Skip to main content

An Insider's Guide: Odd Jobs of the Masters

The history of writing is full of authors striving to succeed in a hyper-competitive publishing world, contending with agents, editors, publishers, critics, and sometimes the greatest challenge of all—overnight success.


David Comfort’s new book, An Insider’s Guide to Publishing, looks at every facet of this journey, and reveals an extraordinary amount of literary hijinks, accomplishments, missteps, and tragedies from some of the greatest writers, editors, and publishers of all time.

Here, David walks us through some of the bizarre and mundane occupations the literary greats held before (and during) their writing peak. Enjoy!

- - -

Odd Jobs of the Masters

by David Comfort

“The best job that was ever offered to me was to become the landlord of a brothel. It’s the perfect milieu for an artist.” - William Faulkner

“Medicine is my lawful wife, and literature is my mistress.” - Anton Chekhov

We have the nightmare jobs of the greats to thank for many masterpieces: Dickens’ stretch in the blacking factory for David Copperfield; marooned seaman Melville’s vacation with the cannibals for Typee; Heller’s tour with the 488th Bomb Squadron for Catch-22; Kesey’s asylum orderly gig for One Flew Over theCuckoo’s Nest, and many more.

A fortunate few were spared employment. The Marquis de Sade, Count Tolstoy, Thackeray, and Virginia Woolf were trust funders. Others found patrons or patronesses. Others became kept lovers. And the most practical—Proust, Flaubert, Lampedusa, etc.—stayed home with their moms.

But the 99-percenters had to do it the hard way: Find the color of their parachute as working stiffs.

Kipling, Twain, Hemingway, Vonnegut, Heller, Wolfe, and many others did newspaper work. As journalists, they learned indispensable skills. The who, when, where, what of a story. How to be clear. How to be brief. How to meet a deadline.

Newspaper work has perks. After his coke-fueled Bright Lights, Big City, Jay McInerny now writes the Wall Street Journal wine column, a natural sequel to his Good Life. Originally, he fact-checked for TheNew Yorker. The job boosted his attention to detail, as well as the contacts necessary to become celebrated, at age twenty-nine, as a generation’s spokesman. The coveted position at The New Yorker has also proved a springboard for other novelists including William Gaddis, Susan Choi, Daniel Menaker, and Roger Hodge.

Other scribes apprenticed in the ad industry. Here they learned how to grab a consumer’s attention. At Ogilvy & Mather, Salman Rushdie wrote copy for Maxwell House coffee and Dove soap. Hemingway pitched for Ballantine Ale and Parker pens. Hart Crane did slogans for his father, the inventor of Lifesavers (though, later, when he jumped off a cruise ship, crying “Goodbye, everybody!” nobody threw him one). After briefly trying his hand at repairing Southern Pacific train roofs, Fitzgerald created signs for Manhattan streetcars. Then, graduating to laundry copy, he wrote “We keep you clean with Muscatine!”

“I was a failure—mediocre at advertising work and unable to get started as a writer,” he recalled. “I got roaring weeping drunk on my last penny and went home.” [1]

Others tried sales. Defoe sold woolens and wine; Faulkner, Lord & Taylor suits and ties; D.H. Lawrence surgical supplies. Thoreau hawked pencils and vegetables. Before teaching, Toole pushed a tamale cart. Before marrying a Vogue editor, Sinclair Lewis sold plots to former oyster pirate and gold prospector, Jack London. Richard Brautigan panhandled his early prose on street corners, as did Henry Miller, who dug graves on the side.

As unfit for sales as his colleagues, Vonnegut—after stacking and burning bodies as a Dresden POW—bankrupted his Saab Cape Cod dealership. Then he went from the frying pan into the fire. “Christ, I did book reviews—I did anything. It was $85 here, $110 there—I was like Molly Bloom: ‘Yes I will, yes I will, yes.’ Whatever anybody wanted done, I did it.”[2] Following, the success of Slaughterhouse-Five, he became a self-sufficient novelist and embarked on a “How to Get a Job Like Mine” national lecture tour.

Deciding that "Writing is the hardest way of earning a living with the possible exception of wrestling alligators," Saroyan sought refuge in the San Francisco Telegraph Company manager’s office. He took early retirement after Story’s check cleared for “The Daring Young Man on the Flying Trapeze” about a starving writer.

For many authors, the medical profession kept the wolf from the door and provided rich life, death, and triage material. Chekhov, Celine, and William Carlos Williams were doctors. Hemingway, Hammett, Maugham, MacLeish, and Cowley were EMTs, otherwise known as the World War I “Literary Ambulance Drivers.”

Zane Grey cut his teeth doing molar extractions with pliers in rural Ohio. He worked his way through dental school as a movie usher and minor league baseball player. After earning his degree, he filled cavities for twenty years, then retired on the proceeds of The Riders of the Purple Sage.

