FIVE FOR WRITING: JEFF PEARLMAN!

Jeff Pearlman is a columnist for SI.com and the author of four sports biographies, including the best-selling Boys Will Be Boys: The Glory Days and Party Nights of the Dallas Cowboys Dynasty.

He was also, back in 1999 or 2000, watching BP from the first-base side at Veterans Stadium before an ordinary afternoon game between the Toronto Blue Jays and Philadelphia Phillies.

At the time, he was one of the youngest writers at Sports Illustrated; I was a beat writer for National Post. Jeff was the guy I aspired to be. For maybe twenty minutes, I stood with my back to the cage—rookie mistake—and asked him many, many questions about how to become a magazine writer. He was very kind and patient in his answers. They were helpful and inspiring. He wore a red hat. The sky was blue. Jeff doesn’t remember our conversation—I checked—but I remember it very well.

Whenever a young writer asks me about my work and how I do it, I think about how generous Jeff was with me that afternoon at the Vet.

And now here he is again, all these years later, still answering my questions.

My thanks, then and now, to Jeff Pearlman.

1. You’ve worked in every corner of the word business—in newspapers, magazines, and online, and most recently, in books. Why have you jumped from what would seem like a succession of dream jobs? And what is it about writing a book—you’re now on number five—that fits you so well?

It’s funny how people often don’t think of themselves a certain way until it’s placed before them. I’ve never, ever, ever considered myself to be a writing vagabond, but when you spell it out like that… I suppose I am. Weird.

This is a tough one to answer, but I’ll give it my best. When I was 13 or 14, I told my mom that one day I would write for Sports Illustrated. I was a Jewish kid growing up in Mahopac, N.Y., and my wonderful Jewish mother said what all wonderful Jewish mothers are required to say: “That’s nice, but you also have to be realistic. Don’t you think being a lawyer would…”

It sounds corny and cliché, but I swear that I’ve never forgotten her words. They truly motivated me. I remember saying, “No, mom, I know I’m gonna write for Sports Illustrated. I just know it.” So, from that age on, my goal in life was to write for SI. It’s why I wrote for my high school paper, my college paper, had a bunch of internships, etc. My first full-time job was at The Tennessean in Nashville, and I was given the open spot—food and fashion writer. I took the job as seriously as I could (I’m a crap dresser and an even worse cook), but I always was thinking, “How can I get to SI?” So I applied and applied and applied and applied until one day they ran a freelance piece I submitted about the time I applied for early entry to the NBA Draft during my junior year at Delaware. The piece ran, and shortly thereafter SI hired me. I cried. I literally sat alone in my Nashville apartment and cried tears of joy. I called my mom and said, “See! See!” Best moment of my life until that point—easily.

Then I got to the magazine, moved up the ranks, loved, loved, loved it. Had such fun, got to cover cool events. I mean, every Christmas they’d fly in all the senior writers from around the country for a State of SI celebration/meeting, and, man, I was in journalistic heaven. Yeah, I was Christian Laettner on the ’92 Dream Team, but I was in the room.

About four years into my time at SI, though, I started getting a tiny bit itchy. I was Tom Verducci’s No. 2 on baseball, which was terrific. But… I don’t know what it was. The players were starting to get younger than I was. The clichés drove me crazy. I dreaded getting blown off so some guy could read his Field & Stream (true story). I went through the inevitable, “Is this as good as it gets?” Udall stage.

Seminal moment came in 2001. I was covering Game 4 of the World Series between the D-backs and Yankees at Yankee Stadium. Great night, amazing energy. Well, early on my stomach starts to hurt. I start cramping up, and I say to Verducci and Steve Cannella, “I’ve gotta go home.” We weren’t filing for that night (at least I wasn’t), so I left and took the train to the apartment I shared with my then-girlfriend/now-wife. The two of us sat on the couch and watched the game—this classic World Series thriller that came down to a 10^th inning homer by Derek Jeter. And as I watched from afar, the fans going nuts, Jeter rounding the bases, the announcers screaming, all I could think was, “I’m so happy I’m not there right now.” That’s the 100% truth—I was thrilled to not deal with the crush; the clichés; the blather. And it was that moment when I officially started thinking about exiting SI. Because if you’re not sad to be missing Game 4 of the World Series, you need a change.

So I eventually left, and landed a gig at Newsday writing 2,500-4,000 word pieces for the cover of their magazine-ish section, Part 2. And it was truly wonderful—“Walk New York City, find unique stories, write them up.” I could have done that forever—but then Newsday went to shit. Literally, one day my editor said, “I hate this, I love what you’re doing—but the paper is changing and we want you to start writing 500 word minis and coming into the office every day.”

That was that. Since then, it’s been ESPN.com, which was great, and SI.com, which has been great. But mainly it’s about the books for me.

As for why books work for me—a bunch of factors. First and foremost, writing books allows me to be a stay-at-home dad, which is certainly the most satisfying part of my life. I’m actually my son Emmett’s “class mom,” and I held the same post in past years for my daughter, Casey. My wife and I never miss a school concert, a dance recital, a parent-teacher conference—nothing. That’s a blessing, because I realize how fast life soars by, and how quickly kids grow up. I have this quirky belief/hope that the more I’m around, the slower it’ll go.

