The Skateboarding Mindset for Business Success

If you want to succeed in business, take a lesson from skateboarders. It might sound like an odd comparison, but hear me out—skateboarding requires resilience, adaptability, and a willingness to fail repeatedly. And those are the same qualities that separate thriving business owners from those who give up too soon.

Think about how a skateboarder approaches a trick. They know they might not land it on the first try, but they commit fully anyway. They fall, get back up, adjust their technique, and try again. The best skateboarders in the world, the ones landing jaw-dropping tricks, have failed thousands—if not millions—of times. But they don’t quit.

In business, the same mindset applies. You’re going to make mistakes. A deal will fall through. A client will ghost you. You’ll spend money on something that doesn’t pan out. But if you let failure stop you, you’ll never reach success.

When I started my construction company, I had no idea how many times I would metaphorically ‘slam’ before I figured things out. The first time I tried to manage multiple projects at once, I felt overwhelmed. The first time I had to fire an underperforming employee, it stung. The first time I lost money on a project, I felt like a failure. But just like skateboarding, I learned from each attempt and kept moving forward.

The key is to treat setbacks as part of the process. Adjust your approach, analyze what went wrong, and then go at it again. There’s no business owner out there who hasn’t ‘hit the pavement’ at some point, but the successful ones are those who keep getting up.

So if you’re running a business—whether it’s construction, real estate, or anything else—adopt the skateboarder’s mindset. Accept that failure is part of the journey, embrace the process, and keep pushing forward. Because just like in skateboarding, the only way to succeed is to keep trying until you land the trick.