'In the Pain Cave': Award-Winning Journos on Long-Form Writing

It wasn't mentioned in journalism school (at least not mine), and isn't raised by NYU professor Robert Boynton in The New New Journalism, his collection of interviews with contemporary masters of long-form nonfiction. The topic is crucial to the writing process, but is almost totally invisible.

In an effort to shine some light on the subject, I asked a quartet of feature writers whose work I admire to explain how they restore and retain the entire sweep of a story as they sit down to write. How do they reintroduce themselves to their notes, prioritize their contents, and then fashion an outline? Three-fourths of them, I was shocked to learn, don't even get that far, and that includes the ones who have won multiple National Magazine Awards.

The writers in question include Charles Fishman, a senior writer for Fast Company, whose stories I read and re-read when it's time to write my own for the magazine (where I'm a contributing writer). He is also the author of The Wal-Mart Effect, a 2006 finalist for The Financial Times/Goldman Sachs Business Book of the Year.

GQ correspondent Lisa DePaulo contributed the title to this story -- she describes the time spent meticulously transcribing notes and wrapping her head around the story as the days and weeks spent in "the pain cave." She has twice been a finalist for an Ellie.

"Any journalism school professor would recoil in horror" at Tom Junod's consistent failure to create an outline, says the writer of his own process. Despite that flaw in his mechanics, the Esquire writer-at-large has been nominated for 10 National Magazine Awards and won two for Feature Writing. He may win a third on May 1 for "The Loved Ones," his profile of the owners of a New Orleans nursing home in which 35 elderly patients perished during Hurricane Katrina.

For 25 years, Gary Smith has been one of the brightest stars in Sports Illustrated's stable of writers. He has won four National Magazines Awards, including one for a story about a photograph taken in the Texas Christian University locker room before their 1957 Cotton Bowl game against Jim Brown's Syracuse team. He essentially won for inverting the old adage about a picture saying a thousand words -- several thousand, in that particular instance.

Charles Fishman

Fishman began his career as a "cops and courts" reporter for The Washington Post, covering trials in Fairfax County, Virginia. As meticulous note-taker under constant deadline pressure, he soon developed a system of meta-note-taking, using a standard notebook to capture every scrap of testimony, while balancing a legal pad on his lap. During breaks, he recalls, "I would keep track of the most important notes, the pages they were on, and also the themes and issues that were emerging in the trial and testimony that day." He'd then use those notes to create a rough outline for that day's story.

Later, in 1986, Fishman was a member of The Washington Post team covering the aftermath of the Challenger space shuttle explosion. He spent more than a month on the road for the paper, assembling the story of how NASA recovered every fragment of the shuttle and its booster rockets from the bottom of the ocean floor. "This was the first really big story of my life, where you knew it was good," Fishman says. But his first draft, at 4,000 words, "felt labored. You felt like you were drinking cod liver oil."

Today, the process begins with the same degree of meticulousness he displayed during his court reporter days ("I write down the whole conversation, and also the color of their clothes, the pictures in their office, and so on.") Then, he transcribes every last page of his notebooks into his computer, a process he's dubbed "doing the notebooks."

While transcribing, he keeps several files open at once. For a story about Toyota and its philosophy of "continuous process improvement," he created a file called "0.0 Toyota Good Stuff" (the 0.0 is meant to ensure that the file is always at the top in an alphabetical listing), into which he transcribes "good stuff" -- quotes under one heading, examples under another, and themes under a third.

Yet another category holds "good stuff" that isn't directly linked to the story's major themes, while every quote or fact is highlighted according to its relative degree of importance -- bolded if good, bolded with a bullet if very good, and bolded with three bullets "if you can't miss it."

"When you've finished panning for gold in your material, you inevitably have a sense of the shape you want your story to take," Fishman says. "The 'good stuff' comes directly from the little anecdotes you want to connect the themes to. Then, you write the story, and everyone has their own approach to that." Armed with the de facto outline that emerged from this process, Fishman wrote a 4,300 word story on Wal-Mart's backing of environmentally-sound lightbulbs in two eight-hour bursts.

Fishman used his technique while writing The Wal-Mart Effect, but the experience left him unsure as to whether it worked well for writing books. "I don't think this method necessarily scales that well. I'm going to consult with someone before I write the next [book]. I love my system for stories, but for books, I need to figure out what the next system is."

Lisa DePaulo

"In a lot of cases, I tend to over-report," DePaulo says. "The more time someone will give me, the more time I will take." As an inveterate taper of interviews, the inevitable result is that by the time "you're ready to write, you have a dozen 120-minute tapes to transcribe." And, DePaulo insists on transcribing every last tape herself.

