This year I entered NYC Midnight’s Short Story Challenge. I’d heard about NYC Midnight before, but I’d never entered any of their writing contests. The entry fee is pretty steep, and they’re really competitive. But with a little bullying encouragement from my mom, I decided to enter.
Before we go any futher: I am not sponsored by NYC Midnight, or anyone. (Pilot Pens, HMU. I will shill for the Juice Up 04 until the day I die.) I just wanted to share my experience with this contest.
The entry fee $69, the highest I’ve seen for a writing contest. On the flip side, the 1st place for 2026 is $8,500, which I think is also the highest prize amount I’ve ever seen. Two percent of your entry fee goes to charity, and you could choose between Doctors Without Borders, Little Free Library, the Natural Resources Defense Council, Save the Children, and World Central Kitchen.
NYC Midnight doesn’t work like most writing contests. There are multiple rounds, and you can’t submit just anything. You’re given an assignment, which determines your genre. Your assignment also includes an object and a character that has to play a significant role in the story. For the first round, assigned genre was fairytale, my object was “donation,” and my character was a tastemaker.
At first I thought I’d lucked out with the genre. I love fairytales and other forms of traditional literature — folklore, fables, myths, legends, the stories that get passed down from generation to generation. Fairytales also have a rigid structure. It was a good start to the contest for me. However, I wasn’t sure what to do with a “donation” and a “tastemaker.”
I only had a week to figure it out and turn it into a workable story. My first step was mind mapping. Mind maps are really great tools that I’ve used for a lot of things. I really recommend it for creative writers. I did three mind maps: one for the genre, one for the object, and one for the character. After my paper was filled up, I decided which bubble on the map felt right, and started connecting them. Once I had that, I wrote a couple paragraphs outlining the story.
My outline had a beginning, a middle, and an end, and included everything that was required. Even so, I knew it was missing something. I reviewed it with my friend Liz, who is an artist, writer, and fairytale aficionado. She helped me figure out what I was missing: the harsh lesson where the main character learns the error of her ways.
Once I had the plot mostly figured out, it was time to write. I finished a draft, read it over, and re-wrote it. Finished a second draft. I won’t say that I was “happy” with it, but I was satisfied.
However, I started hating the story. Everything about it was wrong, weak, terrible. There was no way this was going to win. It was awful. I had only seven days to complete Round 1, and I was pounding away on this story through lunch breaks and after dinner. It was the worst thing that I’d ever written, and needed to be thrown into a well.
But that’s not really the truth. The truth was that I had written it in a short amount of time, and I had no time to let it rest after drafting it. When I finish writing something, I usually let it rest for 2 -6 weeks before I edit. That way, I can come back to it with fresh eyes and less self-loathing. I didn’t have that luxury with this story. I was spending all my free time with it, writing and re-writing, to make the plot stronger while trimming down the word count. Finally, on the last day, I formatted the story and was ready to submit.
Before I did, though, I double-checked the submission rules to make sure I hadn’t missed anything. And I had missed something big. I’d thought the word limit was 2,500. It was actually 2,000. Oh dear God. I was 100 words over the limit. I’d be disqualified on the spot.
I spent the next two hours poring over every word on the page, analyzing every word to decide which ones could be exorcised. I re-wrote entire passages, then re-wrote those re-writes. Every author deals with a certain amount of writing-related hardship, whether it’s a deadline or an editor. But this was an exercise in creative misery like none I’ve ever experienced before.
When I finally—finally—had my word count down to a little less than 2,000, I submitted my story. I threw out all my notes for it because I couldn’t bear to look at them anymore, took a shot of whisky, and swore I wasn’t going to write for a whole week.
I made it about five days of not writing. And they were FABULOUS.
Round 1 had 5,004 contestants, so it took a long time to judge. I wasn’t competing against 5,000 other people, though. I was only competing against the 30ish people who had the same fairytale assignment as I did. If I made it to the Top 5 in my group, I would move on to Round 2.
I didn’t get the results for Round 1 until early April. I was fine with that. I never wanted to look at this story again.
When April rolled around, I stayed up until midnight to see the results. I told myself to be prepared for disappointment. Since I began submitting stories for publication, I’ve received way, way more rejection letters than acceptances.
But I wasn’t rejected. I had made the cut. Not only that — I had placed first in my group! I was ecstatic. It made every hour spent laboring over this story absolutely worth it. I had written something good. I was a good writer. I won because I was a good writer.
I have been telling stories for as long as I can remember. In fifth grade, I discovered poetry. In seventh grade, I discovered fanfiction. In eighth grade, I started thinking about writing as a career. But every writer (except the worst ones, it seems) is plagued by doubts: is this original? Is this the right word? Is this any good, or am I just fooling myself?
To win first place in such a big contest, even if it was only in round 1, was one of the most validating experiences I’ve ever had as a writer.
