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The Freelance Whisperer Explains How He Built a Full-Time, Jet-Setting Career

By Anne Miller July 12th, 2018

David Hochman is a freelancer’s freelancer. He’s penned features for The Times (both New York and Los Angeles), Forbes, and GQ. He’s written about flying (nearly) around the world via private jet—a jaunt that ran $77,000 at the time and landed him in notoriously closed-off Bhutan, among other places. He’s traveled to one of the most remote corners of Africa to learn about the ancient and endangered tribes who cling to existence there. He’s interviewed George Carlin, Ezra Klein, and a pre-White House Donald Trump for Playboy.

And when he’s not snagging bylines, Hochman, who calls himself the Freelance Whisperer, runs Upod Academy. Upod—an acronym for his mantra: Under-promise, over-deliver—hosts small weekend conferences where writers hear from top editors and take part in private coaching sessions.

Talking to Hochman, it’s clear that making such memorable copy comes from a painstaking dedication to craft. The glory of swanning around the globe on someone else’s dime comes with hours dedicated to taking copious notes and recordings while on the road, and months of preparation and communication with editors to earn those assignments.

“This is my superpower,” he said. “I wish it was something else, like managing a hedge fund, but this is my superpower—getting travel editors to send me places.”

Superpower it may be, but that doesn’t mean other freelancers can’t learn from his experience. On the phone from his home in Los Angeles, Hochman shared some of the insights that have helped him land the kind of gigs that make for one hell of a career.

Set your focus daily

“Even if that means timing it out, like putting it on a calendar, where you say from 8 a.m. to 9 a.m. I’m going to exercise. From 9:30 to noon, I’m going to look for ideas and pitch these publications,” Hochman said. “Set your agenda in a way that you can be held accountable.”

Serve the publication first

“It’s about pitching smart—in other words, after you’ve done the research—and not taking no for an answer,” he said. “Study the hell out of that publication, know what the language is, know who the players are.”

Diversify your portfolio of clients

Make a list of who’s paying writers and creative people for the work they need to do, then figure out how you can serve their needs. That may mean mixing some content marketing into your journalism work. “I’ll go to brands or try to work for agencies or do other kinds of work that’s going to feel like it’s worth my time.”

Know your selling points

“Journalists know what journalists do,” Hochman said. But companies focused on branding, for example, may not fully grasp what a seasoned reporter can bring to the table.

“I’m someone who can help tell your story, and I get the sense that your story isn’t being told as well as it can be,” he added. “As journalists, we can listen deeply and connect the dots on data and different strings of ideas that can help our clients make more money.”

Stop waiting for editors to come to you

“If you want to be writing for the New Yorker one day, that day is now,” he said. “The playing field is much more level.”

If you’ve done the legwork, there’s no reason to not pitch those reach publications. “You need to be daring enough so that when the time comes and you’ve done the research and you have a name [of an editor], you can take your thumb and slam it against the ‘return’ key.” (Hochman calls these moments thumb slams.)

If Hochman is any example, the first step in building your freelance career is to pursue great stories tenaciously. Start with your goals and then find the editors and brands who can help you achieve them. Put in the work, craft stories that make them look good, and soon they’ll be calling you. Just be sure to have your passport ready.

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