Why can't I win at anything?

You'll learn more from your losses than you ever will from your wins. Learning more about why you lost is another way of learning about yourself, why you lost; then the better you start to know yourself, the more likely you are to win.

Winning makes us feel important, and more significant. Two very big deals for every human being. We need to feel that we matter. However if you condition your own self worth by comparing yourself to others, you will never feel happy about yourself, because there are always better people at anything. What there are not, are people that are just as good as you in the particular things you are good at. You are probably good at multiple things to some extent, and the combination of those things can be more than the sum of its parts. If you always focus on what you can't do, you'll be blind to what you can. What I mean here is for example, a person who is really good at spriting is never going to win a race, while a person who has really good endurance is unlikely to, either. But a person with just the right combination of both, moderate capabilities overall, could probably win.

Define win? Ask yourself why you want to win? Why it means so much that you do win? and what's wrong with losing? What have you done to ensure you win?

You can, you just might not feel that you can. If you go out thinking "I can't win" , then you will definitely not win. Try to think "I can do this!"

life is not about winning its about learning from your mistakes, but it would be nice to win stuff

Well some times things are hard to win but it's ok to loss winning isn't everything sometimes losing can make you able to try harder

I guess i have a rather nevative attitude which stops me frtom putting my heart fully into much. Besides 7cups, I've never really connected with people or tried to specifically win or strive for succession.

Not everything is a competition, some people work better when they are not under pressure to do so. Sometimes being a winner doesn't necessarily mean winning anything, but taking part. That is what counts.