Reflections on Falling in Love with Skateboarding

As a 6th grader at Aldo Leopold Community School, I witnessed something that would change the trajectory of the rest of my life. One day at dismissal, I saw an older student confidently pushing down the street on a skateboard. I had never talked to him and didn’t even know his name. But he had a presence about him. Lacking height, he drew attention in other ways. He wore baggy clothes, had shaggy, unkempt hair, and was nearly always carrying a skateboard. After being caught for some middle school behavioral infraction, I once heard a frazzled teacher say to him, “You’re in hot water young man!” Goody-two-shoes that I was at the time, a scolding of this sort would have terrified me. But this kid was just stone cold causal about it, like, “Whatever, lady.”

I was impressed.

But to be clear, this kid wasn’t “cool” in any normal sense of the word. He didn’t have a lot of friends and he certainly was not an exemplar student. But I already had those things. What I didn’t have was something he clearly possessed in abundance: confidence. This kid just did what he wanted to do, even if it didn’t fit within the parameters of what the adults around him expected.

I decided I wanted a skateboard.

But a brand new complete is fairly expensive, of course. Even after I shoveled driveways and mowed lawns for six months, I had still only saved about $60 or $70. Then by the grace of the timing of my 12th birthday, Grandma Schmidt stepped in from high on above and kicked in the rest of the funding.

Several weeks later, the long awaited package arrived at my dad’s duplex in Green Bay after having been shipped over halfway across the continental United States from CCS mail order in San Luis Obispo. I ordered the board unassembled, knowing I wanted to put it together myself. Toy Machine deck, Grind King trucks, Spitfire wheels, Bones Reds bearings, Black Magic grip and Shorty’s hardware. I took the tool kit out and got to work.

As soon as the board was set up, I headed to the driveway and proceeded to devote the entirety of my physical and mental energy to learning how to do this powerful, but elusive thing called an ollie. After he got home from work, my dad took the above picture of me trying it and failing miserably.

I’m 30 now, and at this point it’s hard to remember what it felt like to not be able to ollie. Today and for well over half of my lifetime, I’ve never had to think about ollieing ever again. Once you learn it, it essentially becomes an unconscious process, fueled off the muscle memory that’s built through daily practice over the course of many, many years.

But this photo brings me back to my encounter with an experience that’s universal to all skaters. That moment when you are desperately invested in the goal of learning a new trick, but you’re still completely unable to do it. There’s so much to be learned from analyzing this moment because the frustration that comes out of it is extraordinarily motivating. And it turns out that authentic self-motivation is exactly what homo sapiens need in order to learn skills as legitimately complex as ollieing for the first time.

As clearly evidenced in this photograph, on the first day of my possession of a skateboard, I had almost no clue how to properly use it. But that won’t last of course, because I proceeded to spend hours and hours in that driveway, trying it over and over and over again until I finally got it. Exactly no one told me to do this. I just wanted it for myself. I wanted it so bad I didn’t stop trying until I got it. More clearly than any other educational experience in my life, it was through skateboarding that I learned that mere dogged persistence alone could get me pretty far.

Part of what I now suspect sustained this persistence though, was some degree of a longing for identity. Growing up in largely white, middle-class neighborhoods, I don’t think I had much of a sense of communal belonging as a young child. But skateboarding changed that for me. It opened me up to the larger world outside of my immediate surroundings.

In this picture, I’m wearing a non-descript outfit entirely assembled from Kohl’s department store. But looking back on the rest of my childhood skate photos, what’s striking about this one in particular is that it captures me skateboarding, but before I identified as a skateboarder, per se. It’s hard to find another picture of me from ages 12-17 where I’m not wearing a skate hoodie of one brand or another. Why? Because in the days, weeks, months and years after this photo was taken, skateboarding went on to completely consume me.

Sometime around when I was applying for college, I remember wondering, “Who would I be if I didn’t skateboard?” It was almost impossible for me to imagine how else I would have spent the near entirety of my adolescent free time, imagination and money if not on this one thing I’d become so profoundly obsessed with.

And to think, that all of this stems back to a flicker of a memory of a kid I never even talked to in middle school. I have no idea if that kid kept skating, or if it was just a passing phase for him.

What I do know is that without even being aware of it, he inspired me to pursue something I almost certainly would not have otherwise. And furthermore, that the impact this has had on the rest of my life has been profoundly rewarding.

In my youth, skateboarding gave me two of the most valuable things any adolescent can have access to: a framework for learning how to hone a new skill that’s intrinsically rewarding, and group culture through which to develop a positive sense of belonging and identity.

Well into adult years, my life continues to be enormously enriched by skateboarding. For this, all I can say is that I’m extremely grateful.