Is Will Leitch Winning? (Yes.)
When I received the email invitation for the launch of Will Leitch‘s latest book, Are We Winning? Fathers and Sons in the New Golden Age of Baseball, I forwarded it to a friend with this commentary: “Where does he have the time!?!” I hadn’t known that Will was working on another book — his fourth, after his debut collection, Life As A Loser; his YA novel Catch and his superfan bible God Save The Fan — but I certainly didn’t think he was idle, between his prolific work at New York magazine, his continuing work as an “Emeritus” at Deadspin.com, the insanely popular sports blog he founded at Gawker media, and writing loving and meticulous movie reviews on his personal site.
But it shouldn’t have surprised me — I’ve known Leitch since his days before he was a thorn in Buzz Bissinger’s side, since he was the first person to give me an online home for my musings. As one of the founding editors of The Black Table, Leitch gave a start to all sorts of fledgling writers with something to say and attitude about saying it, and from there came some of blogdom’s most familiar names. It is on the Black Table that the original archive of “Life As a Loser” can be found — but wow has Leitch come a long, long way from that.
What do you do? (I know you “do” many things. But, in your own words!)
I type for any publication that will let me type for them. I’m so lucky to get to do this for a living. I spent many years writing for nothing, just trying to get better and get noticed, so to do it now, as a profession, is all I ever wanted.
What do you love about your work?
I love the challenge of sitting down to empty space and having to fill it. If I don’t fill it, it doesn’t get filled. It’s a responsibility I take seriously.
You’ve been a blogger , a columnist/long-form mag writer, and author. Each required you to work within very different structures. How easy/difficult has it been to adapt from/move between each?
Well, I have the same style no matter where I write. The easiest is writing for New York, because their editors are so sharp and smart that they always make me look sharper and smarter than I am. The hardest is blogging, because you’re completely without a net. That’s exciting but terrifying.
Your first love is clearly writing about sports. Does “work” feel different when you’re writing about something that you didn’t wake up knowing?
My first love is actually writing about movies, but film critics are even more endangered than sportswriters these days. I always assume that I know nothing, and try to figure it out through my work. That’s why blogging has always appealed to me as a writer. I like solving problems on the fly.
You used to do work you didn’t love. What felt different about that work?
You know, the work part, that was fine. (I once spent eight hours stuffing envelopes, and lemme tell you, I was a TERRIFIC envelope stuffer.) It’s just the notion that I was wasting time: It’s the notion that I was put here to do something other than this, and this, the envelope stuffing, the answering phones at Telemundo (another fun gig), is getting in the way of that. But the work itself? I loved the work. I just love working. I get very lost when I’m not working. I’ve been at NY mag for almost two years now, and I’ve yet to take a day off. Days off make me uncomfortable.
On the flipside: You used to do work you did love, but didn’t get paid for. (Black Table) How did that work feel different from the kind of work you do now?
It’s the same. I mean that. The only difference is that I have more time to do it now because I’m not distracted by all the envelope stuffing.
The Black Table was powered entirely by free labor: Yours, your co-founders, your writers. What motivated you all to do it? What energized the process?
We came to New York trying to make it as writers and noticed immediately that the traditional channels were not going to be open to us, for a variety of reasons. So we started our own thing, figuring if we were going to go down as failures, we were going to go down as failures on our own terms. It remains, to this day, the most fun thing I’ve ever been a part of.
That was obviously an endeavor marked by collaboration. Writing the book is the opposite. How do you stay motivated and productive?
This is the only thing I know how to do, and, when you really break it down, the only thing I truly enjoy. It’s an old maxim, but it’s true: When you find that thing you want to do, do it over and over for the rest of your life. It’s easy to be motivated when you’re doing what you love.
Whom have you learned from recently?
I listen to everything Roger Ebert says, and pretty much do what he does. There is obvious joy he gets from his work. If you can’t take joy from your work, you’re doomed.
What do you think your former “Life as a Loser” self would say if he could see you now?
I think he’d just be happy I found a nice girl. He’d be disappointed I haven’t stopped smoking, though.
Further Reading:
The Story of LeBron James (2018) [New York Mag]
The History of the Black Table [The Black Table]
The Will Leitch Experience [Tumblr]
Photo via The Will Leitch Experience.
[...] We’ve supplemented this group with expert advisors from different walks of life such as Will Leitch, Jimmy Yaffe, Mark Lazarus and of course Rachel Sklar. It’s important to us to take [...]