When should a person conform to the rules and wishes of others, and when is it best to exercise personal freedom?

This is really asking for your opinion rather than mine. I think the answer depends on how much you are willing to follow conformity. What are you willing to give up in order to fight for your freedom? People are jailed, killed, and punished everyday for fighting for freedom in different parts of the world. Society in the Giver does not tolerate free thinking: it usually leads to being "released" from the community.