Second, I love digging and digging and digging, until I’ve exhausted all research avenues. That’s books. With magazine pieces, there’s usually a short time to work. With newspaper stories, even shorter. But to be able to devote two years to a book project is a digger’s dream. I couldn’t have seen this coming when I started in the business, but I am addicted to picking up a media guide and, one by one, finding every single person. Not just the players, but the executives, the clubhouse guys, the IT expert. Everyone. The moment when I track down a really obscure individual is indescribable.

2. How do you know when you’ve found the right idea for a book? What are you looking for? How do you judge whether it’s good enough to sustain you over those months and years of work? It is work, right?

Tough question. I’ve had four books published. Two on teams, two on individuals with PED ties. The two team books landed on the Times’ bestsellers list. Bonds and Clemens sort of came and went. So how do you know when you’ve found the right idea? I’m not sure. My approach has always been this: A. The subject has to be something that interests me; B. The subject has to have a chance of selling big. There are no guarantees, obviously, but I feel like all of my books have had shots of landing on the list. In hindsight, Bonds and Clemens were doomed, because people don’t want to spend $25 on people they mostly loathe. But they were big names with big resumes.

Because this is my primary way of making a living, I need the books to sell. I feel a lot of pressure in that area. For example, I’d love to write a biography of the USFL. I toy with the idea, mess with the idea, start putting the idea into a proposal—but I just don’t think it’ll sell, and I’m not sure I can survive a bomb.

As for the sustainability—I’ve never thought about it. My general belief is that everyone has a fascinating story, you just have to dig your rear off.

That said, I’ll make this point: Of the books I’ve written, Clemens was the one where I struggled a bit with the sustainability. He just isn’t a very deep man. Extremely surface, only thinks about baseball, trucks and breasts. So I wound up focusing elsewhere a lot—his older brother, his teammates, etc. Which can still work. But there’s a reason that’s my least favorite of the four books.

3. Don’t take this the wrong way, but I’ve always felt that people who write in coffee shops can’t possibly be getting anything done. Yet you’ve written hundreds of thousands of published words in coffee shops. Why coffee shops?

Ha. As I answer this I’m sitting in The Floridian, a diner in Ft. Lauderdale. I’ve got a story due tomorrow morning, but I’m procrastinating by answering these questions and peeking at American Idol on the TV.

Why coffee shops? The illusion of social interaction. I need to hear voices and see people and imagine that I’m at an office. There’s nothing worse for me than the silence at home. The refrigerator is a tremendous distraction, as is the television. In a Starbucks or Panera or Cosi, the chatter somehow soothes me. It’s great background music.

What I hate, though, is the search for an outlet. If you see a gawky balding guy in an STP T-shirt looking under tables at the nearby Starbucks, it’s likely me.

4. You’re very accessible to your readers, through your blog, twitter, and email. But you also seem to be a writer who’s still trying to figure out how best to manage your relationship with your audience. What’s our responsibility to our readers? And do they have any responsibility to us?

Ha, that’s a polite way of saying it. I really struggle in this area. On the one hand, I do enjoy the back and forth. On the other hand, I’m easily bruised at times. I take writing personally. Probably more personally than I should. I never go all Skip Bayless and make points just to argue. I believe what I write, and I want it to be good. So when readers say, “You suck” or “That’s the dumbest thing ever,” well, I actually think about it. I guess that’s me having thin skin, but I do actually care what readers think, and I try really hard to respond to every single e-mail.

But I will say this—our responsibility to the readers is to write good stuff—period. That’s it, that’s all. I’m under no obligation to Tweet, to respond, to anything. I enjoy it, so I do. But I think, in this area, something has really gotten messed up in our world. People are so insanely rude, and they hide behind anonymity. I wrote a cnn.com column about this, and the number of “amen, brother” e-mails from other journalists numbered in the hundreds. You wanna tell me you hate a column? That’s your right. You wanna tell me I’m a donkey ass-sucking piece of dog shit who fucks grandmothers on the streets of Urbana? Uh, no.

5. I’ve read that your dream project would be to write a biography of the late Blind Melon singer Shannon Hoon. That seems like a pretty improbable sentence, but I just wrote it, and I believe it to be true. Shannon Hoon?

I say this with no irony: Shannon Hoon might be the greatest songwriter nobody really knows about.

Exhibit A: http://www.youtube.com/watch?v=g4H5vsQM7z8

Exhibit B: http://www.youtube.com/watch?v=TrxnJzxxEKk

Blind Melon only released two CDs while Hoon was alive, and they’re amazing. Then they came out with a third after he died, with Hoon’s leftover songs, and it’s even better. The Exhibit A song, “Soup,” was supposed to be the title track to their second album. Yet even though the CD was named “Soup,” they left the song off. I love that. Makes no sense.

Hoon also happened to be really tortured. I have yet to meet a writer who doesn’t do torture well.