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On Building a Successful Freelance Writing Career: An Interview with Chadwick Moore

As layoffs of full-time employed writers have plagued the print media industry over the last decade, the freelancing field has become increasingly crowded. For struggling media outlets, freelancers represent a solution to the twin problems of lower budgets and a decline in circulation. But for writers, the absence of full-time employment can mean uncertainty. Learning to navigate this precarious field is a prerequisite of the job. Moreover, the freelance market has become increasingly competitive and now, more than ever, writers have to distinguish themselves from their competition. So, in the interest of sharing some tips on viability in this volatile line of work, we sat down with Chadwick Moore, a young writer and journalist who has, in the six years since publishing his first item in The New York Times, built a successful twenty-first century freelance career. Moore is editor-at large at Out and The Advocate, and a contributor to Playboy and The Times. His article “Wounded but Unbowed, LGBT Orlando Tries to Carry On” is the cover story of the August 2016 issue of The Advocate. In the following interview, Moore shares trade secrets about breaking into the business, navigating relationships with editors, the art of the pitch, and keeping your finances straight.

AG: There are more writers than ever who write freelance pieces, but that’s categorically different than earning a living as a freelance journalist. How does one make the leap from publishing the occasional article to making a career of it? Better yet, how did you make that leap?

CM: It also feels like there are simply more writers than ever, period. Aside from professional writers who occasionally freelance, we’ve also got all these hobbyist writers—corporate litigator by day, thinkpiece wizard by night—many of whom are, frustratingly, very talented. This is a saturated business and, particularly here in New York, where we have the world’s most crowded publishing industry, where there’s a surplus of eager warm bodies, no money, and a limited number of column inches available, I think what it firstly comes down to is having grit, determination, and an absolute passion for your industry.

Here’s my cliché truth: I skipped my college graduation ceremony and hitched a ride to New York from Iowa with two bags and $900. Shortly after coming here I managed to convince a prominent, very generous magazine editor to have coffee with me. He remains one of the kindest people on the planet to me. What I remember most is, when I asked him how to make all this happen, he said something like, “Just keep going. Just keep trying, you’ll figure it out.” At the time, it felt like a throwaway comment but he was absolutely right. He was talking about perseverance, because perseverance is, surprisingly, a rare quality in this business. Perseverance is the thing that will get you raptured. But, of course, wear it with decorum and know your place.

A few years ago Neil Gaiman gave a commencement speech at The University of the Arts where he said—and I’m paraphrasing—that a successful freelancer is three things: They do good work, they’re pleasant to deal with, and they’re on-time. But, he said, the secret is you don’t have to be all three. Two out of three is just fine. I think that’s the most comforting thing ever said about freelancing.


What are the keys to making a good pitch?

The most important thing is to keep it brief! If you’re e-mailing an editor for the first time, they’ve got 9,000 things in their inbox and they do not care that you were editor of your college newspaper and spent a year in India caring for lepers. You swiftly introduce yourself and bang the story idea out as efficiently as possible while providing any relevant backup information. That’s it. And, when you don’t hear back, it’s okay to follow up, but no more than once. You don’t want to be annoying or aggressive.

Secondly, do your research. Know your publications and know the kinds of stories they publish and sculpt your pitch to fit their tone and style and taste. Even if you don’t get a greenlight on a pitch, editors will be impressed if your ideas at least sounds like something they would publish.

I’ve always felt that getting a “thanks but no thanks” response is just as good as a greenlight, because that means the editor is actually interested in you. If he or she takes the time to respond—because they will ignore you, always—you should absolutely keep sending that person ideas. And if they continue to reject, that’s fine. Try harder.

Finally, and most importantly, don’t be intimidated. That’s easier said than done. You need to remember that these editors need you just as much as you need them. Most of the time, you’re reaching out to someone who spends all day sitting at a desk and they rely on people like you to tell them what’s going on out in the world. They need copy, you need a byline.


How long until you began getting pieces commissioned from the publications you’ve written for? Is that something one can actively work toward? How?

