How 5 Famous Freelancers Got Their First Big Breaks

By Michael Tunney November 3rd, 2014

When you’re caught in the grind of churning out work to make a living, it’s easy for us freelancers to lose sight of big-picture goals. As an editor and media strategist for writers, I’m also working toward being a published author myself one day.

Sometimes, it can feel like a big creative break is never going to come. But everyone from Hollywood screenwriters to bestselling novelists has gone through the same career peaks and troughs. What got them through uncertain times is usually a combination of grit, hustle, persistence, and most importantly, opportunity.

Take a look at how these five famous freelances got started, and bring some of their hard-won wisdom to your own career.

1. Upton Sinclair

Known as one of the great muckrakers of the 20th century, Upton Sinclair began his career as a freelancer at 14 years old, writing jokes and dime novels to pay for his tuition at the City College of New York. During the height of his time freelancing, Sinclair churned out 8,000 words of pulp fiction per day with the help of stenographers.

14 years later, he published his first successful novel, The Jungle, at 28. He intended for The Jungle to expose the poor working conditions affecting employees in the meatpacking industry, but instead, readers were fixated on the poor quality of meat the plants produced.

As Sinclair said about the novel’s reception: “I aimed at the public’s heart, and by accident I hit it in the stomach.”

2 . Hunter S. Thompson

Long before he became famous for his Gonzo journalism, Hunter S. Thompson started his writing career as a copyboy for Time, typing Ernest Hemingway and F. Scott Fitzgerald novels at night to learn their writing styles.

After unsuccessful freelancing stints in Middletown, New York, and San Juan, Puerto Rico, Thompson published his first feature in Rogue Magazine. He caught his first big break in 1965 when Los Angeles author and editor Carey McWilliams hired him to write a story on the Hells Angel’s motorcycle gang for The Nation. Thompson spent a year with gang in preparation for what would become his breakout book Hell’s Angels. After the book was released, Thompson began writing features in major magazine like The New York Times Magazine, Esquire, and Harper’s.

He said of the book’s success: “To be able to earn a living as a freelance writer in this country is damned hard; there are very few people who can do that. Hell’s Angels all of a sudden proved to me that, Holy Jesus, maybe I can do this.”

3. Cameron Crowe

Thanks to his semi-autobiographical film Almost Famous, some of us already know writer-director Cameron Crowe was a wunderkind with the pen. At thirteen years old he was writing freelance music reviews for The San Diego Door. He graduated early from high school at age 15, and on a trip to Los Angeles, he met an editor of Rolling Stone, who hired him to freelance for the magazine.

Crowe would go on to interview artists like Bob Dylan, Led Zeppelin, and Eric Clapton for Rolling Stone before writing his first novel, Fast Times at Ridgement High, at 22.

4. Chase Jarvis

Chase Jarvis planned to apply medical school after college, but right before he graduated, his grandfather, who was a photographer, died, and left Chase one of his cameras.

After graduating, Jarvis and his girlfriend—now wife—went on a trip through Europe, camera in tow, and he fell in love with photography. When the pair returned they made another move to Steamboat Springs, Colorado, where Jarvis began photographing professional skiers and snowboarders. Eventually, he was able to license his first photos for $500 and a pair of skis. His first big score came when REI licensed photos that gave him enough money to open up his own shop, Chase Jarvis Photography.

Jarvis has now gone on to produce produce photographs for companies like Nike, Apple, and Red Bull, and he’s also the CEO of Creative Live, an online education company.

5. Aline Brosh McKenna

Now a famous screenwriter in Los Angeles, Aline Brosh McKenna first tried to break in as a freelance writer for women’s magazines in New York after graduating from Harvard.

While in New York, McKenna took a 6-week screenwriting course and was able to get an agent based off a script she wrote for the class. Soon after, she moved to Los Angeles and waited eight years until her first film—Three to Tango—was made in 1999. Since then, she has gone on to write scripts for movies such as The Devil Wears Prada and 27 Dresses. McKenna implores aspiring writers to keep calling when they are trying to get hired for a writing job; to her, persistence is key.

Image by YuryZap
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