Dear Byron, Sincerely Tom Wolfe

My favorite writers block-breaking, inner critic-silencing, creativity-producing methodology is something I call “Dear Byron, Sincerely Tom Wolfe.”

In 1963, an impending deadline coupled with an editor’s desperate suggestion inadvertently created a new style of journalism. Tom Wolfe, working for the New York Herald Tribune, found himself forced to freelance when a newspaper strike hit. He convinced Esquire magazine to fund an article about California’s custom car culture, and they spared no expense, putting him up at the Beverly Wilshire Hotel where he racked up nearly $6,000 in expenses over the course of a month.

But when Wolfe returned to New York, he found himself completely blocked. The pressure was immense. In addition to the hotel, Esquire had already invested $10,000 in color plates for the article. Byron Dobell, Esquire’s managing editor, suggested that Wolfe simply type up his notes so that a “competent writer” could shape them into a proper article. He needed something to take to print.

Feeling guilty about the magazine’s investment, Wolfe sat down to type up his notes. The memo started as you might have guessed, “Dear Byron,” but the ending didn’t come until the wee hours of the morning. Wolfe had become unblocked. He wrote in a fury, nonstop through the night, and composed a 48-page memo describing what he had witnessed at the North Hollywood auto show. When Dobell received these pages, he recognized their brilliance immediately. He simply removed “Dear Byron” from the top and the “Sincerely, Tom Wolfe” from the ending, and published the memo exactly as written. There Goes (Varoom! Varoom!) That Kandy-Kolored (Thphhhhhh!) Tangerine-Flake Streamline Baby (Rahghhh!) Around the Bend (Brummmmmmmmmmmmmmm)…was a sensation.

Wolfe later reflected that his breakthrough came precisely because he wasn’t writing for a large audience, he was writing to a friend. People often freeze up when writing for publication because they worry about others’ opinions, he observed, but are more natural, more authentic, when composing letters, because they’re less self-conscious.

This accidental technique launched New Journalism, a movement Wolfe helped define alongside Joan Didion, Truman Capote, and Hunter S. Thompson, changing American writing through their vivid description of scenes and playful language, capturing the experience, not just the facts.

Listen to Wolfe tell it…

The Hard Part Is Already Done

Why do I like the “Dear Byron, Sincerely Tom Wolfe” technique so much?

It’s not unlike all of those bedtime stories you grew up with. How do they start? Once upon a time. And how do they end? Come on, you already know. Happily ever after, right?

The ghost stories all start on a dark and stormy night and if you tell it well, they end with a horrifying scream.

The start and the finish, those are the hardest parts sometimes. With “Dear Byron,” the start is formed, and with “Sincerely, Tom Wolfe,” so is the finish.

Now it’s just those middle details that need to be worked out.

It lowers the bar. After all, it’s just a letter, just an email, just a list of notes. No pressure.

Editor and author Shawn Coyne will often tell the writers he works with to assume a different perspective, a different character. Write the scene from the perspective of the dog if you need to. And that changing of perspective can be all you need to shake free from your mental constipation.

His longtime collaborator Steven Pressfield has a terrific prompt as well. He’ll start a new piece by writing “A bad version of this looks like….” at the top of the page.

Only one way to go from there.

Squashing Inhibitions

Tim Ferriss said, “My quota is two crappy pages per day. I keep it really low so I’m not so intimidated that I never get started.”

Breaking free from intimidation is a key component in making more work, but sometimes, if you go a week, maybe two, and all you’ve got is a pile of crumpled up notes, it can feel like you’re wasting your life. Crappy pages don’t feel like progress so creatives don’t write them, they freeze up, they stop their practice, and they snag a job at a local diner, telling random customers about their screenplay.

Not a writer? Okay, so you’ll tell them about your band, or your audition, or your sketchbook.

When Ferriss was writing The 4-Hour Workweek, he couldn’t find his voice.

He said, “I threw away four, five chapters and had two glasses of wine and sat down and said I’m going to write this like I would write an email to my best friends. That’s how it started. That’s how I found my voice.”

Instead of trying to write a best seller, he just wrote something helpful to someone specific. He made it personal. Just like Wolfe, he wasn’t writing for a large audience, he was writing to a friend.

All of these tricks and tactics are attempting to do the same thing: quiet your inner bully.

Advertising tycoon David Ogilvy was absolutely terrified of producing something lousy. He wrote, “This causes me to throw away the first 20 attempts. If all else fails, I drink half a bottle of rum and play a Handel oratorio on the gramophone. This generally produces an uncontrollable gush of copy. Next morning I get up early and edit the gush.”

I’m not going to advocate for drinking and writing, but it’s worked for many an author. The ultimate silencer of inhibitions. The prescription may vary, two glasses of wine, half a bottle of rum, to each their own. But you need to do something that will allow you to “gush.”

Just make sure to get up early the next day for edits.