It would depend on if the first man is doing what fills him, or what he "should" do. If it is a should, then he is trapped by having disrespected himself. But if he is there because that's what he wanted out of life, he is the freest of man.

My husband is going for the first kind of free. He has learned that boundaries are good as long as not forced on other people.

Freedom doesn't mean without boundaries, it means to be free to choose respect of self and others.

(There's also other definitions I'm blanking a bit in the real one)