I Want My Kids To Fail (And Get Over It)

Pre-Parenting #2: to watch a skateboarder continuously fail is a learning experience all its own.

Pre-parenting (definition): the attempts by a childless male to add some intentionality to raising his future children. Usually based on his own experiences growing up. Most likely futile.

Carefree Kickflips

I admire the hell out of skateboarders. I’ve seen no other activity where human beings, especially those in the teenage years of oppressive self-consciousness, willingly fail in public. 

I say “fail” because out of the hundreds of times I’ve seen skateboarders around New York, I’ve never seen anyone land anything. That’s not an exaggeration: it’s a constant stream of failure.

But if no one’s landing anything, it means they’re not trying things they know how to do. In fact, it’s the opposite. It means they’re constantly trying things they don’t know how to do. Whether you’re a beginner or an expert, once you knock down a trick, you move on to the next one.

Is there anything else you can think of where people, in public, try something that they will most likely fail at over and over? It seems like for a lot of us being in public is an exercise in not being looked at, in not being judged. Walk down the sidewalk and stub your toe and you immediately look around to make sure no one saw it.

Tense Tennis

Case in point: recently we went to the 12 tennis courts on the East River. First off, if you ever thought tennis players weren’t violent, try cutting in front of someone who’s been waiting for two and a half hours and whose name was clearly on the list; tennis can be a full contact sport. With that type of wait, you can bet that there’s a full crowd of people watching you play. This is especially true when you’re on the courts closest to the entrance, which is where we ended up. 

Now both of us played a bit growing up but we aren’t what people call “good”. Yet. But there’s only one way to get good, and that’s by practicing. Only in this situation, our practice was in front of 40 people, all of whom were most likely better than us and all of whom wanted our court.

In the beginning, I went anti-skateboarder. I hit the softest forehands with just enough power to go over. I’m also pretty sure I made large gestures about the sun being in my eyes after missing a shot. You know, to let the crowd know the kind of odds I was up against.

As the game progressed though, I realized two things: the entire paradigm of these people judging me was almost entirely in my head, and even if it wasn’t, those people really didn’t matter. This was a chance to remove everyone else from the picture. It was just us two, under the shadow of the Williamsburg Bridge, toying around on the tennis court, getting better.

Where It All Started

Growing up I was terrified of judgement. My sixth grade girlfriend (hey Liv!) once showed up at our basketball game and I proceeded to not only miss the first shot I took, but to chuck it clear over the backboard. I didn’t shoot the rest of the game. For that matter, I don’t think I shot much in any sport after that. The fact that a sixth grade memory is still fresh 20 years later shows how emotionally scarring that experience was.

And yet 20 years later I’ve also ended up sharing embarrassing moments in the most public venue possible: the internet. How can I give my kids the gift of shortcutting that process? How can they lose, however much possible, that fear of judgement?

Skateboarding is only one path to teaching shame-less improvement. It just happens to be the one that comes to mind most easily. Drawing, making short films, go-kart racing: who knows what the urge will be, physical or creative. The goal early on will be to find ways for my kids to express, in public, themselves or their work to steady them against the inevitabilities of judgement.

That judgement will come no matter how much they hide, no matter if they are extroverts or introverts. It will come in school and at work. It will come from peers, teachers, bosses, co-workers, and complete strangers.

The thing I want to instill is the mentality of picking up the board and giving that kick-flip one more try.