What Does “Winning” Even Mean?
I started skateboarding when I was 10 years old. While I played some team sports, they never interested me the way skateboarding did.
Gaelic football and hurling was something I did at the weekend. But skateboarding was something I skipped homework to do.
The 1980’s and 90’s in Dublin suburbia was a grim place for skateboarders. There were no skateparks. The weather was rarely our friend. All we had was the street we lived on, some home made ramps and occasional Sunday jaunts into town (at a time when Sunday shopping was not a thing!)
So, you’d really have to be into it, to be a skater in Ireland.
The thing that attracted me the most to skateboarding was that I wasn’t constrained by rules. I was free to create my own skateboarding experience every day. And while the people I skated with weren’t on my “team” they were my peers and contributed more to my development as a skater (and I them, I hope) and as a young person, than any football or hurling team ever did.
They were my crew.
In team sports, I was an outsider. Usually on the sidelines, waiting for my chance to be picked — I wasn’t bad at these sports, I just wasn’t passionate. But with skateboarding, I was actively participating and improving myself. I wasn’t in competition with other players for a game, or other teams for a winning score. I was in competition with myself!
I was simultaneously the only person who could hold me back, and achieve success. And success usually meant landing some trick that I’d not done before. Success was personal to me, defined by me and something that I had control of achieving. And as friends, we actively encouraged each other to achieve.
And the thing about skateboarding is: it’s all an iterative process. Every new trick has its roots in something you’ve already learned. And combining a trick that works on flat ground, with a different environmental context, leads to a new trick or improvement in your style.
Because of skateboarding, I grew up with a different understanding of “winning”. I always felt that with team sports once you won something, you’d then have to defend it. And it felt like once you’re in defensive mode, you’re not really creating.
And that was the best thing about skateboarding for me — having the freedom to create. I understood that if you’re not creating, you’re not improving, and if you’re not improving you might as well give up.
And giving up, is clearly not winning.
I first picked up a skateboard in 1987. Nearly 30 years later, I’ve somehow taken the understandings, insights and lessons that I picked up from skateboarding, and applied it to the rest of my life. I don’t even think it was something I consciously did, but looking back I can see it.
I’ve been creating technology for 20 years now, and while it’s been a few years since I’ve actively skated, there are tell-tale markers of the impact skateboarding has on how I think about products, experiences and my crew.
Just like skateboarding, modern software and product development is an incredibly iterative process. And just like skateboarding, it is accelerated by being surrounded by a crew of good people. People who do, create, imagine, and inspire.
My crew and I have been neck-deep in product development for 5 months, and we’re getting close to being able to share it with people. It’s a pretty complex problem that we’re solving. And like the best skateboard tricks, our job is to take something complex and make it look simple, to feel easy.
For us, winning isn’t something that just happens. It’s something we’ve been preparing our whole lives for. It’s why we get out of bed in the morning. It’s why we obsess about user experience and creating value.
And it’s something we are entirely in charge of.
Shout out to Tony Hawk and Rodney Mullen, childhood heroes of mine, that still continue to inspire me today ✌
