A rule is useful when set boundaries a person can benefit from:
1) The rule must be good &
2) The person must be capable to benefit from it
The 2nd point is important too !
For example ignoring 1) can lead to assertions like
Financial market don't need regulations or ignoring 2) can lead to assertions like
We can export democracy. We all know the results.
On rigid and brittle rules:
ABIDE model: Barriers
On authority, discipline and dissent:
When diversity, dissent and responsibility lack
A book:
Saying no, Asha Phillips
This give me an interesting suggestion on questioning the rules:
First question the rule, challenge it, experience it, understand it, make a good use it. Then evolve it, subvert it.
Everyone can break rules to achieve what others do better following the rules, while it take a touch of genius and lot of experience to break the rules to create something unprecedented.