I've entered my short stories into contests and magazines many times, and have won. Winning contests is wonderful! You will feel confident, and you'll believe that you really can write well!
There is the possibility that you will lose a contest. Finding out that you haven't won is painful and one of the most discouraging things that can happen to a writer. It's like being told that you can't write well at all. What must be understood is that there are hundreds of entries, and yours may not have met the criteria exactly. It doesn't mean that you wrote poorly, it means you didn't write what the judges wanted.
When your short story is rejected, don't give up. Submit your work to other contests, and maybe you'll be lucky.
Some tips on submitting your short story are:
- Make your first sentence capture the judges. I read in a writing book that judges read the first sentence, and either consider it or toss it.
- Keep the judges interested all the way through your short.
- Follow the rules! This rule is critical.
- If you write a cover letter, don't bribe or beg the judges to publish your work.