Working to expand their audience, many ran for public office: Hugo, Trollop, London, H.G. Wells, C.P. Snow, Yeats, Upton Sinclair, Gore Vidal, James Michener, Norman Mailer, Hunter Thompson, etc. Most lost. Speaking for the group, Trollop called his campaign for Parliament, “the most wretched fortnight of my manhood.” Learning his lesson at the ballot box, he invented the street-corner mailbox in anticipation of absentee filing.

Other scriveners tried to become self-made tycoons and inventors, but they fared no better. Balzac tanked his publishing company, then sank a Sardinian slag operation and a Ukrainian oak firewood concession. Twain’s own publishing house nearly bankrupted him. He tried to recoup with his Kaolatype printing machine, but this invention soon fizzled with the arrival of Linotype, leaving him the few dollars he’d made on his adjustable suspenders and baby bed clamps.

Twain’s contemporary, Lewis Carroll, had better luck with his own inventions: The Wonderland Postage-Stamp Case, the Nyctograph (a night-writing palm pilot tablet), a Scrabble prototype, a tricycle steering wheel, and double-sided tape.

Some in the service industry managed well. Before concentrating on the creative end of the business, Shakespeare valet parked horses outside the theater. Chekhov worked his way through med school catching and selling goldfinches. Amy Tan freelanced as a horoscope writer. Dashiel Hammet busted unions for the Pinkerton detective agency. William Borroughs exterminated pests in houses. And Raymond Carver mopped hospital floors.

Nor can we forget the adventurers and gunrunners (Conrad, Melville, Rimbaud); the post office SASE pushers (Faulkner, Bukowski, Richard Wright); or the day laborers who became tramps and rail-riding hobos (Faulkner, Steinbeck, Kerouac).

- - -

The list goes on and on as David Comfort explores this crazy, chaotic, and indispensible world of writing in An Insider’s Guide to Publishing with equal parts humor, wit, and the shocking truth—from the pros and cons of having an agent to handling the inevitable in-fighting among literary giants; from cashing in on the e-book gold rush to navigating the depths of absolute failure with your dignity (or handcuffs) intact. Take a look at An Insider’s Guide to Publishing for more amazing stories of the literary greats!

And what about yourself? What are the strangest jobs you've held while working on your literary masterpiece? Let us know below!

[1] Jeffrey Meyers, Scott Fitzgerald: A Biography (New York: HarperCollins, 2004)

[2]Kurt Vonnegut: The Last Interview: And Other Conversations. (Melville House, 2011)

Lisa Jewell | Writer's Digest Interview Quote

The WD Interview: Lisa Jewell

The New York Times-bestselling British author discusses creating thrilling plot twists and developing characters in her 19th novel, The Night She Disappeared, in this interview from the Jan/Feb 2022 issue of Writer's Digest.

5 Tips for Successfully Pitching Literary Agents in Person (That Worked for Me at the Writer’s Digest Annual Conference)

5 Tips for Successfully Pitching Literary Agents in Person (That Worked for Me at the Writer’s Digest Annual Conference)

Author Anat Deracine found her agent at Writer’s Digest Annual Conference. Now she’s sharing what she’s learned to help other writers become authors. Here are her 5 tips for successfully pitching literary agents in person.

Tips for Reading Poetry in Front of an Audience

8 Tips for Reading Your Poetry in Front of an Audience

Poet's Market editor and published poet Robert Lee Brewer shares eight tips for reading your poetry in front of an audience.

Plot Twist Story Prompts: Strength Lost

Plot Twist Story Prompts: Strength Lost

Every good story needs a nice (or not so nice) turn or two to keep it interesting. This week, let a character lose their powers.

Sharon Short | Point of View Quote 1

Managing Point of View: Mythbusting

In the first of this three-part series, novelist and WD columnist Sharon Short breaks down 7 of the most common myths about choosing which POV is right for your story.

Channel Your Inner Authorpreneur for Your Writing Labor of Love

Channel Your Inner Authorpreneur for Your Writing Labor of Love

As self-publishing continues to become an attractive and popular options for writers, it’s important to know what you’re getting into and to have the right expectations. Here, author and entrepreneur Tom Vaughan shares how to channel your inner “authorpreneur” to help your book find its readers.

Mark Kurlansky: On Coincidences Driving Memoir

Mark Kurlansky: On Coincidences Driving Memoir

Award-winning author, playwright, and journalist Mark Kurlansky discusses the experience of channeling Ernest Hemingway in his new memoir, The Importance of Not Being Ernest.

In-Between: Writer's Digest 2nd Annual Personal Essay Awards Winner

In-Between: Writer's Digest 2nd Annual Personal Essay Awards Winner

Congratulations to Alyssa Rickert, Grand Prize winner of the 2nd Annual Writer's Digest Personal Essay Awards. Here's her winning essay, "In Between."

Things To Consider When Writing About Ghosts and the Supernatural in Fiction

Things To Consider When Writing About Ghosts and the Supernatural in Fiction

From maintaining subtlety to visiting haunted places, author J. Fremont shares everything to consider when writing about ghosts and the supernatural in fiction.