This is a really good question and I’m not qualified to answer it, other than to say “it can be done!” Alan Kay is an example of someone who has a great intuition for answering this kind of question.

My general opinion is that a great coach/mentor can “see” your errors and doesn’t just know what you’re doing wrong but what the best next step is from where you are, to learn the thing that is holding you back.

Deliberate practice never feels easy. You’re always pushing the boundary of what you’re capable of. And you keep going back for more.

Where there are a lot of different styles of doing a thing “well” (e.g. first class lawyer, teaching, writing, 99% of things ) you’ll need to progress through a wider series of different mentors/coaches, sort of “earning” the mentorship of a “better” coach is a good goal in any field.

In fields like you describe it’s not a simple ladder, more like a branching tree of ladders. You’re goal is not just higher and higher but learning (by climbing) where and who is a mentor for you.