Supervisors often prefer rule breakers, up to a point

A more palatable phrasing, "supervisors prefer people that engage with the rules with purpose." That is, choosing to break a rule because you are making a cost call based on what you were able to achieve is not, necessarily, a bad thing.

The "point" where this fails, of course, is where the "cost" call above is such that the supervisor can't agree.

You sound like a supervisor there ;)

“They didn’t break the rule! They engaged in the rules with purpose unlike those rule followers.”

Though I’m not advocating your approach is incorrect.