Asana
Asana was the first program I ever used that made me feel old.  But not in the actually rather good sense of it making me say "wow, they can do this now?"<p>Rather, it made me feel like an old fart using a computer for the first time, bewildered more often than not, most of my instincts rendered useless.<p>There are many examples in Asana of this. Each, taken alone, is banal: kind of annoying, but maybe not too bad. Taken together, though, we have something that a nicer person than I wouldn't wish on his worst enemy, but I'm just not that nice of a person.