Essays on Technology and Culture

Lottery Tickets

I just watched this excellent talk by Darius Kazemi, from XOXO. If you have 20 minutes, I suggest you do the same.



Darius is on to something. When we hear successful people talk about what made them successful, our instinct is to follow their lead. The thing is, there’s no magic formula. It really is about luck. And the bigger the success we want to model our careers upon is, the more luck it takes.

Spike, a comic artist I’ve long followed, posted an excellent 24-hour comic for aspiring cartoonists called “This Is Everything I Know”. If I had to single out one page, it would be this one. Once you buy your lottery ticket, getting to that point is just luck. End of story. Why, then, do we keep sucking down someone else’s success stories, and trying to model our careers on them? And why does it hurt so damn much when success doesn’t come after putting in the work?

Part of the problem is survivorship bias. When all you see is the people who succeeded, talking about how they succeeded, and all you try are the things people did to succeed (in implementation, at least), and you don’t succeed—what then? When I worked for The Startup, I saw this sort of thinking play out on a monthly basis. Someone—usually the founder—would come up with a new feature that would drive user growth and revenue, and the technology side would rush to get it together. And, universally, these ideas were almost always something another, popular Internet Company in an adjacent space was already doing. They often didn’t get traction, and soon we were all distracted by the next shiny object. Looking back, this was the technology equivalent of buying scratch-off tickets.

For two years, my friends and I did a podcast that I was quite proud of. We pushed it to our friends, and we did our damnedest to make it great. In the end, we had double-digit download numbers, and eventually I sunsetted the whole darn thing when it was clear that the work of making it wasn’t worth what I was getting out of it. That was a lottery ticket, and it lost. Instead of trying to win the Podcast Lottery, I’m trying to take the money I spent on those tickets and am using it to buy more tickets in the Blogging Lottery. So far, it’s worked out better, and doing it is a lot more enjoyable.

Instead of success stories, I want to hear from people who failed, especially if they failed by doing the “right” thing. We have more to learn from those who lost the lottery than we do from those who won. I suppose, in the meantime, the self-aware stories from folks like Darius, and to a slightly lesser extent, folks like Justin Hall who succeeded by some measure, and then failed. That’s where the true lessons lie, not about success, but about life. One lesson I have learned, however, is to keep buying lottery tickets, and this is my latest one.