To me, winning isn't what matters.
Of course, it's nice to do well and be the best, but "winning" in the traditional term at the end of the day is empty compared to other things.
Yesterday I participated in VASE (Visual Art Scholastic Event) competition and got a 4. 4 is the highest you can score, and also ensures that I get my letterman(!) jacket. Out of all the 500+ pieces only a fraction of those make 4's, and out of that fraction that makes 4's only 8-10% move on to state competition.
Part of the competition mandates that you have to complete an interview, and my interview, to me, was way better than ever getting into state.
When I first walked in I wasn't nervous, I just smiled, put my piece up, and sat down. My judge instantly recognized my piece, and asked why I had decided to portray Jung and his theory of archetypes.
I went on this long ramble about how I believed that every person is a character in someone's story, and how even though we may not realize it, we categorize people we meet in everyday life into certain archetypes.
Halfway through my elaboration he started to take notes, smiling. He said to me, "I don't care if you chose this room, or got here by accident, but I'm so happy I got to hear you say this. A few days ago my friend and I were talking exactly about this, and you were not only able to vocalize what we were thinking, but you were able to visualize it as well. You're smart, and not in the valedictorian way. You can be at the top of your class and still be an idiot.
"You have something, and are very lucky to have it. If the other judges were here to listen to you, there's no doubt you'd advance to the next level of competition, but they're not. Conceptually you're at a high level, however you're execution must mature also. Lot's of kids just advance because they can draw, or make things pretty, but they lack substance. Your work is not something everyone will understand, but that's ok, because the ones that do understand what you're doing will appreciate it far more than all of the still lifes and self portraits and photographs you'll ever have to compete against."
And I just sat there. I looked that the timer he had set and I knew we were about to go over the interview time, but that was ok.
We spent the next five minutes talking about technique, and he gave me lots of advice on how to control certain mediums.
I think I learned more in that five minutes compared to all the art classes I've ever been in.
I didn't advance onto state. So what? The advice that I got that day will get me farther than any medal or blue ribbon will get me.