Kelsey Stewart: 26th Annual Writer’s Digest Short Short Story Awards Winner

I’ve been writing casually since I was a child, but I only started taking it seriously about two years ago when I entered the creative writing master’s program at Harvard. Before that, writing was always something I loved, but it existed more privately. The program forced me to approach it with real intention instead of treating it as something I only did when inspiration randomly struck. That was the point where I began devoting more than just casual time, thinking seriously about craft, structure, and voice. It shifted writing from simply a personal outlet to something committed.

Short short fiction is both terrifying and completely freeing. You can kiss Freytag’s Pyramid goodbye and abandon the idea that every story needs a perfectly engineered arc. Instead, you can dip into a feeling, a voice, or a single strange character and let it consume the page entirely. The piece becomes less about plot and more about atmosphere, obsession, or emotional residue.

I love that compression. A short short can function almost like an essay or a poem. It allows ambiguity and trusts the reader.

“In Case” is actually a very personal story for me, unlike so many I have written. When I married my husband, he had full-time custody of two children, and I stepped immediately into a mothering role: PTA meetings, team mom duties, packed lunches, the whole domestic relay race. You think this kind of role will be read as selfless, maybe even heroic, but the reality is much messier. There are expectations placed on you, complicated feelings from the children that vary from child to child, and new pressures on the marriage itself. There are no more fun dates for you—only permission slips and dinner negotiations.

I’ve also found that teachers, parents, and other adults respond to step-parenting in wildly different ways. Some people seem offended that you would try to occupy a serious place in a child’s life as a step-parent. Others assume you are one bad bedtime decision away from becoming a Disney villain origin story. Some are deeply condescending while still expecting the world from you.

Recently, I’ve been writing from those experiences and feelings, and it has been fruitful—not only creatively, but emotionally. It feels almost like a diary, or a therapy session: a way to get the gross, complicated feelings out of my body before I start abusing Häagen-Dazs.

I’m the worst person to ask about drafting and revision because my process is painfully slow and probably deeply unhealthy. I move paragraph by paragraph, sentence by sentence, and I usually refuse to continue until I’m satisfied with what’s already on the page. Every workshop professor on earth will tell you this is a terrible way to write. They always say to get the draft down first and revise later. In theory, I completely understand that advice. In practice, I am apparently incapable of following it.

I’m too much of a perfectionist. I obsess over rhythm, tone, and whether a joke lands before I can emotionally move on to the next paragraph. The upside is that, by the time I reach the end of a piece, I usually have less large-scale editing to do because I’ve been actively revising the entire time as I write. The downside is that it takes forever and occasionally feels like building a house one molecule at a time.

So, I am truly a horrible example, and anyone reading this interview should probably do the opposite of whatever I do.

Over the past few years, my professors have encouraged me to start submitting my work to competitions whenever I felt genuinely proud of a piece. At first, I mostly did it to push myself to stop hoarding my work on my laptop. I’ve been honestly shocked by the response. Truly. I don’t really come from a background where I’m used to “winning things,” so every acceptance, placement, or encouraging email still feels slightly surreal to me.

I honestly entered this one on a lark, assuming it was completely unrealistic that anything would come of it. The story felt deeply personal to me, and because of that, I worried it might also be too emotionally tangled for other people to fully connect with. Sometimes the pieces closest to you are the hardest to judge objectively. Needless to say, I was extremely surprised to open my inbox and see an email from Writer’s Digest. It was one of those surreal moments where you reread the message several times because you’re convinced you must have misunderstood it the first time.

Read. Read constantly, and read outside of your comfort zone. Read genres you think you dislike. Read things that initially feel “not for you.” Some of the most useful lessons come from books you would never naturally pick up on your own. I also highly recommend reading craft books, especially writers like George Saunders and Steve Almond, because they talk about writing in a way that feels practical, generous, and alive rather than overly academic.

And try writing in different genres, too. Your writing voice may actually belong somewhere completely different from your reading taste. I think a lot of writers assume the books they enjoy reading most are automatically the books they’re meant to write, and that’s not always true.

