i posed myself this question just now, and i'm pretty sure i've already worked it out.
you are winning at life when you can bloody laugh at yourself.
like... really laugh, call yourself a goose, and wish there was another one of you so you could sufficiently slap yourself in the face for being said goose.
oh gawd, i started a sentence with 'like' and i just lucked out on being a Gen Y (thank heck). no offense to the non-self-centered awesome folk in that generation that i have the pleasure of knowing; that blog that went around recently explaining Gen Y really hit the nail on the head actually; in a parody generalizing kind of way. so i suppose the thing that needs to be added to that well put together piece of stick figure hilarity is that 'if you didn't find the silly in this article you are not winning at life (you fool)'.
i believe you are also winning at life when you are not too proud or too stubborn to ask for help when you need it.
you are winning at life when you are not afraid to speak your mind.
and mostly you are winning at life when you take those small opportunities, brief encounters, and shared moments in time, putting them in a corner of your mind for taking out later and providing a little grin for yourself when you really need it most.
here endeth the ranteth.
though may i present to you this moment in time where i grinned from ear to ear...