Similar to the question I read on Server Fault, what is the biggest mistake you've ever made in an IT related position. Some examples from friends:
I needed to do some work on a production site so I decided to copy over the live database to the beta site. Pretty standard, but when I went to the beta site it was still pulling out-of-date info. OOPS! I had copied the beta database over to the live site! Thank god for backups.
And for me, I created a form for an event that was to be held during a specific time range. Participants would fill out the form for a chance to win, and we would send the event organizers a CSV from the database. I went into the database, and found ONLY 1 ENTRY, MINE. Upon investigating, it appears as though I forgot an auto increment key, and because of the server setup there was no way to recover the lost data.
I am aware this question is similar to ones on Stack Overflow but the ones I found seemed to receive generic answers instead of actual stories :)