I didn't achieve much in school because I was one of thoes kids who rarely went into school. It's a pity I didn't get caught because the kicking I'd have gotten off my dad might have got my head right. But I am proud that despite it being too late for school, I did get my head right eventually and I went to college and got a couple of GNVQ's, 1 at level 2 to make up for school and then one at level 3 which is equal to A levels. Considering how hard I had made it for myself, I'm proud that I came through in the end, and I haven't looked back since. However I definitely took the difficult and stretched out route to get there.
A more recent event, (I'm not sure if this is quite what your after in this thread, but I'm proud of it all the same) is that I was talking to a guy who organises large corporate events, shows, expo's etc and handles related budgets. While we we're chatting, he offered me a job position basically working alongside him. I gave him a call on Saturday and I'm starting mid June and it's very much a new experience for me and I'm looking forwards to it. Now I have to let my current employers down lightly.