First I want to congratulate one of my favorite bloggers, Kimberly Davis. Her poem "Alchemy" won Mid-America Review's James Wright Poetry Award. In her announcement Kimberly, as always, has some useful insights into writing contests.
Opinions regarding contests vary widely among writers. Some feel they are a waste of money since most require a submission fee and the odds of winning are long. Others are downright skeptical assuming that: new writers need not apply; an MFA is required; or winners are usually "in bed" with the judges. This skepticism was fanned a few years back when some dirty linen did fall out of the closet. In one or two cases it appeared judges had awarded former students, and in more than one case the judge determined there were no winners and contest sponsors refused demands for refunds of submission fees.
These situations were truly not the rule. If there were more than three or four that made the writer magazines, I'm not aware of them. However, as often happens, the hue and cry had the further beneficial effect of making contest sponsors even more vigilant for any appearance of favoritism.
Consequently, I would join Kim in encouraging writers to enter competitions, and I would add one additional reason to what she covers in her post. I find that writing for contests can be a great incentive to produce. While I've never come closer than a finalist––a distinction shared by the top 50 entries––some of my best work has been written with the intention of submitting to a specific contest.
I say intention, because I don't always submit the final product. Sometimes I miss the deadline while trying to get it into polished form, sometimes the final version doesn't appear as good a match as I first envisioned it, or I may decide I don't want to tie up a story with potential in a contest that doesn't accept simultaneous submissions. Whether I submit or not, I usually end up with something to show for my efforts.
As far as when and where to submit, contests can become an expensive habit. I encourage writers to set a budget and choose wisely. Keep in mind that choosing wisely doesn't mean the lowest submission fee or the one where winning is most likely. If the award carries little prestige, no amount of money will be worth it. But whether you submit and win, submit and don't win, or don't end up submitting at all, searching out and writing for competitions can be a useful expenditure of a writer's time.