Some classic dropout path for smart American teenagers ("the fall from normiedom") are to realize that
(1) drugs are actually super sick and their parents/the government health council can stuff it
(2) most people around them appear to be incompetent or lazy (which is partly but only partly a misrecognition)
(3) their country is deeply flawed and consistently fails to live up to its idealized freedom/democracy self-portrait
(4) the religious ideology they were brought up in is a sham
(5) doing psychedelics
(6) feeling like you've heard every variation of every argument on hot topic issues from free will to abortion, can trace arguments deterministically like a garden of forking paths which you desperately want to escape
(7) going online and stumbling into a host of heterodox subcultures, positions, attitudes, systems of taste judgment, social norms, vibes, and your space of possibles expanding
Some people hop ship once and desperately pledge loyalty to a new adopted home. They learn to paper over incongruences that slowly emerge over time. Others aren't as good at lying to themselves—they end up hopping and hopping and hopping, from New world to new world (sometimes boy to boy, girl to girl, job to job, scene to scene) looking for the perfect fit.
Nb Im of the opinion Obama and Google were my generations great disillusionments—the propaganda either revealed as propaganda, or the bureaucracy corrupting/swallowing everything good in the world. But you could probably add Pitchfork Media on that list.