How to Sell an Essay or Article: 21 Tips for Writing a Winning Cover Letter

Wondering how to sell an essay? Writing a cover letter that’s short and perfect to introduce your pages will sell a piece faster than submitting an excellent article or essay with an uninspired note.


This article is excerpted from Susan Shapiro’s new book, The Byline Bible: Get Published in Five Weeks.

My writing students are shocked by my belief that sending short, perfect cover letters to introduce mediocre pages will sell an essay faster than submitting a stellar piece with a lousy missive. Of course, I’m not advocating sending out pages that are less than superb. But here’s why writing a cover letter that makes for a great initial presentation is essential: Making mistakes or revealing a bad attitude can lead an editor to delete your e-mail or toss your envelope in the garbage without reading what’s attached. On the other hand, if you manage to charm someone on staff into giving your piece a serious look, that editor may work with you to make it publishable even if it’s not ready for press yet. Here are steps to ensure your first impression isn’t your last.

How to Sell an Essay: 21 Tips for Writing a Winning Cover Letter

1. Be brief. Three to five lines are usually sufficient.

2. Be professional. A cover letter only needs to explain the piece you’ve already written and are attaching. That’s different than a longer query letter, where you summarize what you haven’t written yet but plan to in the future. Either way, “Hey Sarah, how’s it going?” is not how I’d start a business correspondence, even if the editor is twenty-two, looks cool on Instagram, or is a friend of a friend. “Dear Ms. Smith” is more respectful.

3. Save wacky and witty for later. Self-deprecation can be hilarious when it comes from Margaret Cho, Chris Rock, Amy Schumer, or David Sedaris. It can work wonders in a well-crafted essay. But humor is subjective, and it’s hard for novices to pull off in a very short introduction letter. So don’t yuck it up too quickly for the wrong editor. In three-line e-mails and texts, irony, sarcasm, and playfulness can be easily misunderstood, especially when it comes from strangers who might not get your personality or appreciate your familiarity. After one class, a student wanting my help e-mailed me, “You’re an exceptional critic and teacher, though maybe a pain in the butt sometimes.” Instead of funny, I found this off-putting and kept my distance.

Rob Spillman, editor of the acclaimed literary magazine Tin House, once instructed my class: “Don’t act crazy.” Or at least keep the craziness in your pages, not in your letter. There can be a fine line when you’re pitching a piece about your schizophrenia, addictions, manic depression, obsessive-compulsive disorder, or anxiety disorder. Someone I didn’t know once introduced himself as “wildly neurotic alcoholic and chain-smoker.” Not wanting a headache, I told him I was too busy and recommended he work with another teacher.

4. Emulate the voice you want to publish you. When describing my piece, I often use the tone of the publication I’m aiming for. I once sent Cosmopolitan a story on “how I just met the man I wanted to father the children I didn’t want to have.” I would not have described a piece that way to an editor at The Nation. Make sure you read several issues of the publication before throwing your writer’s cap in the ring.

5. Get a name. Although many columns will instruct you to just send your work to generic e-mail addresses (like “op-ed submission”), I never send anything without a specific name on my letter. Otherwise, I can’t follow up with anyone and fear my piece will get lost in a huge folder of unsolicited material. If you must use these addresses, first try to figure out the right editor for the section you’re aiming for. You can usually find this information on mastheads or websites, in an Internet search, or with a quick phone call. When submitting an essay to The New York Times’ “Modern Love” column, I use their standard address, modernlove@nytimes.com, which the editor Daniel Jones prefers, but I begin “Dear Mr. Jones.”

6. Spell that name correctly. Sounds easy. Yet tons of editors tell me that, when they see their named misspelled, they feel they can’t trust the author to be accurate or fact-check anything else. So they say no.

7. Be accessible. Make sure to put your name, full address, phone number and e-mail address on top of your letter, your submission, and all correspondence, even if it’s electronic. Many editors will send cyber rejections, but would rather pick up the phone to say “yes” or ask if you’re willing to rewrite pronto? If they can’t reach you, they might just call someone else. Do not send your piece out then go off the grid, backpacking in Thailand for six weeks. Look up whether your target publication runs daily, weekly, monthly, bi-monthly, annually or is updated on the web 24/7. Many magazines and newspapers now have both a paper and a web division that operate separately. The paper version of Tin House comes out four times a year, offers more remuneration, and can often take six months to reply. TinHouse.com doesn’t pay as well, but it takes more pieces, which translates to more chances. Be conscious of which editor and section you’ve sent your work to and how long they take to respond, info that many post on their submission guidelines.

