That, however, is a separate skill that must also be nurtured and developed.
I feel this is what happened to Louis C.K. After being ousted from the mainstream comedian community for his antics, he's become more beholden to the smaller subset of his audience that will worship him no matter what, so he gets high off his smaller cult following and less receptive to the larger scale waves of feedback and sentiment he got from his forays into the mainstream. As a result his recent specials have been more mediocre.
The frustrating thing is that it seems that the only people allowed to be truly transgressive and also mainstream are the conventionally attractive. We reward handsome and pretty people for "pushing the envelope" because the dopaminergic quality of their face and build allows all the weird stuff to go down easy. That allows those more genetically blessed to be more free to experiment and express their true selves.
Same is true I'd say in certain creative or deep science positions. If your phd computer genius (which I know is a bullshit label, but people get presented that way to businesses) comes in wearing a tailored suit and well groomed, people are going to be suspicious. If someone looking like RMS shows up, people will belive he's legit. Unfortunately most careers involve some acting.