I Stepped on a Skateboard Again After 35 Years. Here’s What Happened.

Standing at the skatepark

Last week I stood in full pads staring down an 8-inch kicker ramp. It looked at least 12 feet tall. My wife and two of our kids were watching. Thankfully, there were no other skaters around to witness the spectacle — an old man wearing body armor, facing a tiny ramp with trepidation. It was a sweltering morning, and the humidity and fear had sweat pouring into my eyes.

I had already made a couple of runs at the ramp. Each time, I didn’t have enough speed to clear it. The front of the board went over the ramp, but then dove nose-first into the ground, sending me jogging forward to bail out.

Thoughts that went through my head:

“This is really dumb.”

“You’re too old for this.”

“There is a distinct possibility that you are going to get hurt.”

That last one was the big one. At 48 years old, I’m not sure if I could recover from a hard fall the way I did when I was a kid. Eons ago, as a teenager, my friends and I built a launch ramp out of scrap plywood we found in a local church parking lot. The pastor was a cool guy and let us skate there. We spent the afternoon flying off the end of the ramp into the grass at the edge of the parking lot. With the soft turf to land in and the invincibility mindset of an adolescent, there was no fear.

Times had changed.

What happens when a middle-aged man gets back on a skateboard after roughly 35 years?

The kid who used to skate

In middle school, I lived for skateboarding. I started with a JCPenney catalog skateboard with questionable build quality, and I was hooked immediately. All my friends had the same routine. We would get off the school bus, grab our boards, and then cruise to a parking lot or the street to skate. I skated every day from 12 to 15 years old.

It was the early 1990s. My small town didn’t have a skatepark, so we had to be resourceful with places to skate. Church parking lots were the usual spots. Most of the time, people were welcoming, but we occasionally had run-ins with irritable neighbors or the police. We never got into any real trouble, though.

Although we didn’t have a skatepark, we did have a great skate shop. Fairman’s Thrash and Threads in West Chester was a great shop. I got my first real skateboards there: a Blockhead Omar Hassan full-size and a Lance Mountain mini. Sadly, it closed a couple of years ago.

I sucked at skating, really. I could ollie and cruise around, but I was never a great skateboarder. I did it because I loved it. It was what all my friends were into, and it was that first taste of freedom as a kid when your parents first start to let you out into the world. It was the unsupervised, “come back when the streetlights go on” world that doesn’t exist anymore.

Eventually high school started, friends moved away, and new interests emerged. I went off to college, got a job, married, and had children. In the back of my mind, fond memories of skateboarding remained.

Why the hell did I decide to do this again?

My preteen daughter thinks I’m an idiot. She calls it “cringey.” I’ll admit that the idea of someone my age skateboarding is difficult to wrap your head around.

Of all the hobbies that a middle-aged man could cultivate, why skateboarding?

I’ve been thinking a lot about getting older, losing my sense of adventure, and learning new things. The typical adult activities of golfing, jogging, and bowling don’t appeal to me. I had a crazy idea. Why not try skateboarding again?

It was a fleeting thought that I dismissed at first, but it kept coming back. Some of it is nostalgia, of course, but really, I just wanted to do something fun. I don’t plan on being any good at it. That doesn’t matter to me. It’s the feeling of disconnection from real-world concerns that does it for me. When I’m skating, all I’m thinking about is skating. It’s a break from everything else in life.

I quit skateboarding just as it was about to explode in popularity. I watched Tony Hawk land a 900 at the X Games; college roommates played Pro Skater on PlayStation. Skateboarding even made it to the Olympics. After years of watching skateboarding on TV, I didn’t want to watch anymore — I wanted to try it again. What I’ve found is that the skateboarding world I left behind is gone. There are now at least a half dozen really nice skateparks within driving distance of where I live. I’d have killed for opportunities like that as a kid.

The first session: Reality arrives

So I bought a skateboard. When I was younger, Powell-Peralta was one of the biggest skate companies. Digging around online, I was glad to see that they still make skateboards and have even reissued some of the older decks that I remember from the ’80s and ’90s. I put together an 8.5-inch Flight deck with Indy trucks and Bones wheels.

In the alley behind my house, I stepped onto my brand new skateboard. Suddenly I realized how difficult this was going to be. It seemed I had forgotten the hours it took as a kid just to keep the board from flying out from under me. I had expected it to be like riding a bike. I thought the muscle memory would still be there.

It wasn’t.

I had to bail out multiple times. Just standing on the board made my feet ache. The little muscles in my feet were firing like crazy just to maintain my balance. Every little pebble seemed to catch the wheels and send me flying. I’m also a lot bigger than I was back then, and the board I chose seemed way narrower than the skateboards of my youth.

