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This is the second of two posts recapping the last 20 months I spent working as a full-time freelance journalist—what worked, what didn’t, and what I’d suggest to others going down the same road. The first post is here.

The thought of sending pitches to an unimpressed editor may have given me the most sleepless nights, but it’s still only a small part of the freelance process. Most of your time will be spent doing two things: 1) actually writing, and 2) haggling over/worrying about/counting/realizing you don’t have enough money.

How to Get Paid

If there is one piece of advice I would give to freelancers (and young people in general), it’s this:

TALK WITH YOUR PEERS ABOUT MONEY—OPENLY AND CONSTANTLY.

This is rarely a comfortable conversation, because we’ve been taught to stigmatize these questions. But freelance journalism right now is a buyers’ market, and it’s easy for young people to get stiffed. The most egregious example is when outlets offer to pay a writer “in exposure.” If you must work for free, do it only as a favor to people you like and respect, and who don’t have a ton of institutional resources behind them. Other outlets will pay you, but at rock-bottom rates—watch out for those guys, too.

Before you negotiate a rate with your editor, do some research and talk to friends who have done similar work so that you can go into the conversation with a rough idea of what the going rate might be for a piece like yours. The most invaluable resource here is the Who Pays Writers blog and Twitter feed, the author of whom deserves a goddamn Nobel Prize. Susie Cagle, a freelance journalist based in Oakland, California, is also a must-follow on this beat.

General trends that I’ve found to be true:

  1. When you are starting out, expect to get paid by the piece, not by the word.
  2. A reported piece will take a lot more time and effort to write than an opinion piece, and therefore you ought to charge more for it — at least double what you’d ask for a non-reported piece of the same length, IMO. (Don’t back down on this point, or you’ll be on the hook for a whole lot of underpaid labor.)
  3. The corollary to trend 2 is that reported pieces are harder to successfully pitch than opinion pieces. This explains the abundance of shitty opinion writing, both in print and online, the rise of the thinkpiece as a major part of the media ecosystem, the number of outlets that are committed to aggregating stories, and so on. Reporting is expensive and time-consuming, and that’s just the way it is.
  4. Remember that you will pay self-employment tax at the end of the year. However much money you need to make a living, try to have a net income of about 20% more than that.
    4A. You should prepare for the possibility that paying your living expenses *plus* setting aside 20% for taxes will not be financially possible. At the end of last year, I knew I was going to owe the IRS a lot of money and was prepared to pay it, but I definitely didn’t break even once my bills were all paid.

And in the interest of practicing what I preach, here are some hard numbers. If you want specifics on who paid me what, shoot me an email and I’ll be happy to talk—seriously.

For straight op-eds, whether they were for fun, bloggy affairs or Very Serious Journalism Endeavors, I could make anywhere from $100 to $500 per piece, with both of those numbers being extreme outliers. When I got $100, I was willing to take a low rate because I really loved the outlet in question, thought the Web Editor there did a great job working with my articles, and knew that they were not exactly flush with cash. (Many outlets will tell you they simply aren’t able to pay you that much—sometimes this will be bullshit, but sometimes there’s truth to it. Use your instinct.)

For reported pieces, it depended on the intensity of the reporting involved, but I’ve netted anywhere from $200 for 800 words (in retrospect, I should have asked for more) to $700 for 1500 words of heavy reporting and interviewing. I should also note that I’ve written heavily reported, 2000+ word pieces that I’m confident could have fetched $1000 or more at established publications. Owing largely to the financial circumstances of the outlets that ran the pieces (I knew they were hard-up and/or had limited freelance budgets), I made in the $250-500 range for each piece.

The point of this isn’t to brag about how magnanimous I am, obviously—it’s to let you know that if a piece is long and detailed enough, many outlets will be happy to pay you a lot of money for it. Whether you want to sell an article to a scrappy web magazine with limited cash or an internationally recognized brand is a call only you can make, and IMO should be done on a case-by-case basis.

Me Write Pretty One Day

This is the part where I feel weirdest about giving advice, because writing is such a deeply personal act that I wouldn’t feel comfortable going all Strunk and White on you. Instead of prose style tips, then, some general thoughts I’ve gathered over the last 20 months about how to write, what to write about, and how to maintain your sanity in a brutally competitive industry.

  • Develop a beat, and stick to it. It took me several months before I realized that “Urban planning and millennials and politics and media and occasional jokes” wasn’t really a compelling personal brand. Narrowing my focus to city-planning issues and local politics benefitted my career in a number of ways: It put me in touch with a group of fellow journalists and wonks whose work I really respect. It allowed me to acquaint myself with the ins and outs of a particular cluster of issues, and become more confident talking about them. It gave me really great reporting opportunities by putting me in the middle of a field where there’s a lot going on at the moment. Being associated with a particular topic, I suspect, also made it easier for editors to approach me when they wanted to commission an article. The handful of times someone came to me and said “Would you like to write on this for us?” it was because I already had a track record writing on housing, gentrification, infrastructure, etc. And speaking of which…
  • Love your editors. There is seriously no substitute for knowing that your article is in capable hands. The more you can establish a consistent working relationship with someone, the better you’ll be able to craft a consistent voice yourself.
  • Pick up the phone. So many outlets now aggregate or repackage news that it’s easy to forget how important (and hard) the act of reporting is. My new year’s resolution for work was to include a piece of reporting or research in everything I wrote. I don’t think I’ve *totally* followed through, but I have no doubt that the “Report first, opine later” mindset has led me to produce consistently higher-quality writing.
  • Don’t be afraid to go long if you need to. A lot of editors and media critics make a great virtue of brevity. (Insert your own “snackable content” joke here.) Looking over what I think is my best work, I’d put it differently: Make your article as long as it needs to be, but no longer. Most of the time you won’t need 1000+ words to make your point. But on the rare occasion that you do, don’t apologize for it.
  • You are not the most interesting part of your story. Good writers who only write about themselves are not actually good writers.. Find other people, let them speak for themselves, and elevate their stories above your own.
  • Be generous with your time and network of contacts, especially when other freelancers are involved. I got pieces published because other people were willing to get coffee with me, make introductions, do favors they didn’t expect me to pay back, etc. Pulling up the ladder behind me would make me officially The Worst. (Caveat: Never send single-opt-in emails!)
  • The best articles are about things that actually happened, not about narratives, discourses, framing, or what we’re really talking about when we talk about x. Finding somebody who said something stupid on the internet is easy. Any one thing can feed into a narrative that posits some other thing if you massage the language enough, or write with enough bad faith. (#CancelDerrida) But to use an example from my own beat, what’s more useful: writing about how we should understand gentrification as a continuation of settler-colonialist discourse, or writing about actual poor people of color who are getting illegally evicted from their homes?
  • Twitter is useful for finding like-minded writers and staying informed on your topic of choice. Tweet about whatever you want, and follow whoever you want, but it’s just Twitter. You don’t owe any one issue, or any one person, your attention.
  • You will almost always have more work than time. Set clear boundaries for work/life balance, and follow them.

That’s all I’ve got. Would love to hear questions/comments/concerns/disagreements—every freelancer has a different story.

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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.