That really depends on the publication and your relationship with it. For a publication with a large staff, it won’t matter how many great stories you write for them, they may never throw you a bone because your value to them is having fresh ideas that are your own.

In other cases, it will probably take a couple of years before you begin to get assignments. It takes time for a publication to trust you and trust that you will make them look good. But stick with it. And you can help that along by always being available and always saying yes. And, if you’ve been around for a few years, don’t be afraid to ask for what you want. Ask for a contract, or ask for some assignments to come your way. We like people who know their value and ask for what they want, don’t we?


In addition to nurturing relationships with editors, you seem to have also carved out a few subject-matter specialties. Is there an advantage to doing so? Is it necessary?

In nonfiction, the more specialized you are, the easier your life will be. This is fact. It is a huge advantage to specialize. I am not specialized. I write a lot about the LGBT community but that’s only because I’m actually gay, and write for two gay publications, and I know way too much about what gay people are up to. But my topics are all over the place. That’s not really specialization so much as general interest writing for a certain audience. I feel I’m at a disadvantage here, to be honest, because I’m absolutely curious about everything under the sun. But, on a good day, I suppose what I bring to the table is a certain perspective that can be applied to a range of topics. And maybe that’s what I’m selling. Maybe that’s a sort of specialization.

Still, if you’re interested in writing about, say, the environment, or fashion, or mental health, God bless you. You’ve got a leg up in—sorry to use this word—“branding” yourself as the go-to person on that issue and, if you do it well, you’ll always have work. You’ve got one field to learn everything in the world about and keep it exciting. I’m quite jealous of writers who are very specialized, I almost feel that’s a more fun and rewarding life, to just nerd-the-hell-out for the next 30 years on economic policy or koala bears or whatever. I can barely stay interested in most people I know for more than a few hours, I couldn’t imagine that sort of dedication to a writing subject.


One of the more notable features of the life of a professional writer is the absence of a regular paycheck. How do you plan financially without that security?

This is tricky. I’m lucky that now, for the moment, I do get a regular paycheck because I’m on retainer from a magazine. But, I still heavily rely on the not-regular paychecks. I was the assistant to a bestselling author for about five years while I was trying to nudge my way in the door to publications. I’m still nudging, for the record. The money and hours were scant, but it was regular and allowed me to pursue other things and that was important. It paid the rent, and then if I wanted to eat or get drunk that month, I had to sell a story. That was tough, but that’s the grit aspect I was speaking of earlier, I think.

I watched how the author I worked for did it. He churned those books out, every couple of years, and he knew what his advance would be, so he was able to plan. He had such regular speaking engagements that there was no insecurity, it did become like any other job. I think that’s how it’s done. Once you get your feet on the ground just a bit, you’ve got to begin to position yourself so that you have many pots on the stove and, therefore, if one falls through you’re still ok. Books, articles, teaching, speaking, television, print. Anything you can think of, you’ve got to look into it.

And, if you need money while you’re getting your writing career off the ground, do not work in an office. You will never write a single word. Work for a book publisher for, like, a year. Just to see that end of it. Then quit and be a bartender. I’ve been a bartender, house painter, tea bagger, and cleaning lady and they were all lovely jobs. Cleaning houses was the best job I’ve ever had.

And, hey, if you have to get on the dole while you’re figuring out your career, then by all means!


As a freelancer, do you file taxes quarterly? Do you have a system in place for tracking your income and expenses? Do you use an accountant? What about deductions—do you write off any “tools of the trade” or a portion of your living space as workspace?

I do have an accountant. I file taxes yearly. Because about 85% of what I write are my own ideas, I have to spend a great deal of time out in the world, talking to people, and that costs food, and drinks, and taxis, and subways. I am, almost quite literally, always working. You’re never off the clock. I can’t tell you how many of my stories have come from conversations in bars with strangers. Often, after a few hours at the bar, I’ve sent myself half a dozen e-mails with ideas for stories and usually at least one of them is really good. If I’m ever stumped for an idea, I’ll cruise up to my local and listen to what people are talking about. So, there is a lot to write off, tax-wise, and to keep track of. I’m not great with financial planning and orderly living in general, but as I enter my mid-thirties I hope to change that. These receipts all go into a stack of envelopes and at the end of the year I sort them. But it’s a good idea to note on each receipt at the time of purchase what was going on, and why this should be an expense, in case you get audited.

