what is it?

So there is all this research to back up what most of us already know. The "everyone wins" mentality just ill prepares children for adulthood.

My parents let me struggle (although everyone did get a trophy the one year I played soccer, but it is a team sport... and we did win....) But I was also told how awesome I was. So I have an administrator who is making me feel un-awesome. Is it because I am ill prepared for criticism'?

I have not been  as good as I should have been at paper work. I am doing the work.. I just have sloppy files. One admin tells me that it is just one of those things. We just have to prove our work. And that was that. I left feeling empowered to do better. The admin who is actually in charge of the files... makes me feel like an idiot for missing a coversheet. What is worse, is now he is constantly checking in on me. Like daily.   And every time he does it makes me feel untrusted and incapable of doing my job. I took his advice directly, and he still is trying to hold my hand. Even if I don't agree with it 100%, I did not do it right the first time, so best to follow the bosses advice. Not that it necessarily bad advice, I just don't think it will work in this case.

He sat in on a meeting (which he would have been invited to anyway) and I felt like I had to look at him constantly to make sure I was saying the right thing, or  asking the right questions or if my ideas were valid. This is where he brought up the idea to change things that I don't really agree with. I have a very distinct feeling that the other admin would agree with me (basically because he has said  as much in the past.) But how do I do that... with out going behind admin 1's back? And if I am right, how do I bring that up?

I feel stupid and incapable- My confidence is gone... this is a first for me.