The most intimidating aspect of skateboarding is still its most appealing—namely, that it is a secret world where culture, fashion, physicality, and self-expression collide (sometimes alongside broken limbs and trespassing tickets). The twenty-first century has been a boomtime for skateboarding, which has grown increasingly professionalized, with corporate sponsors and organized competitions such as the X Games and the Olympics influencing—and, in the eyes of some, altering beyond recognition—a sport that began in the streets of California in the 1950s as a downtime activity for establishment-averse surfers. And while skate culture is extremely tight-knit, skaters have had to contend with this ever-evolving landscape that is in many ways fundamentally at odds with the purity of the scene. That purity begins at first love with the board and quickly blooms with the act of skateboarding itself. But as the ways in which we engage with skateboarding become increasingly monetized and globalized, while professional skateboarders themselves remain unorganized and stratified, how does this change skaters’ relationships with their boards, their streets, and their sport over the course of a career—or life—spent skateboarding?
My first encounter with skateboarding was watching halfpipe skaters flying in the skies of Tom Petty’s “Free Fallin’” music video preceding TV shows like MTV Sports and The Real World. I found a decade-old Price Club skateboard in my garage—a heavy orange-and-black Action Sports Kamikaze board with stiff trucks and oversize black wheels, the board’s graphic a knockoff of pro skateboard legend Christian Hosoi’s iconic Rising Sun board—and started pushing around before the skateboard’s trucks quickly fell apart. Circa 1996, as skateboarding resurged in popularity, I met skaters at school who were more connected to the local scene than I was, friends of friends sponsored by Utility Board Shop, the neighborhood skate shop. They were my entry point into the world of more skilled, locally recognized skateboarders, those who received an occasional free deck and an evergreen discount to UBS. I didn’t get invited to skate with some of them—instead I befriended those in my existing friend groups who had also started skating—but between these crews I accumulated enough hand-me-down parts that collectively, along with a newly purchased blank bargain board from UBS, enabled me to put together my first proper complete modern skateboard. I bought some skateboarding VHS videos from behind the counter at the skate shop and began watching them, memorizing the movements that define skateboarding’s guerrilla film industry. I learned how to push, how to ollie—that foundational move of popping the tail and rising with first the front foot and then the back, balancing into a perfect leap midair—and, quickly, how to fall, tumbling rather than extending my wrists to break the impact. Those friends who kept skating became my accomplices every weekend, finding schoolyards and parking lots to learn and practice tricks in. During the week after school, I’d stay sharp by practicing alone on my block or at the nearby basketball court at the park. A regimented obsession developed, and by the beginning of 1997, just after turning twelve, I was hooked.
When I did get my first proper setup, I made the all-too-common error of putting my trucks on backward, and felt the uneven pull in the board’s direction, not knowing that something was deeply wrong, until I pored over skate magazines and realized my mistake. Like many skaters, my sense of ownership—and my true indoctrination into the sport—began the moment I physically assembled this first board. To do it right, you must avoid any number of pitfalls, as I had discovered. Bearings unevenly slammed into wheels. Air bubbles introduced into the griptape as you go through the act of “gripping your board”—applying the adhesive, sandpaper-like black tape to the top of a skateboard deck. Kyle Beachy writes in his collection The Most Fun Thing: Dispatches From a Skateboard Life, “No skateboarder with any self-respect will let another person apply griptape to their board.” Applying griptape as you see fit establishes your connection to the board you are creating, curating, and preparing for a lifetime of adventure. You come to know your board through this ritual act. Gripping the board is as necessary a skill as ollieing, something you learn once at a skate shop and do for yourself for the rest of your skating life—because it’s your board and this is what skaters do. It’s as much an identifying rite of passage as the act of riding a board itself.
Skateboarding involves putting your trust in a wooden toy and going outside, pushing through the streets, and integrating your environment—curbs, ledges, stairs, potholes—into one more fundamental part of your relationship with the board beneath your feet. Many skaters don’t even use the regulated skateparks designed and legalized for their convenience—most are poorly designed, built without input from skaters after multiple rounds of city council debates on whether to have them in the first place. Why skate there when you can take your board and hit the streets, basking in the temporal ownership you feel as you repurpose underutilized public space, knowing an unmarked red-painted curb first grinded by you and your board is somehow now “yours”?
