Skateboarding seems like the ideal thing to decide to do when you're freaking out about your life. You don't really need that much to get started. Dan Meyer, a seasoned skater who works at VICE, where there are many seasoned skaters, put it this way: "There's no coaches. No rules. No boundaries. No parents."

A month ago, however, I was struck by a vision of myself wearing some kind of fashionable hat while gliding down the street on a skateboard. I immediately knew that I had to become the person in my mind's eye. Maybe once I did, I wouldn't be as deeply depressed, neurotic, or focused on a high-fat, low-carb diet. I would be a skateboarder, a.k.a cool. But before that, I would have to suffer through the indignity of working at it.

I'm currently working on all of this with my therapist because it's the main reason, aside from being generally depressed, that I don't do anything. I own a chameleon, eat paleo foods, write dumb stuff online, and watch the Bachelor franchise . That's my comfort zone. I'll occasionally exercise, and I recently started an acupuncture practice, but the latter just requires me to lie still and the former is becoming increasingly infrequent.

Acquiring a new skill isn't easy. I attempted to take up painting two winters ago, and I cried before every class and then quit. There's nothing worse than being bad, which is a fundamental part of trying something for the first time. I view myself as a generally competent person, and I don't have the fortitude to cope when that belief is challenged.

After about 15 minutes of staring at the selection of standard decks, which were all confusingly different sizes but only by centimeters, Spencer finally asked for help: "Hey, so, we're adults and we want to start skateboarding. What do we do?"

Rion, Spencer, and I walked to our local skate shop as a united front in order to pick out our boards. From the perspective of an adult having a quarter-life crisis, the inside of a skate shop is very scary. There are young people picking out boards confidently. There are relaxed salespeople (all men) in crewneck sweatshirts who "hang back" until you approach them, and you are not going to want to approach them because you're embarrassed.

Luckily, my adult boyfriend, Rion, and my adult roommate, Spencer, also decided that they wanted in on skateboarding's transformative powers, so I had a crew to dull the shame of running into a group of teens—they're always in groups—who are better than me at skateboarding.

There is one rule, though: It's kind of embarrassing to be over the age 14 and learning how to skateboard for the first time.

After I spent a day learning to simply stabilize myself, I found out that skating—as in being able to stand on a board, push yourself forward, and coast—is kind of easy. My next hurdle became learning to turn around smoothly. When you're riding, you can pretty much lean from side to side to maneuver. Doing a full U-turn, however, is a bit more difficult. I spent hours just working on pushing down on my back foot while lifting up with my front foot to "scoot" the board in a circle without falling down, which I did a lot.

For the next few weeks, my crew and I would walk at least four blocks away from our apartment so our neighbors couldn't judge us and practice. (Spencer used an old board that my boyfriend had acquired at some point in his life courtesy of the brand Zico Coconut Water, and we called him "Zico boy" to shame him.) For added drama, we brought a small speaker with us and played Blink 182 songs. Rion and Spencer both skated when they were younger, so they had the basics down. While they were testing out rolling ollies and kick-flips, I would ride up and down the street trying to get the hang of it.

I would later learn that "Lizard King" is the name of a current skater, and the board I picked was "his" board. For a second I felt like a poser, and like I should immediately start working to become Lizard King's biggest fan, but I eventually let that go. I made up my mind to reclaim the name for actual lizards, and even when a friend mentioned to me that my board-sake recently appeared on VICELAND's skate-competition show King of the Road and pooped into a shoe, I remained unfazed. Rion got a board that had drawings of lizards on it, and Spencer declined to get a board because he got cold feet and started to fear that he would rapidly lose interest in skating.

The clerk did not even smile at my roommate's attempt at humor. It's not that he was unfriendly—it was more like he probably hears this inquiry at least once a week from neo-yuppies who had shelved their vague desire to "be an artist" and suddenly realized they've become boring. The clerk explained that the board sizes don't really matter because we're likely not doing any advanced tricks (roasted) so we decided to choose decks based on aesthetics. I got one that had "Lizard King" written as if it was spray-painted in lime green caps amid a purple, sparkling background as an homage to my chameleon, Drake. With the trucks, wheels, and grip tape—the existence and names of which I learned that day—it cost $150. A small price to pay, I thought, for my awesome new life.

Whenever I got bored with that, and a little jealous of the boys' fun, I would attempt an ollie. I'm happy to report that within a few days I achieved what I'm calling "a cute baby ollie," in which I actually got a wisp of air beneath my back wheel! I was starting to feel really good about my new life as skater.

Step Four: Appropriate Skate Fashion

Dressing like a skater essentially means wearing flat shoes and T-shirts. Also if you're wearing shorts, you have to wear high socks, I guess. From what I've gathered, it's all about appearing strategically shitty. Comfort is also key, but a lot of skaters bafflingly wear skinny jeans. Not to brag, but I pretty much already had a cool skater vibe going in my day-to-day wardrobe—during the winter I exclusively wore Converse, sweatshirts, and baggy pants because I was too depressed to look nice.

The only thing I needed was a faddish hat; I decided on a red bucket hat because, out of all the hat styles, it made my hair look the least stupid underneath. If my hair was longer, maybe, I wouldn't mind going for the dad-hat look. For extra flair, I also bought a Vans T-shirt with an iguana on it to compliment my board and my overall brand.

Step Five: Make Your Debut at the Skatepark

Now that I was presentable, I was ready to go to the big show: the skatepark. If I had to describe the skatepark in only three words I would go with "hats" and "boy city." There are so many hats and boys! When I arrived to the scene, teens lined every concrete surface, taking turns dropping in on the ramps, grinding on the rails, and jumping over stuff. Besides me, there was just one girl there. She had dreads, and was wearing wire-rimmed sunglasses, a grungy tank top, and blue track pants—a surprisingly good look. There was guy who looked like he picked out his outfit with help from a mood board comprised of Jaden Smith photographs. A pack of boys stood near the entrance vaping weed and trying to climb a tree. Further back, there was clique of middle schoolers clinging to their Razor scooters, who seemed equally as scared as I was. They stood against the fence, condemned to a life of being the Razor scooter kids at a skatepark.

I related to them because I, too, was an odd person out. Instead of wearing a very cool hat like everyone else, I was wearing a bulky helmet because I didn't want to experience a fatal head injury. I noticed a guy in a bucket hat, the only one in a sea of ball caps and five-panels, and I wished I could somehow signal to him that I also prefer bucket hats. Alas.

Further back, there was clique of middle schoolers clinging to their razor scooters, who seemed equally as scared as I was.

I also related to the razor scooter kids because I did not feel comfortable participating in the action at the skatepark. It was insane. The men and boys were zooming around each other in a chaotic order that seemed determined before I got there and now could not be altered. I couldn't figure out how I would get in there. It was very overwhelming, and my social anxiety was starting to kick in. Additionally, I was, and still am, bad at skateboarding, and I didn't feel like I had enough room to fall or enough time to stand hesitantly before attempting to skate down a ramp for the first time. It was just too much. I went home.

Step Six: Make Your Debut at the Skatepark in the Early Morning to Avoid Teens