Right now, becoming a freelancer is like choosing to fight a battle you know you’ll eventually lose. A lot of us do it anyway. Even though I write regularly for the sports section of the Wall Street Journal and have contributed to publications like The New Yorker, Wired, and Slate, I’ve struggled to support myself with what I earn just from writing. Many of my colleagues at Contently once worked as freelancers and have similar tales of woe. A big part of the problem is freelancers have very few places to go that are dedicated to protecting their unusual careers. We can produce outstanding work, but regardless of our consistency as contract employees, we are at the mercy of editors, clients, and bosses who hold all the power.
Early on in the process of building The Freelancer, Contently Editor in Chief Joe Lazauskas and I kept describing the site as: what we would have wanted when we were freelancing full-time. By that, we meant a media property that would focus not just on providing resources and honest information about compensation and job opportunities, but also, a site that paid attention to people and publications mistreating freelancers. Enforcing at least some amount of accountability is going to be vital to what we do. We have a network of over 30,000 freelancers (including Joe and I), but to succeed, we’ll need to collaborate with many more.
When I tell people I am the editor of The Freelancer, they usually understand my job consists of more than just fixing typos. When I tell them about some of the daily managerial tasks—evaluating pitches, helping writers connect with sources, explaining revisions without crushing egos—they often turn to analogies. You’re like a conductor? A maestro? A teacher? Those are all true to an extent, but we’re big sports fans at Contently HQ, and the analogy that most readily comes to mind to describe my role atop the Freelancer masthead is player-coach.
What makes player-coaches valuable is how deeply they understand what their teams are going through. Indeed, we all still freelance outside of our day jobs at Contently and understand the struggle, which is why we offer substantial rates and pay our writers the moment they submit a first draft. We also want to focus on how we treat our contributors—many of whom we expect to come from our readership.
Player-coaches no longer exist in professional sports, but prior to the 1980s, they used to be fairly common. Now, most jobs are so specialized that it’s hard to fathom how one person could manage himself and his peers. Yet in the MLB, Pete Rose played and managed the Cincinnati Reds from 1984-1986. In the NFL, Dan Reeves played and served as an assistant coach for the Dallas Cowboys from 1970-1972. And in the NBA, which has had 40 player-coaches, Boston Celtics legend Bill Russell even won consecutive championships while occupying both positions in 1968 and 1969.
I’m never going to win an NBA championship—my dreams of playing (or coaching) in the league receded during high school about as quickly as Jeff Van Gundy’s hairline—but I can appreciate the nuances of taking on two related, yet very different tasks, and apply those nuances to what I do, especially when it comes to the freelance industry.
When I was a full-time freelancer, I dealt with some editors who were great and some editors who were bad. But it’s the bad ones who stand out in my mind, and when I began assembling a team of writers and editing the work that will be published on The Freelancer, I promised myself I wouldn’t treat journalists as insignificant cogs in the media machine. I imagine most freelancers have some memorable axes they’d like to grind (I know I do). There’s nothing I can do to fix the slights of the past, but you can bet my memory of them will help me now that I’m editing other writers—and that’s where the awareness of being a player-coach comes in. If we are aiming to create an important publication about all aspects of freelancing, then our top priority is treating all freelancers with the same respect one would treat any staff writer.
Now that we’re ready to launch, I’m excited by the idea of taking over a space in the publishing world that has been neglected for too long. I’m also a little nervous, but perhaps I’m just in good company. Even though Bill Russell was arguably the best player of his era and a title-winning player-coach, he used to throw up before games. He was always prepared and ready to compete, but the intensity took over before tip-off. I’m going to leave my digestive system out of this, but the sentiment still rings true and underlines the passion the entire Contently editorial staff will bring to The Freelancer.
Playing and coaching isn’t easy, but if we were looking for convenience, most of us freelancers would’ve chosen another career a long time ago.
Image via Top Bet