Here's What Happened When a Former Pro Skateboarder Taught Me to Skate In a Day

I remember buying my first skateboard.

It was the second grade, and after begging my mother for three weeks straight to purchase me one, she agreed and took me to our local Toys "R" Us to pick one out.

After scanning through the row of their offered boards, my eye came back to one—it was a black deck with an image of a girl shooting fire out of her fingertips. I knew it then, that was the one. And so I took it home, polished it off, placed it on a shelf in my bedroom and admired it. But you know what I never did? Rode it.

I don't know if it was the fear of falling, fear of having the boys in my neighborhood laugh at me or fear of failure that kept me from riding that board, but it has always been a regret of mine.

Recently, I was given the opportunity to finally hop on a skateboard and accomplish what I dreamed of doing long ago—hitting the pavement.

Want to see if I succeeded? Scroll below to see what happened!

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Meeting Cindy Whitehead and Kyra Williams

You're probably wondering what or who exactly convinced me it was time to give skateboarding a try, right?

Well, a couple months back, I had the opportunity to chat with Cindy Whitehead, a former skateboarder-turned-sports stylist who owns her own empowering brand Girl is NOT a 4 Letter Word and is the author of the book It's Not About Pretty: A Book About Radical Skater Girls.

After talking with Cindy and hearing about all that the young girls she works with have accomplished, I was so inspired. So much so, that I asked her if she would be willing to teach me how to skateboard.

Luckily for me, Cindy agreed and even said she would bring along Kyra Williams, a 16-year-old competitive amateur surfer and skateboarder on Girl is NOT a 4 Letter Word's team. 

I met up with the two at a skatepark in Manhattan Beach, California, and crossed my fingers that I'd make it through the day without ending up in an ambulance (kidding, kind of).

Cindy, Kyra and Brittney at the Manhattan Beach Skate Park

Gearing Up

Before we could get out on the pavement, Cindy and Kyra stressed that I would need to gear up with the proper safety equipment. For newcomers especially, a helmet and pads are a must.

Cindy fitted me with her adorable Girl is NOT a 4 Letter Word matte black helmet and assisted me as I put on both knee pads and elbow pads.

I looked like I was ready for battle with all the gear on.

Brittney putting a helmet on

Brittney putting elbow pads on

Once I was all padded up, Cindy presented me with the skateboard I'd be using for the day—a Girl is NOT a 4 Letter Word x Dusters California cruiser board.

It was beautiful.

Pink leopard skateboard

Cindy explained to me that she wanted me to use this type of board rather than a "Popsicle stick" park or street board because it's more stable with it being a bit wider (8.75 inches wide) and having larger, softer wheels. 

Let's Skate

Now that I had all the right equipment, there was only one thing left to do—skate.

I'm not going to lie, I was pretty nervous and wobbly standing on the board on my first attempt.

I tried longboarding a few months back and started to get the hang of that, but I feared that this would be a totally different experience.

Cindy and Kyra calmed my fears and began walking me through the basic fundamentals of skateboarding.

We identified that I didn't ride with my "goofy" foot (aka my right foot), so I started with my left foot parallel near the top of the board.

Kyra demonstrated for me how I would push off with my left foot, bring my right foot up onto the board at a slight angle, and then once I was moving, would move my left foot to be parallel to my right.

Here I am trying it out for the first time:

Brittney beginning to learn how to skateboard

So far so good.

I continued to practice pushing off and skating ten feet or so until I felt comfortable. Although not pictured, you should know I did fall on my butt twice.

Cindy and Kyra assured me that this was part of the learning process and that I shouldn't let the little tumbles discourage me. I knew if I wanted to continue learning I'd need to pick myself right back up and keep skating—and so I did.

Next, Cindy and Kyra taught me how to turn corners. They explained to me that it was as simple as leaning into the curves of the pavement and bending my knees. To my surprise, I picked this up pretty quickly!

By this point, I had seen both Cindy and Kyra pick up their boards several times by kicking it up, so I asked if they could show me how to do that.

Although they made it look effortless, I struggled with this a little bit. I guess I was stepping down on my board with too much force.

You can see that here:

Brittney trying to kick her skateboard up

I eventually got the hang of it.

For the last portion of my lesson, Cindy and Kyra challenged me to get off the sidewalk and step into the actual skatepark. Oy vey.

With Kyra's help, they wanted me to skate up a little vert ramp and roll back down.

Brittney holding on to Kyra while skateboarding

My first attempt was pretty much a failure—I lost balance and completely fell of the board (taking Kyra with me).

I'm sure you guys will appreciate this visual:

Brittney falling off her skateboard

After a few more tries, I was able to successfully skate up and back without falling. A major accomplishment for me.

I walked off the skate park feeling like I achieved what I came there for that day—progress.

Although I was done for the day, Kyra was just getting started, she grabbed her board and got to skating.

Kyra Williams skateboarding

As I sat and watched her conquer ramp after ramp, I couldn't help but feel an overwhelming amount of pride and accomplishment for not only me, but girl skaters everywhere who kick butt every single day.

Lesson Learned

The main thing I took away from my day at the park was that trying is always the key to success. If I hadn't stepped out there that day, chances are I would have never learned to skate.

No matter how afraid you are, no matter how positive you are that you won't be able to succeed at whatever it is that challenges you, you must try.

I'm so happy that I had the chance to push myself and learn a new skill, and I'm even happier that I fulfilled a childhood dream.

I can't thank Cindy and Kyra enough for showing me that I, too, can be a skater girl.


This isn't the first time I've tried out a new sport! Click HERE to see what happened when I tried to become a roller derby girl.