My 10 Favorite Freelancer Stories of 2014

I’m cheating a little. Since we didn’t relaunch The Freelancer until late May, it hasn’t been a full year of publishing. Still, over the last seven months, we started to hit our editorial stride, mixing useful how-tos with deeper dives about what it’s really like to earn a living as freelancer.

To me, the most interesting part about covering the gig economy is how there’s no real news cycle. It’s not like sports or entertainment—our relevance comes from giving the reader that extra insight about an issue that’s probably evergreen. Below, you’ll find a round-up of our best, from the insightful to the playful. Regardless of the tone, the common thread that ties them all together is an appreciation for the freelance life.

Fiverr, BuckMeUp, and the Future of the $5 Freelance Economy (by Aubre Andrus): From day one, we’ve wanted to hold job marketplaces accountable. Here, Aubre gives a thorough account of how freelancers in various fields deal with services that offer as little as five dollars per project. I knew we had struck a nerve when someone at Fiverr sent me an email that read: “This is why journalists are a hated breed.” On behalf of Aubre, thanks for the compliment.

The Ultimate Guide to Dealing With Unresponsive Editors (by Laura Parker): Just as writers can be too sensitive, editors can be too aloof. Those two traits can make for some pretty dysfunctional relationships. Laura took on the touchy subject of how to communicate with distant editors and injected it with personal anecdotes and careful advice.

Tipping the Pitch: Advice from Today’s Top Newspaper and Magazine Editors (by Will Fenstermaker): We sometimes let veteran freelancers offer their perspectives on pitching. Their insights are important, but who better to give advice than the editors who make the final decision to work with you or not? Will spent a long time reporting and following up to make the advice as sharp as possible, despite some editors not wanting to open up. The result isn’t flashy, but the takeaways from editors who work at places like The Wall Street Journal and The New York Times Magazine can help writers on all levels.

Taylor Swift and 8 Other Celebrities Who Should Become Freelance Columnists (by Jordan Teicher): I had fun with this. Since I edit the site every day, I try to give the meaty stories to the freelance contributors, but when I saw Taylor Swift wrote an article for The Wall Street Journal, my mind immediately jumped to celebrities who should be freelancing. Yes, it’s goofy, but it also reminded me about the value of seeking writers with different voices, something all publications could do more frequently.

Journalism Has a Diversity Problem. How Can We Fix It? (by Gabe Rosenberg): Gabe interned for us during the summer, and he’s now the editor-in-chief of Wesleyan’s student newspaper. He’s going to run your favorite publication one day, and if you want to understand why, check out his absorbing take on how the journalism world can get its act together.

How to Work in an Office, According to Stock Photos (by Jillian Richardson): Jillian also interned for us this summer, and while I don’t expect her to run the Times (because she probably doesn’t want to), there’s a good chance she can become the next Tina Fey. Jillian found humor in the dullest of dulls: stock photography. This, her first piece, was so creative that it made me jealous I hadn’t thought of the idea first.

Ask a Freelancer: How Do You Write 20–30 Pieces Every Week? (by Nicole Dieker): Nicole’s Ask a Freelancer column was this year’s biggest success on The Freelancer. Readers really seemed to respond to her views on how to succeed as a freelancer, and this particular article was her most popular offering. My guess is people didn’t want to believe one freelancer could hustle to such a degree, but Nicole’s strongest skill as a columnist is her openness. I’d like to think readers trust her completely by this point. She even blogs about her exact income, which is something many writers—myself included—aren’t brave enough to do.

I’m a Traveler and a Writer, But I Have a Serious Problem With Travel Writing (by Dana Ter): While we may think of travel writing as some benign genre of beach essays and food reviews, it’s void of intelligent writing. As Dana puts it, “Traveling is supposed to break down barriers, whether they are cultural, linguistic, or gastronomical. Traveling is supposed to help make people more open-minded and aware, but a lot of travel writing has achieved quite the opposite.” This piece truly resonated with our audience.

Cold-Pitching a Story? The Secret Is in the Subject Line (Danielle Elliot): I always think of this piece as a companion to Laura Parker’s article on unresponsive editors. They’re not necessarily related, but to me, they’re the two strongest how-to articles we published. Danielle, an experienced reporter, takes something so simple—an email subject line—and explains why focusing on a handful of words can help freelancers get more work.

Lonely Planet’s 25-Year-Old CEO, the Reclusive Billionaire Who Hired Him, and the Writer Who Told His Story (by Charles Bethea): Writing about writing is hard. Some people get too generic; others ramble. But Charles, who penned the first behind-the-scenes look for our Writer Redux series, nailed the concept perfectly. He built on his outstanding original piece for Outside by recycling whatever was left on the cutting room floor and turning scraps of anecdotes into a primer for how a longform reported piece takes shape over many months.