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Why You Should Enter Writing Competitions Even if You're Sure You'll Lose

Three years ago, I decided to enter an online short story competition. In a way, I had no business entering such a competition since I’d never successfully written a short story in my life. I’d penned plenty of novels, and I’d attempted to write short stories, but they either ended up turning into 60,000 word tomes or I would quit halfway through and leave them to die pitiful deaths in a forgotten computer folder. I just couldn’t wrap my mind around the concept of short story writing—my ideas were all too grandiose…they deserved a feature-length presentation, not a short.

Some concepts are hard to grasp. You’d think that, as long as you like to write, you could write novels and short stories, and both would flow from your pen easily, but that isn’t true. A different part of your brain has to kick in for short story writing, and that part, in my case, was either tucked away in an undiscovered brain lobe or missing completely.

So why enter a short story competition when I couldn’t even write short stories? For the same two reasons I used to enter golf competitions even though I shot in the 100’s (for those of you who don’t play golf, those were horrible scores—I came in dead last in almost every competition). Well, I entered because I wanted to learn, and how else to learn but to dive in and do it, and, like golf, since I knew I was sub-par at short story writing, all pressure was off. I didn’t expect to win. I only wanted the practice.

The short story competition I entered was called the NYC Midnight Short Story Challenge, and it cost fifty bucks just to participate. At first, I balked at this monstrous fee, but then I thought about it: if I had to pay that much to enter the competition, I was damn sure to follow up and actually produce a story. Whether I cranked out a superb or horrible story didn’t matter. The cheapwad in me would insist on getting my fifty dollars-worth, and if fifty bucks was what it took to goad me into finishing at least one short story, it was worth the investment.

The way the NYC Midnight short story competition works is pretty nifty. After you enter, they divide the 3,000+ contestants into heats of twenty. For the first round, you only compete against the twenty people in your particular heat. Everyone in the heat get assigned the same prompts: a genre, a subject, and a character, and then the clock starts ticking. In seven days, you turn in a 2,500 word (or less) short story based on those prompts. If the judges decide your story is in the top five of the twenty stories submitted in your heat, you advance to the next round.

For the first two years, I gamely scribbled out a story and sent it in. The first year, my prompts were: historical fiction, moving to a new city, and a shoeshine boy. I wrote what I thought was a gripping little yarn about a man with a dark past who enters a city and meets up with a seemingly innocent shoeshine boy who turns out to be some sort of devil, but my story didn’t make the cut. Drat.

I had a finished short story though, the first fictional short story I’d ever written, so I exited the competition feeling like I’d done what I set out to do…I created a short story.

I went for it again the next year with higher expectations. At that point, I was halfway through my graduate studies (English and Creative Writing) and thought I now knew a thing or two about how to write a short story (even though I’d only written two more for a short story class, meaning I had a whopping three finished stories as my lifelong grand total). To my shock and horror, I got booted out of the competition after the first round. Again. I obviously didn’t know as much as I thought I knew about short story writing.

So this year, I wasn’t going to enter. I hadn’t written a fictional short story since the last competition, plus I was finishing up the degree, was working on my final graduation project (a novel), and didn’t have the time to muck around with a contest, especially since I apparently didn’t have much luck in writing short stories. I’m not sure what compelled me, on the last day I could enter, to send in my fifty bucks, but I did.

My prompts for the first round were as follows: a romantic comedy, a bakery, a kleptomaniac.

Aaand…go.

Now, I don’t have a romantic bone in my body and I don’t like even reading romances, but I do possess a somewhat smarmy writing style, so I figured I could make the humor part work. I sent in my 2,500-word attempt, wiped my hands, and waited for the rejection email.

And whaddya know…they liked it! I ended up 4th in my heat and advanced to the next round. Amazing.

In the second round, we were again divided into heats of twenty, although I was only one of 500 competitors now, vice 3,000+. And instead of writing a 2,500-word story in seven days, I had to write a 2,000-word story in three days. My prompts were: sci fi (ugh), long-term parking (huh?), and an electrician.

