How I Learned to Freelance Again

It was a Thursday when they summoned me and a dozen of my colleagues into the conference room at a startup news website in Washington, D.C. We were a band of young, eager, and good writers—and we’d just gotten our teeth kicked in by Facebook. The algorithm had decimated our organic web traffic, and our jobs were caught in the crossfire.

When they handed down the news we’d been let go, nobody was surprised. There were a lot of apologies, and a few people cried. I hung my head. But the writing had been on the wall for weeks. Facebook-dependent news outlets like ours had been purging staff.

Later, at a bar, my soon-to-be-ex-coworkers traded the same question: “What are you going to do next?” Some figured they’d go into marketing or PR. Others wanted to leave D.C. for the sunnier climate of Los Angeles. The only answer I had was that I’d keep writing.

In college and my early twenties, before landing a staff position, I’d freelanced here and there. For one brief, thrilling stretch I even lived in a shack on the Outer Banks and surfed daily, writing copy and penning articles at night. On my parents’ health insurance and without college loans, I could sustain myself on cheap booze and hamburgers.

A lot has changed. I now have rent on a D.C. row house. Eating, not to mention socializing or dating, isn’t cheap in our nation’s capitol. But D.C., for the penury it wrought, also honed in me a fine sense of networking. After being fired, I reached out to every writer I knew at a magazine or website in the swamp. I must have called a dozen people at The Washington Post alone. But after a few weeks of unanswered job applications, the guillotine of unemployment fell. I was on my ass.

So I was back to freelancing, back to being a constant presence in the inboxes of editors. But my game needed work. I scored a few freelance bylines during my tenure with my previous employer, but it was mostly side scribbling along the lines of breaking news contributions. And I only landed those because I’d worn down the editors. My freelance pitches weren’t exceptional, because I was comfortable in a staff writer role.

No such luxury existed now. It was time to buckle down.

Great(ish) expectations

I started by making a list of all the magazines and websites where I’d always craved a byline—Rolling Stone, Playboy, The New York Times Magazine, Vanity Fair—and the editors to whom I could pitch. The top magazines were mostly unresponsive. My emails seemed destined for black holes, and I learned almost immediately that I wasn’t going to hear back from these gatekeepers without changing my approach. Even with the pitches I was excited about—silence. Clearly I’d need to start farther down and work my way up.

As I began pitching to more realistic outlets—The Washingtonian, Vice, The New Republic—the responses trickled in. They were rejections but, even in a single sentence, the editors were always helpful. Their emails read like breadcrumbs leading toward a future article: “I love it, but it’s a bit too overarching. Get more specific” or “This is right for us, but not the right theme for this issue.” I never deleted these emails, but instead tagged them in a special file off my inbox—sort of a try-again-later Rolodex.

Re-learning to pitch

It seemed incongruous that after years as a staff writer I’d need to go back to the drawing board, but the truth was I’d never been strong at pitching, and I now depended on it for all of my income.

There was no lack of information on pitching techniques out there—quite the opposite in fact. I sifted through blog after blog about “5 Keys to the Perfect Pitch” until I’d amassed dozens of keys. (That’s right, there are more than five.)

A lot of the blog posts seemed to advocate for pitches that were basically a summary of an article. To me, that felt like a waste of time. There’s a reason that most of us don’t read books after we’ve peeked at the synopsis on the back—summaries are boring as hell.

Another common piece of advice reminded writers to insert their credentials into pitches. I get why, but that seemed like a rather old-school idea to me. Instead, I’ve opted for signing off with my Twitter handle. I’m definitely not Twitter famous, but I’m not famous for my bylines either. I decided that including my social information can let editors see a different part of my voice, review some of my work, and get in touch in a less formal setting.

Speaking of, I also figured out immediately that it helped to reach out over Twitter to editors. A pitch could get buried under email after a few hours, but Twitter offered a more direct line of communication, which elicited some timely responses.

Walking the beat

While freelancing in my early twenties, I was young and hungry, so I took whatever gigs I could, writing everything from copy for clothing brands to horoscopes. I didn’t have the luxury of finding a beat. As I grew into a staff position at a major news organization, I found my niche—politics—and was lucky enough to be able to pursue it. Every day, I read the best political writers in the business. I ate and drank with Hill staffers and other reporters who were writing about Washington.

When it became clear that I would have to rely on freelancing again to pay the bills, I felt plagued by the idea that I should once again take all comers. Problem was, I wasn’t really good at writing about clothing brands or horoscopes anymore. What I am good at, however, is analyzing congressional shake-ups and diving into bills.

I tried to focus on those skills and that expertise in my pursuit of new projects. One of the first pieces I landed as a freelancer dealt with the political eateries of the capitol—where to spot the political elite dining out on the town. As a Washington reporter, I spent years chasing congressmen from barstool to barstool, so I knew a lot about the story before I even touched a keyboard.

As a staff writer, I’d gotten very good at digging through the obscure hide-away corners of the internet and finding nuggets of information. As a freelancer, I began capitalizing on those skills—pitching stories based on factoids gleaned while searching the social media accounts of fringe political actors. For example, I found a pair of old recordings by a notable Trump ally and tracked down the Venmo accounts of a few high-powered aides. And though these stories didn’t get picked up, they made for dynamite pitches that piqued the interest of editors. They were my way of shoving my foot in the door.

Embracing the freelance life

As Facebook and other publishing platforms have changed how they handle news media, many talented journalists have found themselves unemployed. Some of us have been lucky enough to land jobs quickly, but for the rest, we’ve had to teach ourselves how to make a new career. I’m slowly navigating these waters, constantly humbled by the work of other freelancers. I’ve learned to use every rejection as an opening for the next pitch and to keep my eyes peeled for opportunities on the horizon. And if don’t I snag that Rolling Stone byline in the next few months, it won’t be for lack of trying.