How To Make It: 10 Rules For Success From Freelance Writers

Image via Complex Original

Phoebe Lovatt

Editor of Anywhere-Anywhere, Freelance Writer

Has Written For: POP, Harper's BAZAAR, Drapers, Dazed & Confused, Complex, Time Out London, FHM, High Snobiety

Rule: Get out there.

"Being a freelance writer is an incredibly privileged occupation in many senses, not least because you only need a laptop and Internet connection to work anywhere in the world. I'm not saying that you should book a one-way ticket to Tanzania to be a successful writer, but it's definitely a good idea to get out into the world rather than sitting on the sofa in your sweatpants all day (we all do it). Exploring will freshen your perspective, renew your focus and—most crucially—enable you to discover the stories that no one else has."

Favorite Pieces and Projects:

Anywhere-Anywhere (My personal food and travel site)

Paris Haute Couture Reports (Drapers)

"Drifting in LA" (Complex)

Website / @PhoebeLovatt

Shea Serrano

Freelance Writer

Has Written For: Grantland, XXL, The Source, Village Voice, LA Weekly, Houston Press, Four Pins, The Basketball Jones, SLAM, Filter, URB

Rule: Work for (and with) and search out (and attempt to befriend) people who are smarter than you.

"If every so often you don't read something that makes you think, 'Jesus Christ, this is amazing, and everything I've ever written is absolutely the worst in comparison,' then you need to keep better e-company. I've been fortunate enough to write for some positively brilliant people—Margaret Downing, Chris Gray, Ben Westhoff, Mark Lisanti, Rob Harvilla, and Lawrence Schlossman to name a few. It's important to be near that; good begets good, and all that."

Favorite Pieces and Projects:

"Drake Was Whispering Encouragement in My Ear While I Was Having Sex" (LA Weekly)

"Here Are the Songs They Play at a Middle School Dance" (LA Weekly)

Rap Coloring Book (A jumbo coloring and rap activity Tumblr I launched with Bun B last month)

Website / @SheaSerrano

Patrik Sandberg

Senior Editor at V Magazine, Editor-At-Large at DIS Magazine

Has Written For: V, VMAN, Dazed & Confused, The Last Magazine, Anthem, Flaunt, and T Magazine/New York Times Moment Blog

Rule: Decide.

"As an editor—and a perennially impatient person—I cannot emboss the importance of decisiveness enough. Everybody likes to be astonished, hypnotized, moved, and entertained. Nobody likes their time to be wasted. Find the story that needs to be told and tell it—don’t wait for somebody else to do it. If you want to see something, create it yourself. Once you’ve decided, everything else falls into place.

Is that obvious? Don’t answer that."

Favorite Pieces and Projects:

IRL (I wrote a short film called IRL, Coming Soon)

Interview with Damien Echols (VMAN)

Website / @patriksandberg

Photo by Sandy Kim

Mary H.K. Choi

Freelance Writer and Editor

Has Written For: GQ, Wired, Allure, New York Times, MTV Style, Vertigo Comics, Marvel Comics  

Rule: Don't fetishize your output.

"You always feel like a hack and a fraud when you're writing. It's just how it goes. I'm a big believer in puking out all your thoughts in a single sitting and getting some version of the work down, because the alternative just prolongs the agony. The first draft is hideous and ajskdlkdfksjdfslfjk, but it's just a map for where the big blocks go. I'll always find my real thesis dicking around in the fourth graph, and I figure out my ending about halfway in."

Favorite Pieces and Projects:

"Overworked, Overwhelmed, Overscheduled? Work More" (Wired)

"Take It from a Lady: How to Take Home a Lady" (GQ)

"Inside New York's Last Sensory Deprivation Tank" (The Awl)

@choitotheworld

Photo by Estevan Oriol

Julianne Escobedo Shepherd

Freelance Writer and Editor

Has Written For: SPIN, Rolling Stone, New York Times, XXL, MTV, VIBE, Pitchfork, Salon, Interview, The Fader

Rule: Find your voice.

"This can be as simple as listening to yourself and writing down exactly what you feel—so often the writer's tendency, particularly in magazine/online journalism, is to fall back on what's worked before, to structure pieces like they've seen them written through the years. But if you're trying to be the 2013 Gay Talese or Joan Didion, it's important to be true to your impressions, to be honest with yourself. Don't mimic anyone's style, focus on sharpening your own. It will distinguish your writing, and you will also effectively clear the readers' bullshit-o-meter."

Favorite Pieces and Projects:

"Frank Ocean Has a Cold" (SPIN)

"UK Label Night Slugs, Defining a Sound Without a Name" (MTV Hive)

Waka Flocka Cover Story (SPIN)

Website / @jawnita

Kyle Chayka

Senior Editor at Hyperallergic, Freelance Writer

Has Written For: Hyperallergic, Animal New York, Creators Project, ARTINFO, LA Weekly, Modern Painters, ARTnews, Kill Screen, Bygone Bureau

Rule: Pitch like a motherfucker.

