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A neurotic’s guide to skateboarding in your 30s

by Chris Plehal

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I careened down the hill, arms flailing. Trees, dogs and humans whipped by me on both sides. The board felt like it was about to shoot out from under my feet, like a magician pulling a cloth off a table.

I pictured myself crashing into the pavement and breaking every bone in my body, or mowing down a random pedestrian. “This is it,” I thought. “I’m going to die.”

I was skateboarding, for the very first time, at age 33.

I never skated as a kid. Skateboarding was something reserved for the cool kids. I was more of an overachieving, anxiety-prone type. I didn’t have time to hang out behind the 7-Eleven and mess around with ollies and kickflips. There was homework to do! Extracurriculars to attend! College applications to pad!

My anxiety persisted throughout high school, college, and into adulthood. It drove a lot of my success; it also kept me up at night and made me miserable. Eventually, I found myself on a couch across from a therapist named Paul.

“You should try surf therapy,” Paul suggested.

“Sure, let me just buy some beachfront property,” I replied.

“It doesn’t have to be literal surfing. Just any activity where you’re a little bit out of control. You know, like skateboarding, rollerblading, or—what are they called—hoverboards. You could get one of those!”

“I think they explode,” I said.

“Yeah, well. Maybe skateboarding then. Just ride the wave.”

Was this what it’s like to give up control? To “ride the wave”? I hated it.

By the following Saturday, I was armed with an entry-level skateboard and knowledge gleaned from some “Intro to Skateboarding” YouTube videos. My friends were supportive of my new mission. “I like how your midlife crisis is both early and affordable,” my friend Owen said.

I carried my new board to the Schuylkill River Banks, a multi-use path near my apartment in Philadelphia. The path was crowded with the standard joggers, walkers, and bikers. Normally I fit right in with my usual fully-controlled, type-A, achievement-based activities. This time, though, I felt like an impostor. I wore my rattiest jeans and an old hoodie, trying to look like a disaffected teenager and not an anxiety-afflicted adult.

I balanced my left foot on the board and pushed off with my right. I wobbled dangerously but kept moving forward. “Everyone knows you don’t know what you’re doing!” the voice in my head screamed. I told it to shut the hell up and kept pushing. I managed to get both feet on the board and glide. Instantly, I felt like a cool kid. I was Marty McFly. Bart Simpson. That happy bulldog from the internet.

I experimented with turning, shifting my weight and adjusting the angle of the board. Up ahead, I noticed a gap in the pavement. I leaned back on the board to lift the nose (it’s called a nose, right?) in the air. This was a mistake. I slipped backward, like a cartoon character stepping on a banana peel.

I brushed myself off before anyone could notice and soldiered on. Gradually, the path began to slope upward. I could tell because my right leg was fighting gravity to push the board up the hill. So far, this didn’t seem particularly relaxing. How was I supposed to unwind when everything required so much effort?

At the top of the hill, I reached Paine’s Park. It’s a clean, modern skate park full of ramps, half-pipes, and concrete benches, edges stained black from years of grinds. The park was full of skaters and BMX riders—these guys were the real deal. I skated around the periphery, trying to look like I was just taking a break and could, at any minute, perform a sick 360. Eventually, I managed to drop off a five inch-curb without falling off my board. I was proud of myself until I saw a five-year-old in a SpongeBob helmet do the same thing.

After my fifth fall, I decided I’d had enough for one day. I turned back onto the path and headed toward home.

It took me a few seconds to realize something was different. I going downhill and picking up speed. YouTube hadn’t taught me anything about hills. It hadn’t taught me how to stop at all.

I struggled to stay vertical as the board accelerated. The path seemed more crowded than before, an obstacle course of human bodies. I had no pads, no helmet, and no way to stop myself. I could jump off the board, but didn’t know how to land. Plus, the board would keep going and probably steamroll a toddler.

Was this what it’s like to give up control? To “ride the wave”? I hated it. I felt stupid and irresponsible and old and scared. Why had I thought I could do this? My brain conjured up all sorts of wonderful ways this could end, most involving a visit to the ER.

And then the board began to slow. As the hill tapered off, I regained control. My heart rate lowered, and I felt a peaceful feeling. I didn’t have to push. I could just stand there and let the board carry me home. I breezed around the couples strolling along the riverbank. I was cruising, which isn’t a verb normally associated with me. As the sun set pink over the Schuylkill river, I relaxed and rode the wave.

A few days later, I went for a run along the same path. I rounded a bend and saw three badass skateboarders hurtling toward me. They passed under a bridge that amplified the sound of their boards on the pavement.

The old fear gripped me, and I instinctively moved out of the way. But the first skateboarder held up a hand in the universal signal for a high five. I raised my hand and slapped his, then the hands of his buddies: one, two, three.

I’m never going to be a great skateboarder. But the world needs more people who will high five strangers. And if that means I need to “ride the wave” sometimes, it’s worth a few skinned knees. (However, now I wear knee pads, elbow pads, and wrist guards under my jeans and hoodie. Please don’t tell.)

Chris Plehal

Chris Plehal is a writer who believes creativity can change the world for the better. His work has appeared on television, in children's books, in advertising, and on film. He currently splits his time between Philadelphia and New York. Chris has been meditating with Headspace since 2014.