Stew of thought.
Affordances, gifts and possibilities.Open and closed systems and tasks.
First of all, some of the words and ideas came from comments on old posts and I can't remember who wrote what or even when, so I'm sorry if I don't attribute them. If someone wants to point me at the posts, I can fix that in edits.
There are some things that are simple to do and simple to learn. Those are closed systems. Throwing a ball. Learning to write your letters as a child. There are really only a small number of variables. These are things that you can learn by rote. You can actually get proficient merely through repetition.
There are other things, like fighting and, I don't know, LIFE maybe, where the possibilities are nearly endless and the variables are incalculable. Those are the open systems.
Throwing a ball at the garage door or playing catch, the variables are few and you can get better and better. But a million reps of that will only help a little when it is time to throw a pass to a moving player with blockers in the way and big men coming in to tackle you. By the time you've finished first grade you can draw all of your letters, but twelve years of repetition, even into the mechanics of writing doesn't produce authors.
It seems like the key to developing proficiency in the open ended systems is to get in there and play. That's how kids learn video games and they develop a level of proficiency in hours that wouldn't be achieved with months of classroom instruction. That's why immersion teaches languages so much faster. That's why highly trained martial artists sometimes fail.
Part of it is gifts, which is my less-intelligent word for what Edwin calls affordances. You kind of have to learn to see gifts in their natural environment. Rote learning is good for imposing your will on the simple parts of a simple world. When the world doesn't cooperate, you need to be able not only to see that, but to see how...and adapt.
For a class for writers (with Steve Perry) I wrote a few paragraphs about beginners grappling:

Grappling. At first, again, you are like a rag doll in the hands of a good player. Even if you are bigger and stronger, everything you do seems to make his job easier. If you roll away from his pin you roll into a strangle, you pull out of an elbow lock and into a shoulder lock. Everything you do feels anticipated, even expected.

The thing is that a good grappler isn't anticipating everything. There are people way better than me, but I rarely played the game more than three moves ahead. The thing is that once you learn to see it, any move is an opportunity, a gift. A better grappler than you may not be playing you like a puppet so much as just recognizing that any of your options can be played to his benefit. My first judo coach used to say that "Any way you stand and any way you move makes you vulnerable to a throw." You just have to know the right throw.
And grapplers, more than any other traditional martial artists, get in there and play. They play like it's an open-ended system and they tend to be far more adaptable than anyone who learned only by repetition.
And that's an interesting note-- there are levels of openness. Football has far more variables than playing catch, but the variables are far from infinite. Almost any training will limit variables, the system will never be completely 'open'... part of what I do is to try to open things up, at least a bit. And almost all of the carping, telling people that X isn't as realistic as Y boils down to how many variables are excluded.
Which brings up another thought. Living may be the only truly open-ended system... but no one has the balls to live that way. Everyone brings their own rules in to stay in a comfortable zone.
Do you learn faster playing or memorizing? Do you learn deeper playing or memorizing? Is the skill you are trying to ingrain designed for an open or closed problem? Is your training suited to your goal?