I think it is worthwhile for any writer who hasn't published a novel to enter contests. Most contests will not allow entries from writers who have been published in the contest's genre or who have published a novel at all, so this advice mostly applies to those of you who aspire to publish a novel.
(In a moment we'll discuss the Oak Tree Press contests, but hang on; we give equal time.)
There are two major types of contests I want to focus on.
First, there are many contests sponsored by RWA, MWA, or writers' conferences in general*. (*Note here the appropriate use of the passive voice to emphasize the doer of the action.)
These are grand because everyone gets feedback in the form of a ratings sheet with comments from each of the (generally three or four) contest judges. You usually get three ratings sheets that tell you how well you did in the contest (rating you on items such as Dialogue, Plot, Grammar/Punctuation, et alia, on a scale from 1 to 5 or 1 to 10), and each judge should give you comments to some extent. These will be the closest to unbiased remarks you can get, as the judge doesn't know you and presumably has no agenda or preference for a winner. You'll see right away how your work might come across to a new reader.
If you receive low rankings in the Grammar/Punctuation area or Dialogue area from all three judges, then you know you'll need to run your work by someone who is knowledgeable so you can learn what you probably need to learn. (When two judges rank you highly and the third tanks you, the contest coordinator generally throws out the low score and has the entry re-judged by someone else for the new third score, so in most cases, these rankings can be fairly indicative of general problems.) Hearing what people think--even if they don't agree with you and ultimately are not judged to be on target (because it's really something elsewhere in the piece that has influenced their opinions, for example; I talk about this in the latest post on my blog, deniseweeks.blogspot.com)--can be eye-opening.
But better than that, you might win or place. Those whose work places first, second, or third in a contest usually get to send a partial and outline to an agent or editor who is the final judge of the contest win. Sometimes agents and editors who judge these things ask for more than one of the finalists to send work, and writers have sold on these partials. It's worth entering a few of these just to see what people will say.
(Don't immediately assume that everything anyone says is correct, though. But that's a whole 'nother post.)
Note that conferences generally insist that you sign up for the conference before entering certain contests, but not all of them. Also, RWA often charges a nominal fee of $15-20 for entering. This is reasonable.
Then there are the BIG contests, the contests that award you a book contract!
Generally there is also a cash prize plus an advance. You can't lose if you win, in other words.
What could be better than that?
Of course you should look at the contests run by Oak Tree Press. Your romance might be perfect for the romance contest. My book NICE WORK just won the 2011 Dark Oak Mystery contest and thus made the big time. But there are others: the St. Martin's Press/Malice Domestic mystery contest awards a contract with St. Martin's Press, and the Delacorte Prize for a First Young Adult Novel puts you in print with Delacorte. This is the gold ring you have been grabbing for. And if you don't enter, you CAN'T win.
A manuscript that doesn't win may still be very good and publishable. However, if you win, you're on the road for sure. These contests usually do not give feedback, but you will probably hear whether you were shortlisted, and if you place in the top five or ten, that should give you a boost. You're writing at a professional level.
Sometimes you don't win the contest, but you do win an acceptance. Contests are one way some publishers have of finding publishable stories. This used to be more true in the past (Warner Books used to run a First Fantasy Novel contest, and I remember others that have disappeared as well), but you'll still see these, and they're worth entering, IMHO.
If you have written essays, short stories, and poems, you will find many worthy contests sponsored by anyone from a prestigious literary journal to a university press to Writer's Digest and Writers of the Future. Just about the only way to get poems seen is to win some sort of contest, so most poets are fairly familiar with contesting.
I still enter short story contests, by the way. On occasion I'm struck with an idea for a literary short story, and there's nowhere for those to go except to literary journals, the New Yorker (ha), and contests. I've also won or placed in various essay contests. For example, my essay about my approach to gift wrapping made me one of eight finalists in the Scotch Brand Most Gifted Wrapper contest, and I was whisked to New York City for the final round at Rockefeller Center just before Christmas 2008. That was a peak experience for me (I touched the Algonquin Round Table on that trip. There are photos.) I have placed second and fourth in the Robert Benchley Society's essay contest, and I have the charming note from Bob Newhart (who was the final judge one year) to prove it. I even placed an essay in a medical school's journal (about my experience with treatments). I've won small cash prizes and various trophies, including a gold-plated rose from the Golden Rose contest sponsored by RWA.
So it's well worth your time to enter things you've written (things you feel are exceptional, I mean--often you're correct) in various contests. You may already be a winner!
In fact, if you are writing seriously, you already are a winner. You are fulfilling your mission in life. Who can say what your destiny will be? I'm still waiting to see how I will fulfill mine. Remember: if you don't play . . . you can't score.
(Not THAT kind of scoring! Get your minds out of the gutter now and go enter a contest.)
--Denise Weeks, author of NICE WORK, winner of the 2011 Dark Oak Mystery Contest
* Go enter the 2012 contests at http://oaktreebooks.com/ (link opens in new window) *