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    Why are you afraid to let me fail?
no don't take that question back... but you might want to frame it in the positive: Why do you want me to do well in everything I do?

The answer might be "When I was your age I had to carry water up to the tenth floor of a building. Poverty sucks and poverty and totalitarianism suck worse. I want you to have the tools for success and freedom."

Your question #2 is a good one too.