To begin, I would like to tell a story of when I was a teenager. I had been taking classical piano lessons, from the time that I was five years old, and I had achieved a certain high level of competency on the piano, especially during memorization. Now, I did not feel myself up to challenge of learning increasingly difficult piano pieces, even after I had successfully memorized extremely advanced pieces which were 14 to 17 pages long. So, rather than increase the challenge which was given to me, I instead increased a different type of challenge: the amount of time it took me to memorize a specific piece. My lack of belief in my competency in one area led me to become extremely competent in another area: the time involved in memorization. I was so afraid of making the piano pieces any more difficult than they had been, that I decreased the amount of practice time before a piano recital more and more, until I was memorizing every single one of my piano pieces the day before the recital. Actually, it was usually the night before.
The above story is an example of an extremely stunted and unbalanced method of challenging yourself. It is always best to challenge yourself, when developing a skill, from many different directions, rather than just one direction. If you feel yourself being averse, or even afraid, of using one type of method, then consciously choose to use it. It means that you have become somewhat competent in some areas, and less competent in others. It means that you ARE succeeding, and that you just need to turn the system around and use it on your former strengths now.
Challenging yourself has to be purely intrinsically motivated. You cannot truly challenge who you are by doing things for others or for outside motivation, since it is not a direct cause-and-effect type of situation. Rather, challenge yourself in ways that only you will ever know about and that only you will be able to enjoy. You can mix your personal challenges with external motivation later on, when your motives are pure and have been practiced over and over again.
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