There are advantages and disadvantages to breaking rules. Innovation and progress are closely tied to doing things people are told they’re not to or at least think they aren’t supposed to do. At the same time, parking and speeding tickets are almost entirely the result of people breaking rules.
If you are an artist, an organization, a business, a parent, or just some random person trying to make something great happen on a Tuesday you’ll probably find times when breaking rules is the very best thing you can do. The difficulty is in determining when those best times come up and then having the confidence or openness to failure enough to see those rule-breaking choices through.