How to succeed by failing

When I was eight years old, my older brother was the coolest person in the world. So naturally, when he started skateboarding I had to learn also. In the driveway one evening after dinner, (and after I’d convinced my mother to purchase a board my size) I tried my very best to appear calm and collected. My knees were shaking from fear; I would surely appear to be the lamest ever. But then he said something that would change my life forever.

“You have to want to fall.”

We spent that evening trying to fall over and over again. Twenty years later, I’m no pro skater, but I am successful because wanting to fall taught me the most important lesson of my professional career. Failure is cool. The ability to totally fail and get up and do it again means you’re confident enough to take a risk.

Today, my colleague and I were chatting about friends of ours who say “why can’t I get my career going?”. Smart, witty, wonderfully talented people who are frustrated that they’re still living with their parents. And we thought, what’s up with this?! Simply put: Why are some people finding success and some are feeling stuck?

We swapped anecdotes from how many times we’d failed chasing the strangest leads. My colleague Amy moved to NY and took a design job she saw in a tweet! I got my first UX job from critiquing a product to the person who built it. Finally, we realized why we “made it”. We constantly took risks, knowing failure was a possibility.

It’s the pure act of going after it. Taking the leap when it’s not a sure thing: that’s what brought us success. Today, these accomplishments stand on the back of a hundred unanswered e-mails, botched ideas, abandoned projects, and failures both large and small- but somehow all of those slip away and it’s the successes people are talking about.

Some of your ideas are lame and some of your work will be bad. But. who. really. cares? It’s terrifying, sure. But it also doesn’t have to be. It doesn’t have to be terrifying at all, because you aren’t that fragile.


Instead, make failure fun. Here’s how:

  1. realize that failures don’t define your intelligence, ability, or personal self.
  2. know that nothing is precious. no single idea is so great that it shouldn’t be torn apart. get used to generating ideas, so that they aren’t everything to you.
  3. want to fall. take all the risks and see what tricks you can land when you aren’t overthinking it.
  4. failure is inevitable. you’re going to fuck up. you’re going to feel horrible and let people down, but that’s how you learn what NOT to do.

After years of collaborating and training with creatives, mentors and professionals, I always come back to that moment in the driveway where falling was cool and suddenly it’s all a little simpler. Fail as much as possible. Fail over and over again until you’re kick flipping over all the haters (especially yourself).

Bye-bye, going over here to succeed now.