The Skateboarder’s Mindset

Falling, Getting Back Up, and Trying Again

Every skateboarder knows the drill. You try a trick, you fall. You try again, you fall harder. You keep at it, sometimes for hours, days, even weeks. And then, when you least expect it—when frustration has set in, when your legs are sore, and your board feels like an enemy rather than an extension of yourself—you land it. The feeling is pure euphoria. Every slam, every scraped knee, every moment of doubt vanishes in that instant.

That feeling, that process of failing, adjusting, and pushing through, has shaped who I am today. Skateboarding isn’t just a sport. It’s a mindset. A way of looking at the world that has helped me in more ways than I can count—whether in business, creative work, or just life’s inevitable setbacks.

The Lessons Skateboarding Taught Me

Skateboarding is relentless. There’s no coach telling you how to get better, no team to rely on, no shortcuts. It’s just you, your board, and your willingness to keep going. That kind of persistence seeps into everything.

I see it in how I tackle projects now. If something doesn’t work the first time (which, let’s be honest, it rarely does), I don’t just walk away. I tweak, I experiment, I try a different approach—just like I did when learning kickflips in the driveway for what felt like an eternity.

I see it in how I approach challenges. When you’ve slammed into concrete enough times, you start to build a different relationship with failure. It stops feeling like an ending and starts feeling like part of the process. Whether it’s running a business, developing a new skill, or figuring out how to parent (a whole different kind of challenge), I know that frustration and setbacks are just steps along the way.

And now, more than ever, I want to pass that lesson on to my kids.

Teaching Resilience Through Skateboarding

I want my kids to know that failure isn’t something to fear. That the most rewarding moments in life come after struggle. That it’s okay to fall—as long as you get back up.

Skateboarding teaches that in a way nothing else really does. It doesn’t matter how many times I tell them to “keep trying” or that “mistakes help you learn.” But when they step on a skateboard, take a few falls, and eventually feel that rush of landing something they’ve worked for? That’s when the lesson really sticks!

The Feeling of Finally Landing It

There’s something almost magical about finally nailing that trick you’ve fought so hard for. It’s not just about the trick itself—it’s about everything that led up to that moment. The patience, the frustration, the determination. That sense of proving to yourself that you can do it.

That’s why I still love skateboarding, even after all these years. And that’s why I want my kids to experience it, too. Not just for the fun of it, but for the resilience it builds, the lessons it teaches, and the mindset it creates.

Because in the end, life is a lot like skateboarding. You fall, you get back up, and you try again. And the ones who keep trying? They’re the ones who make it.