How a Skateboarder Teaches Us to be Better Creators and Overcome Our Obstacles

Photo: Devin Avery via Unsplash

By any metric, I was an awful student. Quiet and respectful but disinterested in anything written on a chalkboard or spoken by an adult. So it came as a shock to me that one of the favorite expressions of math teachers everywhere, “show your work” would become one of the most inspiring phrases for me in my 40s.

Austin Kleon cleverly repurposed the expression for his book Show Your Work which has nothing to do with whether you’re cheating on your homework… or just clairvoyant; it’s about sharing your creative process with your audience, instead of just the end result.

Aren’t you a little old for that?

Some people might be surprised to know that I ride a skateboard. It certainly gets me some odd looks at the skate park. I rode as a kid and then I took a 30-year break until my daughters got me back into it. They gave me a board for Christmas a few years ago with the expectation that I would show them some tricks. I was terrified.

My first instinct was to open YouTube and search for a tutorial, which is how I found Chad Caruso. Chad is in his 30s and makes videos both to teach others and to document his own progression as a skateboarder. He is possibly the best example I have seen of what Kleon is advising artists to do in Show Your Work.

The fine art of skateboarding

I’ve always thought of skateboarding as a creative sport that could be considered an art form. For instance, no one can deny the creativity of Rodney Mullen who invented and perfected over 30 tricks, many of which formed the basis for the innovations of generations to come.

Caruso embodies this quest for learning and experimentation, combining different tricks to come up with something new (sometimes by accident) and filming all the while. He challenged himself to learn a new trick every day for a month which was impressive, to say the least. Then he exceeded all expectations and embarked on a tour of the United States during which he learned 50 tricks in 50 days in all 50 states.

Always let them see you sweat

All of this Caruso does in the spirit of service. Some of his videos are tutorials, but in all of them, he is letting us watch him overcome obstacles in the hopes that it will inspire us to overcome our own. Occasionally, he runs into another skater trying to learn a trick and Caruso will say something like “I’ll give you 20 bucks if you land it next try” and most of the time the skater will land it.

It’s this approach to life that has earned him over 50,000 YouTube subscribers and allowed him to start Karma Wheel Company. As Austin Kleon wrote:

“When you teach someone how to do your work, you are, in effect, generating more interest in your work. People feel closer to your work because you’re letting them in on what you know.”

As artists, we can learn from his example. Opening up about what we’re making, our creative process, our failures, our struggles, and challenging ourselves publicly can only help us make stronger connections with our audiences and potentially help a lot of people.

Moreover, we can also benefit creatively by making ourselves accountable, like my weekly drum solos. Sometimes I’m not at all inspired to play a drum solo, but I turn the camera on and suddenly it’s time to perform. When it’s done I’m ready to keep playing. Having that expectation to show up every week and make something has made me a better drummer.

Another thing that stood out to me when watching one of Chad’s early videos was when he remarked about how strange it was to be talking about his thought process. I’ve also been making videos of myself composing music and found talking about what I was thinking very odd at first. Then as it became less awkward I realized it was helping me clarify my thoughts and actually helping me compose. And again, having the expectation of posting a video of me composing makes it way more likely that I’ll actually write some music.


In my last article I pointed out how Jerry Seinfeld’s creative process should serve as inspiration for all creatives and now, looking at the creative output of a skateboarder on YouTube, we see that inspiration really is all around us. Austin Kleon’s books are a wonderful resource for artists and really any creative person, but we can also see examples of creative excellence and inspiration in the most unusual of places.

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