Winning to me does not necessarily mean coming first, although that would be nice. It’s more about being recognised i.e. making it onto the long or short list of a big competition, and just as being rejected can make me feel rather flat for a good chunk of that day (although it’s definitely getting easier to manage), achieving any level of success can feel wonderful.
I think I’ve reached the stage where I’m able to recognise good writing, certainly writing that’s more deserving of mine to win, and this is great as it only makes me want to improve.
However, it can get slightly disheartening when you feel your story is as good as the winners (I find this more with magazine stories), especially when you’re not sure exactly what you need to do to get better. I think it’s sometimes down to luck or simply the fact that the judge or fiction editor has already read something similar or prefers another style of writing to yours.
The thing I find difficult is that you hardly ever know what the problem was or how close (or far!) you were to/from the winners. That can be frustrating. I suppose the answer is just to get on with another piece of writing. Not giving up can take you one step closer to winning.