A couple years ago, I was skateboarding down a beautiful slope of connecting suburban streets. At one point, my route ran past the house of a childhood friend, who was watching me from her large living room window. She was curious: What was I doing out there? What led me to launch downhill on a skateboard, particularly at age 50-something, and float through the Maryland countryside?

When she asked me that question in person, my answer was at first very technical. I ride a Carver skateboard, I told her, because they have this fantastic patented swivel design in the front truck that makes it move like a surfboard, great graphic designs, and it’s good for balance. Skateboarding is good exercise and a hobby I’ve loved since I was a kid in the 1970s. 

“That’s great,” she replied—but I could see she was after more. She wanted to know why, in my heart, did I still choose to skateboard? I love the feeling of the air against my face, I said, and how the streets look as you ride by, and the funny dogs that come to greet you, and the feeling of being in motion even as the earth is in motion and God’s wondrous cosmos is in motion.

“Oh,” she said. “So you’re out there praying.”

I just looked at her, a bit stunned. Why, yes. I had never thought about it that way. But, yes. Skateboarding is like praying. My friend and I had both gone to Jesuit schools, and didn’t the men of that order teach us to be “contemplatives in action?” That was as good a description or, rather, decryption of skateboarding as any. 

Shortly after our conversation I wrote an essay for Modern Age in which I reflected on my own history with skateboarding, how the sport has reappeared at different times in my life to reentrance and mesmerize me. One rider I quoted in the piece described in the journal Buddha Weekly how when he stopped worrying about doing tricks and simply rode his board home without bells and whistles, he experienced a feeling of blissful Zen peace. The rider, Sonic Mike, was present (you have to be when riding). His breathing became steady, regulated. He was noticing the world around him. 

He was, in fact, praying.

My story would certainly be appreciated by Kyle Beachy, the author of the recently published book The Most Fun Thing: Dispatches from a Skateboard Life. Beachy, cohost of the skateboarding podcast “Vent City,” observes that even as a married 41-year-old man, skateboarding “continues to fill a necessary if difficult-to-name void.” 

The essays in The Most Fun Thing were published in various forms and in literary and sports journals between 2010 and 2020. Beachy’s style might not be for everyone; he can often use too many words where fewer will do and his imagery can sometimes bleed a bit purple. Yet, at its best, The Most Fun Thing is a collection crackling with intensity and love for the hobby that has defined his life and helped form his philosophy.

Beachy is a novelist and a writing teacher, as well as something of a philosopher, so The Most Fun Thing is not an adolescent, superficial read about ollies and power slides—although Beachy does know his lingo. For example, when he describes Belgian pro Youness Amrani’s “backside noseblunt and kickflip manny,” connoisseurs of the sport will feel at home. 

For Beachy, the “sacred” act of skateboarding helps him move through the difficulties and joys of life with “rhythm and harmony.” The different riding styles can reflect the different aspects of human nature—sometimes cautious, sometimes daring, sometimes foolhardy. 

Visiting a favorite Chicago spot where he rides, Beachy reaches for the metaphysical: 

This is where the meaningless activity [of skateboarding] has brought me. Via a long sequence of questions about selfhood and performance, about watching and comprehending, I have come to think that the style skateboarders speak of might, in fact, be a tool for understanding what mankind used to call the soul.

Indeed. There has long been a correlation between human movement, whether it’s dance, play, or lovemaking (which John Paul II called “an icon of the interior life of God” ) and the soul. Skateboarding is an Olympic sport, a billion-dollar industry, and an edgy subculture. It’s also an expression of the soul. In this way it is like another great American original art form, jazz.

Like jazz, skateboarding has certain rules and traditions that need to be mastered while also expecting and celebrating innovation and improvisation. Also like jazz, skateboarding started as something of an outsider activity, somewhat disreputable, a subculture of misfits and outcasts. 

Arising out of the early 1960s Southern California surfing scene, it quickly developed a reputation for danger and iconoclasm. In 1965, the California Medical Association called skateboarding “a new medical menace.” Cities banned riding on public sidewalks and streets. Yet, as Beachy reveals, skateboarding, like jazz, also has a feeling of the spiritual at its core. Its practitioners, like jazz musicians, tend to have their lives transformed by the activity in question. In The Most Fun Thing, Beachy gazes upon famous skateboarding sites the way a jazz disciple might view the Village Vanguard or the birthplace of John Coltrane.

And just as it’s impossible to fake jazz chops, one can’t fake skateboarding. One of the best essays in The Most Fun Thing is a profile of Jeff Grosso, the sport’s unofficial ambassador. Grosso died in March 2021 and was described as “the soul of skateboarding.” Like Beachy, Grosso sought to understand this thing, skateboarding, that still held him in thrall well into adulthood. “It’s a total rush,” Grosso told the St. Louis Dispatch in 1986. “It’s the feeling that when you go out there with your board, it’s a no-hero type of thing. And you either accomplish something or you don’t.”

That last sentence, about how when you ride you either accomplish something or you don’t, may account for why skateboarding is more popular today than ever. It stands out as an activity that requires total integrity in a world that seems largely compromised. In Little League, everybody gets a trophy. A transgender swimmer who was a man the day before yesterday is shattering women’s records, and he thinks that makes him honorable. Simone Biles dropped out of the Olympics because “there’s more to life than just gymnastics.”

For many skateboarders, “just” riding is important for personal integrity because it is such a genuine, soulful, and uncompromising part of life itself. You can’t fake it. When you are at the top of a hill about to push off, or looking down at a concrete staircase about to attempt a rail slide, or even just attempting an ollie, there is no way to cheat or fudge. As Jeff Grosso said, either you will accomplish something, or you won’t. Kyle Beachy puts it well in the best passage from The Most Fun Thing:

How many of us, I wonder, are lucky enough or doomed enough to have a force such as this in our lives? A practice, I mean, or pursuit or activity, an entity, or really any kind of thing whatsoever, that we fear or respect enough that we will not lie to it, or try to trick it, or approach it with anything short of total candor? A thing that we know can see through us, that will laugh at our folly without reserve, revealing sharp and yellow teeth, pointing a long finger to mock our reality? And will just as readily offer an embrace for our persistence and reward us with a joy that has no cognate, that is its own unique end?

Not many.

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