When does it become normal to humiliate a man instead of letting him grow alongside his peers and build properties the same as them?

What does it really mean to "just enjoy the ride" in life? How can this approach lead to a more fulfilling and stress-free existence?
What are some signs that it's okay to let your emotions out, even if you've been taught to hold them in?
Why is it so hard to cry or show emotions in certain environments, like gang neighborhoods, and how do people cope with that?