Skip to main content

Meet Short Short Story Competition Winner Gregory Jeffers

The winner of the 20th Annual Writer’s Digest Short Short Story Competition reveals his strategies for writing award-winning short fiction.

When returning to the Puerto Rican island Vieques after Hurricane Maria, Gregory Jeffers noticed not only the horrific destruction left by the storm; he also saw things around him starting to sprout back to life. The scenes were so inspiring that he wove the imagery into his short story, “Quitting Time.”

“A fourth horse limped into view and stood under a hurricane-bonsaied mango that once probably towered sixty feet. Its new leaves sprouted in bobs the size of beach balls,” he writes.

“Quitting Time” is a tale of destruction and rebirth set on Vieques after the hurricane. It explores the power of the natural world to cure itself and some human miseries, as well as shed light on larger existential questions. It won first place in the 20th Annual Writer’s Digest Short Short Story Competition.

Read Jeffers' winning short story.

Jeffers’ winnings include $3,000 and a pass to the Writer’s Digest Annual Conference.

Jeffers has been visiting the island for more than 30 years, so he is pretty familiar with the natural world there. He was originally brought to the island—and many other settings that have inspired his writing—by his work as a contractor for the construction industry. 

Another work setting that has inspired Jeffers to write stories is an old orphanage in Vermont. The four days he spent evaluating the building conjured up the sounds and smells of 1880, and along with it, inspiration for a novel he wrote about a person in a similar situation being visited by a young ghost from that time period. 

“It turns into a parallel storyline, the changes that occur in this man and the other tale of the young woman and her siblings as orphans in 1880. The two stories converge in a horrifically magical way,” he says. But, “it’s a very complicated piece and that’s why it’s still not published.” 

Jeffers turned to writing short stories when an editor he sent a draft of his novel to suggested that he try writing short stories to perfect his craft. He found that short fiction is a good practice in learning to honor readers’ time. His editing—whether for short stories or novel writing—focuses mostly on reduction.

He says the challenge of flash fiction is making a piece a story, not just presenting a situation that ends in a joke.

“It seems like a lot of flash fiction is a situation looking for a punchline,” Jeffers says. “To make a story whole, the story needs an arc and character. That’s difficult in a short work. The people that are best at it are the folks that have the ability to create the iceberg, with 10 percent of the story showing up and the other 90 percent below the water.”

To overcome the challenge of coming up with ideas for short stories, Jeffers keeps a list of every idea that comes to his mind. He jots many of these ideas onto notecards that he uses to generate story ideas. He categorizes these cards into three sets. The first is a list of settings.

“It can be anything as broad as the word prehistoric to something more specific like Sherwood Forest,” he says.

The second set of cards lists characters, and the third lists story genres. When he is ready to begin a story, Jeffers picks a card from each pile and puts them together. 

Jeffers admits that story endings are also hard for him to pin down. He tries to focus on two things that signal resolution: a change in character or circumstances, or a signal that change is within reach; and the rhythm of the sentences.

“It has more to do with syntax and how the words are put together and the length of sentences,” he says. “The best way to say it is that it’s a rhythmic quality to the ending. That can help signal the story has some kind of resolution.”

See the official 20th Annual Short Short Story Competition winner list.

Going From Me to We: Collaborating on the Writing of a Novel

Going From Me to We: Collaborating on the Writing of a Novel

Past experiences taught bestselling author Alan Russell to tread lightly when it came to collaborating on projects. Here, he discusses how the right person and the right story helped him go from a “me” to a “we.”

From Script

Short Film Goals, Writing the Cinematic Experience on the Page and Sundance Film Festival 2022 (From Script)

In this week’s round up brought to us by Script magazine, set your creative goals with a monthly guide to write and produce your short film, provided by Script contributor Rebecca Norris Resnick. Plus, an exclusive interview with Academy Award-winning screenwriter William Monahan, a Sundance Film Festival 2022 day one recap, and more!

Your Story Writing Prompts

94 Your Story Writing Prompts

Due to popular demand, we've assembled all the Your Story writing prompts on in one post. Click the link to find each prompt, the winners, and more.

How Inspiration and Research Shape a Novel

How Inspiration and Research Shape a Novel

Historical fiction relies on research to help a story’s authenticity—but it can also lead to developments in the story itself. Here, author Lora Davies discusses how inspiration and research helped shape her new novel, The Widow’s Last Secret.

Poetic Forms

Saraband: Poetic Forms

Poetic Form Fridays are made to share various poetic forms. This week, we look at the saraband, a septet (or seven-line) form based on a forbidden dance.

Karen Hamilton: On Cause and Effect

Karen Hamilton: On Cause and Effect

International bestselling author Karen Hamilton discusses the “then and now” format of her new domestic thriller, The Ex-Husband.

Plot Twist Story Prompts: The Ultimatum

Plot Twist Story Prompts: The Ultimatum

Every good story needs a nice (or not so nice) turn or two to keep it interesting. This week, have a character give or face an ultimatum.

6 Things Every Writer Should Know About Sylvia Beach and Shakespeare and Company

6 Things Every Writer Should Know About Sylvia Beach and Shakespeare and Company

Sylvia Beach was friend to many writers who wrote what we consider classics today. Here, author Kerri Maher shares six things everyone should know about her and Shakespeare and Company.

How Writers Can Apply Business Tools to Their Writing

How Writers Can Apply Business Tools to Their Writing

Author Katherine Quevedo takes an analytical look at the creative process in hopes to help other writers find writing success.