Many monumental breakthroughs were accomplished by disregarding permission, and rebellious attributes are attributed to people like Stephen Wolfram[0] and Albert Einstein. The MIT Media Lab even has an award for disobedience [1].
This mindset, though, can manifest into an unhealthy obsession with breaking the rules. An uncontrolled expectation to "ask forgiveness" can lead to murky moral territories. Where do you draw the line between accepting rebelliousness and enforcing the law?
[0] https://en.wikipedia.org/wiki/Stephen_Wolfram#Education_and_...