8. Pay respect. Don’t begin a missive by launching into your accomplishments, ideas, or needs. Do your homework and spend time researching so you can offer homage to the higher-up you want help from by saying you’re a fan of something she’s recently run or written. (Many editors also write.) Don’t pick the first thing that comes up on Google or something from 10 years ago. To submit to the “Modern Love” editor Daniel Jones, I’d start with something like:

“Dear Mr. Jones, I love the column (especially the essay ‘You May Want to Marry My Husband,’ which made me made me cry), the new podcast (Colin Farrell’s segment was my favorite), and your insightful book Love Illuminated. I hope you’ll consider my piece about how, after thirteen years of marriage, my husband decided to move in with me.”

(That was my exact 15-word essay description that worked.)

Editors are sharp and can smell phony praise. Don’t vaguely mention that you adored a piece or a book you didn’t read (or at least skim). A New York Times editor friend recalled being impressed with a cover letter by a new writer who told him, “I thought your section’s handling of the recent mayoral scandal was much smarter than The New Yorker’s version.”

9. Emphasize connections. If you’re lucky enough to have a go-between or insider’s link to the publication you’re querying, don’t wait until the end of your letter to mention it. Many readers won’t get that far. When someone starts an e-mail to me, “My friend Gerry Jonas gave me your name,” I immediately think: Damn, I have to be nice to this person. Why? Because I trust Gerry’s judgment, he helped me, and I return the favor every time, even if I’m busy. Another person made the mistake of e-mailing me, “Marla recommended I call you. I guess she’s too busy and important now to work with me.” I contacted Marla, who (not surprisingly) reported that this aspiring writer was needy and inappropriate. So I didn’t work with her either. Lavishly praising your mutual acquaintance is common sense. Anything negative is self-destructive. If you don’t know anyone, look up the editors’ bios to see if you can find common ground. Throwing in “as your Midwest neighbor,” “as a fellow Yalie,” or “I’m another working mom from Montclair” might establish a bond.

10. The harder you work, the luckier you’ll get. Planning a book publishing charity panel, my fantasy panelist was former New Yorker and Random House Editor-in-Chief Daniel Menaker. Although I’d met him years before, it was an ambitious choice. I could have started by saying how much I’d enjoyed his novel The Treatment (which I did). Yet on a quick Internet search for an update, I discovered the film version of his book was opening that night at a nearby theater. I waited 24 hours until I could see his movie. Then I wrote a fresh, timely letter that received an immediate affirmative response. He may have said “yes” regardless, but why chance it? I prefer to work at lightning speed, but sometimes it’s better to be patient and better prepared.

11. Say why you. Make sure to mention any expertise or experience you have in a short bio that might make the editor more likely to take your work. “As an Iranian expat who speaks Farsi, I hope you’ll consider my essay on the personal stakes of the Iran missile crisis” will get attention. “I majored in philosophy and minored in English at NYU, worked in banking for three years until I married, had two children, and moved to New Jersey,” not so much. Only include information that is relevant and may sell your essay, not your entire resume. If you have clips, you could say, “My writing has appeared in the Daily News and Post,” but don’t list a dozen small zines nobody has heard of, or letters to the editor, which don’t count as clips. You could include one or two related links you’re proud of, if they are recent, but not ten. A colleague once told me the most confident, successful writers do the shortest cover letters. Understate, don’t overstate.

12. Figure out the lead time. Since Psychology Today only comes out four times a year, they plan way ahead. In March, they are closing their fall issue. A monthly like Esquire often closes each issue four to five months in advance. A weekly like The Village Voice may only need ten days’ notice to rush a piece through. A webzine like Slate, which is updated daily, could take a piece on Tuesday that goes live Wednesday morning. Be conscious of the math because it could determine the numbers in your bank account.

13. Say why now. If there is anything in your essay that is timely, exclusive, or in the news, make that clear up front. When my student Darnycya Smith sent her piece “My Molotov Christmas in Brooklyn” to an editor at The Frisky webzine, she wrote in her cover letter and subject heading “Timely Christmas piece/December 25,” which was the day it ran. Another student, Danielle Gelfand, sent her essay “Years of Atonement,” about her father’s death on Yom Kippur, to The New York Times’ Opinion section, she told the editor, “I hope this might work for Yom Kippur, on October 7 this year.” She mentioned her topical hook in the subject heading (“Yom Kippur pitch, October 7.”) It went live on October 5. My colleague Amy Klein submitted “Looking for a Blessing to Marry,” about her rabbi’s prediction that she’d meet her husband on Hanukkah, to The New York Times’ “Modern Love” editor, saying, “I thought this may work for the upcoming Jewish Festival of Lights.” It ran that December. It doesn’t just have to be a holiday. My student Stephanie Siu tagged her New York Times essay to Donald Trump’s presidency, which ran on the day of his inauguration. I submitted an essay to Salon called “My Personal Michigan Recount” about the presidential recount on December 9, 2016, the day it was posted. A topical peg will always run faster than a generic timeless piece that editors call “an evergreen.”