And then the Round 2 assignments were given out. Once again, I stayed up until midnight to receive mine. I knew it was unlikely that I’d get that lucky with a genre I was so familiar with again.
And I was right. My genre was thriller.
Here’s the thing about thrillers: I don’t read them.
Okay, I have read a handful, two of which you can read about on this blog. While I know what a thriller should look like, it’s not a genre I know the ins and outs of, like fairytales. I also had to include a breaking point and a card player.
I decided to write a YA story, because that’s what I know well. YA stories have to be fast-paced, but they also leave room for overwrought emotions and characters making questionable decisions. I needed both for my story to work.
I went to mind-mapping again, but it wasn’t as helpful as it was before. I was too worried about the genre, and the very short amount of time I had to plan, write, and edit.1 I figured out the role the card players (yes, there were multiple ones now) would have, and decided that the “breaking point” would be literal. I didn’t make an outline, but started with the opening image, and hoped that the rest would come to me as I wrote.
Almost none of this made it into the final version of the story. The only thing that did was the main character’s name.
But I thought it was a good opener, and that it’s a shame to let it waste away, unread, on a forgotten file somewhere. So here is the original intro scene.
If it’s you versus Newton, Newton always wins. That’s the first lesson I learned in archery. As I release the arrow from my bow, I wonder what Isaac Newton would think of me using my physics test as target practice. My arrow skewers the paper and sinks into the bag with a satisfying thunk. I smile, and nock another arrow.
I shoot five more, each further shredding the test. When Kody and I go to retrieve the arrows, the papers fall apart. “Damn, Amber,” he says, nudging a scrap with his foot. “You really hated that test.”
Kody lives out in the boonies, so it’s not a big deal if there’s litter on the ground, but we pick up the papers anyway. I make sure to snag the piece where my score is still partially intact – a whopping 32% – before he can guess what my final grade was.
“Don’t even get me started.” I move the target a few feet up for him, which he rolls his eyes at. I started taking archery classes when I was ten. I thought it was a beautiful sport, graceful and powerful all at once. Kody doesn’t see it that way. A couple years ago he got an idea in his head that he had to be a bad-ass, and so he started practicing with me. To be honest, his attitude is annoying.
In the final version, there’s no Kody, there’s no failed test, and there’s no archery.
As I wrote, things started to take shape. I decided to tell the story non-linearly, which was either a genius or a terrible idea. But the writing was painful. Remember when I said that Round 1 was one of the most validating experiences I’d had as a writer? Round 2 was the opposite. I was back to questioning every word, hating everything I put on the page, and generally feeling like I was the worst writer ever.
If you decided to do this contest, I have two pieces of advice. Use mind maps, and don’t go it alone. Obviously, you’ll be doing the writing by yourself, but I wouldn’t have been able to complete this story without my friends, my husband, and my sister. While my husband and sister helped by leaving me alone and making sure I ate and slept, two friends in particular helped me reach the finish line.
The first was Audrey, who was brave enough to read the raw, unedited first draft. It was 700 words over the limit with a plot hole you could drive a truck through. But heaven-sent Audrey told me she liked it, and really liked the non-linear timeline. From the depths of my despair, I could see the light. I don’t know if I could have found it in my to continue working on the story without that pep talk.
The other was Chanelle, whom I’ve interviewed about her job as an audio describer here. Chanelle is a certified Cool Person who helped me so much with the “breaking point” – now a broken fencing foil rather than an arrow tip. Her fencing experience was invaluable, and she helped edit one of the most critical scenes in the story.
It was a very long, stressful weekend, especially because I work on Sundays. I decided that if I make it to the final round, I might have to call in sick to work. I gave the story one last editing pass on Saturday night, then submitted it around 10 PM.
Then I had a well-deserved cocktail.
Round 2 was a lot harder. While the shortened time frame and smaller word count were the biggest stressors, my first attempts at writing this story didn’t feel like me. But by the time I submitted the story, I had found my voice. Despite everything, the story still felt like something I – and only I – could have written.
The judging was also going to be harder. Some of this is just odds. The people who went over the word limit, didn’t make the deadline, or strayed too far from their assigned genres would have already been eliminated in Round 1. There would be no easy eliminations in Round 2.
The results for Round 2 wouldn’t come out until June, so I had plenty of time to distract myself with work and other projects.
I got the results on June 3. I placed second in my group.
My first reaction should have been joy and excitement. Instead it was a quiet, “oh shit.” I was already anticipating the two days of writing hell that awaited me, but I had an extra challenge that would make writing over the weekend even harder: preparing to sell my house. My house didn’t need to just be clean for photos. It needed to be look like no one lived there at all. Between the contest and the cleaning and packing, there was a real possibility that I would implode from all the stress.
Which is why I was so grateful that I got a straightforward genre for Round 3: romantic comedy.
