What skateboarding taught me about failure
a methodology for approaching calculated risks and incremental progress
In skateboarding, you fall—a lot. Unsurprisingly, the better you get, the more talented you are at falling gracefully. Falling in skateboarding isn’t failure itself; it’s a powerful tool for navigating failure. There is an art to falling. When you are working on a new trick, you always know you might fail, and a big part of learning to be comfortable on a skateboard is learning how to deal with situations going sideways. As you get better, you learn more tricks, develop better technique and style, and learn how to deal with the myriad ways you will fail while on your journey.
In the startup world, you hear “fail fast, fail often.” This phrase is quite polarizing to many folks, and I sympathize with perspectives for and against this saying. I think some folks miss the point of this saying, though. It’s not about failing; it’s about the practice of navigating failure. If I take this perspective as a skateboarder, I’ll frame this as “be willing to fail when you're confident you can deal with that failure in your efforts for greater things.”
I was never the type of skateboarder who could ollie down a “20 stair” (skateboarders measure the size of stairs by the step count). Stairs that big were not something I was not equipped to deal with a failure on that level, and I knew that. I was more of a “5 stair” skateboarder. I was prepared to deal with failure at that level. I spent much more time working on mini-ramps, technical tricks on ledges, small rails, manual pads, and gaps. Things that were readily available in my small town. When you learn to fall, you lower the risks of your progression for better things. You know how to get out of a situation at the final moments, maybe roll out of the way, or push your board out so you don’t compound things and make it worse. This is called “bailing” on a trick, and if you watch a talented skateboarder, they are masters of bailing. Learning to bail gives them more time to work on difficult tricks under challenging situations without getting hurt. Of course, your ability to bail fails at some point, and you might get hurt. Skateboarders get hurt a lot, but they also get hurt significantly less than folks who might try those same tricks and aren’t nearly as skilled in bailing.
Learning to fall also gets you over two other vital factors: fear of falling and social embarrassment of failing in front of others. When you skate with friends, it’s inspiring to see a progression, to watch someone fail and fail and fail, and then have a breakthrough and land a new trick. Nothing is embarrassing about this “failure” amongst your peers because we all understand it’s part of the progress. You also develop an intuition on whether or not someone might be close to landing a trick or whether it’s aspirational.
As I’ve grown older, I’ve come to appreciate what skateboarding has done for me when taking calculated risks. I still enjoy finding challenges that encourage me to constantly push myself to get better. I still strive to push the boundaries of what is possible at my ability level, and I strive to get immediate feedback for improvement.
When skating, if I landed the trick and rode away, it was so satisfying. Maybe next time, I will add a flip trick or try a slighter, more difficult grind. But if I tried something way out of my league, I would get the immediate feedback of getting hurt or having a scary near miss. So you get better and make incremental progress. Maybe I work on a simpler trick on a lower ledge and work my way up. Maybe I kickflip a three-stair until I’m comfortable, then move to a five-stair, and perhaps a seven-stair.
I’ve brought this approach to calculated risks and incremental progress into my professional work. I’ve learned this pattern; can I apply that over here in a new context? What would happen if we deploy code this way? What if we try this in our observability stack? So, you take calculated risks and learn the correct way to get feedback loops and make progressions. You learn how to fail gracefully, so it’s easy to get back up and try again. You do that in a way that reduces the risk of hurting yourself or others. And because of this, the frequency of breakthroughs goes up. You end up being able to do stuff that looks magical sometimes, but it’s because you’ve also gotten good at reducing your risk of failure while you push through, gain skills, and express yourself in new ways in the world.
Notable Links this week
Steve Mould never disappoints in his approach to working through surprising phenomena.
Philosophy of Physics: Space and Time by Tim Maudlin (affiliate link)
I finished Tim Mauldin’s book on space and time this week. I’ll write more about this in the coming weeks. His framing of the topics and his clarity of thought is second to none. When need more philosophers in Physics. He is a welcome counterbalance to the “shut up and compute” crowd.
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