"You won't get it if you never ask. Pitching, or proposing stories you want to write, is basically the job of any freelance writer—you need to have ideas, a lot of them, and know how to present them well. Even if you know all the right publications and editors, you need to spend time honing your story ideas, figuring out what your story style is, and learning how to present it in a compelling way. Keep a list in your notebook, keep it on your iPhone, keep it in your head—just keep thinking."

Favorite Pieces and Projects:

"A Short History of Death on the New York City Subway" (Animal New York)

"eMPty3" (Bygone Bureau)

"Yoshi’s Fauvist Island" (Kill Screen)

Website / @chaykak

Joshua M. Bernstein

Author and Freelance Food, Drink, and Travel Journalist

Has Written For: Details, Saveur, New York, New York Times, Time Out New York, New York Daily News, New York Post, Gourmet.com

Rule: Be prepared to face continuous rejection and failure.

"I spent years and years pitching magazines, newspapers, and websites, only to receive 'no' after 'no' after 'no'—or no response at all, which is even more heartbreaking. But you know what? All it took was a single 'yes' for me to forget all those failures. Too often, people take these failures personally and give up. Instead, I looked at a 'no' response as another opportunity to find a way for an editor to say 'yes.' One success will sustain you through months and months of failures. And one more note: Always, always value your work. No matter how small the assignment, always ask to get paid."

Favorite Pieces and Projects:

Brewed Awakening: Behind the Beers and Brewers Leading the World's Craft Brewing Revolution (My book)

"Will Bike for Beer" (Imbibe)

"Captain of Industry" (ReadyMade)

"Indigenous Industry: KelSo of Brooklyn" (Edible Brooklyn)

Website / @joshmbernstein

Clinton Yates

Local News Editor at Washington Post Express, Columnist at The Root DC

Rule: If you don't want to read it, nobody else does either.

"If you're trying too hard to write for an audience, everyone will be able to tell if you're faking it. You don't have to be the smartest or wittiest, but if you're being dishonest about your interest, it's obvious. Write what makes sense to you. If that doesn't work, re-evaluate yourself or your audience. Or both."

Favorite Pieces and Projects:

The 3 Wise Men Show (A podcast I co-host)

"good kid, m.A.A.d city: Instant Masterpiece" (Washington Post)

"Famous 5: Clinton Yates" (Interview)

Website / @clintonyates

Paul Boutin

Freelance Writer

Has Written For: New York Times, Wall Street Journal, Wired, Slate, Valleywag, AdWeek, VentureBeat, The Industry Standard, Reader's Digest, MIT Technology Review, Engadget, The New Republic, MSNBC, Salon, Outside, Cargo, Business 2.0, InfoWorld, PC World, Independent Film & Video Monthly, The Content Strategist, California Legal Secretary, TechWeb, Samsung Beacon, BusinessWeek, occasional ghostwriter, and involuntary Huffington Post contributor

Rule: Get published as widely as possible.

"My best gigs don't come from networking or self-promotion. They come from editors who have read something I wrote elsewhere and want more of it for themselves. The new writers I mentor often spend too much time at social events, or on social media, when they should be cranking out a few more underpaid freelance articles or blog posts instead. Editors look for writers by reading other publications, not by going to parties or trolling Twitter. Write for as many publications as you can, to spread your clips as widely as possible. Say yes to assignments you're iffy about. Embrace publications that your hipster friends ridicule—I learned a lot writing for Reader's Digest. In a few years, when you're established and have a prestigious gig, then it will make sense to be picky."

Favorite Pieces and Projects:

"Video Mad Libs With the Right Software" (New York Times)

"Read My Mail, Please" (Slate)

"The Law of Online Sharing" (Technology Review)

Website / @paulboutin

Katie Baker

Staff Writer at Grantland

Has Written For: Grantland, New York Times Magazine, Deadspin, New York, Gawker, Wall Street Journal

Rule: Read.

"Read at least one thing every day that isn't yours. If you spend your days dissecting music, read about the latest business scandal. If you're a beat writer for the Bulls, read romance novels. Read the way you did as a child: Don't obsess; don't dismissively compare it to your own work or despair that it was written by another—just read it and move on. And ideally, when you're finished with one thing, read two or ten more things after that."

Favorite Pieces and Projects:

"Gridiron Girls" (New York Times)

"The Confessions Of A Former Adolescent Puck Tease" (Deadspin)

"Coldhearted: Los Angeles, at Last!" (Grantland)

Website / @katiebakes