Five years ago, writer Will Leitch was publicly humiliated on national television. Leitch, now an editor at the culture website The Black Table, was dumped by his fiancée the night before he was set to be a contestant on Win Ben Stein's Money, and Jimmy Kimmel announced the break-up to America as a hapless Leitch looked on in confusion. But Leitch managed to turn embarrassment into inspiration—"Consolation Prize," the essay he wrote about that particular heartbreak, became the first in a string of Internet columns that Leitch published in various forums under the name "Life As a Loser." The columns mostly chronicle Leitch's itinerant early twenties, as he rode the late-nineties Internet boom from small-town Illinois to New York City, only to be laid off after five months and forced to move back home. Leitch has gathered the best of these columns in a new collection, also called Life As a Loser, released earlier this week by Arriviste Press. Taken together, the collection forms a familiar tale of "early promise squandered and hard lessons learned," as author Tom Perrotta writes in the book's foreword. Leitch recently spoke to mediabistro about idiots, luck, and the role of both in Internet journalism.
Let's start with the obvious question: Do you really think you're a loser?
I have a lot of stories where I'm the idiot, and the columns started with a couple of those. As it went along, it evolved from being less about me and more about how we've all been in situations like this, which is good. It's not an online diary. That's always been my fear, that it would be perceived as just about me, me, glorious me. Particularly in the book, I tried not to make it too one note, where it's all like, "And at the end, Will gets kicked in the groin!" It's supposed to be, you know, we've all been the guy who's picked last in kickball, we've all been laid off, we've all been the one who doesn't get the girl. In that way, it evolved to where it became, by the end, very easy for people to relate to.
But there is a lot of self-deprecation, this "Will gets kicked in the groin" thing. In the intro to the book, you basically say, "I'm a totally uninteresting guy," which doesn't seem like the best marketing ploy. But is that what you wanted your hook to be—sort of "I am the common man"?
The thing is—I mean, "Life As a Loser" is a really good title. It's snappy, it's catchy. But when I first started doing the column, it wasn't, like, a gimmick. It was legitimately like—"Okay, seriously, I suck." And it's not that I don't still suck, but after 10 or 15 columns, I ran out of stories where I completely humiliate myself. We kept the title, which is a hook, it is a catch, but the moral of the book is not: "Boy, look how much of a dork this guy is. I'm glad I'm not him."
The book's premise is this classic "small-town boy tries to make it in the big city" set-up. Do you ever play that up for fictional purposes or is it all relatively genuine?
It's funny, I was talking to a friend of mine the other day—who's also from small-town Illinois—about how when he got out here, he was just going to completely reinvent himself. He did not want to have anything to do with where he was from. And he said, "Will, you're like living in the permanent Midwest embassy." And I like that idea that I'm still a small-town kid. I've been out of Mattoon for 11, 12 years, but it's so ingrained in me, and I think in a lot of people who come here. Even now, in terms of people who have only known me out here, when I've been here longer than they have—they know me as the midwestern guy. And I'm not walking around going, "Oh, wow! There are no sheep here—I'm confused!" But there's a certain vibe you give off and that's just what you are. Some people are really uncomfortable with that, like my friend, who is so determined to be taken seriously and never be labeled like that. I really think if you asked him if he's from the Midwest, he would lie. I can't imagine living like that. To me, the most important part of keeping that midwestern part is knowing that no matter what, you're just a dumb idiot from nowhere, so don't take yourself too seriously. It's part of the idea of the book, too, being comfortable with who you are, and not trying to be something you're not—particularly when you've been laid off a thousand times, and everyone's telling you: "We don't want you around. Go away." The job market hasn't been too great in the last few years, and we were all bouncing around. I'm sure a lot of mediabistro readers have been bounced around. At a certain point, you have to realize: "I'm okay. I believe in what in what I'm doing."
Well, obviously you're doing pretty well for yourself. Most self-described "dumb idiots" don't parlay their Internet diaries into a book deal—
Not a diary!
Okay, your Internet musings. So tell me how the deal came about. In the book, you allude to a manuscript and a deal with a big-shot publisher. Was that this book?
Yeah, that was back in 2000, when I'd been out here for, like, five months. Someone approached me and signed me up to do something a little different from this, with more of a narrative running through the whole thing. But then we all got laid off, and I started to realize I love this little book project I'm doing, but I might want to worry about getting a job first. And the book ended up getting put on the back burner. Frankly, I just wasn't ready yet. I was a kid! I hadn't been here at all, I hadn't struggled, I hadn't gone through any of it. It's just a chance that I blew. But I kind of had to—if I'd have written something then, it would have been so self-important. I'd been working for dot-com jobs, thinking this is the easiest place in the world—like I'd suckered these people into letting me do anything. You came to New York, you were making more money than your parents, getting off work at 3, and drinking with everyone you worked with. In that mindset, in that kind of environment—it's no way to write a book.
