Reflections on an Unusual Short Story Competition
Planning, drafting, and editing a 2,500-word story in one week for the NYC Midnight Short Story Challenge
💡 If you’re looking to improve your storytelling or overcome perfectionism, you’ll find this one useful.
This past week, I took part in the 2024 NYC Midnight Short Story Challenge.
In this competition, you only have one week to write the best story possible with a maximum word-count of 2,500.
But there’s a catch…
Every entrant gets assigned a genre, subject, and a specific trait that one of their characters must have.
If you’re an over-writer, and/or struggle with perfectionism, you’ll hopefully agree this is a great way to work through those bad habits.
The assignments were announced on a long list of all the entrants. Since my surname is Westacott, I had to scroll all the way to the bottom, highlighting just how many writers were competing.
Scrolling through around 6,000 entrants, I wasn’t getting my hopes up too high. When I found my assignment next to my name at the bottom of the list, my chances got even slimmer.
My assignment was:
Genre — Comedy
Subject — Bromance
Character Trait — Ex-smoker.
This is about as far out my comfort zone as I could be taken. Not only have I never written comedy, I don’t read much of it either. A funny ‘bromance’ is also a severe change of pace for me as a writer.
A tough challenge, to say the least. But, actually, it wasn’t as difficult as I was expecting.
Here are some insights from working through the process of planning, drafting, and editing a 2,500-word short story in one week for the competition:
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How to Write Outside Your Comfort Zone
When I first saw my assignment, I was a bit disheartened. But I quickly recalled some advice I’d once read from comedy genius Judd Apatow.
To paraphrase, it goes something like this:
Don’t approach comedy by trying to write a funny story. Most great comedies could also pass for dramas if you read them through a different lens. Just focus on writing a good story first and foremost.
Give your protagonist relatable character flaws, put them up against plenty of conflict and antagonistic forces, and use their frustrating circumstances and misfortune to generate humour.
Approaching the challenge without focusing too much on the comedy aspect, just trying to write a good story, removed a huge obstacle for me early on in the process.
Use “Write What You Know” as Leverage
Since the competition only allowed one week to write your story, I felt it was critical to follow the timeless advice of “write what you know” to expedite the process.
A bromance had to be a key driver of the plot, so I searched my brain for personal experiences with bromances, ideally ones that could be seen as funny.
In October, I went to my girlfriend’s best friend’s wedding, and ended up making friends with a nice guy from Wigan who was about 20 years older than me. We spent most of the night chatting, and my girlfriend found it hilarious because we were a bit of an odd couple. At the time, I figured it could make an interesting short story one day.
So, I leveraged this recent experience as the basis of my story, which gave me a valuable head-start and made the writing process easier.
Start with Character
A character-driven story is usually more engaging than a plot-driven one.
So, I decided to use my assigned character trait — ex-smoker — as a fundamental flaw for my protagonist.
This gave me lots of opportunities to challenge the protagonist with antagonistic forces and conflict, which are essential to a compelling short story.
An ex-smoker stuck in a situation where they’re constantly tempted to smoke is a great way to build tension (and humour, in this case).
That helped me tie my assigned subject directly to my protagonist’s character trait, which should make the story a strong entry in the context of the competition’s rules.
Select the Most Effective Structure
I feel you should always select a narrative structure that enhances the story you’re going to tell. This creates the best possible reading experience for the audience.
So, I chose to structure this story in a Fichtean Curve.
A Fichtean Curve begins with an inciting incident, then follows a series of escalating crises, each one building more tension. This all leads to a climax at the apex of the curve, followed by a short section for falling action at the end.
I chose this structure because it felt like the best way to build rising tension for someone trying to resist temptation to smoke in an uncomfortable situation. His frustration keeps intensifying with each crisis until he reaches breaking point.
Keep it Simple
For the past few months, I’ve been taking a break from my novel to write short stories.
As part of this exercise, I’ve spent a lot of time studying the vital components of a compelling, effective short story. From all that research, I’ve built a pretty comprehensive checklist for planning my stories out.
I used this planning document to plan my story on the first day of the competition.
Remember, when planning a short story, keeping it simple is almost always the best approach.
Don’t over-complicate things, don’t include more than two or three characters, get to the action immediately, stick to one core, focused idea, etc.
Edit Ruthlessly
Once I had my plan in place, I wrote out all the story beats in bullet points, giving me an initial outline.
On the Monday, I took that set of rough bullet points and expanded each one in the correct narrative voice and point-of-view.
Narrative point-of-view and tense should be chosen to enhance the story and give the reader a better experience, just like narrative structure.
I chose to write in first-person, present-tense, placing the reader directly in the protagonist’s perspective. This will make the reader feel as immersed in the situation as possible and create a sense of urgency to enhance the rising tension.
Expanding on those story beats until they formed a cohesive narrative, my first draft came in around 3,600 words two days later.
I reviewed that rough first draft against my story plan to ensure it all aligned with the story I was trying to tell.
I then printed the draft and edited it with a red pen, as I do with all my draft short stories, novel chapters, etc. Editing a printed version of your drafts on paper is so much easier than trying to edit on a laptop, in my opinion.
Naturally, I’m a terrible over-writer. It’s one of the reasons I’ve paused my novel, to practice being more concise with short stories. With that in mind, the hardest thing about the editing process for me was cutting my story down to 2,500 words.
I was really happy with a penultimate draft that reached around 2,900 words, but I think the final draft (at 2,492 words) was actually stronger.
The lesson here? Edit ruthlessly, beyond what feels natural.
Even when you've edited your story extensively, and you’re really happy with the draft, there’s almost always some more dead weight that can be cut.
Ignore the instinct that tells you to explain a not-so-important point in full detail, or leave in that long passage of description that does nothing to advance the plot.
Just because it’s well written, doesn’t mean it should be kept in your final draft.
Every sentence in a short story should either:
Drive the story forward
Reveal something important about the character
Reinforce the theme.
Or, ideally, a combination of the three. Anything else is redundant.
What Next?
Planning, writing, editing, and submitting a 2,500-word short story in one week was a big achievement for me.
The last short story I wrote took me around three months. I tend to spend too much time planning, and my perfectionism usually compels me to revise my drafts an excessive number of times.
But participating in this competition has achieved exactly what I’d hoped it would. I’ve proved (to myself) it’s possible to produce a good story in one week.
I’ll now replicate the process to help me write my next short stories much quicker than usual.
Finding Creative Ways to Improve
This NYC Midnight Short Story Challenge was such a valuable learning experience.
Their next short story competition won’t begin now until January next year. But my writing group and I are going to use the same format and hold our own version of the challenge amongst ourselves later this year.
Give it a try if you have a group of writers you can do that with. Just place a selection of assignments — genre, subject, and character trait — in a hat and pick them out at random.
I’ll share the story I submitted here when the competition allows us to, for anyone who’s interested.
In the mean-time, please consider subscribing if you found this interesting or useful.