: that’s a terrible business strategy.
While I was busy figuring out how many ads I could cram onto a page, Facebook showed up. Clean, no ads, intuitive. And the rest is history.
I failed. Spectacularly.
And now, years later, I love telling that story. Because it’s real. It’s messy. And it’s mine.
The Myth of “If Only”
Here’s what we don’t talk about enough: the “if only” trap.
“If only I’d reinvested in the business, I’d be a billionaire.”
“If only I’d focused on users, I’d have built the next Facebook.”
It’s easy to torture yourself with alternate realities. But here’s the truth: there’s no guarantee those choices would’ve led to success. Maybe I’d have moved to Silicon Valley, burned through cash, and ended up exactly where I am today—with a bunch of stories and zero regrets.
Stories Over Success
That’s the thing about failure—it’s fertile ground for stories. And stories connect us.
Think about it: when someone shares their success, you admire them. When someone shares their failure, you relate to them.
That’s why I lean into failure. It’s not about glorifying mistakes; it’s about embracing the idea that our failures are what make us interesting. They give us texture, depth, character.
Why We Should Fail More
Look, failure gets a bad rap. It’s not a dead end. It’s a recalibration. A redirection. Sometimes it’s a punchline.
But the best part? Every failure teaches you something. And sometimes, it gives you the spark for your next big thing.
So go ahead, fail at something. Fail hard. Fail weird. Fail publicly. Just don’t let it stop you. Because one day, you’ll tell the story, and someone will lean in and say, “That’s incredible.”
And if you don’t believe me, let me leave you with this: I could’ve been Facebook. I could’ve been Tinder. I could’ve been … well, a lot of things.
Instead, I’m here. Writing this. Smiling at how it all played out.
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