Falling on Your Face (and Laughing About It Later)

You ever watch one of those old cartoons where a character walks off a cliff, hangs in midair for a beat, and only falls once they realize there’s nothing beneath them? That’s what starting something new often feels like.

And honestly, I’ve learned to love it.

While co-founding SXSW, I’ve taken more than a few leaps that felt like cliff jumps, with no safety net and absolutely no guarantee we’d land on our feet. And we didn’t always. Sometimes we face-planted. Spectacularly.

But here’s the thing: those failures? They’re where all the good stories come from. They’re where you find out what you’re made of, what matters, and how to build something that actually lasts.

SXSW Was Built on Glorious Missteps

People see the SXSW of today and assume it was always this polished, globally recognized machine. But back in the early days, it was more like a band of rebels trying to throw a party we hoped people would show up for.

We made so many mistakes. Wrong speakers. Wrong rooms. Wrong assumptions. We’d book a panel that only two people would show up to, or overestimate interest and end up with a line around the block and no seats left.

There were moments I thought: “Well, this might be the year we crash and burn.” But every time we got something wrong, we learned something right.

And that’s the point: failure didn’t stop us, it shaped us.

Fear Is the Real Killer of Creativity

What keeps most people from doing the thing they dream about isn’t lack of talent. It’s fear.

Fear of looking stupid. Fear of not being taken seriously. Fear of trying and falling flat.

But if you’re building anything worthwhile, especially in creative industries you have to get comfortable with that fear. Better yet, you have to invite it in, offer it a drink, and then get to work anyway.

Failing doesn’t mean you’re wrong. It means you’re trying.

And I’d take a messy, heart-filled attempt over a perfect idea that never leaves the notebook any day.

You Can’t Innovate Without Falling Down First

Here’s something I’ve learned again and again: you can’t play it safe and build something new at the same time.

Whether it’s launching a new format, backing a weird idea, or trusting an unknown artist—you have to be willing to risk the flop.

Some of the biggest wins I’ve ever been part of started as “are-we-sure-this-isn’t-terrible?” conversations. That tension, that creative discomfort is the birthplace of originality.

And yeah, sometimes it doesn’t work. But the lessons you gain from trying and failing are the exact tools you’ll need to get it right the next time.

Laughing in the Wreckage

I’ve also learned not to take failure personally. Or too seriously.

If you’re going to fall on your face, do it with style. Laugh about it. Own it. Then get back up and go again.

Some of my favorite memories from the early years aren’t the successes, they’re the disasters that we turned into jokes and war stories. The time the sound system failed. The time the wrong bio got printed. The time someone asked us if this “little conference” was even worth attending.

The ability to find humor in those moments is what keeps you going.

Failure Bonds People

There’s a secret side effect to failing: it brings your team closer.

When things go wrong and they always will, it forces you to trust each other, communicate better, and solve problems together. You stop pretending to be perfect and start becoming real collaborators.

Some of the most loyal, talented people I’ve ever worked with are people I’ve shared failures with. We’ve been in the trenches together. And we came out the other side with grit, perspective, and a hell of a lot more respect for one another.

A Culture That Welcomes Flaws Lasts Longer

In hindsight, I’m proud that SXSW and other projects I’ve been part of didn’t start out polished. They were scrappy, flawed, and totally human. And that’s what gave them soul.

If you build something with the expectation of perfection, it will crack the first time real pressure hits. But if you build something knowing it will evolve, that you’ll learn as you go, you create something durable. Something with space for growth.

Failure builds resilience. It builds adaptability. It builds culture.

Jump Anyway

If you’re standing on the edge of your own cliff—thinking about launching something, saying something, creating something, let me say this:

You’re probably going to mess up.
It might get embarrassing.
You might fall a few times.

But you’ll survive it. And more than that, you’ll grow from it. You’ll gain clarity. You’ll find unexpected allies. And you’ll create something that matters, even if it’s a little dented around the edges.

“Cartoon deaths” and cliff jumps are part of the process. And the sooner you learn to fail with your whole heart, the faster you’ll discover what you’re really capable of.

So go ahead, take the leap.

The net doesn’t appear until after you jump.