Get That Cool Job: freelance writer

Joseph Bien-Kahn recently hit a literary milestone: his one-year anniversary as a freelancer. Within the past year, the Oakland-based writer rode the Baja 1000, went behind the scenes with a bunch of wrestlers, and got slapped in the face by a Thai couple for body modification-purposes—all in the name of journalism. 

“The biggest perk of journalism is that you get to learn about something, or do something, and get paid for it,” says Bien-Kahn of these odd, fringe stories that are his forte. “The work becomes worth it—even though it’s tough, it’s a lot of rejection, and it’s not much pay—because you get to see these parts of the world as you learn.”

Bien-Kahn now has a steady gig with Vice, but he admits to having a shaky freelance career at the beginning.

“I always wanted to write, but I wasn’t sure exactly how,” he says. “There isn’t a good guidebook for how to become a journalist without grad school.”

Many pitches later with not-so-much luck, a stumped Bien-Kahn reached out to a friend in New York for tips, one of the most helpful being: “Make sure it’s the first pitch in the editor’s inbox.”

“I’m out on the West Coast, so I started waking up at 5 a.m. to pitch, so it could be there at 8,” he explains.

So how can you tell when a story is worth pitching?

Taffy Brodesser-Akner, who contributes to many publications including GQ and the New York Times Magazine, says pay attention to how you feel.

According to Brodesser-Akner, “We all have a mechanism that goes huh­—like ‘Huh, that’s interesting.’ Writers have many jobs. One of the jobs is to learn how to listen for the ‘huh’ and know that’s your story.”

As an example, she cites her story about The Bachelor—a story no one had thought to write a big, reported feature on previously—and how that show has played out in culture.

Brodesser-Akner is reminded of something every kid is taught in school: that each person is unique, and no two people think and behave in the same way. Thanks to freelancing, Brodesser-Akner discovered that this lesson isn’t exactly true. And that just might be the key to good storytelling.

“What I learned from having ideas, and putting them out in the world, and receiving feedback from the world is that we’re actually at our core the same,” she says. “The same things make us laugh. The same things make us cry. My reactions to things are legitimate.”

What Devin Gordon, the Senior Articles Editor at GQ, looks for in a freelancer is “Someone who has an original sense of story and an ability to write an amazing sentence.”

Gordon, Brodesser-Akner’s editor, says that “There are a lot of good stories out there, but only a few special ones, and Taffy is good at telling the difference. She is breathtakingly funny. She has a very, very specific voice that I think you can tell the moment you’re reading it. It’s not enough to be good. You have to be singular.”

Brodesser-Akner only began freelancing five years ago, after she had been home with her oldest son for a year after he was born, realizing it was necessary financially to go back to work.

“I started writing personal essays because I was home with the baby,” she says. “I started doing it kind of knowing my life depended on it. I knew if I didn’t do it well and quickly, I’d have to go back to the office.”

Brodesser-Akner recalls advice she once received from Rob Brunner, the senior editor at Fast Company: “A freelancer should always be good, nice, and on time. But if you’re any two of those, you’ll always work.”

Rae Alexandra has been freelancing for the past 13 years. She has written for many music-based publications and websites, such as Kerrang!,, Rock Sound, and—“which is hilarious,” she says, “given my years covering nothing but punk and hardcore bands.”

For Alexandra, “Music is the constant, but I’ll also go where the paycheck is.” She now writes mostly for SF Weekly, as well as the Village Voice and, plus she also works with two authors: one whose focus is on holistic health and the other who is a neurologist writing a book about Alzheimer’s.

For writers testing the freelance water, Alexandra clearly practices what she preaches: “be on the lookout for work constantly,” she says. “My job at came about because of a chance meeting with the editor in the ladies room of a dive bar. You never know!”

Or, as absurd as it might sound, peep Craigslist. “Whenever I think my bank balance is in jeopardy, I hit up Craigslist,” says Alexandra. “There are a surprising number of good writing gigs on there. You just have to sift through the crap to find them.”

It’s not just locking down gigs that defines a good freelancer. Alexandra stresses that “consistency, courtesy, and never, ever missing a deadline” are must-have qualities.

When asked what she has learned about herself from freelancing, Alexandra says, “I’ve learned that freedom and flexibility is more important to me than a steady paycheck and benefits.”

So now, Alexandra doesn’t always have to deal with mornings and can sleep in. Bien-Kahn isn’t totally chained to his computer—he drives around the Bay as a Lyft driver part-time. And Brodesser-Akner?

“Today, I’m going to take my kids for ice cream at about 2 o’clock,” she says. “I always knew I’d want to take them for ice cream at 2 o’clock and hear about their day.”

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