Carol took her time accepting that she was an evil stepmother.

She had the makings of a sympathetic prequel: a career abandoned, a life rerouted. But a stepdaughter, hands soft from an iPad and a lack of chores, was steadily draining her. Emma’s real mother, gone by way of abandonment—a decision that made more sense to Carol the longer she lived among them, leaving Carol to explain, repeatedly, to dentists and pediatricians why a stepmother had been placed in charge of matters like fluoride.

After a particularly sour review involving a forgotten Elf on the Shelf, Carol sat in a large armchair near the back door with a book. The washing machine sang its lengthy tune, beckoning her to move the clothes to the dryer before they soured, and Paul sat in the living room watching cartoons with Emma, laughing along at the appropriate moments.

Carol would be expected to make love to him. But she still had time.

The fridge opened and closed. The grunt of a small person lifting something too large. Something falling. Then the unmistakable glug glug glug. Rivers of white trailed across the wood floors and pooled beneath the dishwasher. Emma grinned, daring Carol to say something.

“What’s wrong, sweetheart?” Paul asked.

“Carol dropped the milk on me,” she wailed.

Carol knew better than to engage a terrorist in Elmo pajamas.

Paul sighed with the weary authority of a man convinced he carried the family alone, despite not knowing how to make spaghetti. Carol let the anger settle into a dull ache at her temple, then perched on the living room sofa, aggressively ticking items off her daily agenda.

She stared at the word laundry.

Let it sour.

Half-hour increments of grating character voices dragged on. Later and later, on a school night. Eight thirty. Nine thirty. Ten thirty. Popcorn was popped. Carol sighed. Emma would be a nightmare to wake in the morning. At eleven thirty, Paul met her at the fridge, she held up her phone and pointed at the time. Paul only grinned, pouring M&M’s into the popcorn.

Carol leaned back against the refrigerator, sending a small piece of paper skittering across the floor. She had forgotten. The holiday play—specifically not a Christmas play. Emma was supposed to be a snowflake. An angel? She couldn’t remember whether the school provided costumes or whether she was expected to.

As Paul returned to the sofa, Emma grabbed a handful of popcorn, chocolate melting across her palm. She met Carol’s eyes and wiped it onto the back of the couch. Eventually, Emma’s head sank toward her chest, and Paul carried her to bed. He came downstairs to review the day.

“You know,” he said, and Carol shifted, “She was pretty upset about the milk. You could have apologized.”

“I didn’t do anything,” Carol said. “She dropped it herself.”

“Even so, she wouldn’t have needed to get the milk if you’d been more attentive.”

Carol tried to respond. Nothing useful came out.

“This isn’t how I thought this would go.”

Carol wasn’t sure whether he meant the evening or the marriage.

After clinical lovemaking, Paul rolled over and slept. Carol rubbed the awful birthday cake–scented lotion her mother-in-law had given her into the cracks in her hands and feet. It had come as part of a set—the kind of present you give someone you don’t really know or don’t particularly like. Birthday cake scents were usually on sale. Carol wiped her greasy hands on one of Paul’s shirts strewn beside the bed. Dry cleaner tomorrow, she thought, then lay back.

By morning, it was as bad as she had predicted. She lightly barbed Paul about keeping Emma up too late as he grabbed his briefcase and left, kissing the top of her head in a priestly gesture.

“Don’t be so negative first thing in the morning,” he said. “You’re exhausting.”

After he left, Carol rubbed her arm where Emma had kicked her for waking her. She refused to brush her teeth. She dumped out a toy chest for good measure. Carol retreated to the kitchen, but Emma marched in and threw a shirt in Carol’s face, complaining that it hadn’t been washed.

Carol realized then that she didn’t have to make pancakes. She thought of the mother in the Eggo waffle commercials: perky, pleasant, heroic. The kind who only rolled her eyes when her kids skateboarded through the kitchen. Carol went to the fridge. Strawberry yogurt. She reached into the cabinet for cereal. Emma knew where the silverware drawer was. She knew how to spray juice across the counter, trying to force straws into Capri Suns.

