Yesterday during lunch with a colleague, the topic of skateboarding came up. And I was reminded of how much I used to love it. There was a time when I used to skateboard everyday. If I missed a day or two, I felt rusty.

What I loved about it was how incredibly challenging it was to learn and perfect new tricks. And there were always ways to continually push yourself to the next level, whether it was the number of boards you could ollie (jump) or the number of steps you could ollie down. You’d start with 3 stairs. Then it was 4. Then 5. Then 2 sets of 5. And so on. Once you mastered those, you could then introduce a kickflip to make it even more challenging. The possibilities were endless. And so—to borrow Daniel Pink’s terminology—it was all about mastery for me.

Here are a few of my old skate decks (they’re on the wall in my apartment):

But in addition to teaching me that there’s no substitute for discipline and practice, skateboarding also helped shape my love of cities (either that, or I was a born urbanist and skateboarding was a symptom). 

Street skating is an inherently urban activity. There’s no defined field or rink. The entire city is at your disposal. And so as a skateboarder, you’re always on the look out for interesting things “to skate.” You want steps, ledges, edges, and changes in grade. You also look for sequences. What tricks can I string together across this urban landscape? You wouldn’t believe how exciting these features can be to a skateboarder.

In fact, I’d even go so far as to say that skateboarders are probably some of the finest surveyors of public space around. How many people do you know go around counting stairs, examining railings and measuring ledge heights? Skateboarders do.

But as much as street skating is all about the city, that relationship is often an acrimonious one. Skateboarding is viewed as a property destroyer, an annoyance and, in some cases, a criminal activity.

A perfect example of this is the story of LOVE Park in Philadelphia (it was a public plaza, not a park). LOVE Park was a legendary space in the skateboarding community. It put Philadelphia skateboarding on the map. It was iconic. If you skated during that era, you knew about LOVE Park.

However, on April 25th, 2002, the Mayor of Philadelphia ordered that the park be closed off and remodelled to remove all the elements that skateboarders loved about it. It was decided that skateboarding was not an acceptable behaviour in an urban public plaza.

That act made a huge dent in the Philadelphia skate community. And the park became essentially a homeless shelter. 

As a former skateboarder, urbanist and ex-resident of Philadelphia, this always baffled me. Cities all around the world spend a great deal of time and money trying to create spaces that people will actually use. And here you not only had an intensely used one, but one that spurred a grassroots global phenomenon. It’s precisely what makes cities so great.

Thankfully, many cities have woken up to the benefits of street skating by building purpose built skate parks. But in my view, those spaces lack something that places like LOVE Park had. LOVE Park was authentic. It was about a serendipitous repurposing. It had a sense of place.