What were some of the expectations you had about New York before you arrived, and how did that mesh with reality?
I never really had a romanticized view of it, because at that point New York was in such terrible condition. A lot of my sense of New York came out of Johnny Carson monologues. It was always about muggers, about Central Park. I remember a piece in The Village Voice when I was early on there about spending the night in Central Park. And I think it was a cover story. That's how dangerous it was. When I came to the city, you were told, "Do not go to most of Riverside Park at night. Do not cross this part of Union Square Park." So I didn't have a terribly romanticized idea of the city at all, but what I did romanticize was I thought that, based on movies I saw, the literary world was going to be this glittering, witty, sharp place. Instead, you realize, no, it was just jockeying for power and possession. It wasn't people holding drinks in their hands saying witty things. Sometimes when you met people you looked up to, it was [disappointing.] Like, this is it? All they are doing is complaining about the food.

There are phrases tucked throughout the book that seem to be social commentaries on, not only the direction of young writers, but the direction of young culture in New York. "Nothing makes writers happy very long," or "That's why we're all so lonely," in a reference to editing on computers all the time.
There really is no mentoring. I don't even know if I'd call what I got mentoring, but I certainly got really, really good editing. There were certainly people who were mentored. There is a whole group of writers who, in a sense, were mentored by Bob Christgau. Mind you, that's a positive and a negative aspect. I'm sure they were slapped down like bear cubs every once and awhile. But there was that sense. There's a much greater sense now that you're totally on your own. You're totally a freelancer.

What impact does that have?
It means you don't really have a grasp as to where the next thing is coming from. If you're starting out as a freelancer, you can hope that you do enough freelance work and, back then at least, some magazine would pick you up. There was almost a ladder, a progression, where if you got a lot of attention in the Voice, this other magazine might pick up on you. That's what happened with me. I wrote for the Voice, but then Esquire hired me, and Harpers. Now, no one is hiring basically. No matter how well you do, it's very iffy whether or not you'll get any type of regular gig. I think it makes people feel like they're constantly starting over and at square one. Also, the other thing is that when I started out, we didn't have Twitter or Facebook or any social media. There was no way you could dissolve yourself into that. Every writer has their procrastination habits, but now these make it even more insidious because you're procrastinating, but you can also tell yourself that you're writing. It makes people feel, kind of, "Where does it go?" I think what happens now is people are hoping that they do freelance, get enough attention, and then maybe they get a book contract. But of course, those aren't the money they used to be. I've been very fortunate because I've always been based in some magazine. But a lot of people I know who used to be based in a magazine, they got let go and now they're freelancing in their forties, fifties, and sixties, and they're not going to pick up that much work.


Lucking Out
272 pages

How have you seen social media affect readers of counterculture journalism?
I think it's pretty much killed investigative reporting, because now no one has the resources to do it, so you get a lot more opinion stuff. On the most basic level, I find that because I read so quickly online, I have to be really careful because, now, I tend to drop words out of sentences. It's like my brain is doing shorthand and jumping ahead. If you do a lot of texting and emailing, it's very easy to start writing in code. That can be a real problem.

What kind of code?
You're assuming that everybody knows certain shorthand phrases. Twitter is full of loaded phrases and catchphrases, and so it's very easy to fall into that, and not write more formal writing. It's also a real temptation to have a very splintered approach. You're attacking something from this angle, but you're not building a whole, like a writer like John McPhee or others who really assemble a piece. You don't really see the structure, but it's there. Writing on the Internet can really dissolve structure and turn everything into assertion. Plus, a lot of people get sucked into battles on Facebook and Twitter that are going to do them no good. It's not like you're arguing something out in The New York Times, where a lot of people are going to see it. It basically becomes a series of running feuds. I've seen so many people get sidetracked, and you can tell they're spending their whole afternoon in a state of indignation on Twitter, firing back at people. It's not going to do you any good, and on the most basic level, you have to say, "Am I going to make any money? If I need to write for money, how is arguing with a guy with a semi-obscene nickname on Twitter with 48 followers going to help me? What is the point?"

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