The Obsessive List Approach: How to Write a Winning Short Story
Written by Lori Twining
Editor’s note: Lori was a finalist in the Blank Spaces 2021 Fiction Anthology Contest and her story was published in The Things We Leave Behind, released by Chicken House Press on April 30, 2022.
Since being chosen as "one of the lucky ones" to be included in the anthology published by Chicken House Press, I have had a few writers ask me about my process for creating a winning short story.
The question makes me laugh because there are probably 101 different ways to tackle this task, and only a tiny percentage of writers want to attempt it my way: The Obsessive List Approach. I always start with five interrogative or question words: who, what, where, when, and why (not necessarily in that order). Each one gets a whole page where I list things of interest or intrigue out in point-form, so it is easy to cross-reference from one list to the next. Let me explain in more detail:
Last year's theme for the Blank Spaces Literary Magazine short story contest was "The Things We Leave Behind." Here is the breakdown of how I figured out what my story would be about:
WHAT - I thought about those words for a few days while making a list on my yellow legal pad of what kind of things people leave behind. My first list included everything from forgotten items, such as a kid's favourite teddy bear or a suitcase full of cash, to things left behind on purpose, like a pair of ugly shoes or a dead body. I circled the top five items of interest, and in the end, I chose a simple weighted blanket left by her father, and the main character was also left behind by her boyfriend.
WHERE - The second list included all the random places where people leave things behind: hotel rooms, restaurants, the morgue, the playground, the beach, the forest, or sitting on the train tracks. I highlighted the top three places that intrigued me. I gravitated toward a sandy beach—sometimes a vacation destination for the Toronto people—but the story was about the ordinary people living there, working close by, and sometimes needing to deal with extraordinary circumstances.
WHO - The third list included the possible characters involved. One of my favourite topics is the relationship between parents and their children. In my story, I wanted to focus on the mother-daughter connection. There is always so much conflict to draw from when dissecting the bond between different generations of women. The mental anguish of allowing one person to control the other, the advice given, or the advice not taken. When you add in some turmoil and relationship problems, the results could be either challenging or comforting.
WHY - I made the fourth list about the emotions people experience when they realize they have forgotten or left an item of value behind accidentally. I scrutinized people's feelings when the relationship sours and their partner disappears from their life. I added the sentiments of the mean-spirited people who had a crime on their minds and did terrible things for money, greed, or revenge. People do what they do for a reason, which strongly indicates who they are and what they might become.
WHEN - Every story needs to be rooted in time, such as the season, the month, and the year. It can be historical, contemporary, near-futuristic, or millions of light-years in the future. Most of my stories occur in the here-and-now, with a few flashbacks to the past.
As you have noticed, I am obsessive about making lists. After making decisions about the top five "W" questions, I made the sixth list of details regarding everything you might see, hear, smell, taste, and feel while strolling along the sandy beach. I circled the unique ones that someone visiting the town might not notice, but someone who lived there would recognize them as familiar. I sprinkled the facts throughout the story anchoring it into a real-life situation, even though the story was fictional. Details included the temperature on a hot summer day, the kinds of birds who frequent the shoreline, and the plants that grow in sand.
Lastly, I made a bonus list of what people fear besides being left behind. I wanted the main character to overcome another fear, even though her mind and heart were not making the decision unanimously. I gave the daughter one of my personal fears. I have galeophobia, which is a fear of sharks. I currently live near Georgian Bay and Lake Huron, and I grew up on the shores of Lake Erie, so sharks are not something I need to be afraid of in the Great Lakes. However, I cannot shake the fear since I watched the movie, Jaws, at a drive-in when I was a teenager. I was a lifeguard for decades, and I still have anxiety with elevated heart rates, shortness of breath, shaking, sweating, nausea, and dizziness when I am near a large body of open water. I gave all these emotions to my character. The struggle to conquer her fear (and mine) was real.
Therefore, the title, "Fins, Teeth, and Broken Surfboards," came to me naturally after I figured out the daughter's fear of the sharks. Then, I decided that the mother would be a Marine Biologist who surfs and constantly tries to calm her daughter's anxiety about the water. I assigned the mother and daughter a typical situation of dealing with a separation/divorce from their significant others and went with opposite emotions when dealing with the water. It added some common ground between them and some well-placed conflict.
Once I figured out all these things, I could write the story. My first draft came in around 6000-words, and the contest had a maximum of 3000-words—quite a challenging task. There were plenty of edits to do. As the saying goes, the real magic happens in the re-writing of the story. With each passing revision, I better understood what the story would be about, which made it easier to reduce the number of words by cutting sentences that didn't make any difference. I chopped complete scenes out, dismissed unnecessary words, deleted adverbs, reduced adjectives, and changed long phrases to one or two words that meant the same thing.
Overall, I studied the seven lists of random things, circling my favourite ideas, before I found the key ingredients to start mixing words on the page to form the fictitious story. From start to finish, it took approximately one month to create, which included seven days of meticulous editing, to meet the maximum 3000-word count. It seems like a tremendous amount of time to put into one short story, but it was worth it. I have had many people comment about how much they enjoyed reading it, and if they were lying to me, I’m okay with that. At least my self-doubt has disappeared for a few minutes and I am so grateful for that.
My Obsessive List Approach is just one way to develop a short story, but it might help you write something for the next anthology contest, "Small Town Summer Nights," with the deadline of August 31st. I wish you good luck, and I look forward to reading your winning story.
To support Lori’s writing and to read the story that put her in the finalist circle — “Fins, Teeth, and Broken Surfboards” — purchase your copy of The Things We Leave Behind from the CHP bookstore. A Kindle version is available through Amazon and a KOBO version is available through the Kobo store.
Interested in the 2022 Anthology Contest? Learn more HERE.
*this post contains Amazon links - any purchases made through these links returns ad dollars to Chicken House Press
You can listen to Lori sharing a little excerpt from her story in this clip from the winner reveal event. (Beginning at 40:45)
Lori Twining is a writer and storyteller whose work encompasses fiction, nonfiction, and poetry. Her stories appear in various print media, including Blank Spaces Canadian Literary Arts Magazine, Chicken Soup for the Soul: Christmas in Canada, Just Words: Best Canadian Literature, and Nefariam: The Elements of Crime. She’s an active member of many writing groups, such as International Thriller Writers, Crime Writers of Canada, Sisters In Crime, Toronto Romance Writers, and Ascribe Writers. She’s a lover of books, sports, and bird watching; and a hater of slithering reptiles and beady-eyed rodents. You can learn more about Lori at www.lvtwriter.com and/or www.ascribewriters.com.