I think the larger issue is that it is hard to learn how to use rules effectively if you haven't learned hard lessons by breaking them.

Part of the problem is that human language is by nature imprecise as is human knowledge. The rules have very fuzzy edges and people need to be introspective about these sometimes. But you can't be introspective about the rules if you aren't pushing the limits. Otherwise you are in safe territory and there's nothing to be introspective about.