I have a two bedroom apartment and my second bedroom is entirely used as my office, so I’m able to deduct that from my taxes, based on square footage, but I have no idea how much of a break that gives me or how any of that works. This also applies, I’m told, to Internet connection, some utilities, and some of my cell phone. I’m also allowed, I’m told, to include my bathroom in those deductions. If you’re living this sort of life, a trustworthy accountant is required.


Are you able to negotiate a kill fee for your stories? Is the kill fee still standard practice in the industry?

As far as I can tell, a kill fee is still, thank God, very much standard practice. I believe it’s only happened to me once, that a story was killed, and I was paid the full amount, which was nice. I still believe a standard kill fee should be 50%. I’ve had contracts that offered 20% and when I asked to raise it to 50% it was not an issue.


Authors Guild members often ask our legal department for help when a publisher is slow to pay. How do you approach that problem?

Oy. With strong-willed and persistent, but polite, nagging. Many years ago when I was writing for some nightlife website I did show up at the office and ask for a check after months of neglect. That worked. I’ve seen writers really lose it over this issue, taking to social media to call out, embarrass, and harass editors for tardy payments. That is not the look, in my opinion. You’re only embarrassing yourself. I know some people have gone to small claims court. Assess with a clear head how much this means to you and what you’re willing to sacrifice. Tardy payment is something you will have to deal with in this business, and you need to be tough and prepared. This is also why it is so important to have several pots on the stove. So much of this industry is about relationships and if you want to burn bridges, good luck to you. I think a nice cup of coffee with your editor is a better idea. Maybe you can ask him or her, “Hey, is everything ok? Are you good on money?” See what they say. Maybe they haven’t been paid in months either.


Is legal liability a concern for the type of stories you write? If so, is that something you address with the publication that will be carrying the piece? Do you use any sort of media liability insurance?

Legal liability is not a huge concern. I’ve had sources get very upset with me for stories that were published—one incident led to hideous and completely made-up allegations against me—but this all took the form of nasty e-mails and texts to me and my co-workers. In fact, I could have sued her, rather than the other way around. I’ve always felt I’ve portrayed everyone fairly and honestly and to the best of my ability. Speaking to the press in the age of the Internet is a terrifying thing and so I understand people’s concerns, and I try to make them comfortable, and I’m always thankful when they do speak with me.

But, you’re never going to make everyone happy. As long as you identify yourself as a journalist and as being on-record, and you record every conversation and choose your language around sources very carefully, no one can say you misrepresented them and have a legal case. I find that all 8.5 million New Yorkers are very media savvy, and they know the game and they know what they are signing up for when they speak to you. When you get out into the middle of the country, it’s a different story and you might need to be more delicate. I’ve been blessed to always have very astute fact-checkers at the publications I work for and I always send them my transcripts—and then it is pretty much on them if a legal issue arises.


What have you learned along the way about marketing yourself and promoting your work?

Social media is great, but not every writer needs it. Sure, if you’re an opinion writer, for example, you should probably be blasting off opinions on Twitter like a crazy person, and most of them do.

Some writers are wonderful on Twitter. I’m not one of them. The most important marketing and self-promotion you can do, I believe, is with your flesh and blood peers. People, especially in this industry, want to help the fledglings, if they like you enough, because many people helped them along the way and they know the struggle is real. I’ve begun taking on writers for a magazine I work for, and some of them aren’t entirely there yet, but it’s a great feeling.


Do you work with an agent?

Not yet, but soon, hopefully, for a potential book project. Do you know any?

Where can we find your work?

I publish frequently in Out, The Advocate, Playboy, and The New York Times. I keep most of my clips on my website,

Thanks for your time, Chadwick.

My pleasure.



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Photo credits:
Chadwick Moore courtesy of Chadwick Moore
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