Rising ConFusion

In writing we spend a lot of time being told what the 'rules' are. What constitutes good writing, what should never be done, what should always be done. Yet time and time again, success seems to follow people who pay no attention to these constraints. Is this a situation where you must know the rules to break them or are there advantages to having never learned said rules to begin with? And how does this bias work either for or against artists and creatures around the world? What is the price we pay for self-censoring? Are there rules that should always be followed, or are they more like 'guidelines'?