I've always had issues with authority, which doesn't make me very special in this day and age; the default stance of modern people is to be skeptical of authority, independent of it as possible. We don't have very good models for authority, our political and economic leaders do not as a rule inspire much devotion.
In my youth I got my disrespect from MAD Magazine and the National Lampoon, from the underground press. I was too young to be an actual hippie, but I was a preteen wannabie, Abbie Hoffman was a childhood here. Later I was fond of anarchism, although I never was really an -ist, the problems and contradictions of a complete lack of authority were too evident.
In my time I've had some quite monumental fights with authorities – I walked out of middle school to attend an antiwar rally; much later in grad school I was in an epic battle over IP and freedom to publish with the director of the MIT Media Lab (an extremely powerful and high-status person; I was in the right but frankly was a fucking idiot to fight him, it severely derailed my academic career).
I'm older now, at an age when most of my peers have become bosses of one kind or another. I've managed to avoid that almost perfectly (my one short stint as an actual manager was not a complete disaster, I actually enjoyed aspects of it, but clearly not my path). I try to make my peace with authority and in fact I'm fortunate enough for the moment to work in a place where I actually do respect the bosses (it's a science non-profit which makes a big difference).
But even in the recent past I've had these issues where, despite my best efforts to actually go with the flow, to be part of the organization, to be a good member of the hierarchy, to do my job while respecting the managerial powers – most of the time I end up in fights with the authorities anyway, without meaning to and in some cases without even being aware I was pissing them off. I call this being authority-deaf, I think it's linked to my latent autism, I just don't pick up on the social cues the way you are supposed to, I don't signal submission and dominance the right way. Or something. Part of such disabilities is that you are stupid about those aspects of yourself, compared to normies.