People keep saying things are getting worse, but today I was thinking about why so many folks aren’t seeing the expanding universe of opportunities unfolding in the wake of disruption.
And then it hit me: y’all aren’t skateboarders. That’s why y’all aren’t as excited as we are about the future.
See, most people were conditioned early (through school, sports, social and professional circles) to follow rules inside a fixed system. They were taught that success comes from playing within the lines. It’s orderly, hierarchical, and mostly imaginary.
Skateboarders never bought into that.
We habitually scan the city for hidden lines: ledges, stairs, rails, embankments - urban architecture as an evolving playground. We see possibility where others see concrete.
We train ourselves to notice what’s been overlooked, and no one gives us permission. Indeed we become good at begging for forgiveness.
There are no referees, just friction, gravity, and imagination, within an activity where fortune rewards the bold.
So when the economy cracks, or institutions lose legitimacy, skateboarders don’t freeze, we adapt, because we’ve been doing it our whole lives.
In this documentary clip from 20+ years ago, Edmund Bacon (the father of modern Philadelphia and dad to Kevin Bacon) talks about how skateboarders represent the leading edge of human interaction with modern design.
And yeah: that’s me in the clip.
The documentary was shot back when I ran a nonprofit that helped grassroots advocates scale their local efforts using lessons from manufacturing and systems design. It’s the work that earned me a board seat at the Tony Hawk Foundation.
I’ve always been drawn to the space where economics meets political science, but the traditional top-down version? Super boring. As a guy who hates team sports, it’s the American football of civics.
What fascinates me is how self-organizing systems take shape at the selvages and the edges; at the last mile, where trust and discretion often hold more value than money.
That’s why skateboarding was such a useful training ground.
Our work reframed the city’s master plan around a marginalized group: non-voting, non-taxpaying youth, mostly kids of color aged 9–14, and we did it by weaving together unlikely allies: parents, business owners, neighborhood groups, and law enforcement, at the last mile and from the bottom-up.
We learned the same schema can help successfully launch “renegade DIY farmers markets,” which merges improvisational gameplay of busking (street performance) with food-based job creation, to deliver a persistent expression of economic justice…at least when it’s done well.
Twenty-five years later, we're using the same playbook, constantly testing and adapting the model until we find one that sticks.
Only now, it’s not about skateparks, and it’s not exactly about farmers markets, but food and workforce development is definitely on the menu.
It’s about affordable housing, or rather: the ability to afford a high-quality and sustainable life, and the first trick is boldly stepping into opportunity where others only see crisis and fear.
I have the highest confidence that ours is a happy ending, provided we fearlessly embrace our shared future, with an authentic joie de vivre.
