I was working at a private school for the children of wealthy families; the median income was north of $250,000, with a healthy dose of CEOs and Presidents from local businesses represented. I came into work feeling a bit under the weather; no big deal, I figured it would break off after a couple hours. Unfortunately, it just got worse, and I developed a rapid fever. It was bad enough that I was almost passing out. My boss ordered me home (which was sensible), and I begrudgingly complied.
I get in my car, check my mirrors, throw the car into reverse, turn the wheel to the left and hear the sickening crunch of metal slamming into metal. Turns out that there is a brand new minivan sitting next to me that I somehow managed to overlook in my flu-induced hallucinations. I walk back into the office to grab some paper, leave a note and a number for the owner, and drive home (which, at that point, I probably was in no shape to do).
Turns out the van belonged to one of the trustees. Whoops. Fortunately she was very nice about the whole thing (probably because insurance footed the entire bill). But she'd occasionally come into our office and I'd have to duck my head in shame. Not only was it embarrassing, but it jacked my insurance rates for the next couple years. Double deuce.
There was also a time in college I was working paint crew in the summer months. A buddy and I had hoisted a 5 gallon bucket of 5770 (your typical eggshell white classroom color) onto the back of a golf cart and driven off to join the other student workers. Well, we didn't secure the paint, and the jolt from acceleration tipped the bucket over, where the paint proceeded to trickle out and leave a nice eggshell streak 100 yards long across the parking lot. Our bosses made us clean it up with wire brushes while everyone else was standing around drinking soda and laughing at us (we got through about 30 yards of it before they decided they'd let us blast it with a hose and call it good).