A professional’s approach to the writing life

Author James Kaplan’s James-Kaplanmonumental, two-volume biography of Frank Sinatra checks in at 1,600 pages of narrative, plus more than 100 pages of notes and bibliography. Researching, reporting and writing Frank: The Voice (2010) and Sinatra: The Chairman (2015), both published by Doubleday, took a decade. The Fairfield Writer’s Blog is pleased and honored to welcome James Kaplan back as our first returning expert in the series of interviews about the craft and art of writing that we’ve been publishing over the past five-plus years.

In the Sinatra books, Kaplan not only tells the detailed story of a great singer’s life and his alternately charming and boorish personality, he does so amid the richly rendered context of many facets of 20th century American history: the American Songbook era of popular music and its composers, lyricists, arrangers, conductors and singers; the growth of movies, radio and television in the everyday lives of performers and patrons; presidential politics and international crises; organized crime; the ring-a-ding-ding heydays of Hollywood and Las Vegas as entertainment playgrounds; and, of course, the public’s unending fascination with celebrity life. The skill, style and flow of Kaplan’s writing make the books eminently readable. To select just a few words from a very long roll of praise, Frank: The Voice was described as “vivid” in The New York Times and “monumental” in The Wall Street Journal, and Sinatra: The Chairman was called “riveting” by The Boston Globe and “magisterial” by The Washington Post, which named it one of 2015’s notable biographies.ChairmanCoverfrank-voice-kaplan-200x300

In 2010, in the wake of the publication of Frank: The Voice, Kaplan answered questions about the creative side of writing. Now, following the publication of Sinatra: The Chairman, in a second exclusive email Q & A with the FWB, he offers examples and advice about how to be a more conscientious, disciplined writer—in short, how to approach the art and craft of writing like a pro.

  • Routine. How do you set the parameters of a work day, so that you treat your writing as a job as well as an artistic endeavor? Do you keep regular hours, and how do other considerations such as family, exercise, etc., fit into them?

I’m sometimes asked where I get my inspiration. The mortgage, I say, is a great inspiration. Accordingly I am boringly regular in my habits, finding a fixed routine both calms me and reminds me that I’m doing a job.

I work in the attic of my house, a very pleasant space under the eaves with skylights and treehouse views. On weekday mornings I get to my desk between 8 and 9 and work until my stomach starts to grumble, about 11. I have a snack and walk around the block, then go back to work until lunch, which is anywhere from 12:30 to 2 p.m., depending on how the work is going. I do my floor exercises: pushups, crunches or planks, light weights. Lunch is light and brief, a half-hour tops. If possible I try to close my eyes for 20-25 minutes after lunch. It’s not often possible (deadlines and other distractions), but it sure is nice when I can work it in. I exercise (gym or tennis) in the late afternoon, 3-4 times a week. If it all sounds like being in training, that’s because it is.

My wife and I have three sons: two are out of the house, and the youngest has a foot out the door. When they were small, since my attic office has a pull-down staircase, I used to call myself The Man in the Ceiling. But the blessing of working at home was being able to see a lot of my kids, changing diapers, walking/driving them to school, etc.

  • Quotas. During interviews for Sinatra: The Chairman, you spoke of a goal of writing 1,000 words per day. Did you stop once you got there?

I copied the thousand-word-a-day quota from [John] Updike, an excellent model of productivity! With both my Sinatra volumes I felt a great deal of pressure due to the enormous amount of material (and with the second volume, his upcoming centennial), so I was rigorous about hitting quota. Sometimes I went over, but never under. But when I hit quota, I allowed myself to stop for the day. Conserves energy. Plus, as Hemingway famously said: Always leave the story hanging so you know where to start the next morning.

  • Editing. Do you edit your own writing as you go, or get it all down and then go back and revise? On the Sinatra books you worked with two editorial “legends” (your word), Phyllis Grann and Gerald Howard, at Doubleday. How much did you stay in touch with them during the creative process? Any basic rules of thumb for the new writer working with an editor for the first time?

My mentor William Maxwell [1908-2000, fiction editor at The New Yorker and author of novels, short stories, memoirs, essays, etc.] told me, about novel-writing: “Don’t revise and polish as you write it, just head for the ending. Once you have it down roughly you can fine-tune it, but rewriting slows the pace and leads to self-doubt and other disasters.” This is excellent advice for fiction, where confidence and the imagination are intertwined. With nonfiction, though, I give myself a running start each morning by glancing over the previous day’s work and spot-polishing it. The logic is that it almost always looks better the next morning than it did the day before, and this gives me confidence to move forward.

