It especially happens after a student has just begun to understand that they can only move in some directions relative to the wind, and they feel stuck with the boat pointed straight into the wind. You have to move to change your heading, and you have to change your heading to move? The first reaction is to feel like the rudder is broken.
Ways to make this faster include pushing the main sail on a small boat out to the "wrong" side, tightening the front sail on the "wrong" side of a larger boat, and positioning the rudder only a little off center so that the slowly moving water relative to the boat is less turbulent.
Probably the only time when it is an actual problem is when people are drifting into some obstacle. It seemed to take students a matter of seconds to regain control of their boat when they were surrounded by large expanses of water. When they were frantic, their intuition about what they needed to do when in a hurry prolonged their loss of control.
http://www.sailing.org/tools/documents/42Interpretationsforb...
I feel like a much better metaphor is the difference between understanding that turning the steering wheel turns the car and understanding that turning the steering wheel turns the front wheels. You can drive a car without knowing that, but at some point you will find that not knowing that prevents you from having an intuitive grasp of things like parallel parking.
In software engineering, an even more apt analogy is understanding how compilers/interpreters work. You can do a lot of programming treating those as black boxes that make your program run, but eventually you have to have the deeper understanding.