I got news for you Debussey, no one wins in life but it is easy to feel like a loser. Never envy anyone else because they might have a toothache.
Why you are given a voice on any public forum is beyond me. If I owned this site you would never post your filth here.
You are not correct about your "winning" statement. What constitutes "winning" in life in the first place is a matter of how we define it, and since you don't have the power to make an all-reaching definition of diffuse matters like this, you are not in a position to make such a statement.
In this life we really don't know much. As Debussey has stated before, finding the answers to the "big questions" in life = practically impossible (can you really prove much besides the fact that you are aware right now?), at least today. What we do "know" is that you have your life, and that the quality of it is determined by the emotional states you experience. If going by this, what constitutes "winning" in life should mean being as happy as you can, and if you feel like a loser you are certainly not on the winning side. Doing what it takes to live a happy life will at least maximize some part of it you can feel pretty sure about (again, this is just Debussey's "life maxim". Very hedonistic, eh?

).
If you on top of this accepts the brutal facts about life (you will get old, you will die, your loved ones will die and so on), then you can still "win" because you maximized your happiness within the frame of something resembling reality.
They have done studies on people who's been on their death bed, and it seems like there are two groups: A minority that achieved what they set out to achieve (family, education, business, friends, loads of great experiences ect and so on, a bit like "maximizing" ) and they usually accepts death and are ok with it. The majority dies a bitter death though, feeling that they came out short (this group will include a loser like you)

Addition: The "happy minority" are supposedly less fearful about their transition into death too (but Debussey has to check up on this though, don't take this for granted yet).
Arnold understood that how you feel and what you achieve is up to you (there will of course be unforseen external factors that can help or screw you over, but these should be accepted nevertheless. Getting the best output from yourself, despite what's going on elsewhere is still up to you), and even though many people thinks of him as an arse he still made them feel like losers

The purpose of life is to live it, to taste experience to the utmost, to reach out eagerly and without fear for newer and richer experience.
Eleanor Roosevelt
And just for you Vince, you loser:
No one can make you feel inferior without your consent.
Eleanor Roosevelt
Addition: The post is not meant to contain "universal answers", this is just what Debussey chooses to live its life by, nothing more, and Debussey has to accept the consequences of living its life based on this way of thinking.