Skateboarding terrifies me.

As a kid, I think I tried once, quickly fell hard, and vowed never to try again. And it's especially horrifying to me now, as a 33-year-old out-of-work standup comic. I'm used to plenty of emotional pain, but bombing onstage hardly ever ends in broken bones.

It's not that I'm completely uncoordinated—I do play Ultimate Frisbee, after all—I've just always preferred sports where a small mistake doesn't lead to lots of blood loss. But after seeing way too many "inspirational" posts about learning new skills during the pandemic, I felt I couldn't leave all the good vibes to people learning how to bake bread.

My task was to teach myself to skate in a week. If nothing else, it'll get me out of the house and back into my comfort zone of feeling like an impostor. And honestly, my bar for accomplishment is pretty low—I'll be happy with not killing myself.

Day 1

I've never skateboarded, but I do own a skateboard.

I live in a place that's been inhabited—some might say infested—by comics since 2013. The board has been there for years. I imagine it must have been left behind by one of the countless drunk open-mikers who've crashed on the living room floor. I don't know who it belongs to, but it does have "FUCKO" written on the bottom.

I need someone to show me the ropes, or the wheels or whatever, so I set up a Zoom chat with my friend Bill Conway, the formerly Portland-based co-founder of satirical website The Hard Times, who now lives in Los Angeles. Bill shows me how to get on the board and push—as best one can through a phone screen, anyway. His main advice? "Get used to the fact that you're going to be intimately familiar with hitting the ground," he says, "and you're gonna hit it hard."

Around 11:15 that night, I take my board out for its first spin in the parking garage outside my apartment. My girlfriend accompanies me to make sure there's someone to call the ambulance and/or laugh at me if and when I fall. I dress in what I think skaters wear: skinny jeans and suede Adidas. I also wear a helmet, which seems decidedly uncool, but I'm also not trying to concuss myself on night one.

I get on the board. I wobble, I shake. This is going to be a long week.

I get going a little faster than I want and have to bail. The board kicks up and misses my neighbor's Jaguar by inches.

Before I head back in, I try that trick where you kick the end of the board so it flips effortlessly into your hands, but I keep getting scared it's going to hit me in the balls. I bend over and pick it up in shame.

Day 2

I feel like a dork searching YouTube for "skating videos" because it feels like typing "boobs" into Pornhub, but I don't really know any skaters besides Tony Hawk, and I know I'm not dropping into any half-pipes this week. I end up watching a guy named "Jaws" jump off a 25-stair set. These guys are simply a different breed from me.

Bill said a good place to start would be a smooth basketball court, so I head over to Irving Park. I push around for a while, at one point panicking when a group of kids comes by to shoot hoops. Thankfully, they either sensed how nervous I was that they might see me fall or were simply too embarrassed to be in such close proximity to a grown man with a dorky helmet in skinny jeans trying to recapture his youth, and decide to go elsewhere.

After clumsily rolling around the court for a bit, I noticed how little momentum I was getting. I turn the board over to spin the wheels and noticed they stop rotating  rather quickly. That means a visit to a skate shop tomorrow.

DIE OR SKATE: Jake Silberman, shredder. (Annie Schutz)
DIE OR SKATE: Jake Silberman, shredder. (Annie Schutz)

Day 3

I decide I need a teacher who can actually see me in person, so I call up my friend Alex, who is more of a casual, not-into-tricks skater. He takes me over to Woodstock Hardware where they have a small skating section. We buy new bearings, which are much easier to install than I anticipated. My wheels are now spinning freely.

Alex takes me for a lesson around his neighborhood and shows me how to properly push and where to keep my feet on the board. He shows me how to ride off a curb, and I make this my goal to do by the end of the week. I try a few times but am just too nervous to commit.

I vow to conquer that fear no matter what. Besides, there's no better time to break a limb or two than during a pandemic when I'm supposed to be at home anyways.

Day 4

I wake up sore and stiff.  After resting most of the day, I head out to skate at Irvington Elementary, which has a big, mostly flat schoolyard perfect for not busting my ass in public. I still can't really make any sharp turns, so when I need to change direction I either make a very big loop or just hop off the board and turn it around.

Some kid walking his dog across the lot waves at me. Does he think I'm a skater? Do I fit in? Why am I so worried about a middle schooler's approval?

Another skater shows up. We do the head nod and I watch him out of the corner of my eye as he effortlessly glides around and pops a few tricks.

Somewhere during this time I've become my own Vitamin Water sponsor, buying a 32-ounce Tropical Citrus from the overcharging neighborhood corner market near my house after nearly every session. I may not be a skater, but I'm gonna hydrate like one.

Day 5

I'm sore as hell, in odd places like my left pec, which must be from all the flailing. As I'm getting ready to go out, I cut my foot on a random piece of broken glass left on the floor of my living room—living with comics rules!—and I start bleeding all over the carpet.

No skating for me today, and I worry that this might be it for my week.

Day 6

The cut on my foot has healed up much better than I thought. I head back to Irvington, my new skating home, and I can feel the rust—one day off seems to have robbed me of my hard-earned "skills."

I push around lightly, trying to regain my confidence. There's another skater here, wearing one of those "guy who's still trying to hoop even though his knee said 'Dear God, please quit' years ago" leg braces. This makes me nervous because my knees are already shot after some hard years on the Ultimate Frisbee field.

A bit later, a guy in his early 40s shows up on one of those one-wheeler things, wearing a T-shirt that says "Epic Husband Since 2000." I imagine what lucky gal is waiting at home for her man to ride up on a Sharper Image toy. Then I realize I'm also an adult who can barely stay upright on a small board with wheels and decide to shut my mouth.

I see a short curb and decide to try to ride it. I straighten my board and push off. I hit the curb and commit. I make it to the street! I didn't stay on the board, but I'm not dead! I've broken the seal of fear!

I head back up the sidewalk a few more times and eventually nail it.

Day 7

My girlfriend and I head to Irvington so she can witness the hot skater bro her boyfriend has transformed into. She films me failing going off the curb a bunch until I finally land one. She hops on the board in sandals and instantly has more balance than I've had all week. I blame it on my big feet. As we're leaving the park, I try to ollie in the bark chips of the playground, coming nowhere close.

As I skate home, I don't consider myself a skater since I never fully ate shit, which leaves me feeling like a true poser. I'm not sure how many times I'll get back on the board in the future. But I do know I'm still getting that overpriced Vitamin Water.