Being mission focused can help in this regard. Knowing what you are trying to do and why you are trying to do it can guide you when to break the rules. This requires you to understand the business/organization and how the organization works. If a rule was set up to protect the company from breaking the law, you do not break those rules (unless you work in finance). If a rule was set up because someone with bad judgment did something dumb in the past which caused a snafu, make sure you aren’t being dumb.

If you aren’t sure if you are being dumb or not, you are probably dumb. If you are sure you are not dumb, you are probably dumb. If you think you may not be dumb, you may in fact not be dumb.