It’s all in the title. I thought I had trained well for this particular contest. I haven’t done a list in a while. This one is short, but makes for a great jumping off point.
Background: This past weekend, I was busy writing a short story for the 2nd round of the 2019 NYC Midnight Short Story Challenge. Each writer in the challenge is given three things to incorporate into their stories; a genre, a character, a subject. We were then given 72 hours turnaround time to submit a 2,000 word maximum short story to the contest. Round 1 of the contest whittled the pool of writers down from about 4,900 to the 750 writers who took part in this past weekend’s 2nd round.
Reasons Why I Should Have Aced the NYC Midnight Short Story Challenge
- I took part in the Trafalgar24 Play Creation Festival in Whitby, Ontario SIX TIMES. In this festival, the playwrights are locked inside a castle for 8 hours. In that time, they each have to create a 10-minute play that will be performed in front of six rotating audiences the very next evening
- I took part in the Muskoka Novel Marathon in Huntsville, Ontario TEN TIMES. In this marathon, the writers are locked inside a room for 72 hours. In that time, they each have to create a full novel that will be judged by industry professionals in the months immediately following the marathon.

That’s it. That’s my list. I was so certain that those two things were enough to get me into the shape I needed to be in to pown this NYC Midnight thing. Or is it pwn? Either way, I thought I was going to ace this.

I have always said that of all the writing assignments a creative writer could have, the short story is the hardest. I have pounded out novels in one sitting TEN TIMES now. I’ve written plays while beating the clock multiple times, for various festivals. And the thing that finally got to me, the thing that defeated me, was this short story challenge.
I submitted with one hour and fifteen minutes to spare. It was a 72hr time frame for 2,000 words. I’m not a mathematical genius or anything, but that’s a far cry from writing 50,000 words in the same number of hours at the Muskoka Novel Marathon. Let’s see…carry the one, add the 3, subtract the 7 and multiply by 11 and what do you get? 694.44 words and hour for the MNM and 27.77 words an hour for the NYC Midnight challenge. The pressure should be stronger at the MNM, shouldn’t it?
Above are pictures from one of the many Muskoka Novel Marathons that I have participated in over the years. 40 writers + 72hrs = 40 novels! AND, we typically raise $30,000+ for area literacy programs each and every year.
Sadly, it doesn’t work that way. The real secret about the comparison between the short story and the novel is that you have to fit the exact same amount of story into each receptacle. And that’s only one of the factors going into my perceived failure this past weekend. You well and truly need to get the whole story into a short story…squeeze 50,000 words into its itty bitty living space and condense them down to 2,000 (or 2,500 , or 3,000 or whatever your limit is). This is not an easy task, and to go into it thinking it is an easy task is folly. The takeaway lesson should be—never be cocky about your ability as a writer. Every challenge is another series of wrenches thrown at you. You’re never ready for hurled wrenches…don’t make the mistake of thinking you are.
So, to review, NOTHING can prepare a writer for an on-the-spot writing challenge. I guess that’s why these contests work so well. It’s an amazing feeling when you push yourself to take a leap into the unknown. And I guess the thought behind the NYC Midnight challenge is… a writer is a writer is a writer. Any good one should be able to take what they’re given and pump out a result that is both entertaining and worthy of a read.
Boy, did I struggle with this one. It doesn’t matter whether you read regularly in every genre or not. If you’re not comfortable writing in each of them and you’re tasked to take one of them on…it’s bound to be difficult. That’s the thing that got me this weekend. By the luck of the draw I received a genre to write in that I have read voraciously over the years, but never once wrote it. I was afloat on a sea of confused desperation for the past 72 hours.
We shall see how this round of the challenge goes. If anything, I’m thrilled to have made the first cut. I can’t imagine that it’s an easy task to move forward in this challenge. I did it, and I should be happy about that. It’s all I can ask for.
To all those who pushed themselves to enter the challenge, congratulations! You took a leap and I guarantee you it made you a better writer. To those of you who moved forward into round two with me, even more congratulations! You did it. That’s an amazing achievement in itself. I wish all 749 of you the best of luck in this next round of judging! If a miracle should occur, I might see some of you in the 3rd and final round. But if not, do your best. You got this!