How do we learn to swim? This example that pops up on several occasions throughout Deleuze's work, and here on page 23.
The movement of the swimmer does not resemble that of the wave, in particular, the movements of the swimming instructor which we reproduce on the sand bear no relation to the movements of the wave, which we learn to deal with only by grasping the former in practice as signs. That is why it is so difficult to say how someone learns: there is an innate or acquired practical familiarity with signs, which means that there is something amorous - but also something fatal - about all education. We learn nothing from those who say: 'Do as I do'. Our only teachers are those who tell us to 'do with me', and are able to emit signs to be developed in heterogeneity rather than propose gestures for us to reproduce.
I think he chooses the example of swimming in particular to illustrate the general failure of the idea of imitation to account for learning. Someone shows you the movements are involved in the crawl stroke. You mime them on the beach. It's actually a very simple pattern. You imitate the instructor till everything looks exactly the same. Then you get in the water and try to reproduce those movements and you sink like a stone. You can't learn to swim by imitating the motions of someone who knows how to swim. If you could, there wouldn't be any process of learning to swim at all; someone would tell you or show you how to do it, and you'd just do it.
What you're actually doing when you learn to swim is learning to fit the pattern of your motions together with the patterns of how the water moves. You're not copying an external model like the swim instructor. That is just providing you with a set of signs that will hopefully enable you to grasp how you can interact successfully with the water. A good teacher is not just someone who knows how to do something well, and so provides a good model, but someone who knows how to explain it in a way that triggers your ability to fit your motions together with the world. If they are transmitting some sort of information to you, it is at best in the manner that a seed transmits information to the next generation of tree -- not like a copy, but like a recipe.
I think it's easy to acknowledge this distinction in the case of learning a new physical skill like swimming or playing tennis. But what about areas where we seem to be able to just learn that as opposed to learning how? Aren't there plenty of situations where we learn the right answer more or less instantaneously just by someone telling us what it is? We do seem to learn information or facts this way, and certainly a lot of our schooling seems to revolve around force feeding people these facts. I think these situations may actually be the exception that proves the rule though. Inevitably the new information we acquire so quickly by copying it is actually just a small new modification within a very large framework that took us a long time to build up, just like acquiring physical skills.
You might call this sort of thing "propositional learning". Where you learn, say, the definition of something, or what formula to use to calculate the internal rate of return on an investment, or even what Plato said about the concept of repetition. We tend to think of a lot of "higher" learning as propositional learning, perhaps because it's only this type of learning that can end with a right or a wrong answer. You either correctly copy the instructor, or you don't.
In fact, a lot of philosophy is taught as if it were a form of propositional learning. Was Descartes "right" when he said that the pineal gland was the seat of the soul? Was Kant "correct" when he said that we can never know a thing-in-itself? Obviously, in philosophy the answer is up for debate in a way it usually is not in physics. But the discipline is still mainly taught as if there were a right answer that we will somehow eventually come to. So the other reason I think Deleuze invokes his swimming example early on in the book is to alert us to the fact that he does not see philosophy in this mold. We are meant to "do it with him" and not just "do it as he does". Perhaps this helps us appreciate his unique writing style a little more? It's a lot easier to simply agree or disagree with Plain English than it is with French Philosophy, where you have to struggle over a sentence just to figure out what it might mean. I don't think the goal is obscurity, so much as to try and unfold the complexity of the problem, instead of simply offering a ready made solution.