Let’s talk about … Failing Up (and Finally Getting It)

There’s a certain kind of person who simply can’t lose for trying. You know the ones — they show up late, unprepared, halfway holding a latte and still manage to walk out of the meeting with a new title and an expense account. They don’t fall; they float. Life, for them, is an endless series of banana peels that somehow turn into red carpets.

We’ve all got one in our orbit. Maybe it’s a friend, a coworker, a cousin — or if the universe has a sense of humor, all three. The kind who shrugs their way into opportunity. The ones who say, “Oh, I just kinda fell into it,” as if the universe itself is their HR department.

Meanwhile, the rest of us are sitting there with our color-coded planners and emotional homework, whispering affirmations into our oat-milk lattes, trying to manifest something that might be mistaken for momentum. And yet these folks — the fail-uppers — they just… go. Unphased. Unpolished. Utterly unbothered.

It’s not arrogance — it’s something purer, stranger. It’s that baked-in self-assurance that the ground will always rise to meet them. It’s the kind of confidence that seems to exist on a cellular level, like a secret genetic upgrade the rest of us missed in the shuffle. They’re out here saying, “I’ll figure it out,” and then — wild concept — they actually do.

Historically, sure, this energy had a particular zip code. A certain demographic came factory-installed with a trampoline for failure while the rest of us got concrete. But somewhere in the last decade, this thing went global. Confidence has gone viral. Everyone from yoga instructors to TikTok philosophers has caught it. The artist who’s been “launching their brand” since 2019, the friend with a half-finished screenplay and a full-time belief system, the woman who quits her job on a Wednesday to start a candle company — all glowing with the same untouchable certainty: something good is coming.

And the best part? Sometimes, they’re right.

Because life does seem to reward motion more than mastery. While some of us are still workshopping the perfect version, they’ve already failed twice, learned once, and somehow ended up on a panel talking about “resilience.”

But here’s the plot twist: I used to laugh at that kind of audacity — until I found myself getting a taste of it.

For years, I said I was going to walk across the country. Said it with conviction. Said it like people say they’re going to start journaling or learn Italian — it was always next season. And then one day, I got tired of hearing myself talk about it. So I just… went. No perfect timing, no detailed plan, no committee meeting with myself. Just a pair of shoes, a stubborn heart, and my lime-green emotional support chariot, Gertrude.

From California to South Carolina — 2,900-ish miles of proving to myself that motion beats motivation every single time. Somewhere between the deserts and the diners, I finally understood what “failing up” really means. It’s not luck. It’s not entitlement. It’s movement.

Those people we love to marvel at? They don’t wait to feel ready. They don’t ask permission to begin. They don’t sit around waiting for clarity to strike like lightning; they light the match and start walking. They’ve learned that confidence doesn’t come before the leap — it’s built mid-air.

And I’m not saying I’ve joined their top echelon just yet. I still overthink my overthinking. But somewhere on the road, I caught a glimpse of what it feels like to live with that quiet inner nod that says, You’ll figure it out as you go.That’s what the fail-uppers already know. That’s their superpower.

So here’s to them — the people who move first and refine later. The stumble-and-smilers. The “I meant to do that” crowd. The ones who trust themselves loudly enough that the rest of the world believes them too.

And here’s to the rest of us — the recovering perfectionists, the late bloomers, the cautious dreamers — finally learning that progress doesn’t require perfection. You don’t need a guarantee. You just need a start.

Because once you’ve walked across a country, you realize no one’s keeping score. The road doesn’t care if you trip — only that you keep showing up. And somewhere along the way, your fear softens into faith.

You stop chasing confidence and start creating it.

You stop waiting for permission and start walking your proof.

You stop striving for balance and find your rhythm — maybe even a little sway.

And that’s when it hits you: the people who can’t lose for trying aren’t chosen — they’re just consistent. They move through the world like it’s okay to fall, and maybe that’s why the ground keeps catching them.

That’s the secret. Not luck. Not lineage. Not a LinkedIn connection. Just motion — and the courage to keep it.

Because sometimes, failing up isn’t about defying gravity. It’s about trusting your own momentum.

And when you finally stop fighting the fall and let yourself swing a little — you realize you’ve been held all along.

Somewhere between courage and surrender, between chaos and calm… there’s a hammock.

And it’s got your name on it.

😜