Humans have evolved an over-the-top obsession with what others think of thema craving for social approval and admiration, and a paralysing fear of being disliked.
It seems to me that there is a delicate balance (an art) in both being able to question any level of social agreement (explicit or implicit) while acknowledging that all culture, language and technology is, at many different levels, reliant upon such agreements.
To both acknowledge and be responsible for that relatedness, and to be able to go beyond it when it seems necessary – that seems to be both ultimate freedom, and ultimate responsibility.
Exactly where those boundaries lie must be a very personal and individual thing.
For me it ultimately resolves down to a probabilistic interpretation of everything, and a choice of values – individual life, and individual liberty (my own and everyone else’s). And finding a balance between the minimum set of rules or agreements necessary for social survival and maximising individual liberty is a very uncertain art, one that seems to this individual to demand the highest levels of awareness and responsibility from every one of us.