With Phyllis Grann on Sinatra Volume 1, I only showed her the first chapter—to win her confidence that I was on the right track—then the complete manuscript. She was pretty hands-on about marking up the pages, but always told me to only change what I felt like changing. I took her at her word. I might as well confess here that I’ve always been able to produce a pretty clean first draft. Chalk it up to fussiness, but that and being good about hitting deadlines got me a lot of magazine work during my magazine-writing career (circa 1985-2000).

With Gerry Howard, the process was different. Since we had this big deadline of the Sinatra centennial [December 12, 2015], I sent him the manuscript chapter by chapter so he could keep up with me. I think it’s safe to say that Gerry’s a fan of my writing, but as a hardworking line editor and an excellent writer himself, he never hesitated about telling me when I’d written a little purple—excessively or over-expressively. And I learned with Phyllis and continued to learn from Gerry the sheer pleasure of cutting words and trimming the story to its essence. It may sound unreasonably sunny, but I can’t remember a serious disagreement with either of them about textual matters.

Advice about working with an editor for the first time would vary widely depending on the writer and the editor, but in general I’d say: know well ahead of the work who the editor is and what she or he is likely to like and dislike. And pay very careful attention to her or his suggestions: you may be very good, but the editor may still be right.

  • Distractions. How do you avoid the lure of the internet? Do you keep up on reading? Do you listen to music as you write?

When writing, it’s crucial to have steely discipline about the internet. I allow myself to look at my email once before I start in the morning, again at my 11 a.m. break, and then just before lunch, at 12:35. If you’re going to let yourself get sidetracked by cute cat videos or naughty pictures, you’re just being self-defeating: work it out. Since I had the huge advantage of using online newspaper archives for the Sinatra books, one of my biggest temptations was getting lost in those old newspaper pages: I could gaze all day at refrigerator and automobile ads and comic-strips and human-interest items from 1953 all day. All I can say is that I strapped myself to the mast and got on with the work because I had to.

When I’m writing, I like to read the opposite of what I’m doing—fiction if I’m writing nonfiction, and vice versa. The reason is simple: anxiety of influence. Don’t want to pick up some other writer’s rhythms, or get intimidated by masters in your field. While working on Sinatra, I began reading Proust! It was as different as could be, but the length of it gave me hope that I could persevere. And the depth of human understanding is incomparable.

I can’t listen to music as I write (though I listened to tons of Sinatra for reference). Since I write for my own ear—the sentences have to sound good to me—having other melodies and rhythms in my head as I composed would be distracting, if not crazy-making.

  • Commerce. Should newer writers turn down assignments or sales if they feel the payment offered is not enough, or is earning the credit worth accepting the job? You were awarded a Guggenheim Fellowship for the Sinatra project; any advice for writers applying for grants or residencies? How much do you rely on your agent to handle the commerce part of being a professional writer?

A writer has to establish a market for him- or herself. This is a very daunting, chicken-and-egg process: you can’t get established till you’ve been paid, and you can’t get paid till you’re established. (The same is true of getting an agent: can’t get one till you’ve been published, hard to get published without one.) To get a foothold in the beginning, you need clips—samples of your published work. Do anything at first, for free or for pennies, if you can do it well and produce clips you’re reasonably proud of. You can then begin to negotiate your price upward. Advice on applying for grants: Persevere. I applied for the Guggenheim four times before I got it.

I rely utterly on my agent to handle my writing business. I expect her to negotiate the best possible deals for me, and to be a tiger in negotiations. She does and she is.

  • Quantity vs. Quality. With the long-term scope of a big project like a book, how do you set aside those concerns of “getting it done” and focus on turning your writing into art?

Make it manageable. Write an outline: know exactly where you’re going. Then break the work down into doable pieces. Calculate how much you can write a day, per week, per month (and be realistic about it). If all you can think about is the Himalaya in front of you, it’s too easy to intimidate yourself into paralysis. Stay as healthy and positive as possible, and time will be on your side.

  • Personal Characteristics. You are unfailing polite, friendly, soft-spoken and good-humored. To have success such as yours, one also must be committed, persistent and ambitious. Do these two sides ever conflict, and if so, how do you keep them in balance?

I am a gentleman to the outside world, and in the privacy of my office (and my inner life), a driven, ambitious, competitive S.O.B. I believe all successful writers share those less than savory qualities—some are just more clever about hiding it than others.

Alex McNab

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Published in: on May 18, 2016 at 12:26 am  Leave a Comment  
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