The Making of a Full-Time Freelancer

The reason I’ve been so bad about updating this personal blog in the last 18 months is that I’ve been a full-time freelance journalist. My first priority, to be perfectly vulgar, is getting paid for everything I do, so I only put original content up on this site as a last resort. I’d like to think I got the hang of it eventually, but it took quite a lot of time and anxiety.

Freelancing full-time is not glamorous, and it was never something I really wanted to do myself. I was thrown into this situation after I was abruptly laid off from a full-time job at a digital-news site, decided to really give it a go after a few months thinking about my future, and since then I’ve just kept plugging away at it. Now that I’m moving away from New York, beginning graduate school, and changing career paths, I thought it would be useful to follow in the footsteps of many freelance journalists who I admire, and write down some closing thoughts on what’s worked for me, what hasn’t, and what I would say to someone who’s embarking on a freelance career, voluntarily or no.

Pitching.

I am pretty confident in my ability to string sentences together, but I am terrified of pitching. It’s always been my least favorite part of the freelance process. I think it has to do with some repressed fear that an editor will read my thoughts on what is interesting, disagree vehemently, and then decide that I myself must not be that interesting either.

My favorite advice on this topic comes from Alana Massey, who likes pitching much more than I do. I’m going to just ape her shamelessly and go through some notable articles I pitched, explaining why they did or didn’t work out.

Pitch 1. My first story as a full-time freelancer. This is the pitch that ended up getting accepted:

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Who read the pitch? I emailed it cold to an editor in chief after Googling websites that covered urbanism and transportation.

Did it work? Yes. The article ran in UBM Future Cities, an urban-planning website (sadly now defunct) that focused on issues of interest to industry professionals. Versions of this pitch were rejected by Atlantic Cities, Fast Company Transportation, and Next City. Future Cities, which read more like a trade publication than a general-interest outlet on urbanism, was willing to let me go into the details.

Lessons: If you’re going to email someone cold, make sure you’re not pitching a topic the outlet has covered in detail before (Next City and FastCo both rejected the pitch because they’d covered Bus Rapid Transit and/or Mexico City transpo before).

Also, if you’re new to freelancing, Google websites that cover the topic you’re writing about, and keep Googling. UBM was the 6th or 7th website I pitched this article to, I’d never heard of them otherwise, and I ended up writing for them a bunch of times in the rest of 2014.

Pitch 2. I pitched this only a few months into my freelance career, but had been thinking about the issue for a long time.

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Who read the pitch? An Al-Jazeera America opinion editor, who I knew personally through a couple mutual friends. She invited me to pitch this to her after we had an in-person conversation about the media industry.

Did it work? Yes. AJAM ran the article and it remains one of my two or three best-performing pieces.

Lessons: Punch up, and strike while the iron is hot. This came out when it looked like Upworthy was going to destroy us all, so it touched on the concerns of a lot of very talented writers in a very timely way. Also, this article (and my work at AJAM in general) is a testament to the importance of good editors. I really enjoyed writing for the Opinion team there because they had a good sense of the tone and style I was going for, and knew how to curb my excesses. I was really confident pitching to AJAM because I knew my articles would be in good hands.

Pitch 3. Another case study in the importance of a good editor.

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Who read the pitch? An editor who I’d never met in person, but she and I shared some interests and mutual friends—cities, millennials, etc. She was launching a new vertical for feature writing, and invited me to pitch her after she read and liked an essay I wrote on gentrification the previous fall.

Did it work? Yes and no. I’d been trying to land this article for months, with little success, but in a very different form: a righteous, snarky rant about how much I hated this phrase, with a brief side appearance from the professor in question. The editor read my pitch and realized that this professor, Julia Hobsbawm, was the most interesting character in the story. Making my story largely about Hobsbawm allowed me to get my point across without having to write a self-indulgent thinkpiece.

Lessons: Pick up the damn phone, and when you do it, talk to people with empathy and respect. Looking back on older drafts of this article, I’m struck by several major errors: Shitting on somebody without giving them the chance to speak on their own behalf, assuming that the author’s feelings are inherently interesting, etc. Interviewing Hobsbawm and making her the center of the story made my arguments more broadly applicable, and while I was up-front with her about my strong priors on this topic, she spoke to me anyway, and I tried to give her room to tell her story at length. The final product, as far as I’m concerned, was infinitely more nuanced and fair than my rough drafts were.

Pitch 4. When at first you don’t succeed…

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Who read the pitch? A features editor at The New Republic. The editor and I had never interacted before, and I got his email address from a friend who wrote a freelance article for TNR a couple months earlier.

Did it work? No. I pitched a thinkpiece on House of Cards and The West Wing to five or six outlets in February 2014, just after Season 2 came out, and nobody took it. By the time my pitch got rejected from TNR, I realized that the window of opportunity for HoC reactions had basically closed, and I put the essay up on my personal blog. (Read it here.)

BUT! I tweeted out a link to the blog post, and in the link I tagged Chris Hayes, whose book “Twilight of the Elites” plays a central role in the essay. He retweeted me, which turned the article into a sleeper hit (by my standards, anyway). It’s still the most-viewed article on my blog, and it’s not even close. I’m still weirded out (but flattered) by all of it.

Lessons: The bar for a good thinkpiece is really high, especially when you’re taking on a major pop-culture phenomenon. If you aren’t able to place one, don’t despair—post it yourself and promote it on Twitter like you would any other article. Tag people who you think would find it interesting. You never know what will happen.

Pitch 5. How to frame a piece of straight-up reporting.

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Who read the pitch? A features editor at Gothamist who emailed me about a month earlier, asking for pitches on urban planning, infrastructure, and general “city life” issues.

Did it work? Yes, with tweaks. I pitched this while I was trying to focus less on opinion writing and more on reporting, and what’s noteworthy about this pitch is the way it was focused and refined over time. You’ll see two pitches in my original email: one on subway countdown clocks, and one on bus headways and rider information more generally. After some back and forth with the editor, we agreed that the former was the more compelling and under-covered story, and lent itself better to a concrete investigation. We decided to proceed with a look at why most subway lines in NYC don’t have countdown clocks, a pretty niche topic that still affects day-to-day life for millions of New Yorkers.

Lessons: When you’re trying to answer a question, tailor the question narrowly. An “article” on why NYC is bad at running a reliable bus system could easily turn into a novella. Given my budget of 800 words, subway countdown clocks was a way better pick: I was able to go to the MTA spokesman with a single, concrete question, and I could tie the article to a general feeling that the subways had gotten considerably worse during the past winter.

—–

The moral of all these stories? Pick your editors carefully, and when you find a good one, keep pitching them. The impulse to spread your work far and wide, and keep looking for new outlets, is a totally understandable one. But if I hadn’t gotten into a consistent routine with a handful of editors and publications, it’s anyone’s guess how many of my pitches would have turned into published articles.

Coming up in another post on leaving the full-time freelance life: Thoughts on how to make sure you get paid well, and some things I’ve learned in the last 18 months that I think have made me better at the writing and reporting process once a pitch has been accepted.

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