I was eight years old when I tried skateboarding for the first time. It was 1998 and skateboarding seeped its way into peak popularity within pop culture. Tony Hawk Pro Skater was a new game on Nintendo 64. I would watch the X-games on TV and dream about how cool it would be to zoom down a ramp or land a trick. 

I saved up money and went to Toys R Us to purchase my first skateboard. It was about $30 (a lot of allowance money, at the time). It had plastic wheels, no grip tape, and a glittery sticker design of angry eyes. I think the sticker was supposed to look “hardcore” but really it just looked painfully cheesy. 

I consider myself naturally athletic, and tend to pick up sports easily. This was not the case with skateboarding. I spent hours in my garage trying to do an ollie. I would go back to the Tony Hawk video game and make the character do an ollie over and over so I could figure out the body positioning, and then go back outside to try for myself. I failed every time. And then I gave up.

Last year, I went to Target with my friend Amy. Like most Target trips, we didn’t have a real purpose for being there aside from killing time. We looked at clothes, got a few necessities like milk or laundry detergent, and scanned for random accessories to add to our living rooms. 

We passed the aisle with the plastic skateboards and I told her about the one I bought when I was a kid. She and I both exchanged stories of how we tried to skateboard when we were younger, and quickly gave it up because we were too self-conscious. As we talked about our previous dreams of being the next female Tony Hawk, I started to wonder… What if I tried it again? 

Me, being the impulse buyer that I am, blurted out, “Wait… what if we got skateboards today...?” I was half joking but half serious. And by “half serious” I mean I put a skateboard in my shopping cart. Amy took the bait. Luckily, she is much more responsible than I am, and said “well, if we’re going to buy skateboards, we definitely shouldn’t get them here. We should get LEGIT skateboards.” We both didn’t really know what “legit” skateboards meant, but figured it probably didn’t entail cheap, dinky wheels. 

Onward we charged to the local skate shop. We were both nervous to go in, afraid the workers wouldn’t be nice to us or take us seriously because we were girls. After mentally preparing  ourselves outside the store, we finally made it past the door. Amy and I were pleasantly surprised when they spent over an hour helping us pick out a top quality skateboard. They walked us through all of the details, and gave advice on picking the right trucks, wheels, bearings, and decks. Their enthusiasm for us to learn how to skateboard was infectious, but would the same ring true when we actually stepped foot in the skatepark? 

For a while, we didn’t feel comfortable going to the skatepark, so we would meet in the dark and secretly practice in deserted areas around my neighborhood, free from the mockery of “youths”. I remembered someone telling me about an all women’s skateboarding clinic called Skate Like A Girl, so we signed up and went to our first lesson. The rest is history. 

It sounds like the story would have a happy ending there, but the more clinics I went to, the more frustrated I got. The coaches were amazing, and gave me tips and tricks to focus on. Women of all ages were supportive of me, and cheered me on. I even made some new friends who invited me to skate outside of the clinics so we could practice together as beginners in solidarity. I made a lot of progress, but the one trick I wanted to accomplish was still out of my grasp. 

As a competitive person, it’s hard for me to stick with something when I’m not good at it. I like to win. I like to be the best at everything I try. If I’m honest with myself, the deeper issue is I feel self-conscious and embarrassed when it appears like I don’t know what I’m doing or feel out of control. 

I would wake up on the morning of the Skate Like a Girl clinics and wish that I had never signed up. Eventually, I would feel too guilty and go. After the clinic, I would tell myself, “that was awesome, I need to sign up for another one!” For the next year, the cycle repeated with me waking up with the same reluctance, followed by the same excitement after the session.

This morning was no different. My alarm went off and I pressed snooze, weighing the options in my head. I thought about cancelling last minute. As always, my deep-rooted guilt won, and I showed up for another lesson. 

The coaches helped me with turns, and encouraged me to try a backside kickturn. I tried dropping in for the first time. I saw my confidence rising, and decided to try an ollie. Per usual, I failed. And I failed again. And again. And again. I’ve been working on this trick tirelessly and I still couldn’t get it. Frustrated (and sweaty) I decided to work on it until the session ended in 20 minutes, and then give up again. 

And then somehow, I didn’t fail. I actually got it. I didn’t expect it to happen and was immediately skeptical. Did I actually do it or was it in my head? Did my wheels really get off the ground? 

I tried again. And I landed it again. And then another time. And another time. After 18 years, I finally nailed the one trick I had my heart set on. I couldn’t stop smiling and was “stoked” beyond words (...Am I a skater yet?). 

But my real joy was for a different reason than I anticipated. Aside from the personal achievement, I was happiest to tell my friends about it because I knew they would be proud of me. I texted Amy. I texted the new friends from previous lessons. I told the group at the clinic, and they cheered for me. My inbox flooded with texts of “YESSS!!!” or “OMG CONGRATS!”. 

In that moment, I wasn’t grateful that I completed the trick – I was most appreciative for the supportive people surrounding me and helping me along the way. I was thankful for the girls who invited me to skate with them because it kept me going, and without them I probably would have stopped trying. I was grateful for the newfound confidence and bravery I didn’t know I had. I was thankful for not giving up and challenging myself. I was grateful for the humility I learned from not being the best. 

In the grand scheme of skateboarding, an ollie is an extremely basic trick that most people can figure out within a few tries. But for the little girl who spent hours in the garage in 1998 on a shoddy skateboard, it meant so much more. 



Skate Like a Girl did not ask me to write this story, but I had to give them a shoutout because I love what they do. I've seen first hand the impact they have on the community. If you want to donate, Skate Like a Girl PDX is in the Willamette Week Give Guide. Make a donation through Willamette Week or at the Skate Like a Girl Portland website.