Context:

The subject is a white male and a lifelong New Yorker from Manhattan and Queens. He is my twin brother and we attended the boarding school Choate Rosemary Hall in Connecticut. Before this we were discussing boarding school and teen culture and how low levels of depression was a large part of that. We made a lot of jokes about it which led to this proverb. This proverb interests me because it is a youth proverb and those are very rare as we associate proverbs with age and wiseness. And it is a proverb that was created by youth and only used by youth in a sort of rebellion against that proverbial wisdom.

Piece:

“What we’d used to say, you know after something pretty shitty happened. Like you got a bad grade on a test or like you, it became really stupid after a while like you’d stub your toe and say “win some, lose most” and everyone would just agree with you. You know, it’s like “win some, lose some” but like true. It was sorta a joke”