Fall Forward

What Skateboarding Can Teach Us About Leadership Culture

Skateboarding. Yes, the coolest of all sports, offers some surprisingly profound insights for leadership. Take the simplest of instruments: a maple plank, metal trucks, four wheels. From that, skateboarders create an endlessly inventive language of movement.

And what’s the first thing all skateboarders learn? Not how to ride. Not how to turn. How to fall.

Rodney Mullen, often called the most influential skateboarder in history, speaks with humility and precision about the craft. His career, and the stories of his peers, reveal a truth we can apply to any organisation: progress comes from repeated failure, creativity thrives when disbelief is broken, and culture shapes performance more than raw talent.

As Mullen explains, skateboarders “take simple movements and chunk them together” until they become complex, instinctive, automatic. This is muscle memory forged through repetition, and in leadership, it’s no different. Teams need the basics so ingrained that they can adapt and innovate without hesitation. Before asking for bold ideas, leaders must ensure their teams share a common ‘language’ of skills, processes, and values. Only then can they create something truly new.

He also reminds us that the biggest obstacle to creativity is breaking through the barrier of disbelief. Watching someone else achieve the impossible changes what you believe is possible, not because they showed you how to do it, but because they proved it can be done. This is why role models and breakthrough moments matter so much. Every success in an organisation doesn’t just hit a target, it expands the horizon for everyone else.

Mullen tells the story of a young skater who, simply by spending time with high-level peers, began doing tricks he never thought possible. The “new normal” became extraordinary. Culture is contagious. Surrounding a team with driven, creative, high-performing individuals will naturally raise the bar. People adapt to the standards around them, whether those standards are high or low.

For every “make”, a landed trick, there are hours, days, even weeks of failed attempts. Skateboarders fall all the time. They override fear, override instinct, and try again. Resilience isn’t just a nice idea, it’s a habit. The real challenge for leaders is to build systems that make failure safe, expected, and part of progress. If we want teams to push boundaries, we have to make sure they can fall without being finished.

Many of Mullen’s peers faced career-ending injuries, and came back stronger, not by doing the same thing as before, but by reinventing their approach. One skater changed his style entirely. Another, paralysed, learned to walk and skate again through sheer persistence. Setbacks are invitations to evolve. A disruption to your usual way of working can be the catalyst for a breakthrough, if you’re willing to re-engineer your method.

Mullen closes with a powerful analogy: many people have the ‘gears’, talent, skill, balance, courage. But what drives them is the ‘engine’. The act of getting up again and again is what builds that engine. Talent without drive goes nowhere. Persistence turns potential into performance.

Skateboarding might look like rebellion on wheels, but behind it lies discipline, creativity, and community, the same foundations any thriving organisation needs. In leadership, as on the board, success depends not on never falling, but on getting up faster, learning from each slam, and daring to try the next trick.

The Power of Possibility

One of the most fascinating aspects of progress, in skateboarding, in leadership, in life, is how something almost impossibly difficult can, once achieved, suddenly feel within reach for many others.

Tony Hawk’s landing of the first 900 in competition on 27 June 1999 was one of those moments. For years, the 900 (a 2.5-revolution aerial spin) had been attempted and abandoned. Hawk’s successful landing during the X Games in San Francisco was the product of countless failed tries, injuries, and a level of persistence few could match. At 31 years old, he became the first skateboarder in history to pull it off under competition pressure.

In that moment, Hawk didn’t just land a trick, he broke through the barrier of disbelief for an entire community. He showed that it could be done.

Fast forward to 15 June 2024. At Tony Hawk’s own Vert Alert competition in Salt Lake City, nine-year-old Ema Kawakami made history by landing three back-to-back 900s. The skateboarding world was astonished, not just because of his age, but because of how quickly he had closed the gap between possibility and mastery. When Tony Hawk asked how long it took him to learn the 900 after mastering the 720, Ema’s reply was as casual as it was revealing: “One day.”

The trick that had taken years of collective striving, trial, and failure to accomplish for the first time had become something a child could learn in 24 hours. The leap in performance wasn’t down to luck or even raw talent alone, it was the fact that someone had already proven it could be done. The mental barrier had been removed.

In leadership, this same principle applies. Once a challenge is shown to be achievable, the path to it becomes dramatically shorter for those who follow. The breakthrough of one becomes the baseline for the next. Leaders who can show, not just tell, what is possible remove layers of fear and uncertainty for their teams. The result is an acceleration of progress that can seem almost magical, until you realise it’s the direct result of belief replacing doubt.

When Ema Kawakami told Tony Hawk it had taken him just one day to master what Hawk had once fought for years to achieve, Hawk didn’t bristle or try to defend his own struggle. He laughed. His face showed genuine pleasure mixed with disbelief. This is the reaction to the impossible that fuels high-functioning teams, where someone else’s leap forward is met with joy, not jealousy. It’s a culture that celebrates progress, no matter who achieves it first, and it’s in this culture that existential leaps, the kind that change the game entirely, become possible.