The Power of the Prompt

March 28, 2022 § 5 Comments

By Colleen Kinder

I’m one of those writing teachers who swears by prompts. Narrative directives like, “Write about a childhood memory, set in a car.” or “Begin every single sentence with ‘I remember.’” (Hat tip, Joe Brainard). “Write an apology letter to a place.” 500 words, tops. Ready-set-go.

Usually, the more specific the prompt, the more magnificent the outcome. Students I would not have called exceptional writers burst out with essayettes I’ll remember for years. In ten minutes, they slide under the spell of voices so unmistakably their own, grounded in the radiant particulars of their lives. Again and again, it astonishes me: how writing students churn out their finest, most strident work when forced to create inside what seems like a box. All I have to do is design the walls of the container, then flip over the egg timer. Go.

I know teachers who take these constraint principles even further, assigning lipograms—essays or poems in which only one vowel is fair game—and pushing students to the point of exasperation, to the sense of handicap, which only disarms them for amazement at what they improbably produce.

“I’m jealous of your prompts!” I’ve joked many times to my students, because I’m one of those writers who chronically craves more time, more space. When I start a writing project, I easily get lost in it for years, paying zero heed to my snow-balling word count let alone the modest figures in my bank account. In short: I’ve always known, deep down, that the very creative limits I dole out to pupils would do me good.

Seven years ago, I finally acted on that hunch. What if “the prompt” wasn’t such a rudimentary tool, exclusively impactful in the classroom? Perhaps other writers also stood to benefit from some creative straightjacketing. When I asked around, my peers responded to these questions and theories with some version of “Amen,” or “yes, please.” With their help, I co-founded a literary magazine, Off Assignment, whose every column is rooted in a specific prompt.

Of all our early columns, “Letter to a Stranger” was the mightiest, the most universally generative. Write a letter to someone you’ve met in passing but still think about, we challenged writers. Write it in letter form, in the second person. 800-1200 words was the sweet spot, we said, setting a deadline that was arbitrary, but a deadline nonetheless.

Leslie Jamison was the first writer to submit a “Letter to a Stranger” essay. “Immediately, I knew the stranger I would write about: a one-legged traveling magician I’d crossed paths with several times when I lived in Nicaragua,” Jamison writes in the Foreword to Letter to a Stranger: Essays to the Ones Who Haunt Us (Algonquin Books, March 2022), a collection inspired by this flagship column. Like so many writers I’ve by now worked with on “Letter to a Stranger” essays, Leslie didn’t have to mull the prompt over—not for a month, or a day. Memory had done the work of distilling the scene, casting a strobe light on that one, glinting figure.

“Honestly I didn’t really know what [my letter] would be about,” Jamison goes on. “I just knew it would be a letter to him. And when I wrote it, several weeks later, it came out dark and gleaming and alive, as if it had already existed inside of me, fully formed. A secret stowaway. It just needed a home. The invitation of a letter had given it a home. This invitation said: Write to this man, even if you don’t know why you want to. It said: Write into that mystery.”

Another letter, from Lavinia Spalding, rolled in shortly after—a focused and searing account of a dalliance on a Thai beach. As for journalist Ted Conover, he sort of already had a “Letter to a Stranger” in progress, a side-story jotted down while on a New Yorker assignment in Rwanda almost twenty years earlier.

These seminal letters, published in the inaugural batch of essays in Off Assignment’s “Letter to a Stranger” column, opened the floodgates for hundreds more missives. Stories about missed connections and near-death scrapes; stories featuring gamblers and widows and DHL drivers; scenes set in the northern reaches of Norway, the rainstorms of Benin, Caracas at night, the South Pacific at age 22. 

The letter, it turned out, was the perfect vessel for these particular tales: a form brief and intimate, one keen on collapsing distance. What electrified Off Assignment early on was the sense that we’d found a literary shape that corresponded with a species of story already alive inside the writer. The letter form works like a whispered summons, coaxing out the long-dormant story. Come out. Here’s your place. Come, ghost: fill this nook out here in the world. If you’re going to haunt so persistently, then haunt us all. 

I no longer worry that we might exhaust the form of the “Letter to a Stranger,” thanks to the endless parade of writers who have since walloped me with surprises, bending our prompt in fresh ways. Writers like Anna Vodicka, who wrote not to one stranger, but to a room full of them at a Bolivian hostel; and Rachel Yoder, who penned a letter to the man who stalked her in high school, a fuming missive that felt destined for our collection, and yet entirely unforeseen.

I learned so much from editing the 65 essays that comprise Letter to a Stranger: Essays to the Ones Who Haunt Us: namely, that any nagging ghost makes for a glorious muse; that memory goes to work on the rough drafts of our pasts like a ruthless editor, whittling them down until all we see clearly are the scenes that glint with significance; and that there’s a great kingdom of narrative at the terminus of a simple, specific question: “Who haunts you?”

I’m convinced now that we “seasoned professionals” often need a dose of the medicine we prescribe to our apprentices. When our students amaze us with their output and their focus, their sudden lyricism and the singularity of their sentences, we’re wise to pay heed to what triggered it: those narrow instructions that sent them right on their way.


Colleen Kinder is an essayist whose work has appeared in The New York Times Magazine, The New Republic, National Geographic Traveler, Virginia Quarterly Review, AFAR,, Los Angeles Review of Books, Creative Nonfiction, A Public Space, and The Best American Travel Writing. She is the editor of the forthcoming anthology Letter to a Stranger: Essays to the Ones Who Haunt Us (Algonquin Books, 2022), and the co-founder of the nonprofit magazine Off Assignment. A former Fulbright scholar and MacDowell fellow, Kinder has taught writing at Yale University, the Chautauqua Institution, and Semester at Sea.

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