I fall a lot

I started figure skating when I was 4 or 5. It was my Mom’s idea. She wanted something of her own to do with the kids.

The first thing you learn when you’re taking skating lessons is how to fall. My sister would even stick a pillow in the back of her pants to cushion herself.

Nothing cushioned the fall she took on her chin. Blood on the ice. Stitches.

Almost two years ago I went through Y Combinator a second time (S2011). We built some pretty cool technology to help companies brand their own versions of popular games. Games like Bejeweled. Imagine if a company like The Gap let you play their version of Bejeweled, but instead of jewels they were Gap logos, and pictures of models wearing the latest shirts, and you could even win a prize.

We had people playing an average of two hours a day. I was pretty damn excited and hopeful.

But we weren’t getting enough repeat business. The product remained in experimental marketing budgets and never got any serious traction. It also wasn’t something I would personally use every day. The product didn’t have my soul.

We shuttered the work. It was a very, very hard fall. This time on my chin.

The other day I was sitting with a friend, getting pizza and talking about children. He told me he and his wife play a game with their toddler son: they act like buffoons.

They make fools of themselves and fall around on the ground. The kid loves it. He said his son has started mimicking them. This little toddler will act like a buffoon himself, fall, and then look over at his parents to see their reaction, expecting smiles.

It sounded very cute.

But what struck me though was the lesson my friend was teaching his son. It’s OK to act like a goofball. Not everything needs to be bottled up and perfect. It’s OK to fall. It doesn’t hurt that bad. It can be funny too.

You probably wouldn’t be surprised to know my buddy is an entrepreneur. He’s taken his share of falls.

I was figure skating pretty frequently up until about the age of 16. When you skate that long, you’re doing an incredible amount of jumping and falling. Mostly falling. There’s even an apparatus you start using with your coach: they can hold you up in a harness while you attempt to jump so that you don’t fall. You use that a fraction of the time when you’re practicing. The rest of time, you spend picking up new bruises and feeling cold from the ice. You’re lucky if the Zamboni didn’t just resurface the ice. Because then you’re wet and cold.

But you keep jumping. And you keep falling.

Sometimes it took months. Sometimes there was blood. More often there were bruises. But every time I fell ice-skating, I was trying to accomplish a jump I eventually figured out.

My sister still skated for a decade after those stitches.

After shuttering the branded games we were doing at Cityposh, I was stuck in a dark place groping for ideas. That’s what entrepreneurs do. I know that. But it doesn’t help the loneliness and sense of failure you feel.

I played with a couple things, nothing worked. And then I got an offer to help the tech team at the Obama re-election campaign. It was a great break. Not relaxing on most levels. But a break from the groping nonetheless. A break to let me get up off the ice and let my bruises heal.

I’m up again. I’m in the game again. I’m working on a project I’m damn proud of that many other writers seem to enjoy.

I have no idea how it’s going to turn out. What I am sure about is that I’m going to fall again. It’s going to hurt. It’s going to bruise. There’s probably going to be blood.

But that’s what we do. We try. We play. We act like buffoons. Because it’s fun. It doesn’t hurt that long. Not when you realize you’re surrounded by people supporting you – all they want is to see you enjoy yourself. They don’t care if you fall. They just want to see that smile as you try.

P.S. You might enjoy following me on Twitter: here.


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