5 Tips to Help You Win a Writing Contest

For the past year, I’ve had the pleasure of judging a weekly writing contest. This involves reading dozens of short stories all written to themed prompts, culling the good from the bad, and agonizing over which of my favorites is truly the best.

Some days I’m overwhelmed with quality submissions — which is honestly the best kind of torture. I could easily see a number of our participants going on to publish their own books. But while we’re blessed to get so many amazing stories every week, I’ve also seen plenty that is, well… less than stellar.

Today, I’m going to take you behind the curtain and show the kinds of things I watch for while judging. To be sure, while there’s no “one weird trick” to guarantee you’ve penned a winning story in either my contest or any other. However, these tips will at least make your story a much more solid and compelling entry — no matter where you’re submitting.

Tip #1: Keep your copy clean

Nothing will drag me out of a story faster than dumb mistakes.

By this, I don’t mean you’re not allowed a single typo — though you should be sure to edit your story as best as you can before submitting. But when I open a story and immediately see a wall of text with no paragraph breaks, misplaced quotation marks, and half the sentences beginning with lowercase letters, I know I’m not dealing with a professional writer.

Tip #2: Punch up your dialogue

I judge short fiction, so every sentence has to count. This goes double for dialogue. There’s not much time for me to get to know a character, and the worst sin you can commit is writing conversations just to fill space.

It’s true that real people rarely talk in deeply revealing, meaningful exchanges or pithy quips that tell the reader everything about the speaker. If we’re honest, we often don’t speak in complete sentences, at least not around the people to whom we’re close. But, fair or not, characters get held to a higher standard — each line they speak should not only carry the story forward, but also provide insight into who they are.

Tip #3: Understand your form

This may seem self-evident, but if you’re submitting to a short story contest, be sure that you’ve written a short story — not the opening chapter of a novel, and not a summary of a larger work!

Different formats can be tricky to understand, especially if you’re not used to writing in them. But it’s important to wrap your head around the fact that a short story is fundamentally different from a novel: not just in pacing, but in structure, tone, and where the crux of the story lies.

Similarly, poems, flash fiction, and novellas all have their own rules. Be conscious of what you’re writing — and what you’re not writing — when you submit to a contest.

Tip #4: Know the rules

Much like writing clean copy, this is another “quality signal” that judges watch for, whether they realize it or not.

I don’t mean to say there’s no room for creativity — quite the contrary, as we’ll get to in my next tip! But there’s a difference between purposefully breaking convention for artistic reasons and just… not understanding the basic rules of storytelling and grammar.

Before you submit to a contest, make sure your story follows these basics: use strong verbs, show don’t tell, and avoid “purple prose,” among others. Not sure if your work is up to snuff? Before you submit, you could always run it by a professional editor.

Tip #5: But don’t be afraid to experiment!

The best short stories I’ve read in our contest — the stories I still think about months later — are the ones that surprise me. Whether that’s a perfectly spun second-person narrative about the fear women face when confronted by strange men, or a love story about a pill bug, I love to read something I’ve never seen before.

Taking this approach does run the risk that your experimental prose will rub people the wrong way. Still, I don’t think I’ve ever voted for a winner who played it safe. So long as you know what you’re doing, feel free to let your imagination run wild and your prose spool out in thrilling new directions.

So go ahead — take that big swing. And good luck!

Desiree Villena is a writer with Reedsy, a marketplace that connects self-publishing authors with the world's best editors, designers, and marketers. In her spare time, Desiree enjoys reading fiction, writing short stories, and giving (mostly) solicited advice to her fellow writers.

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