14. Be humble. Despite your conviction that you’re a genius worthy of instant attention, be careful not to come across as presumptuous, self-involved, flippant, demanding, or delusional. I’m not an editor who buys or sells anything. Yet I get many requests to read unsolicited manuscripts and proposals in emphatic language that certain publishing guides mistakenly promote. After the release of my first memoir, Five Men Who Broke My Heart, my bemused editor mailed me the thick copy of a five-hundred-page manuscript from a male stranger in Texas. His letter bragged, “Hey there, I’m enclosing my great memoir, about the five women who broke my heart. I hoped you’d plug it to your editor and agent.” He’d sent the male equivalent of my memoir—which he neglected to mention he’d bought, skimmed through, or even liked. He was sure I’d want to read his project cloning mine to help him get published. He wasted postage and killed trees, since I put his pages in the trash.

While it’s good to sound confident, I wouldn’t start with “Here’s my fantastic work that I know your readers will relate to.” Instead of “I’m sure you’ll love this,” try to pay respect (see #8), or at least tone down your self-importance to “I hope you will consider this.”

15. Perfecting your Hollywood movie pitch may lead to a movie. Along with including what exactly you want, a good cover letter will entice an editor or agent into reading your submission. So describe the story you send in a very short, engaging way. I often quote my former student Katie Naylon’s pithy, successful cover letter to Jerry Portwood, who at the time was the editor of New York Press, a small out-there Manhattan weekly newspaper. She wrote, “Dear Mr. Portwood, I love your recent theatre reviews. Attached please find my essay on how I ran a phone sex operation in college when I was still a virgin. I hope it might work for your ‘8 Million Stories’ column.” It did! Portwood told me he wanted the piece from the description alone. (Naylon later recycled the comic premise for her hilarious 2012 rom-com For a Good Time, Call…)

16. Be artful. I am much better at writing than I am at “pitching,” which is writing about what I am going to be writing. Since I recommend completing an entire essay before you start writing a cover letter, here’s a trick I learned: You can use the best lines of your piece to describe it to the editor. When I submitted my New York Times piece “The Bride Wore White—and Black,” I began my explanation, “I was married twice last summer. I wore two different dresses in two different colors in two different cities …” Those were the first two lines of the essay I’d spent months completing.

17. Be a little mysterious. In that letter, I didn’t share the next part of the sentence: “…where I said ‘I do’ to the same man. The first wedding was for me. The second was for my mother.” I left it out so the editor would be more intrigued. If you map out every single twist and turn in your short recap, there’s no incentive to read on. Some editors prefer to see pitches, not the entire piece. In that case, if I’m describing an original story, I keep it vague. Sharing all details, addresses, and sources will make my exclusive newsflash easier to steal. For my Time Out New York piece on kooky ways New Yorkers like me tried to quit smoking, I mentioned a nameless addiction specialist, hypnotherapist, and Smokenders and Nicotine Anonymous groups without providing names or e-mails. Instead of overstuffing, whet the editor’s appetite.

18. Stick to e-mail and snail mail. Don’t phone publishing staff you don’t know. I wasn’t surprised to learn a student was hung up on when an editor was on deadline and had no time for an unsolicited call. Some editors accept faxes, especially if they are overseas. Try to suss out which way a publication wants to be pitched. Otherwise mail is usually way to go.

19. Have a smart heading. Try to see the world from an editor’s point of view and make his life easier. If you are sending a piece to a Salon editor, in the line for “Subject” do not write “Salon submission” (as five million others will). Also don’t use the editor’s name. Instead I use the topical reminder and my own title. “Michigan Recount essay Dec. 9” worked quickly for Salon. If your piece has no timely reference, say something fun or unusual. “My Best Friend Married My Brother essay submission” worked. But don’t swear, be sexual, or sound like an advertisement—or it could get caught in the spam filter. Editors get bombarded by PR e-mails, so make sure yours makes it clear it’s from an author, not a public relations firm.

20. Don’t tell the co-op board about your two abortions. This is a euphemism I use for: Don’t offer unrelated facts about yourself that could sabotage your chances. Mentioning that you are going through a lousy divorce will only be relevant if you submit a piece about relationships. Sharing that you used to be an alcoholic or drug addict is only necessary if that’s what your essay is about. Even saying that you have a Harvard M.F.A. might be a turnoff if you are trying a literary editor with an unrelated story about an illness you lived through. Editors aren’t shrinks; keep your personal shares to a minimum with people you don’t yet know.

21. Start small. When making initial contact to sell an essay, I ask the editor to read one short piece, nothing more. Not two pieces attached, or five ideas, or three versions of the same essay. Suggesting a weekly column to an editor you’ve never met is like asking a cute stranger, “Will you go out with me every Saturday night for the next three years?” Coming off desperate or demanding is a losing strategy. Like a first date, if all goes well, you’ll get another chance.


Learn more tips on how to write and sell an essay or article in The Byline Bible by Susan Shapiro, and if you’re in NYC, catch her Secrets of Publishing Panel at Barnes and Noble on September 21, 2018.

 

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