This originally appeared in my friend Pat’s blog A World of Logical Consequences in April of 2006.

I’ve had a short story in mind for a while now. Here’s the opening line: On my thirtieth birthday, I bought a skateboard. It was going to be a Cheever-esque exploration of immaturity, juxtaposing the narrator with his friends, all married with children with real jobs and real adult lives. I didn’t have an idea for the poignant realization part of the short story but at least I had the first line. I figured something would occur to me through successive drafts.

Perhaps I’ll still write it. However, it won’t be fiction. Yes. I bought a skateboard a week and a day after my twenty-ninth birthday, one year early.

The defining feeling of my twenties has been one of time running out. There’s a battle between what we can get away with at different ages. What’s appropriate? When should you marry? Get a real job? Settle down? When can you no longer purchase your first skateboard? While I haven’t declared a position on the former questions, I think I have a handle on the latter: thirty is pushing it. So, I gave myself a twenty-ninth birthday present.

I’ve also given myself a mission. The mission is to learn to ollie before I turn thirty. Now, I haven’t skateboarded since I was about twelve or thirteen. I couldn’t ollie then and I can’t ollie now. I had a cheap toy store skateboard unlike my friend Austin who had a Vision Gator skateboard. But I won’t let the blame rest on my inferior equipment. I was also a pussy afraid of falling on pavement. Besides, I had TV to watch.

Is this just my quarterlife version of a Porsche and hair plugs? (You’ll notice that I left out the trophy bimbo that completes the triumvirate of the midlife crisis cliché. At my age, a trophy bimbo is still very welcome and doesn’t necessarily veer into the realm of pathetic. In fact, I think it’s still considered, quite simply, awesome.) I don’t think so. I think it’s just an interesting challenge in the vein of, “man who catch fly with chopstick accomplish anything”. (Daniel San had a BMX bike, not a skateboard, but I digress…)

My mother never wanted me to get a skateboard. I idolized Marty McFly in Back to the Future and his skateboarding skills – holding on to the backs of cars to get around town. Damn he was cool. My mother feared for my life just watching that movie. And, now that I’m older, I suppose I can see the danger in holding on to the bumpers of cars while riding a skateboard. But, at the time, even the thought of me on a skateboard in the driveway scared her. When we watched Big with Tom Hanks and the twelve year olds had skateboards, she leaned over to me and said “don’t even think about it”. So, here I am, a modern day Ralphie Parker, attempting to go against the grain of accepted parental wisdom. I’m a man now, damn it. If I want a skateboard, I can get a skateboard.

Also, I haven’t told her about it.

Last year, I picked up Dogtown and Z-boys on DVD and started watching it obsessively. I’ve always been fascinated by people coming out of a certain scene whether it’s the writers and painters from Greenwich Village in the fifties or the musicians coming out of Manchester in the late seventies and early eighties. The story of the Zephyr Skate team is pretty compelling – the confluence of circumstance that led to the birth of pool skating as well as the meteoric rise of Stacy Peralta, Tony Alva and Jay Adams.

While watching the documentary, I felt the pull towards skating. Now, there is nary an ollie in the movie. They were all surfers and vert skaters. The ollie would be invented and perfected by the next generation of skaters in the Bones Brigade era by the likes of Tony Hawk et al. But let’s not get into a semantic argument over skateboarding history. It really doesn’t serve our purposes here. The point is, I realized that I have unfinished business. I never learned to ollie.

I have to give myself credit for overcoming one hurdle already. I actually purchased the skateboard from a skateboarding store. I have a chip on my shoulder about feeling out of place – whether it’s self-esteem issues or the remnants from too much punishment from middle school tormentors, I don’t know. Again, let’s not get off topic. I’m a reasonable person and I know in my head that my feelings of inadequacy are unfounded. No one actually cares or notices. However, in the case of a skateboarding store, I really don’t belong. I am the unthinkable, unmentionable, untouchable. I am the pariah of the skateboarding world. I am a poseur.

I walked into the East Village skateboarding establishment with the same mix of shame and self-righteousness as the guys I saw coming through the salon doors of the adult section of Champagne Video when I lived on the Upper East Side. The skateboard store was small and narrow with boards up on the wall above a long rack of t-shirts. To the left were shoes and skateboarding DVD’s. I browsed the boards while the lone employee made conversation with some customers, neither of whom looked as out of place as me.

After about fifteen minutes of awkward browsing without anyone offering help, I knew I had to make my move.
“Hey, I’d, uh, like to buy a skateboard,” I said. Now, just to take a peek into my psyche, this request actually caused me some anxiety. Did I say it wrong? By not calling a “deck” or a “rig” or some shit, was I just screaming “poseur”?
“Sure, what size?” the guy asked. Size is the width. The lengths are all the same.

“Uh, I’m not sure.”

“Have you done a lot of skating before?” he asked. We both knew the answer, obviously, and I had already nixed the idea of inventing a phantom little brother who was going to receive this as a present, so, I just admitted it.

“Nope.”

“All right, what are you going to use it for? Tricks or just cruising?”

“Um, a little bit of both, I guess.” I’ll just save the “learning to ollie before I’m thirty” bit for myself, my close friends and readers (who, frankly, are probably one in the same).

Then we picked out some wheels and he put it together. Then I dropped my credit card down, paid for it and walked out of the store.

I’ve started on my mission and here’s what I’ve learned. First of all, I’m going to spending a lot of time on my ass. Second of all, those kids who skate in Union Square, the ones who never land a trick – those kids are incredible compared to me. So far, I’ve perfected a few embarrassing pseudo ollies. The first is where I just jump up in the air and the board goes nowhere. The second attempt is where I kick the board up but it flies out from under my feet. The good attempts – the ones where I actually land with both feet on the board – end with me falling backwards onto my ass, scraping the heels of my hands, with the board skidding away from me.

I can’t bring myself to wear pads or a helmet. Even though my anxiety filled mind replays nightmare injuries where I become the first person to breaks his neck from attempting an ollie. The worst part of the fantasy isn’t the nurses and doctors asking me how I did it, then saying “aren’t you a little old to be riding a skateboard?” It’s not even my mother’s hard earned “I told you so.” The worst part is, years later, close acquaintances in private moments leaning in to me and saying, “I don’t mean to pry, but how did you end up in that wheelchair?”

Then I have to reply, “Well, on my 29th birthday, I bought a skateboard…”