I think acknowledging and encouraging his growth is a good thing! Even when he thinks he fails, you can let him know how wonderful, creative and productive it is to be courageous and bold -- and let him know that there is no failure, only feedback.
I'm not in favor of "little" and "big." I have a cousin who in his forties is still known as "Little Steven" and he's pretty screwed up. Napoleon complex, you know?
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