Making it up as you go along.
I think that's when you know that you have broken free. It implies that you are out front, pioneering, and exploring the unknown. It may also mean that you are not moving according to predefined rules or following a specific track. Lateral moves are just as important as moving up or out.
You are probably aware of what you are capable of doing and know how far you can extend yourself. And if you push too far, then you know what to do next. Remaining calm and flexible is the key to survival.
It's not for everyone, especially if you thrive in structure and rigidity.
But, that's the interesting thing: the most intensely creative people have an internal code and structure that they follow that enables them to move freely in their external world. They know themselves.