Hard to see the negatives. Rule breakers allow you to reap the rewards while removing liability.
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Same supervisor when caught breaking rules: Rogue employee. Nothing to do with me. Will fire them.
Looking at uber, any number of social media companies, etc., having some good lobbyists works wonders.
"You should understand the reason why the rule exists, so that you can decide when to follow it" -- yeah, then why is the reason not explained in the book containing the rules, including an explicit note that if the situation does not match the example, you are allowed to ignore the rule?