Freelancing, Rejection and Chess: An Interview with Author Michael Weinreb

Freelancing, Rejection and Chess: An Interview with Author Michael Weinreb

Media Gossip/Musings

Freelancing, Rejection and Chess: An Interview with Author Michael Weinreb

Most of the time, our interviews focus on established newspaper writers, pillars in the sports media industry, or just folks we like (Norman Chad!). Today, a curveball comes in the form of Michael Weinreb, an author/freelancer hybrid whose name we kept seeing on the byline of stories we enjoyed (we’re closeted chess freaks). And as you’ll soon see in the line of questioning below, we harbor the hope of one day having the courage to abandon the full-time job and steady paycheck for a life of freelancing. Or even full-time blogging.

Q: From the looks of it, you have what every writer wants: the freelance life. Our big fear is making that leap of faith from having a secure paycheck to hoping to land one. Can you talk us through your move?

I cannot say I made a conscious effort to reach this point: I always assumed I’d have a real job of some sort–in fact, my dad is still waiting for me to get one. But I landed at the Akron Beacon Journal in Ohio straight out of Penn State, back when the B-J was actually one of the better newspapers in the midwest. I spent five years there, covered far too much golf, and worked with many talented people — including Terry Pluto (he is to Ohio sportswriting as Reilly is to SI), Greg Couch (now a columnist at the Sun-Times), David Giffels (a feature writer who recently got a major book contract), and some underachiever named Klosterman (I think he’s herding roosters on a farm in North Dakota these days). By 2000, I was restless and couldn’t stand living in Akron anymore, so I went to graduate school for fiction writing at Boston University, studied with a man named Leslie Epstein (whose son Theo would later take a job with the Red Sox), wrote a few short stories, did some work at Boston Magazine, interviewed for a feature-writing job at Newsday (hiring freeze), moved to New York three months after September 11, took a job at a trade magazine aimed at sales managers, interviewed for a feature-writing job at a newspaper in New Jersey (hiring freeze), took a sort of full-time part-time gig at Newsday and awaited some sort of full-time full-time gig (hiring freeze), published a book of short stories (good editor, terrible publisher), and then stumbled across this great story about a championship high-school chess team in Brooklyn. I knew absolutely nothing about chess, but I sold the book proposal (the book itself came out in March of ’07), and this allowed me to quit Newsday just as it was coming apart at the seams.

So in a way, it was the reality of the business that drove me to this point as much as my own free will; of course, I was stubborn, too, and I wanted to write long-form features (I am not focused enough to cover a beat, I think, though I admire those who do it well), and those jobs don’t really exist anymore. Especially not at newspapers.

That’s why I’ve had a lot of fun contributing some pieces to the E-Ticket section on; it’s a pretty rare opportunity for a writer, and it’s proof that people will read a long feature online if it’s got an interesting angle and it’s packaged very well.

I always figured I would find another full-time job sometime–I guess I still think I’ll have to at some point, though probably not at a newspaper–but I’m hoping to fool enough people for as long as I can.

Q: If you were trying to coax somebody into making that leap of faith, how do you talk them off – or onto – that ledge?

I don’t think you can do it unless you have some sort of guaranteed income–a book contract, or a magazine contract, or enough steady work from a few different outlets, or a very wealthy spouse. It’s hard enough just covering the health insurance. The most difficult part, at least for me, is that I never know how much money I should be saving, so I’m afraid to spend at all. Though I’m probably just cheap. (I’m told it runs in the genes.) Of course, there’s something to be said for being able to break away and spend an entire afternoon playing EA Sports College Football. With a mobile quarterback, I am unbeatable.

Q: Now that you’ve established yourself as a freelancer, how difficult is it to juggle everything? What are the biggest pros and cons of freelancing?

The interesting thing about it is the way the work often tends to pile up all at once. Then you’ll suddenly find yourself with a week where you have nothing to do, and you have to motivate yourself to get started on something new. There’s always angst–I’m working on a new book that is very research-intensive (it’s about the year 1986 in sports), and I worry about that every night now. It can be difficult during certain periods, but I tend to write in spurts, anyway, so it kind of works for me. You also have to be ridiculously aggressive at times. I still find the whole experience of pitching something blind to be incredibly humbling. I thought perhaps once I had written a book and gotten a few decent credits, I would at least get a response from most editors, but it doesn’t always happen. There are times when your e-mails seem to vanish into thin air.

At this point, I’m just happy to have work. And most of it is fun work. When you’ve worked at a magazine called Sales and Marketing Management, you learn that sportswriting isn’t such a bad day job.

Q: We looked you up in nexis and found an interesting piece on Elena Della Donne. She’s the female version of LeBron James, supposedly. You buy the hype?

I actually was working in Akron when LeBron was a freshman in high school; his coach at the time, Keith Dambrot, told anyone who would listen that this kid was going to be a first-round draft pick. I don’t think I believed him, which tells you how much my opinion matters. I wonder if Candace Parker might already be the female LeBron James, but Delle Donne is 6-5 and can play almost anywhere on the floor–perhaps she could be the female version of Dirk Nowitzki?

