Tom Wolfe died earlier this year. He was one of the originators of the so-called New Journalism of the 1960s and 70s (so, yes, he inspired a lot of really bad imitations, but I don't see how we can blame him for that). His novel The Bonfire of the Vanities was an important chronicle of the excesses of Manhattan's financial class in the 1980s. Also, he was exceedingly good at putting sentences together when he had a mind to.
My first exposure to Tom Wolfe was an article, originally published in Esquire, called "The Last American Hero Is Junior Johnson. Yes!" By telling the story of NASCAR driver Junior Johnson, the piece traces the origins of stock-car racing, which grew out of moonshine-running in much the same way that rodeo grew out of cowboying. It's a pretty fascinating read; I commend it to you.
Tom Wolfe was famous for his dapper clothes. But when he went to the wilds of North Carolina to write the Junior Johnson story, he decided to dress down, the better to fit in with the locals. He wore a green tweed suit and a black knit tie to various garages and diners and moonshine operations around North Wilkesboro until Junior Johnson pulled him aside and asked him to reconsider his wardrobe. Junior had grown tired of answering questions about the "little green man" who was following him around.
According to Tom Wolfe, that was the last time he ever tried to fit in with his subjects while doing research for a story. At some point, in fact, he started wearing a white linen suit everywhere he went. Since he seemed to be terrible at fitting in anyway, this was probably a good decision. But more importantly, he found it helpful to come into a situation as "a man from Mars" who didn't even pretend to know what was going on. It gave him permission to ask dumb questions. So if you're a journalist or otherwise have reason to ask questions for your writing, there's a pro-tip you can try.
But there's another thing I learned from Tom Wolfe that has broader application for writers. One of his first big articles for Esquire was "The Kandy-Kolored Tangerine-Flake Streamline Baby," about the custom-car culture of Southern California. After spending four weeks at an expensive hotel in Los Angeles, burning through lots of his publisher's money, and taking pages and pages of notes, he was flattened by a bad case of writer's block. He had piles of ideas and facts, and some great turns of phrase, but he just couldn't seem to find the place to start. After weeks of wrestling around with it, he finally gave up. He told his editor, Byron Dobell, that he needed to drop the assignment. According to an interview Wolfe did with Terry Gross, Dobell told him just to hand over his notes so they could find a "competent writer" to make an article out of them.
So at about 9:00 that night, Tom Wolfe started writing a memo to his editor:
The first place I saw customized cars was at a teen fair in North Hollywood, California...
He wrote through the night, producing fifty type-written pages. He sent them over toEsquiremagazine in the morning. Later that day, Byron Dobell called to say that he was just going to remove the "Dear Byron," and run the whole memo as the article.
As Tom Wolfe told Terry Gross,
By writing what I thought was a memorandum to a single individual who was about my own age, I had liberated myself from all the fears and all the constraints that you feel when you're writing something as formal as a magazine article for a national audience.
Most of us aren't writing magazine articles for national audiences. Nevertheless, there are all sorts of fears and constraints that can keep a writer from writing. For reasons I don't entirely understand, many of the blocks go away when you write directly to or for a real person. Tom Wolfe said it can work for anybody once.
I can attest that it has worked for me at least once. When I was writing (or, rather, failing to write)The Terrible Speed of Mercy, a "spiritual biography" of Flannery O'Connor, I spent hours and hours of desk time thinking of people who were more qualified for the task than I, then wondering what they would think of my book if they read it. I also spent more hours than I would care to count wondering what Flannery O'Connor would think.
At the time I was in a lunchtime bowling league with Andy Osenga (Andy, by the way, now has a podcast called The Pivot that you absolutely have to listen to). He asked what kind of book I was writing, and I told him it was a book for intelligent, well-read Christians who had heard they were supposed to like Flannery O'Connor but could never quite managed to do so. Andy said that described him exactly.
So when I went back to my desk that afternoon, instead of wondering what the "real" Flannery O'Connor scholars would think about my book, or, worse, fearing that they would never think about my book one way or another, I wrote some things I thought Andy Osenga ought to know about Flannery O'Connor. And the next morning I wrote some more things for Andy. And I kept on that way until I had written a whole book.
I don't know whether Andy ever read it or not.