"I transcribe verbatim -- the coughs and 'ums' and 'maybes' and 'sort ofs' are all included," she says. The results is a more complete picture of the interview she can share with her editor and fact-checker, minus the off-the-record portions, which are not transcribed. ("Nobody should hear that -- not my editors, and not transcribers, certainly.")

Once transcription is complete, DePaulo enters what she calls "the pain cave" -- "the point between transcribing and typing your notes, and thinking about where you're going to begin, and trying out leads."

"The pain cave" can last for days, or even weeks, as DePaulo scours her notes and neglects to do the dishes or return emails. She doesn't outline, preferring to inserts asterisks into her transcripts denoting quotes and facts she wants to see in the final piece. "When I'm done with the story, before I hand it in, I go through it again -- searching for the stars -- to make sure everything I found while transcribing was included."

Her stay in "the pain cave" continues until she hits upon the first few sentences of her lede. "Once I'm at the first line break and the next sentence, I'm fine, and then that sentence pours out of me," she says. "The important thing is getting the tone from the start. Every writer has their own voice, but what you want to do with the tone is get the voice of the subject. Then, I'm out of 'the pain cave' and into 'the semi-pain cave' of actual writing."

Tom Junod

"Whenever I re-read the beginning of The John McPhee Reader, and read about his extensive organization using index cards, I wish I was that kind of journalist," says Junod, "as it would save me so many problems."

His typical approach to a first draft is to ignore the notes entirely, and write from pure memory, instead. (On a side note, this approach is also endorsed by Calvin Trillin.) "I tend to write from memory, and if I remember it, it's probably good, and probably worth writing about." This draft, written without any recourse to notes, "begins to function as a sort of outline. But then, there are riches in [my] notes that I did forget, so I go back and find them, which makes things more complicated."

"I wind up writing more drafts than I probably should," he concedes. In the case of "The Loved Ones," "I wrote a beginning that was an overture -- my own parents are elderly, and I started the story writing about them. I got halfway through the piece and ran completely out of gas, as right after I wrote about the personal stuff, I had this section on New Orleans lawyers, and after that, it seemed to dwindle down to obligation, or boredom, or nothing."

On his second attempt, he assembled the interviews from his New Orleans visit and resolved "to tell their stories from those voices, assembling it like a documentary filmmaker would." He handed that draft into Esquire editor-in-chief David Granger, who asked for a revised version that would guide the reader through the piece. "Now, I had a second draft which functioned as my outline, so I used the story as a road map for leading the reader from voice to voice. It's an intuitive, experimental process of trial and error. Because of that, I wind up writing too many drafts.

He does report and record extensively: "I have notebook upon notebook, and sometimes tapes, but I generally write from memory," Junod says. "When you finish the reporting with a memory of what you have seen, you're able to tell it in ways that entertain people, and completely attract people, and tell it as a story. What I try to do is maintain that force while writing." Not a minor point, "A lot of my working method is a function of me hating transcription," he adds.

Gary Smith

"I don't outline either," says Smith. "After I get back with all my notes, I'll start making categories that fit for that particular story, and just start typing everything from the notepads into it. It offers me more familiarity with the material, places things into boxes for when the writing begins."

Some stories may produce more than 100 typewritten pages, filed under 10 to 16 categories. "Sometimes one could be something as mundane as 'childhood.' Sometimes it's a little more psychologically significant. Sometimes it's chronological, or a section of a person's life. Sometimes it's a critical theme."

This process can last as long as three weeks, generating new questions that Smith jots down for later interviews. The emergence of a critical scene could mean, "I need to call everyone who's remotely close to this, to add flesh and blood to the notes." This can take another week, according to Smith.

"All along, stuff is starting to crystallize more and more on what the main theme is here," he says. "What do you want to say and what can you say besides the details of this person's life? How can you show it, and not just say it? What do you want to say with this piece? That question can lead you to some ideas of how the layering of the story works."

"I don't think I ever feel close to an outline," he continues. "You get a feel for how you want it to go. You want to set up that central question, sometimes blatantly, sometimes fairly early." It also helps with establishing the correct point of view -- "It could be setting up camp a thousand miles away, or it could be right inside the gut of somebody. Obviously, different stories have different ways of doing it."

The entire process typically consists of a week or two of research, followed by a week or two weeks in the field, interviewing. Then comes a month of transcribing notes and making follow-up calls, followed by another month of writing. "If you get it right the first time, that's it. It can be anywhere from two to three months for a piece, and sometimes even longer."

On the subject of outlines, he says, "I've had outlines with very general stuff, but never the details. I know that people writing features in college are always writing outlines, but I don't know where the outline disappeared along the line for me. I wish I had a good answer why I don't."

Greg Lindsay is a freelancer writer.