Q: Trying to settle a score with friends: which is the best New York season? Not necessarily for weather or sports, but just all around life?

I think it’s impossible to separate my all-around life from weather or sports, which I will admit is somewhat pathetic. Winter (especially post-Christmas) is generally miserable, and thanks to Al Gore, we no longer have spring – one day, you wake up to four inches of snow, and the next day it is 98 degrees and elderly ladies are passing out on subway platforms. Summer weekends (when all the people you hated in high school go to the Hamptons) are kind of nice, but then, this past weekend I think every damned subway line in the city was under construction. I still find fall to be the best time around here. Of course, I’m basing that largely on sports (the MLB playoffs, and the start of the college football season), and on weather. I don’t get out much anymore.

Q: What are your three favorite non-sports blogs?

I think the guy who writes Talking Points Memo is brilliant, and he’s proof that the good blogs advance far beyond navel-gazing; I guess he’s actually driven the political news cycle a couple of times, as with the Gonzales firings.

Since I (kind of) own an apartment, I often check in on Curbed (about NYC real estate) and Brownstoner (about Brooklyn real estate), though the commenters are constantly falling into bitter disagreements about the impending crash of the market–it’s like an episode of Mad Money. And since my girlfriend essentially owns 90 percent of the apartment I’m sitting in at this moment, she is my Jackie Christie, and I am contractually obligated to read Cheryl Shops.

Q: World is ending, and you can have any meal on the planet. Your choice is …

The Golden Wok, in my hometown of State College, Pennsylvania. Still the best Chinese food I’ve ever had. In fact, my one great disappointment about New York is the baffling lack of transcendent Chinese food — I find it’s all either too Americanized, or too “authentic.” I actually ate more consistently good Chinese food in Akron than I have here. (I suppose if newspapers hired Chinese food critics, I would aspire to that job. And I would have a triple bypass at age 37.)

Q: Favorite 1980s sitcom?

Well, the only sincere answer to this question is Cheers, the third-best television comedy of all-time. I also think it holds up surprisingly well. I’m not sure if I can say the same thing about the Wonder Years, but it has been amusing to watch those re-runs on a “family channel” that advertises Native American aging cures.

Q: The easiest class you took in college.

Man, I went to a state school. And I believe I got a B-minus in the History of Television, thanks.

Q: After the big three sports (Football, basketball, baseball), what are your two favorites?

What else is there? I watch Sundays of major golf tournaments, usually if Tiger is involved. I have no animosity toward hockey fans, but I could not tell you if the NHL still exists. I cannot believe how much I enjoyed watching the World Cup, even though I had virtually no idea what was going on, but I have a friend who “adopted” a Premier League team and I am constantly calling him a poser, so it’s too late to turn back now.

I once covered an electric football tournament, and won third place in a bowling writers’ contest. It’s funny, because the features I most like to write are often the ones that are far off the path beaten by the big three–one of my favorite stories I’ve written was about street handball players in New York. Another was about the roller-derby renaissance. Halberstam wrote a great book about rowing; Stefan Fatsis wrote a great book about Scrabble. That’s how I came to write about chess, I suppose, and that’s why I have no problem with ESPN televising poker or darts or diminutive Japanese men regurgitating – put in the proper context, I think any competitive pursuit can be made interesting, and that’s the whole reason we watch any sport in the first place, isn’t it? Although you could also argue that these things are what have ruined the once-great ESPN Classic. Because despite what I just said, if any ESPN programming types are reading this, there is no such thing as “classic karate.”

Q: You’ve got a book about chess that looks rather compelling. Since bloggers are nerds and nerds play chess … did you ask if any of the chess-playing kids were bloggers as well? And do you feel your chess skills have improved since writing the book?

I don’t think any of the kids have blogs, but there’s a story in the book about one of them, Oscar Santana, who pulled a move straight out of War Games and actually managed to break into the Board of Education’s computer and change his grades. I did use the word “geek” in the subtitle of the hardcover (it’s being changed for the paperback, but that’s out of my hands), and people would ask me whether I thought that was an insult, but I really don’t think it is anymore.

One of the things I hope this book does, though, is break down any stereotypes surrounding the kids in the chess club. That’s why I always try to convince people that it’s not really a book about chess–I actually structured it in the vein of all those great books about high-school athletes, like Friday Night Lights (I BEG you to watch the TV show, if you aren’t already) and The Last Shot and The Miracle of St. Anthony (arguably three of the top 10 or 15 sports books ever written), because these kids had the same struggles, and the same obsession with their chosen game–often to the neglect of their schoolwork.

As for my chess skills, I am, and have always been, absolutely awful, which is yet another reason why the book is very light on technical detail. I actually spent several weeks in the midst of the writing process trying to beat a computerized chess engine that would not only defeat me, but talk trash in the process. It was like Deep Blue meets Shannon Sharpe.

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