What was your school experience like?
I was the obnoxious-outspoken-bullied-nerdy kid. I joined a lot of clubs and stuff, but didn’t have a lot of friends. I had incredible parents who pushed my sisters and me to lead and to be as generous as we could be, but put very little pressure on us to be popular, be on the sports team, et cetera. They really pushed us to be out in the world. To explore a city we’d never been to before by ourselves at the age of 14 kind of stuff.
Wow, that’s amazing.
Yeah. When I got to college, I shifted gears a little bit, but I ended up co-founding a business there that grew to 400 employees. That’s where I learned the knack of starting stuff. We started 15 different divisions in a six-month period of time. Ticket bureau, snack bar, travel agency, magazine stand, a little business that did on-campus concert promotion. I had nothing to lose. I got hooked on that idea that the world is more open to a new thing than we think it is, as long as we can accept the fact that it’s never going to be really popular. It’s just going to make a small difference and give us the privilege to do it again.
There’s a quote I read recently, which says you know you’re a good parent if your children don’t want to be famous. I think that’s an idea that goes against the grain of how a lot of kids grow up—with this idea of stardom, of the YouTube video that has a billion hits.
Yeah. I’ll tell you an anecdote that blows me away. A kid that my kids grew up with ends up at an Ivy League school. He auditions for the improvisation troupe. The troupe announces its results—he came in 12th, and they only let 11 people into the troupe. He was very disappointed. I said, “Why don’t you start your own troupe? It is improvisation after all! Just put some signs up around campus! You’ll have a troupe within a week!” He couldn’t do it. He couldn’t find it in himself to start his own troupe, because it would mean that he would have to pick himself as opposed to getting picked, and he needed the authority to do that. He didn’t feel he had it.
I guess if you pick yourself then you put yourself on the line and a lot of people are really scared of failing, of being the one that doesn’t make it..
Right. Which means they’re going to fail. The people who aren’t willing to put themselves on the line have already announced they are failing.
You have two choices: you might fail, or you will fail. It feels to me it’s better to “might fail.”
But you can “will fail” quietly, while you have to “might fail” loudly.
Correct! And what I have found is the cost of that isn’t nearly as high as people think it is.
Right. It is always easier to look back on failure in hindsight and say “that was a great learning curve.” But the emotional experience of failing— is that something you’ve ever struggled with?
Oh constantly! I still struggle with it every day! That’s my job. But what I say to people is: start a blog, under another name, don’t tell anybody, no one will read it, write every single day, no one will read it. You are failing, completely in private, completely quietly. And then, through the magic of search, someone will read it. They might hate it! So you have failed again—almost silently. But over time, 10 people, 15 people, will engage with your work. That is about as quiet a failure as one can hope for, as quiet a success as one can imagine. But it inoculates you against being stuck.
My first book sold for $5000. I didn’t sell another book for a year. I sold my second book for $3000. It took me 20 years to become an overnight success. I’m really glad it took a while because if it had happened the first day, I would have been completely unprepared for the criticism that would have followed. But at the beginning, when no one’s watching, when you’re just getting quiet, private rejection letters, you learn that it’s not fatal.
What was it like struggling with it when you were not a success for so long?
You know, the big challenge here is how much support do you get from people who care about you.
Do you get a lot of support?
Well, my Mum died about 15 years ago. She was extraordinary in understanding what I wanted to do, and in giving me the right amount of quiet support. I was living in New York, surrounded by investment bankers and lawyers and fancy people, it was tough…