The same can be said for many professions, certainly my own (programming) you should learn the basics and best practices before you can know when it is okay to break them. And like singing or painting it can come down to personal preference whether the rule breaking works or not.

Did I just equate my work to Picasso? . . . I think I did!

I don't think you need to master the rules before you can break them, you certainly need to be aware of the rules though! How else would you even know you are breaking them?

You don't need to be aware of the rules. You might not even care whether or not you're breaking them.

By "The Rules" I think we mean an accumulation of techniques and practices developed and refined by many people over time because they have proved useful. If one has any interest at all in the ones art one will surely be aware of its history and of what others have done. How else does one become interested in the first place? In this respect some awareness of this heritage seems to me to be unavoidable.

It doesn't necessarily have to go back centuries, though. If you're doing rock, you might be intimately familiar with the past 50 years of rock, punk, metal, post-punk, grunge, etc., without having a clue about opera.

I have always been fond of this description:

"Picasso didn't start with painting women with three eyes and square breasts. He knew how to paint a cow."