When talking with my writer friends about entering contests, one said you should look at it as if you were buying a chance, because if you are lucky enough to get two or three judges who like your story, you may very well final or win, but if you get at least one who hates it, you won't. It's not that your story or writing stinks, it's just that that particular judge didn't care for it.
After taking a break from contests because of mixed results, I've decided to dip my toe into the water and give them another try. But I'm going to anticipate that I won't be a finalist or winner. Then if I'm lucky enough to get judges who like my story and writing, I'll have a pleasant surprise.
It works when I buy chances. I always assume I won't win and on those occasions when I do, I'm ecstatic. No matter how small the prize, I won something I never expected to win.
This is my new approach and I'm sticking with it.