They give me Outlook at work which is used enterprise wide.
At home it's nice to get away from such things, but my wife runs an awsome wall calendar with a neat manual birthday update routine that runs at the start of each year!!
Mom does much the same.
So much more practical i would say.
For Outlook users, DeskTask is a nice freeware for quick access to the program without having to open it. Airset is just excellent for Calendar and Contacts sync (prefer it to Plaxo as it also syncs your Notes and Tasks which Airset does not).
Have tried a variety of things like Google's Calendar, Rainlendar, EssentialPIM, WinPIM and other online services but in the end... perhaps a mom style calendar would be the best!
Ooops! I did forget to mention Barca which has a nice Calendar with easy 1,2,3 back-up/restore process and great search capabilities. Except for the exporting feature of .ics file, it fails to sync with anything online.