Collectivism in an individualistic society

For me I think it all boils down to this. I’ve come to terms that it’s all our parents knew, but growing up with 2 pretty much opposite cultures, at school and the outside world, and at home is what the biggest issue is for me

I never properly learned to ask for things, it was all assumed that sharing was always a thing, we’d do things for the enjoyment of everyone at home. It manifested in toxic ways, but I think the culture clash as a second generation immigration is the biggest thing.

How do I find my way in an individualistic society, is it even the right thing to become so individualistic? It’s what’s expected of us in society. As a man, we need to be the ones approaching women and dating and taking the initiative at all times, and this is completely ignored in Asian culture where a lot of the time it’s taboo and you get put into a random (and probably toxic) relationship that you live with for the rest of your life?

I don’t know, I feel like it’s hard. I like some aspects of collectivism, I like some aspects of individualism, but it seems like the world is very either/or. I guess the most important thing is learning to make my own boundaries, thinking about myself more and my own needs. Has anyone figured this stuff out yet?