I’ve watched plenty of rom-coms, so I know the formula pretty well: meet-cute, fall in love, misunderstanding, big romantic gesture, big damn kiss. Keep it light and cute. The assignments are announced at midnight, so I was pretty tired, but I jotted down some dialogue and even the first joke before I went to bed. When I woke up, the joke still made me laugh, so I knew I was on to something.
I still did my mind maps, but they didn’t feel as needed this time. They did help me figure out what I thought was going to be the main conflict between the couple. As I wrote, that changed, but it gave me some direction during the beginning stages of writing.
The stories for the first two rounds were very stressful for me to write, but working on my rom-com became the most relaxing part of my weekend. My husband, Mom, and I spent the weekend furiously cleaning and packing to get my house on the market by the end of the following week. Writing became my escape from the hard, emotional work. I am very grateful to my mom and my husband for respecting my writing time and giving me the time and space I needed to complete the story. I am also grateful that I got a straight-forward genre.
I sent my first draft to my friend Audrey to look at, asking what she liked and if there were any gaps that she saw. Her feedback was helpful, and though her suggestion only added one sentence to the story, it was an important sentence.
I edited, re-edited, and finally gave the story one last look-over before submitting. It felt good to get it in. But it also felt strange. Unlike my first two entries, I didn’t loathe this story with every fiber of my being. In fact, I…kind of liked it? I didn’t even feel the need to take a break from writing after it was in.
This worried me a little bit. I hated my fairytale when I submitted. I still don’t like my thriller, even though I wrote it months ago. But both of those stories got me through the previous rounds. What if writing a story that I liked meant that I wouldn’t succeed in making it to the final round? I know that sounds silly, but are you ever more superstitious than when you’re in a competition?
The results for round 3 were announced in July, and I’d placed fourth in my group. Not as high as I hoped, but I’d still made it to the final round. This was huge. I had started this competition with over 5,000 other writers, and now, there were only 35 left. Including me. To be totally honest, I didn’t think I would make it this far. Of course I hoped that I would, but that felt like a dream.
The final round is different from the previous three. It’s open genre, which means that you can write whatever genre you want, or even blend them, which was discouraged in previous rounds. Everyone got the same subject and character. This year, it was overindulgence, and an ingrate. It’s also the shortest round: I had 24 hours to write and edit the story, and a word limit of 1,250. This blog post is already 1,000 words over that limit. Things had to be tight.
I stayed up til midnight to see the assignment when it came out, then went to bed already mulling over ideas. I had a concept I liked, set in the real world with a sci-fi slant.
I woke up, decided the character I had thought of the night before wouldn’t be a cop, she’d be a social worker. No, she’d be CPS. Called my mom. No, stick with social worker. I wrote the opening scene. Too long, made editing notes.
Who was the ingrate? I still didn’t know.
My idea did not work. If I had more time, or more words, I think I could have turned it into something. Instead, I had to file that story idea away for another time. I made mind maps again, and discovered the opening line: “I can say no.”
That became the basis of the story. It morphed from what I thought would be a story about addiction to a story of emotional abuse and manipulation. It is one of the most personal and vulnerable fiction pieces I’ve ever written because of my own experiences with emotional abuse.**2 (Don’t worry, I’m fine now!)
I was fortunate to have no distractions. I spent most of the day alone, focusing on my writing. At noon, my sister surprised me by sending a DoorDash order to my house for lunch. I took a lunch break, and shortly after, had the first draft completed. I called my friend Audrey, talked her through the story, and she assured me that it was not hot garbage. She read over my second draft later, gave me a few ideas and some grammatical corrections, and once again reassured me that what I’d written was not shit.3
Despite all this, I felt strangely relaxed throughout the process. Maybe it was because I used the day before to utterly spoil myself, but I think it’s in a large part because I’d reached the finish line. Anything I wrote would place, or it would not place. All I could do was my best, and then it was out of my hands. After making some final changes and running the story through a wordcount checker twice, I submitted it around 10 PM.
Of course I worried that my story was cliché, or that it wasn’t subtle. The next day, I thought of a hundred better story ideas, or at least that’s what it felt like.
Of course I dreamed of winning, but I didn’t think my story had what it took to win. I hoped I would place.
But if I didn’t, that was okay. I was proud of what I’d achieved and that I’d made it to the final round of such a big contest. It felt like I already won.
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- One of my friends suggested to read summaries of Freida McFadden books, and my reflexive response was “Fuck Freida McFadden!” ↩︎
- Visit loveisrespect.org to learn more about healthy and unhealthy relationships and find resources and support. ↩︎
- At this point, I think I could have a best-selling novel with a 30-city tour and I’d still be calling her before every book signing. And she would assure me every time. Girls, get yourself a friend like this. She is the BEST. ↩︎
Overlooked Books 