I've got a bad feeling about this

It's a very distressing feeling when you're telling your boss that you understand what he wants you to do and that you have no problem getting it done in the required timeframe while looking him in the eye and getting the feeling that hes disappointed in you.

I had that feeling today and the only thing I can think that he's thinking is that I should've thought to do what he was telling me to do already.

The Deep Beam candid answer is that I had thought of much of what he was saying, but since it involved the Special Permit that we've been working on for months I was hesitant because I wasn't sure what the City wanted to see.

I hate this feeling because while I, and you True Believers, know that I'll do better next time, the next time I get into this kind of situation with this boss is likely to be a long time from now. What do I do in the meantime to let him know that I'm learning from my mistakes and from his experience?

One way is to simply lead, which is the theme of 2011, but that's not easy for me. I need some backbone building exercises.

I am trying to lead and in some situations I've done so effectively, but me taking the lead on a problem often means that my bosses don't find out there was a problem in the first place. Nice catch 22 huh? In don't really want to be That Guy who goes around telling stories about how awesome he is for handling things.

I guess I keep thanklessly going on trying my best.