Conforming to Non-Conformity? Ugh.
The point of the more common version of that question, substituting "everybody" for "nobody", is that an idea is wise or not wise irrespective of how many other folks are doing it. That applies both ways.
Many high schoolers and other young people, feeling (rightly or wrongly) disenfranchised and forced to behave in particular ways, so they try to break conformity. It seems a natural process: the young try to find their own place and make marked differences with the older generation. I think it especially true in our society, that seems so polarized and divided such that no generation knows much about it successors or predecessors (such as in the Left, when some of the brightest minds of the anarchist movement claim to be doing something totally novel when in fact they're simply borrowing from the worst of the '60s, and then the '30s, and then the...). But that seems ironic, because it is in fact the cliques made by high schoolers (though often supported by the values of the broader society and particularly administrators) that seem to be the worst at generating conformity or ridiculous concern for one's place in the pecking order.
But it will not do, as my friend Kyle does, to say that these people are contradicting themselves by conforming to non-conformity.
Why? These are different usages of the word "conform". The first sense is the notion of tailoring one's behavior, thought, speech, etc. to appeal to a perceived norm. The second sense is the notion of altering one's behavior to any external influence, including a notion that one has internalized for oneself or the facts of the surrounding universe.
Many groups that say they're non-conformist in fact conform to a subculture, but that's neither here nor there for this argument. But it is important, and I believe Kyle's true argument, that in fact many of the subcultures who consider themselves most antagonistic to the existing structures (Goths, hipsters, punks, etc.) often have their own internal rules that are far worse and more restrictive than the rules that affect the broader culture. This is the unfortunate result of a sect attitude. Solidarity becomes transmuted into homogeneity. After all, these oppressed must band together somehow and show that they're the same, correct? With smaller groups that deliberately break off from larger cultures, there seems to be innate pressures (surmountable to be sure) for groupthink, a deeply defensive attitude even to those who have very similar attitudes, elitism, a selective clique, and a charismatic demagogue taking over. And it would be wrong to think this only happens in high school.
This notion of conformity is in fact not a concern that only young people listening to Mars Volta and wearing black lipstick have. It is a concern of every serious libertarian and truth-seeker who wants people to find their own path and wants to hedge against tyrannical domination.
The important insight for me has been: What matters to non-conformity is the process, not the conclusion. There are many times when every rational person, accepting a few premises (say: "I don't want to die. Few people do. So we should try to stop death."), will arrive at a similar conclusion ("Jumping off that bridge, from what I remember about falls and what I consciously understand of gravity and biology, would be a bad idea."). But the key is that they should arrive at it independently.
There is no independent value in something new or not accepted that's any more so than an old thing. One could say a new false thing could open one's mind and expand it, but contemplation more deeply of classics can do the same thing. Novelty, creativity, originality, etc. should be applauded, but it is not a necessary or a sufficient condition to establish a good idea. In some fields, that which is old is typically bland: take art. But even in art, a homage or something that incorporates the best of the old is in fact often superior for it.