Gosh, this is what I'm facing at home. DS started and stopped the piano because it was difficult, yes. I didn't think he had much interest in music to begin with, so I agreed for him to stop.

He loves math, but he's at a point where there are multiple operations to be done, and if he stumbles, he wants to stop. Well, not! I think his ideas about himself (that he's very bright) is a major hurdle in learning - he doesn't like the feeling that he's on uncertain ground.

What is helping somewhat is this diagram I found here:
http://learningandteaching.info/learning/resistan.htm

I'm sure someone who has a degree in education can explain this better. I use it to tell him that old skills become boring or stale after awhile, and to obtain a new level of satisfaction, he sometimes has to step off his comfort zone, feel disoriented, but with effort, he can reach new heights for himself. Hopefully he can talk himself through for difficult tasks as he gets older, *crossing fingers*.