At 7:35, Emma came into the kitchen, hair wild. She looked at the bowl. No one spoke. Emma reached for the fridge handle. She spilled milk. No one apologized.

At school drop-off, Emma shoved open the car door. As Carol was about to pull away, a hand waved in her direction, followed by a neon vest. Carol rolled down her window.

“Hiiii,” the woman—Emma’s teacher—said slowly.

“Hi.”

“Look,” she said, lowering her voice, “I realize you aren’t Emma’s real mom.”

Carol waited.

“I just want to make sure I’m talking to the right person. To handle these matters.”

“You can talk to me,” Carol said.

“Great,” the woman said quickly. “It’s just—the holiday play is a big deal.”

Carol waited.

“And Emma hasn’t had her costume for rehearsals.”

“I see.”

“The other mothers understand,” the woman said. “The children look forward to it all year.”

“Do they.”

“Yes. It’s the highlight of their—Christmas,” she corrected herself. “Holiday season.”

The sounds of aggravated drivers rose behind them.

“I’ll just send the information home,” the woman said. “In case.”

Carol nodded.

At the grocery store, Carol went straight to the freezer cases. Waffles. Nuggets. She did not linger in produce. She did not touch anything that required washing. At checkout, she forgot which credit card she was supposed to be using that month and used the debit card instead. She had no idea the balance. They could be on the verge of losing the house.

The goth checkout girl printed the receipt and held it out.

Carol took it. She folded it once.

That evening, Paul and Emma ate floppy microwaved chicken nuggets and pushed peas around their plates. Emma dragged her finger through the ketchup and wiped it on the table. Dinner conversation involved the holiday play. Carol listened for hints about whether Emma was a snowflake or an angel, then found herself tuning in and out.

While Paul went upstairs to read to Emma, Carol completed a forgotten math worksheet in crayon, using her left hand to imitate the numbers. When he came back downstairs, he sat at the kitchen table while Carol rinsed the dinner dishes.

“Emma seemed off tonight,” he said. “She mentioned breakfast. I just think consistency matters.”

Carol nodded. She dried her hands on a dish towel. The folded receipt made a hard edge in her pocket.

“This isn’t meant to be a criticism. I just want us to be on the same page.”

Carol reached into her pocket and set the receipt on the counter beside the sink.

“You don’t have anything to say?” he asked.

“Not really.”

That night, Paul reached for her and fell asleep before she decided what to do. She reached for the lotion and put some on her hands.

The next morning, Carol stood over the lunchbox—unicorn. She looked at the white bread. The star cookie cutter. The heart. Bread was already a shape, she decided. She put the uncut sandwich into a bag. Chips, portioned by Lay’s. Two pudding cups. She picked up the notepad where she usually wrote Have a good day and found herself without anything to say.

By afternoon, Carol was sitting in the dry cleaner’s parking lot when her phone rang. The school number was programmed into her phone. She assumed it was the nurse.

“Hi there. I’m Sandra Pinkerton, the school counselor.”

“Hi.”

“First, I just want to say how supportive we are of stepparents. It takes a village.”

“Sure.”

“Transitions can be hard for kiddos,” she continued.

Carol waited, aware that the woman was not asking a question.

“I wanted to check in about lunch today.”

“Her lunch?”

“Some of it was prepackaged.”

“OK.”

“We’ve found that food choices can affect focus,” she said. “Most of the mothers pack something fresh.”

Carol waited.

The counselor said she’d send the list home, in case.

That night, when the dishes were done, the CPAP machine was already humming. Carol turned on her bedside lamp. Paul didn’t stir. She opened the drawer for lotion and found the tube empty—just a putter of air, a small spurt. She shook the tube, then it slipped from her hand and rolled behind the bedside table.

She did not reach for it.

Maybe it would disappear. Like socks.

In the kitchen, the receipt lay where she had placed it.