Still, unlike surfing, where regardless of the size of an ocean’s tide, few citizens bat an eye at the sight of surfers paddling in the water, skateboarding on the streets can anger civilians. The sound alone of skaters mobbing down the street is enough to make pedestrians shake their heads in disapproval at what they view as reckless vandalism. But skating belongs in the streets, in relationship with an environment where skaters can find and accumulate “spots”— public locations not intended for skateboarding that lend themselves to particular, nuanced tricks. These spots are chosen for the creativity their features engender—staircases to descend, handrails to grind or slide, ledges with straight ends for more effortless dismounts. Skaters seek spots wherever they go, and once they find them, they calculate whether to take the concomitant risks: tickets from cops, physical injury, even getting hit by a car if the landing of a spot is in a busy place. They also learn the unspoken rules of ownership as they frequent these spots, weighing the balance of foot traffic and the possible presence of law enforcement against ample opportunities to execute an intended trick. If a spot is central, like a city hall or courthouse steps, skaters will schedule their skate sessions against the tide of civilians’ routines in urban spaces. These aren’t turf battles, as you might see in surfing, due to a kind of etiquette. If you’re sponsored, don’t repeat a legendary trick in the same legendary spot. Don’t “blow up the spot” by littering, graffitiing nearby businesses. One could call this “owning” the spot, but many skaters know such ownership is brief.
This dynamic relationship with public space speaks to what skaters always own: the knowledge that unless you fully submit to the act of skateboarding itself, you will never truly understand the culture—let alone the cockiness and confidence acquired when falling becomes an option, however controllable, scabs on elbows like encrusted merit badges, earned by trying to learn something new. This new thing is often something that seemed unachievable mere days earlier—an idea that is transformed into a physical, accomplished act. When landing a trick after hours of trying, you feel not so much a celebration but an exhalation, a release of relief. The skill and humility involved in learning to skate create a velvet rope between skater and civilian that lies glamorously across schoolyards, back alleys, and downtown ledges, daring and welcoming anyone to enter.
Many begin the sport and quit after their first bad fall, which often happens the same day they buy their first board. But as in most sports, it’s easy to become proficient with a bit of persistence, although exceedingly difficult to go pro. Unlike most sports, skateboarding at the professional level offers practically no security. Sponsored skaters—pro, amateur, and aspiring alike—have few safeguards or safety nets besides saving paychecks. Skaters have no union. Unlike professional sports like baseball, football, or hockey, pro skaters’ salaries are often opaque—and salary may be the wrong word; it’s more a mosaic of contractor checks. There is no salary cap nor is there a guaranteed minimum, other than that sponsors might offer free product and beer “for life.” I’ve commonly heard rumors about pros driving Lyfts or Ubers to make ends meet.
Even though municipalities attempt to constrain skateboarding with statutes and laws, the sport itself is completely unregulated. With the exception of skateboarding competitions like the Olympics, there are no rules and no referee, however informal. There is no time limit nor predetermined selection of performed tricks, let alone a shot/serve/pitch clock. There’s no governing body regulating COVID protocol. There are no coaches and no prescribed goals other than to progress individually in the act of skateboarding itself.
Indeed, with so few rules and so little structure, this vague idea of what it means to be a skater—someone who takes comfort in the solitary endeavor, who shares a worldview that embraces the possibilities and peril that pursuing this activity can manifest—maybe the one thing holding us skaters together. It’s fitting that in a sport inherently imbued with—and dominated by—risk, skaters are comfortable with this arrangement. What’s ironic is that as skate culture has traditionally rejected rules and convention, high-profile contest skaters competing on television and featured in video games now increasingly rely on corporate structures to execute their professional skateboarding. Pro skating is, in a sense, an opportunistic caste system, with a top tier of current or legacy pros making a lot of money by way of contest circuits such as Street League Skateboarding, Van Park Series, and the Olympics, and wide-ranging corporate endorsement (even Weedmaps briefly had a skate team).
Whatever cohabitation exists between skater and corporate sponsor, skater and city, skater and citizen, or skater and urban developer, skaters have the power to be alchemists anywhere. It’s truly electric that the path of least resistance is often the way street skateboarding finds its place in the world. Part of the power of stepping on a board is feeling like a conduit to an energy loop of skater, board, and movement through space. And to make our sport more progressive is to acknowledge how much we are part of larger movements changing all spaces, skate spots and parks included, and their new identities.
Maybe we’re just efficient survivalists. Dedicated urban parasites turned sponsored craftspeople. If there’s anything skaters own more than the streets, it’s knowing when collective action is necessary. We recognize that as a group we can help save public spaces from forces of gentrification, as when the Lower Manhattan crew powered by the website Quartersnacks prevented the astroturfing of the legendary Tompkins Square Park in the East Village, one of the few paved park spaces left for skaters and pedestrians alike. The efforts of the Long Live Southbank coalition of London skaters not only preserved but remodeled and expanded the undercroft that gave birth to British street skating so that all could enjoy it. Recognizing this influential role in our communities, we’ve stepped up to have conversations and raise awareness around issues like gender-based violence, sexual consent, suicide prevention, and LGBTQIA+ rights.
I’m glad I can even say these things now, as a skater, without hesitation. It’s nice to see more Joy and less Cool. I never started skating to become cool but because skateboarding—the visceral act of seemingly flying, self-propelling across the streets—was indescribable and addictive. Something worth falling for, a chance to own a slice of its possibility.