What Falling Off a Skateboard a Thousand Times Teaches You About Life

Every skateboarder learns the same lesson on day one: you're going to fall. A lot. Scraped palms, bruised hips, and bails that make everyone watching wince are simply part of the deal. The only question is whether you get back on the board.

Brett Sorem got back on the board over and over, and it shaped his whole life. In Land on Both Feet: Grind Through Life with a Skateboarder's Mindset, he looks back on his years in the renegade mid-'90s skate scene and the lessons it taught him about failure, persistence, and growing up.

Sorem wasn't a casual skater. As a young man, he was a sponsored skateboarder with backing from brands like Billabong, Oakley, and Savier, and he had real opportunities in front of him. At twenty, he made a surprising choice: instead of chasing full-time competition, he chose education. Today he's a writer, producer, and creative director, and he has called nearly every major U.S. city home, from the skate scenes of San Diego to the streets of New York. This book, his debut, is the story of what he carried with him from those years.

It's a fascinating time to look back. The mid-1990s were a raw, do-it-yourself era for skateboarding. Skaters built their own spots, filmed their own videos, and lived on the edges of mainstream culture. The sport's journey since then has been remarkable. Skateboarding exploded into global popularity, and it made its Olympic debut at the Tokyo Games in 2021, something that would have seemed almost unthinkable to the skaters of Sorem's generation. Readers who were there will feel the nostalgia of that era, and younger skaters will get a vivid look at the culture that made today's scene possible.

The heart of the book is organized around eleven lessons, ranging from embracing failure to mastering the art of persistence, and even knowing when to stop and appreciate the moment. Each one shows how the challenges and triumphs of skateboarding mirror the complexities of life. And it's easy to see why. Learning a new trick is a perfect model for learning anything difficult. You try, you fail, you figure out what went wrong, you adjust, and you try again, sometimes hundreds of times, before it finally clicks. Skaters build an almost unusual comfort with failure, treating each fall as information rather than defeat. That mindset, as Sorem shows, turns out to be incredibly useful long after you've stepped off the board, whether you're building a career, starting a business, or getting through a rough patch in life.

What keeps the book from feeling like a lecture is Sorem's voice. He's funny, self-aware, and honest about his own mistakes, and the stories from his skating days are packed with the kind of humor and chaos you'd expect from a group of teenagers throwing themselves down stairs for fun. The wisdom sneaks up on you in between the laughs.

It's also a book about growing up and letting go of one dream to discover another. Sorem reflects on what remains valuable from an early passion even when life takes a different direction, a question that will resonate with anyone who once poured everything into a sport, a band, or an ambition that eventually changed shape.

Land on Both Feet is written for core skateboarders, skate enthusiasts, and anyone looking for a fresh perspective on personal growth. It's a nostalgic, witty, and inspiring read about learning to fall, getting back up, and ultimately landing on both feet.

Land on Both Feet: Grind Through Life with a Skateboarder's Mindset by Brett Sorem is available now in paperback and hardcover.