To skateboard is to see the world as a challenge, a series of obstacles to overcome, a new terrain to master. You read curbs as a dare. A staircase? A hill? Let's go. You fall and you get up and you fall again, an endless loop of pain and frustration until, finally, elation. You miss and you miss and you miss until at long last you hit the landing and that feeling—that feeling of beating the odds—will have you chasing it all over again no matter how many times you go down in the process.
I've been a lot of things, but I was a skater first. Third grade on a thin wood plank, wobbly on my way down one of the few hills in the flatlands I grew up in. That feeling of speed as the board wavered uneasily beneath me. Middle School on a Lance Mountain "Future Privative" deck. Watching dubs of dubs of dubs of Bones Brigade videos with friends before going out and trying everything we saw and failing at most of it. Thrasher magazines piled in my bedroom—I fell in love with print then. Fast forward a couple decades and friends were meeting up before our jobs and skating at a park on the lake in Chicago. None of us very good, all of us a touch too old, every one having fun, that feeling of a deck beneath your feet the same as it always had been. Jump forward again to this past summer, my kid learning to skate, teaching himself, seeing all those same feelings flash across his face. Frustration. Determination. Freedom.
So far my 2023 has been defined by waiting. The parents of a college-bound kid, we're in an endless loop of waiting to hear back on his applications. My partner spent too much of January waiting to hear from a job interview. I've been waiting to hear back on freelance pitches that have dragged on too long and on the greenlight on another project that could deeply change my day-to-day.
Tom Petty was right: The waiting is the hardest part.
To ride a skateboard is to get hassled. To get chased off of spots. To have cars stop and yell at you. Or worse: to try and run you off the road. Cities are rebuilt to keep you out. Benches and curbs marred forever just to stop you. It doesn't stop you.
It's easy to get caught up in that waiting, to feel like everything is on hold until you hear back. Looking into a future, as my son is right now, and just seeing haze feels impossible. I'll be honest: I haven't been writing posts these last couple weeks because I've been stuck waiting. The longer I wait, the less I write, the worse I feel, a great spiral to get stuck in. When work for yourself, often your head is your biggest hindrance.
Skating reorients your brain forever. Even if you fall out of the habit—as I have for years at a time—you will always see every bend in a road in a different way from other people. It teaches you to see everything with a potential that doesn't exist otherwise, a life viewed through a lens you can never take off.
The waiting is terrible, excruciating, and the outcomes may not all be good ones. I've been a lot of things, but I was a skater first and from the endless pattern of falling and getting up again I've learned one thing: No matter what happens, you kick and push and it's left behind.
Published February 09, 2023.
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