J-School Confidential: A Magazine Vet Struggles to Write His First Book

In our new AG series, freelancer Greg Lindsay discusses writing his first book. He’s filing monthly dispatches detailing the struggles and successes of writing the first draft of Aerotropolis, due this spring. In this second installment, he describes the “growing pains” he feels transitioning from magazine-speak to book-length prose.

Keep on keepin’ on

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The words “Day 23” are dutifully taped to the wall above my desk, as Charles Fishman advised, but I wouldn’t have guessed those words would look so recriminatory so early in writing my book.

Just to quickly recap: I started writing Aerotropolis on October 1, starting from Chapter 2, which is set in and around the FedEx and UPS package sorting hubs in Memphis and Louisville, respectively. I budgeted two weeks and 10,000 words for the chapter, assuming I could churn out a thousand respectable words worth keeping each day.

That assumption was wrong on several counts. I am 12,000 words in, and there is still no end in sight. (I have an outline, but I’m afraid it’s an outline for a 20,000-word chapter). I’ve struggled to hit my self-imposed daily deadlines. That’s in spite of the fact that I’ve become a zealot about word count, if you define a zealot as “one who redoubles his efforts while losing sight of the goal.” Writing 1,000 words a day (a la Anthony Burgess, who could write twice as much before the pubs opened) has become a goal unto itself on some days, and that’s usually the copy I throw out the next day because I veered off the outline and stopped paying attention to the greater goal.

I’d like to think I’m experiencing the same growing pains that every magazine writer feels the first time he or she sits down to write a book. The rhythms are all different; there is no self-imposed tone by the editor or publication, and the “luxury” of so much white space is very deceiving. And so I find myself adopting different tones midway through the chapter; the John McPhee-style lead now seems self-indulgent and overwrought, and I’m refusing to cut the chapter down myself because I recognize the impulse to chop it into a 3,000-word feature with easy nut grafs up front.

I have made some good decisions. For example, I roped my research assistant into spending several days in my living room transcribing the first portion of my notebooks, which has proven to be invaluable for shaking loose quotes and nuggets of information I would have otherwise forgotten. I can’t wait until he finishes the rest.

Battling bad habits

But the bad habits outweigh the good ones for now. The worst I’ve picked up is my compulsive writing and rewriting of prose that I will probably throw out now that the overall shape of the chapter is finally coming into view. There are certain sentences and paragraphs that essentially make my brain itch, and so I scratch them, over and over, with niggling little tweaks that I’ve only just realized are a waste of time.

This past Monday (October 22nd) was my best day of writing yet, because I had used to the weekend to hole up in a Dean & Deluca with my notes and two large iced lattes, which provided the fuel for extensive paper-and-pen outlining. Armed with that on Monday morning, I just dumped words onto the page from 9 a.m. until 3:30 p.m., followed by an hour of errands and emailing, and then another hour of revising for quality. That produced 1,800 words worth keeping and, more important, some propulsive momentum. Can I keep up that pace, or will my writing inevitably suffer for it?

Pacing is everything

To answer that question, I called Will Leitch. Will is the author of three books, including the forthcoming God Save The Fan, which he wrote when he wasn’t blogging at Deadspin. I have seen Will write at twice the speed of Burgess in settings in which I would find it impossible to work — while listening to music in a beach house filled with eight other people, for example. I’ve pooh-poohed his speed in the past, but now I wish I could emulate it. But I wondered whether all the time he saves writing with a fire hose is then spent on rewriting and editing.

“The rewriting is never that heavy,” Leitch says. “I know exactly what I’m going to write, and how long it should be. Once I have an idea of what I’m shooting for, I know whether I can go long on some parts, while recognizing that I’m wasting too much time on others and need to wrap those sections up. For the Fan book, because it was broken up into segments [it’s a series of original essays], I had a clear finishing point in each case. If it was going to be 3,000 words, I knew I needed to keep writing to hit that figure, and I knew I needed to stop not long after I reached it. With Catch, [his second book, a novel] I knew it would be 70,000-80,000 words total, and I have broken it up into three sections, so each one had to be 25,000 words.”

By focusing relentlessly on his word count maximums and minimums, Leitch was able to keep a much tighter grip over the shape of his narratives than I have so far. But I still couldn’t believe that he rewrites as little as he does. “Certainly, I have self-doubt about it,” he says, “but one thing about writing for the Web that has really helped me is that editors tend to like me — and online writers in general — because they are not divas, and because they are so used to putting up their writing immediately. They don’t agonize about other ways to tell the story. If it feels wrong, I’ll change it. If it doesn’t, I won’t.”

A lot of my first chapter feels wrong right now, but I’m not yet inclined to blow it up and start over. That’s what editors are for, and I’m meeting with him later this week. We’ll see how much survives.

Tips on keeping the words flowing:
1. Don’t narrow your focus to daily word counts. Hitting your self-imposed quota doesn’t matter if you’ve failed to move the story forward that day. If churning out raw copy is all that matters, then you’ll never end up cutting anything. And there’s probably a lot that needs cutting.
2. Find a healthy balance between fixing mistakes immediately and scratching an itch just to feel productive. I already wish I could have all the hours I’ve spent making tweaks back. Until you’re certain you’re keeping that prose in its current form, more or less, there is no need to tweak at the sentence level.
3. Don’t luxuriate in the space you’ve been given. At first blush, 120,000 words looks like an enormous amount of room. But here I am, a tenth of the way there, and I haven’t finished telling even a piece of the story yet. Just because it’s hard to blow your word count doesn’t mean your readers (and editor) won’t be bored while you prattle on forever.

Greg Lindsay is a frequent contributor to mediabistro.com and other publications. He’s working on his first book.