So the publisher put it on the back burner—but you were glad for it?
Yeah. In retrospect, I'm happy about it. I'm actually ending the "Loser" column in March once I hit 200, and this book is a good way to cap it off. A lot that was in the original book is in this, but I've been able to take it and do it the way I wanted to, rather than try to force it into something it's not. I have another deal going on with another publisher for something after this, which is good, because I'm not stupid—well, I'm still stupid—but I'm not as stupid anymore. For a time, everyone I talked to, I'd be like, "Hi, I'm Will. I have a book deal—did I mention that?" I was an asshole. And it's just because I didn't know. And now, I recognize that it's just work, just like everything else is work, and I'm in a much better position now to put stuff together than I was then.
How did you find your new publisher?
They contacted me through The Black Table. Actually, a lot of stuff has happened like that. I was contacted a few months ago to write a story for The New York Times Magazine, simply because of something I'd written for The Black Table that was linked off of Gawker.
Oh, that's great.
Yeah, it ended up getting killed. But I still have contacts over there, and I'm still working on stuff with them. That's one of the reasons we did The Black Table in the first place—we publish a lot of stuff that's been killed in other magazines. The notion of writing on the Internet as online diaries—that's something we've tried to change with The Black Table. We try to do real journalism, just on the web. Mind you, there are more copyediting mistakes, and it's harder to read on the subway.
You actually mention something in the intro to your book about how you're afraid that people think the Internet lessens the import of journalism. Do you really think that's the general perception?
Yeah. There is just a stigma. You saw it when the big gossip item came out about how Jodi Kantor was doing a terrible job as the Times' Arts & Leisure editor because she was hiring all these web writers. The worst insult that could be given to her was that she was out hiring web writers at the great New York Times. But the fact is, that's where they are now. Not to get Marxist, but the workers do have the means of production now. But the term "web writer" freaks people out. They think it's some guy in the basement, sending out screeds about Star Trek. You and I know that's ridiculous, but most people don't. I go back to the Midwest, I tell them I write on the Internet—and half of my family still thinks I'm doing a porn site.
I've been writing on the web for five years, and finally, there are people who are like, "Oh, he has a book out. I guess he's a real writer now!" It's strange. Even web editors have this idea: "Well, someday we'd love to get into print!" Like it's like the holy grail. But I guarantee you that something on The Black Table, or The Morning News, or Haypenny, or Flak is far better than most of the stuff you're going to get in newspapers and magazines—and we're doing it for free. I think people are starting to realize that good writers are going to the web. Why wouldn't they? You have absolute freedom to do whatever you want, and if you're talented, that's gonna shine through.
In the book, you say that growing up, your heroes were small ones—in one essay you devote whole paragraphs to a contestant on Press Your Luck. But did you have any sort of literary heroes in mind when you were writing these essays?
There are certain writers I really admire, but frankly, most of my heroes are not big literary names. I've read every single one of Andy Rooney's books. The man's a genius. I'm telling you, if we can get anything across to the readers of mediabistro, it's how much of a genius Andy Rooney is. I know, he's just the old guy on 60 Minutes, but I like his kind of no-nonsense writing. And sure, I love Jonathan Letham, I love Dave Eggers, I'm into David Foster Wallace, I'm into those sort of people—I've got my smart street cred. But the people I really admire aren't trying to show off to anybody and are simply just writing stories. I wouldn't say Andy Rooney is my biggest hero, but he's probably my most indicative hero.
You also talk about your relationship with Roger Ebert. How did that come about?
He worked for The Daily Illini, as I did. Ebert was someone, who, as a kid, I looked up to. He doesn't have to write full-length reviews of all this stuff, plus do the "Movie Answer Man," plus do the "Great Movies," plus do the TV stuff, but he does. You have to admire that. There's a website called Professor Barnhart's Journal, run by a man in Boston named Bob Sassone, and he sent something out to a bunch of writers called "Why I Write." I wrote some goofy, self-involved thing, and Ebert wrote in: "This is my job." To me, that's the only way you can do it—he doesn't have to do this, but he does have to do this. The fact that he has that much good perspective on who he is, and what his place in all this is, is pretty impressive.
Is that how you feel too, that you're just compelled to do this?
Yeah. I'm still in the, "Wow, I can't believe I can actually call this work" mindset. With the Internet stuff, I can write something and have it fact-checked and up in like six hours. I don't have to worry about pitching it, I can just do it. And yeah, the process of pitching is very important, and obviously more magazines pay than websites pay, so that's a factor. But to me, the idea of not writing on the web would be like not writing.
Jill Singer is deputy editor of mediabistro.com. You can buy Life as a Loser here.