5 Winning Writing Contest Strategies

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The website Vocal Media held a writing competition to attract more viewers to the platform. Dubbed “The Little Black Book Challenge”, users were encouraged to craft a short story involving the titular black book, and the grand prize offered was $20,000.

Well, the contest came and went, but not without its fair share of controversy. I won’t go into specifics on why people were upset with the results, but suffice to say that there was a “vocal” minority airing their grievances about it towards Vocal Media.

In return, Vocal Media was disappointed with the response, as evidenced in the slyly-placed passage inserted into a User Spotlight Post for writer Laquesha Bailey:

Thanks for taking the time to talk with us, Laquesha! The connection you’ve built with your readers is as genuine as it gets — how could we NOT fall in love with a creator as dedicated, passionate, and empathetic as you?!

Take your latest piece, a righteous response to ill-mannered creators and their reception of “The Delicate Art of Counting to Three”, the winning article in Little Black Book challenge, for example.

To All the Ill-Mannered Creators Who Enter Writing Contests

The line gave me pause, and not because it called out unsuccessful entrants of a competition to which Bailey herself was not a winner.

It reminded me of the appropriate etiquette writers must follow when subjecting themselves to a writing competition.

One of the first things that must be understood is that it is very likely you won’t win. Therefore, you should know how to react if and when the moment comes.

That said, there are ways to increase one’s odds of success when entering a writing contest. Here five strategies you can implement the next time you enter a writing competition

1. Read the Guidelines

This is the simplest bit of advice, but it’s often the most overlooked.

If a competition sets a word count limit, it’s in your best interest not to surpass it.

If the contest requires writers to write within a theme, or to include a specific word or phrase or setting, then to ignore it would be to shoot yourself in the foot.

Keep in mind that writing competitions are inundated with entries. If you ignore clear guidelines, then you’re just making it easier for the contest runners to discard your entry.

Disregard contest guidelines at your own peril.

2. Research the Judges

Sometimes, a contest will reveal the judge or judges responsible for selecting a winner.

This can be valuable information, as it means you can do your research beforehand to get a feel for a judge’s tastes and writing style.

If a particular judge is well-known in the writing community, that added celebrity may mean their time is limited, which could mean he or she will only read the cream of the crop. That means you should make sure your story truly stands out before entering.

3. Don’t Enter Contests with a High Entrant Pool / Low Threshold of Entry

Want a better chance at winning money from a contest? Don’t enter high-profile contests with large cash prizes; they tend to attract A LOT of competition.

Case in point: The Little Black Book Challenge had a First Place Prize of $20,000. The response? Over 12,000 entries.

Even if you’re an extremely talented writer, it would be hard to stand out in an entrant pool of that magnitude.

A better strategy would be to enter local contests, or contests confined to a certain geographical area or demographic (i.e. Canadian entrants only, or BIPOC writers only). Entering contests with a low to modest cash prize means a more reasonable competition size.

4. Enter Paid Contests / Contests that Require Mail-In Submissions

The easiest way to get lost in a sea of other writers is to enter a free contest.

With low to no barrier of entry, the temptation to enter just to see what happens can be high; as a result, you can expect a ridiculous number of submissions and a low chance of visibility by the judges.

Conversely, entering a contest that requires a fee that will discourage writers who submit impulsively to anything and everything.

Even fewer people will enter contests that opt for mail-in submissions instead of email, as that comes with the added cost of postage.

5. Don’t Write a Story Just to Enter a Contest

For myself, I find the best ideas come naturally and independent of an impending contest’s deadline. I tend to create my best work when I’m writing for myself and not forced to be creative.

That’s why I don’t think it’s a good idea to submit work you wouldn’t have written otherwise if it weren’t for a contest. When you write for yourself, you allow your story to breathe and have time to develop.

That’s not to say you can’t take a pre-existing story and modify it to satisfy the parameters of certain writing competitions. But I believe you would have more confidence in your work if you developed it on your own terms and not to satisfy a deadline.

So, to recap…

  1. Read the Guidelines
  2. Research the Judges
  3. Avoid Contests with High Entrant Pool/ Low Threshold of Entry
  4. Enter Paid Contests or Contests that Require Mail-in Submissions
  5. Don’t Write Specifically For a Contest

What do you think? Have you entered any writing competitions? Did you enter Vocal Media’s Little Black Book Challenge? And do you consider yourself an ill-mannered creator? Leave your thoughts in the comments below!

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