One of my local clubs, the Richmond Amateur Radio Club (RARC), sponsored a "challenge" (not really a contest) that was called the "Radio Run". The goal of the "Radio Run" was to have a QSO every day of the month of June - mode, band, power didn't really matter - what was important was to have the QSO!
(See "rules" here - Radio Run Rules)
So, yes! I did manage to complete the "Radio Run" successfully. Mostly the guilt and imagining the amount of greif that I would get if I didn't finish really helped me keep it going!
Ok, on a serious note - it was a lot of fun. The challenge really made me think of ways to incorporate radio into my daily activity; even when it wasn't so easy to do. (Like traveling on a business trip! - Long live the D-Star DVAP!!!)