After about a half hour, I was tired and sore. I was able to push, turn a little in the narrow alley, and get a little comfortable rolling down the street. Fear was there, though. Fear of falling and getting hurt was something new for me. I wasn’t sure if this was something I would be able to get over.

The surprising part: I went back

I realized that the road behind my house was not an ideal place to skate. I found a skatepark just a few miles from my house and did something I never got the chance to do as a kid. I drove there and went skating.

Now I was no longer in the safety of my own backyard. I was out there in the world where judgment and ridicule happen. Luckily, I was the only one there. I skated around a little, just taking it all in. There were various ramps and halfpipes constructed of metal on an old tennis court surface. It wasn’t the smoothest, but a lot better than the road behind my house. I tried skating up and turning on some of the quarter-pipes, but I lost my balance often and had to bail.

After a while, another guy showed up. Interestingly, he wasn’t all that young either. My guess was mid-thirties. I told him to let me know if I got in the way, but there was plenty of space. I kept off to the side where I could just practice rolling around. If the guy thought I was goofy, he didn’t say anything about it. I skated a little while longer, then went home exhausted.

But I went skating again. This time to a tiny concrete park in a small town. I had the whole place to myself. The really cool thing about the park was its small pump track. Until recently, I’d never been to a skatepark and never been on a pump track. It was awesome. I fell really hard a bunch of times. I was sore for the better part of a week, but I went back to the pump track again. Skating that thing really improved my balance. I tried skating the small bowl there, with less success. I fell a lot and started wearing pads religiously.

At home, I started spending more and more time thinking about skating. I try to go at least once a week for an hour or so. My wife and kids usually come along to play on the playgrounds or just watch dad skate. I’ve gone from someone who used to skate to being a skateboarder again.

Being scared at 48 is different

The fear is a real thing. I’ve taken some absolutely bone-jarring falls since I’ve been skating again. I don’t remember ever being more than a little sore when I was younger.

There are times when I look at an obstacle and my ego tells me, “Go ahead and do it,” but I chicken out. As a kid, I had no fear and did a lot of stupid things on a skateboard.

At my age, I’ve started thinking about the consequences of an injury. Missed work time, insurance copayments, pain, and recovery are real. Despite the fear, I keep going.

And I am improving. I did my first real ramp trick ever the other day. It was a rock to fakie on the little ramp that I’m afraid to jump off. It’s a simple trick, but it’s progress. I’ll take it at my age.

Progress looks different now

I’m not trying to be the best skater around. Instead of looking at others and measuring my progress against theirs, I’m trying to be a better skateboarder than I was the day before.

I have smaller goals that still have meaning. I’d love to be able to make it all the way around the pump track without losing momentum. It would be great to learn to drop in on that little bowl and ride around. And I need to be able to jump off that little ramp.

I’ll take the small victories. Adults often feel pressure to turn hobbies into accomplishments—times, scores, rankings, productivity, something to show for the effort. I’m choosing an activity that makes me look a little silly, but makes me happy.

I don’t need to be as good as I was at 15. I don’t even need to be particularly good now. If someday all I can do is cruise around the park, I’ll cruise around the park.

Nobody cares that I’m an old guy at the skatepark

This was a legitimate concern for me. It turns out that no one other than my children (who are only teasing) thinks anything much about the old guy at the skatepark.

I usually go to the skatepark very early in the morning, before it gets crowded and I get run over. There’s often no one else there. The folks who are there are usually so focused on their own skating that, other than saying hello, not much happens. No one points and laughs. I might be the only one wearing head-to-toe pads, but no one seems to care.

Skate culture seems to have lightened up a bit since I was a kid in that it’s much more inclusive. That’s a good thing. I soon discovered that I wasn’t the only person skateboarding again after 40. There are whole groups and forums online dedicated to middle-aged skateboarding.

The thing I didn’t expect

As kids, we always seemed to be looking forward to something new. Everything was exciting. There was anticipation in Christmas, summer vacation, seeing friends, Saturday morning cartoons.

As adults, we lose some of that. We have work, bills, home repairs, appointments, and overall less fun. Skateboarding has given me back that anticipation of something that is just plain fun. Something simple and pure to look forward to.

By Thursday evening, I’m already thinking about whether I can get to the park Saturday morning. When I drive somewhere, I make detours to see that community’s skatepark. I watch the weather to see if it’s good for skating. And I think about that damn ramp.

I hadn’t realized how much I missed looking forward to doing something for no reason other than that it was fun.

So there I was. Eyeing up that tiny kicker ramp. I lined up to give it one more try. I pushed off, reached the top of the ramp, lost speed, hung up, and came crashing to the ground. My wife asked, “Are you OK?” I answered yes and meant it. I told her it was time to quit for the day. I’ve learned at my age when enough is enough. I was tired and sore, but happy. I’ll be there again this weekend. Just need a little more speed.

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