I just have a comment on the "glass half empty" thing. There is a difference between people who are highly skeptical, and people who hate themselves and have no motivation. The former is often attractive while the latter almost never is.

Also, Hold, is there any reason for your performance at work other than the fact that your job doesn't interest you that much? I haven't read the whole thread, but could you have a learning disability or ADD or anything? I know a lot of people with ADD who are your age grew up always feeling like they had fallen short of their potential even if they got good grades and sort of hating themselves without knowing why.