Freelancer: Thank you, Will Leitch, for talking me off the ledge

Letter to Romenesko

From RYAN GLASSPIEGEL, founder of As every Romenesko reader undoubtedly knows, freelance journalist Nate Thayer set off a firestorm — at least in our corners of the Internet — earlier in the week when he published an email exchange with Atlantic global editor Olga Khazan.

Ryan Glasspiegel

Ryan Glasspiegel

Khazan asked him to repurpose an NK News piece about Dennis Rodman’s trip to North Korea and the history of basketball’s role in U.S.-North Korea diplomacy. For free. (Well, “exposure,” which, as Mr. Thayer, a journalist with 25 years of experience, told NY Mag, “doesn’t feed my fucking children.”)

A lot of folks chimed in, and it was fascinating:

Choire Sicha hosted a discussion about freelance payments that eventually included more than 70 journalists and editors and over 15,000 words; Paul Carr explained why journalists need to be paid and should not support themselves with side gigs; Ann Friedman gave guidelines on when writers should work for free; and there much more (including discussions about Thayer’s alleged plagiarism).

I’m 26 years old and I’ve been a freelance writer for a little less than two years. I don’t really know if I’d call myself a journalist. I have no formal training. In my major foray into legitimate reporting — a 6,000 word story on medical marijuana industry and policy that ended up at Huffington Post — I discovered that financial incentives for creating these pieces independently were misaligned. I couldn’t find anybody who would pay me anything to publish a project that took me over a month to create./CONTINUES

That I was not ultimately compensated for this work does not mean that the experience was not worthwhile. I met brilliant people connected with the industry, from doctors to patients to advocacy lawyers to care center operators. I learned an unbelievable amount about something I was naturally interested in and shared the education with others. Because of the work I did, medical marijuana is now a topic that I am passionate about. The article would be the cornerstone of my portfolio. Ideally, it would show future editors that I am capable of doing high-quality work and that I am worth collaborating with on different projects. It did indeed directly lead to my highest-paying writing job.

Mostly, I write about sports. Except for college when I wanted to work in Finance because I wanted to be rich so I could buy lots of stuff, it has been my lifelong dream to be a sportswriter.

While many feel much differently, I’m ecstatic to live in this day and age. All you really need to get started is a computer. I have my doubts as to how well I would have fit into a hierarchical newspaper structure. I appreciate how special it is that we live in an era where we have access to every game in every sport on television and can inundate ourselves with real-time information flow. Individual writers — in sports and elsewhere — are more empowered than ever to develop personal brands and capitalize on them. Surely, I’ve thought, I could carve out a niche for myself and make this hustle sustainable before it’s all said and done. Even if not, I owed it to myself to try long and hard enough that I would not look back on my 20’s with wistful regret.

But reading everything this week has been harrowing, and really made me question my belief that I will “make it,” whatever that means — is my writing good and universally interesting enough that the regular readers I am searching for will recognize my byline? Will it ever be? How long should I try to make it before I risk compromising my long-term goal of raising a family? Am I being irresponsible right now? If I were even able to obtain staff writing position at a pageview factory, would it honestly be more fulfilling than a job at, say, an advertising agency?

To be fully candid, these questions burn stronger because I am not financially independent. When I left my straight job, I had about a year’s worth of savings. I’ve earned some money writing, but not nearly enough to continue to pursue this full-time without a) taking on a side job like bartending or serving, or b) having an inheritance.

I’m not, like, a rich kid of Instagram, but my parents have been wonderfully supportive — both emotionally and financially — of these endeavors. I’m unbelievably lucky. I’m aware that my dream would be impossible, or significantly decelerated, if this weren’t the case. These opportunities are not available to everyone. It is not something that I deserve — it is completely out of your control when, where, and to whom in the world you are born — but it is a part of my reality that I consider when I make decisions. As illustrated above, I do still struggle with my identity as a writer within the parlance of how I want to build my career. Financially, the support is not indefinite or unconditional, and I must constantly grapple with whether I would have more confidence and be a happier person if I were a self-sustaining adult with a more societally acceptable job. I have no idea what my situation says about the state of journalism because, again, I do not know if I would classify myself as a journalist.

It was a series of tweets by Will Leitch that would talk me off the ledge and remind me why this is what I want to do:

Now, obviously, I am in a completely different position from Nate Thayer. I don’t have mouths to feed. I have substantially less experience. I write about sports, not international diplomacy. I’m trying to build my own site and I still benefit from “exposure,” especially if I am working with an editor who takes the time to help me become a better writer and promotes my work through his/her distribution networks. The process of writing can be agonizing, but there is no greater exhilaration than having written–especially, though not exclusively, when it’s well-received.

So the rhetorical questions are of course still there, but they are compartmentalized instead of all-consuming. Perhaps I won’t develop a broad readership beyond my friends and family, won’t derive enough income from the craft to raise a family. Worse things have happened in human history. I’ll find other ways to support myself. I’ll still be a writer.

Ryan Glasspiegel has been published in The Classical, The Awl, Outkick the Coverage, Chicagoist, and The Daily Meal. Find his regular writing at Follow him on Twitter: @SportsRapport.