A little more than four years ago, I interviewed journalist Will Leitch to debut my first web site! This week, let’s revisit my conversation with him for two reasons: First, Will offered some great insights. Second, this is the first interview on Dreaming Made Simple.
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Sam Miller: What is your dream?
Will Leitch: All I ever wanted to do was write for a living. More accurately, all I ever wanted to do was to write about things that I care about. For me to have the opportunity to write about what I want in a lot of different places, it is a dream. My dream is to be able to keep doing this as long as I can. It’s not so simple as “OK, you made it. You’re all done now.” I have to keep working hard to sustain that.
Sam Miller: When did you realize you were living your dream?
Will Leitch: If you had told me six years ago, “Will, you’re going to be able to do a movie site with your friend Tim [Grierson]; you’re going to be able to write for New York magazine, one of your favorite magazines; and you’re going to be able to write a big story about Michael Vick for GQ,” I would have been like “Holy crap, I’m living the dream.” Once you’re actually doing it, it’s just work, which is good. I think people have a bad connotation with work. They equate work with job. I like to work. That’s what gets me up in the morning.
Sam Miller: What are the steps you’ve taken to get where you are?
Will Leitch: A large percentage of everything that happens for anyone is luck. You make your own luck, don’t get me wrong. Once you are given an opportunity, you have to take advantage of it. As it happened, Hugo Lindgren was a deputy editor at The New York Times Magazine. (He now runs the Magazine.) He stumbled across one thing I had written at The Black Table and was like, “Hey, this is kind of funny. I’ll e-mail this guy and see if he wants to do something.” That was absolute luck. The funny thing was I got assigned a huge story, a big huge story, that to be honest I am not sure I was quite ready for, but I worked my ass off on it. It was luck that he even stumbled across me in the first place. On the one hand, he did come across the story. On the other hand, I also wrote a million other things that he did not just stumble across. People misunderstand luck. They think, “That person’s just lucky.” No, you have to put yourself in a position to be lucky.
The first step was deciding that this was what I was going to do. I don’t know if I had necessarily decided that when I moved to New York. I think I knew it in college, but there is a difference in knowing what you want to do and to be, like “I’d do this forever even if I die.” I remember a lot of people in my journ program or different English programs that wanted to be writers, wanted to be journalists. They’d say, “I’ll give this [career] until I’m 27 or 28, then I’m going to law school.” Well, in my opinion, you’ve already lost when that happens. I remember a conversation that me and [Deadspin editor, A.J. Daulerio] had. I was 26, he was 27, and we were both really struggling. We had a friend of ours who was a lot older than us. He was not doing well with his career. We thought, “He was a failure. Are we willing to be failures?” We both decided yes. We were willing to have it not work because we wanted to do it and believed in it.
I think that’s the most important thing – to be willing to go down with the ship. You can’t look for an escape hatch.
If my wife had met me in 2003, I was the biggest loser you could find. I could barely afford rent, I had a crap job, I was writing for free, I was a mess. But I knew what I wanted to do eventually, so I had to put in the work and hope that I caught a break and, if I did, to take advantage of that break.
Sam Miller: What lessons have you learned?
Will Leitch: The main one is not to get distracted and not to give up. I find a lot of people act like a job is owed to them, or they deserve it, or they’re special. A lot of the people who have a really hard time are people who are not ready to deal with setbacks.
A lot of people want to be writers but they don’t realize that requires a ton of work. I don’t think there’s a mystery to it. I think people want there to be. I know a lot of people who love the vision of themselves as writers, but really, you’re committed to it or you’re not.
You don’t even want to know how many years my parents thought, “Why is he in New York? What is he doing there? We send this kid to college, and he’s working in a doctor’s office. What a waste of time this was.” I was a total failure for a long time.
Sam Miller: What’s next?
Will Leitch: All I want to do is to keep doing this and to make it work with my life. I want to be able to do the things I want to do while making sure it doesn’t take away from the things I need to be as a husband and a father. That’s my next goal, to figure that out.
There’s no point where you hit a finish line. That’s something I didn’t realize when I was 25 or 26. I always thought I’d hit a point where I made it. You never hit it.
Thanks for reading! Keep watching this space for more interviews like this one and for more about Dreaming Made Simple