Like romance, I’m not that big into sci-fi, so I figured that since writing a light, humorous ditty for the first round got me through, I’d try that strategy again. I had figured out quite a bit about writing short stories by then, but worried that my story wasn’t really sci fi in the end, and this would be the last round I’d be competing in. But hey…I got to the second round! Two short stories completed! Woohoo for me!

So when they announced the results, and this time I got third in my heat of twenty, which advanced me to the final round, I started thinking: hey, I know what I’m doing! I’ve got this short story thing down-pat. And I somewhat cockily plunged into the final round.

Now that we were down to only 80 contestants, the competition got even trickier. We all competed against each other in this last round, and the top 20 would win prizes—the top prize being $3,500 in cash. I was confident by now that I knew my stuff and I’d be in the top 20 for sure, even though now we only had twenty-four hours to write a 1,500-word story, and our prompts were: any genre we liked (woot!), a sunrise, an undertaker.

For twenty-four hours, I wrote and edited. I came up with an awesome story. I had all the elements in there: snappy dialogue, cool characters, an inspirational ending, good thematic elements, the works. It was my finest short story creation.

It didn’t make the top twenty.

Luckily, I found out that I didn’t make top twenty about five minutes before I had to go into the dental chair. Being the wuss that I am when it comes to anything dental related, I had taken a prescribed valium about an hour before I woozily read the news. So I was totally chill and accepting of the fact that my story didn’t make the cut. And even after I came out of my drug-induced stupor, I still felt proud. How could I not?

For one thing, even though ever since I made it to the final round, I’d been dreaming of winning the big prize, it’s probably good I didn’t win. I had started pinning all my professional writing aspirations on the idea that if I could call myself an award-winning writer, the doors to fame and fortune would magically burst open, and that expectation probably wouldn’t have happened, although winning sure wouldn’t have hurt. And frankly, I’d gone way over and above where I thought I’d end up in this competition. I was somewhere in the top 80 of over 3,000 contestants, which is nothing to sneeze at. And more importantly, somewhere in the five-month journey from the first round to the last in this competition, I discovered that I not only could write a decent short story, but I enjoyed writing short stories and plan to write more.

The interesting (and sometimes daunting) aspect of writing is that it’s a learned skill, and the more you write, the better you get. So with six short-stories behind me, I cheerfully admit I’m a complete novice at this medium, and probably don’t deserve to win a competition yet. I need to keep perfecting this new craft, and so I am excited to announce that I’ve parted with another fifty bucks and have signed up for NYC Midnight’s Flash Fiction Challenge. That’s a competition for short stories 1,000 words or less. Let’s see how I handle that!

Now for the preachy part: here’s what I’ve learned that I’d like to impart:

The best time to enter a competition is when you don’t think you’ll win. Why? Because your expectations are more focusing on learning your craft, not winning. You’re more open to accepting criticism from others and you’re less apt to get upset if you don’t lose. You weren’t expecting it anyway.

While it’s nice to dream of all that would happen if you do win a competition, it’s also important to focus on what rewards you’ll receive even if you don’t win. In my case, the following happened:

  • By just the mere process of having to write short stories during this competition, I learned that I could.

  • I began the process of honing my short story skills.

  • I received some great and helpful critiques from fellow competitors and the judges.

  • I now have three sort stories that, with a bit more editing and tweaking, I can send out to publishers of magazines and anthologies.

  • I got back in the groove of writing at least 1,000 words a day on either a blog post or a short story or a novel (I’m working on all three as we speak!)

  • I met some great folks on the forums and read some amazing short stories that have bolstered my resolve to up my game level when it comes to writing.

So, if you’re hesitant about entering a competition—any kind of competition—because you think you’re not quite good enough to win it, that isn’t and shouldn’t be the point. The point is to learn. And to grow. You’re never too inexperienced to try a competition. You might be too inexperienced to win it, but the advantage is still all yours because you’ll always learn something new that will improve your skills. And that’s what it’s all about.

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