The pursuit of conformity is a foolish quest that everyone seeks at one point or another. If everyone jumped off a bridge would you? Clichéd as it is, this question gets to a disturbing truism, and if one were honest, the answer would likely be a tepid acquiescence. Thinking of this not in a literal sense, but a symbolic one. Given a less extreme question, the answer is more likely to be a resounding yes.
The problem with conformity is that it can take an individual away from their true self. Succumbing to the pressure to conform diverts one from the path they should travel. Pressure to conform is the strongest of social pulls, because most people would rather avoid the pangs of isolation. Living life this we betrays the person we should become.
If one were to conform to expectations-what is the reward? In all likelihood it would be a feeling of acceptance and emotional security. However, if individual problems arise, would the herd be there to lend support? Why would they if we are a society of rugged individuals. As a society we promote the idea that everyone should be self-sufficient and pull themselves up by their bootstraps.
A contradiction, to be sure, but that is the strange way modern society works. One should seek to join the herd mentality, but solve their own problems because solving personal problems is a matter of personal responsibility. True happiness and self-fulfillment can be found in a spiritual, individualistic sense. Being a free and critical thinker prevents others from exerting control for their selfish purpose(s). Being controlled/conforming to expectations is a subservience no person should endure.