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The best $150 I ever spent: Roller skates

I hated being bad at new things, but skating rewards falling down.

One night in March 2019, my friend Angela posted a video of herself roller skating on Instagram. She’s Australian, so the video was sunny and bright, the kind of weather it is hard to believe exists anywhere at the end of a long, bleak Boston winter. I’d already been thinking about buying roller skates, and Angela looked calm, happy, cool. I’d always admired her; she’s someone who just seems happy to be here, alive in the world, and is always ready to accept joy and new experiences. I wanted to be more like that.

I’d been hesitating because I knew myself, and I knew I had a trail of abandoned hobbies behind me like bread crumbs of poor follow-through. I hate starting something new and sucking at it; I’m not humble enough to sit in the discomfort of being bad at things. I was once taught to knit, but something didn’t stick and I couldn’t help adding or dropping stitches at the end of every row, and instead of learning how to correct the mistake, I just stopped knitting.

When it turns out that a new skill takes patience to learn and not just an initial fervor, I’m over it. And when something else catches my eye, I promise myself that I will try, that I will practice, and eventually I’ll make it to a place where I can at least enjoy it. But invariably, I use about a quarter of my new yarn or my new origami paper or my new 10 pounds of wax flakes and then never touch them again.

Ever since I’d begun to dream about roller skating, before seeing Angela gliding serenely along, Instagram had been serving me ads for skates. The ads were hard to distinguish from the joyful, colorful feed I’d curated from my friends and aesthetic accounts, which probably made me even weaker for them. Girls in high socks and teal skates, in jean shorts and bright pink wheels, sped across my feed ... on boardwalks and on long, empty streets. By the time I was ready to buy skates, I had a few brands in mind and ultimately asked Angela for a recommendation. I chose the less expensive of the two she suggested.

The skates I wanted were about $150, plus the pads. It wasn’t a ridiculous amount of money for me at the time, but I wasn’t being paid well at my job, and I was extremely careful with nonessential purchases. It would be a frivolous amount for another abandoned hobby. If I didn’t end up using the skates, I knew they’d radiate shame from wherever I ended up dumping them, reminding me of the money that could’ve been a couple of nice dinners or some new summer clothes, instead of yet another embarrassing attempt to be a different person. I sat on the idea for a few weeks while Boston’s winter slowly wound down.

I wanted to be okay with sucking at things, because I knew that being terrible at something is the only way to eventually be great at it, but it felt particularly hard then. I had found myself in tense, less-than-ideal situations both at work and at home with one of my roommates. Every day I went from one uncomfortable situation to another, and I was often around people who really didn’t think much of me. I was in my mid-20s and already felt like I was failing pretty much constantly. The idea of choosing to be bad at yet another thing in my free time seemed misguided, as if I’d be trading in the very last of my self-esteem for no real reason.

When I saw Angela soaring through pools of bright sunshine looking so at peace, it felt like my final push. I ordered my skates at the end of March and they came a few weeks later, in a rad box showing a cool girl in skates, radiating groovy waves of color. I rolled around my apartment when my roommates weren’t home, but I had to wait to start practicing, because Boston took its time transitioning from winter to warmer weather with a long stretch of cold rain. I worked until 6 and the sun set around 7, so even on rare sunny days, my window of opportunity was narrow. I checked the weather several times a day, hoping in vain that the gray evenings would clear up.

When I finally did get to practice, on the basketball courts by the Dougherty playground, I knew immediately that I had made a good decision. One of many great things about roller skating is that it is pretty easy to get your feet under you in order to glide around in big, fast loops, so even on my first day, I was able to move my body in this brand new, blissful way. Skating felt like dancing or swimming; a kind of movement that’s pure celebration.

It’s much harder to learn to turn or slalom or skate backward, and those were the things I had to practice, over and over, until my brain and my ankles and my knees all finally agreed with one another. Really, the first thing you learn when you start roller skating is how to fall. You learn to drop your butt low when you feel unsteady, so if you fall, it’s from a low squat, instead of your full height. There’s even a correct way to stand up after falling, and you have to learn that, too. I watched YouTube videos of women with thick thighs telling me it was okay to fall, that I was going to fall a lot, and that I needed to get used to it. They told me to always look where I wanted to go. There are some incredible roller skating communities, and hopefully one day, post-pandemic, I’ll be able to learn from them, but at the outset, these bossy women on YouTube were my treasured mentors.

The weather got better; the sun set later. Instead of dreading going back to my apartment after a demoralizing day at work, I was rushing home to get my skates and practice for as long as I could. When I went to the gym, I spent extra time working out my quads and calves and inner thighs. I began to appreciate my body for what it was capable of, instead of criticizing how it looked. I started noticing smooth new pavement all over the city. I made a playlist of songs to skate to, songs that make it feel impossible not to move: Robyn, Charli XCX, Missy Elliot, and Abba.

I practiced most often on those basketball courts on Bunker Hill Street, where the buses run from the North End to Sullivan Square. It’s a busy commuter route, and I imagine folks got used to seeing me fall on my ass on their daily bus ride home. The great thing was, I didn’t care. I didn’t spare a thought to how silly I looked, because I felt amazing. If one of the courts was occupied, I didn’t hesitate to take up the empty one, skating and falling beside groups of teenage boys.

Unlike my other abandoned hobbies, every time I fell or failed on my skates made me more determined to keep going. Falling feels personal, and when I crashed onto my palms or knees, I’d get up immediately, with fresh “fuck you!” determination. I liked the scuffs on my skates and the scrapes on my knees, because I was falling and falling and falling, and I was getting better. I had to keep falling to keep getting better, and I went to the basketball courts every day excited to eat shit.

Roller skating reminded me that all I can do is practice. After spending hours just trying to learn how to turn around, suddenly mastering the motion of lifting my toes and flipping my body at the right time felt incredible, as if I were a clock and all my gears suddenly met and moved exactly as they were meant to. It’s a simple, wonderful, “I did it!” I was driven inside at the end of the day because the sun set or because my quads were cramping, not because I felt ready to give up.

Impostor syndrome is not possible on roller skates: You can do something, or you can’t. And if you can do it, you have nothing but yourself and your body to thank. I’m not the best at roller skating — I would honestly say I’m still not even very good at it, more than a year later — but I do still enjoy getting better at it. I live in Colorado now, where I hardly ever have to wait for sunshine, and I found a park with abandoned basketball courts that look out toward the Rocky Mountains. The pavement is so smooth, I can’t even feel my wheels humming against it. I fell last week, literally punched the cement as I landed, and now I have a row of gnarly bruises across my knuckles like a boxer. I drove home an hour later with streaks of dried blood down the back of my hand, so, so happy.

Katie Cunningham is a writer and nanny currently quarantined in Denver, Colorado.


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