Last month, I came across a sentence in Cal Newport’s A World Without Email that took my breath away: Outsource what you don’t do well. Newport describes how one entrepreneur’s decision to hire a part-time assistant swiftly drove up the startup’s efficiency and the entrepreneur’s satisfaction with his job. I put down the book and watched two dogs wrestle in my neighbor’s yard. Newport’s dictum had sparked an idea that seemed so scandalous, so alluring, so taboo, that it might just work…
What if I could find the funds in my teaching salary to hire a writing assistant for a few hours a week? Namely, someone to submit my stories and essays for me?
Creating work has never been an issue. I began composing short stories and poems as a kid, majored in creative writing in college, and attended an MFA program, where I largely worked on fiction. I rarely submitted the stories that I’d spent months and years polishing.
Professors urged us to submit regularly, to create Excel spreadsheets, to amass rejections and keep going. But the whole system felt so obtuse and unrewarding: you submitted a story, waited for months on end, then received a polite form rejection, if that. Every now and then a personal note would come through, suggesting that you send something else. Discouraged by the rejections, I rarely did.
When I managed to actually publish work, the path to success seemed difficult to repeat. In one instance, a college professor kindly nominated me for an Emerging Writers issue. Afterward, a magazine editor at a tiny lit mag reached out, urging me to submit a story. I did so, and somehow the piece wound up being selected as an O’Henry Prize Story that year. All of it—the professor’s nomination, the solicitation, the prize—came down to incredible, unthinkable luck, and no real work on my part, aside from writing and editing the piece itself.
When it came time to look for an agent, a friend offered to put me in touch with his. She eventually agreed to shop my story collection around, but didn’t get any bites. And since the agent regularly misspelled my name in emails, I figured I wasn’t her first priority. Then another friend from grad school, who had since begun agenting, reached out and offered to represent me. I said yes, and she recommended I try my hand at a novel before selling the story collection. I wrote the novel in a couple years, she sold it, and I wound up with a generous book deal and a great editor, even if the novel itself didn’t sell very well.
I assumed that this method would continue for the rest of my career: I’d write another novel, she’d sell it, basta. But none of my drafts seemed to satisfy her, and after five years, we parted ways. Now, on my own (cue the Les Mis soundtrack), with 20 years of writing and publishing under my belt, I still feel squeamish when it comes to submissions. I’ve begun writing more nonfiction, and have had some luck placing personal essays, although this, too, feels scattershot.
Meanwhile, there’s a groaning file labeled WRITING on my computer that contains, I swear, dozens of standalone pieces—poems, short stories, flash fiction and nonfiction, essays, novel drafts, a memoir—all of which silently rebuke me whenever I open Microsoft Word. I’m proud of that work. I think most of it holds up (even if, skimming an old short story the other day, I realized I’d need to substitute a character’s “CD-burning” for a Spotify mix.)
Agentless, as the majority of writers are, how do we find our own agency? My fiancé, Alejandro, ironically, is exactly where I was 10 years ago: poised to finish and publish his first novel. He has done well with submissions: an American Short Fiction prize two years ago turned into a Best American prize last year. He seems less fazed by the whole slush pile prospect: as I type this, he’s in his office next door, shortening a short story for a Guernica submission. Is it his scrappy, thick-skinned approach (he applied to the Michener Program four years in a row before an acceptance) or is he innocent of an industry weariness that my 20 years in the biz has conferred, like a professional tennis player’s sore shoulder?
I love reading business and productivity books because they’re reassuringly matter of fact. But Newport’s suggestion to outsource your headaches is complicated when it comes to submitting creative writing. How can I instruct someone on how to submit my work if I don’t have a reliable process in place? Should I hire a marketer? A college student? A virtual assistant? A freelance publicist?
Ideally, I would hand my teeming file of writing to a deeply organized soul who would go to town organizing it, strategizing about where to submit, and then send work out like mad, using my cover letters. I could offer bonuses for work that was accepted, along with a fair hourly wage. But with such an enormous lag time between submitting and hearing back, and with acceptance rates so low, it’s hard to create an appealing incentive. And the prospect of sacrificing therapy sessions for a publishing assistant seems dubious, to say the least.
Another one of my favorite productivity gurus, Greg McKeown, whose latest tome, Effortless, I devoured in the way I no longer devour novels (see: industry weariness), suggests asking yourself these questions when approaching a thorny task: How could this be easy? And: How am I making this too complicated?
After finishing Newport’s book, I spent a full week trying to come up with a job description for a writing assistant before deciding I probably just need to do the work. Last week, during a lull from teaching responsibilities, I decided I would look over old pieces and edit them in the morning, and then send each story out to five places in the afternoon. Simple, right? Log into Submittable, copy and paste the cover letter, attach the short story file, basta! (Sadly, anytime my plans end with basta, it’s usually a sign that they’re not going to work out.)
Sitting down at my laptop to submit again reminded me why I always avoided it. Trying to figure out if a magazine is in a reading period. Trying to scout out the appropriate editor on the masthead. (Alejandro, scandalously, told me that he just addresses his letters to an anonymous Editor. Ballsy.) Trying to decide what my list of publications should be. Do I attempt a college admissions approach, with reaches and safeties? But if I’m sending out a bunch of work over the course of several weeks, including several short stories, how to choose which magazine should receive what?
For a long time after my divorce, six years ago, I refused to date online. I didn’t want to go through the drama of meeting people who wouldn’t work out. I wanted connection to happen naturally, in the real world. Unfortunately, this meant I jumped at every odd encounter that occasionally crossed my path, just to prove to myself that this organic method was serving me well.
When I finally took the plunge and signed up for dating apps, it took six months of good, shitty, and largely underwhelming dates before meeting Alejandro. I was his first Bumble date, go figure. I told you he was lucky when it came to submissions. And now that I think about it, he totally lured me by touting that recent ASF short story prize in his dating profile, as if I were another magazine editor instead of a romantic prospect.
But maybe there’s something to thinking about submitting as a kind of matchmaking for my creative work rather than as a test of its fundamental worth. Scrolling through lit mags the way I once swiped through faces and profiles. We’re told to go for the most selective publications first, but maybe looking for the friendliest and most intriguing journals would be a more enjoyable prospect. Over the years, my writing has gotten more experimental, and prospective publishers for later work will likely look much different than publishers for work from my 20s and early 30s, just as my romantic partners have changed along with shifts in my personality and my priorities.
The first definition of “submission,” according to Oxford Languages, is “the action or fact of accepting or yielding to a superior force or to the will or authority of another person.” Part of why I’ve avoided submitting in the past is that it always makes me feel so powerless, so… submissive. But perhaps submitting is also about yielding to the truth that my work isn’t for everybody, just as my style of clothing (I’m newly obsessed with vests.) or taste in music (‘90s country forever!) is off-putting to some.
Okay. New plan. I’m going to approach submissions as an online dating adventure for my writing, and see if I can set my pieces up on some alluring blind dates. After all, it’s way better to imagine my story sipping wine at a candlelit Italian restaurant than drowning in a “slush pile.” First step: submit this essay on submitting.
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