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Can't speak for the Millies, but I think for GenX the defining cultural touchstone is "Ferris Bueller's Day Off" (and I hate that movie with a passion, I hate the lead character, I hate the assumptions underpinning it) and I think you're correct: you can goof off but still expect, since you are on the 'right' path, to have a comfortable life just like your parents ahead of you. You can rebel against the authority of The Man, but we all know that this is not genuine rebellion and you will follow the path of 'go to college, get the degree, get the job, get the life'. I think the position of Dean Rooney in the movie is intriguing; he has no real authority. Ferris can trick him and expect to get away with it, and nobody in similar positions of authority (the police) will back him up. Teachers have gone from being respected to being regarded as losers, in a sense; Ferris will move on in his life (probably into a cushy PMC job like his dad and his friends' dads) and be successful, while the teachers are stuck in (low-paid) repetitive jobs doing the same thing with the same age groups over and over again. Cameron's father can own a Ferrari, at the end of the movie Rooney has to hitch a ride on a school bus.
Authority can be mocked but the social bargain still applies, is what the movie ends up saying; you are owed the Good Life if you follow the Rules, even if you bend the rules about "respect authority" and "tell the truth" and "do the work". Being smart and knowing which rules are for chumps and how to game the system gets rewarded. If you want a day of self-indulgence, go for it. Truancy records? Missing school? Who cares? You don't need that, you just need to be charming and know how to socially engineer relationships.
Then the bottom all fell out of that, certainly in the economic slump, and so the Millennials onwards feel cheated. They were promised the Good Life! Why aren't they getting what was promised? Well, turns out if you keep mocking authority for being old-school fuddy-duddy about 'do the right thing and don't cheat and don't break the rules', eventually you end up with other forces in its place that operate on the same "keeping to the rules is only for suckers" level, and they won't stick to the bargain of "follow the path laid out for you, you get the Good Life, you can then indulge yourself as a self-actualised individual whose only responsibility is to yourself and what makes you happy and fulfilled".
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