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A Love Letter to Kissing the Concrete: How Skateboarding Resurfaced My Motivation

Aug. 13, 2019 at 7:36PM

It was far too late when I realized how silly I must have looked standing in my underwear in the parking lot of a skatepark. I had just come from an interview for an editing job and had decided to go skateboarding immediately after — a perfect storm of adolescence meeting adulthood.

The author, sitting curbside near his Riverwest home. July 2019.
The author, sitting curbside near his Riverwest home. July 2019.

Using my open car door as a changing-room curtain, I swapped out my “formal” outfit for a band t-shirt, black skinny jeans, and black Vans (which describes about 90% of my wardrobe’s potential outfits). My head was pulsing from a goose-egg-sized bruise on the top of my skull and a crescent-shaped cut under my left eye from a pointless scuffle I had gotten into at a show the night before. Looking at me, I must have appeared a mess; but on the inside, I felt on top of the world.

I didn’t end up getting that editing job. I don’t think I even came close.

In fact, I still don’t have a full-time Journalism gig. I’ve been searching on and off ever since the newspaper I worked at ceased publications in September of last year. On top of that, some other major life changes seemed to suggest that everything that I thought was good in my life must end and that all of my efforts are just frugal attempts that made me question why I even went to college in the first place. I kept landing interviews, but wasn’t landing jobs. That’s when skateboarding decided to (literally) crash back into my life.

I hadn’t seriously skateboarded in around five years — maybe even longer. It started as just a conversation between friends. “We need to get back into it this Summer.” I would have never guessed that it would’ve have taken off with the enthusiasm that it did. I started getting back out to skate parks at least once a week. My friends were equally on board, starting group chats to schedule weekly sessions and even crafting their own obstacles to skate at home What started as a three-person group quickly expanded into a group of about a dozen old dudes giving it their all.

It all began to come back to me. All of the tricks, the fun, and most importantly: the drive. I’m learning new tricks that I was never able to land before, even back in my “prime” when I was skateboarding almost every day (when I was around 17, maybe?)

Now in my late-twenties, I’m realizing that the most important lesson I ever took away from skateboarding was to shrug it off, get back up and try again. It’s something that I subconsciously understood when I was first learning to skateboard, but didn’t fully grasp until now when other areas of my life could benefit from that same sort of mentality. I used to spend hours trying to get that one trick on the flat bar at the skatepark. I used to bruise up my shins dedicating days to landing that one flip trick in my mother’s driveway.

So why do I now let things like having my resume disregarded after a few tries make me feel hopeless? Why do I ever doubt myself? I used to throw myself down staircases trying to land a trick over and over and over.

Did I lose that determination just because I now have a few gray hairs?
The leg tattoo illustrated by the author's Dad.
The leg tattoo illustrated by the author's Dad.

My parents taught me many important life lessons. But I honestly believe that only skateboarding could have humbled me in this way. Sometimes I really hate that moment when I’m trying my hardest only to end up kissing the concrete. But hell, I really don’t know what I would do without it. To those who have never skateboarded, there truly isn’t anything I can compare what it’s like to land a trick you’ve been trying all day to. What I can tell you is that even now, that feeling is exactly the same as it was when I was a teenager. Getting back into skateboarding has resurfaced a sense of drive that at some point in the past couple of years was buried deep inside of me just because a few things in my life didn’t quite stick the landing.

Maybe all I needed was a reminder — kind of like a younger version of me, traveling into the future to laugh and say, “Time to get back up and try again, old man.”

About the author

Mike Holloway

Mike Holloway was the music editor for The Wisconsin Gazette until it ceased publication in Sept. He currently writes for 88Nine Radio Milwaukee, Milwaukee Record and Urban Milwaukee.