Not only am I a sysadmin, but I'm also a family man. I've spoken of my love for the Exchange connector which syncs my Treo with my Outlook calendar; but that doesn't help my wife who would like to know where I am too...
Enter Google Calendar.
Both my wife and I have Google acounts which allows us to share our calendars. I can find out where she is and she can find out where I am. It's a nice complement to the calendar that's stuck on the fridge when I'm not near the fridge.
However, it's been a hassle double-entering my stuff.. once in Outlook and once in Google Calendar (or GCal for you hipsters).
Companion Link software, maker of many fine sync products, had an Outlook to GCal sync program, and I ponied up the $20 or $30 for it, and it worked for awile... but things got horribly out of synch and I ended up with like 7 copies ofbirthdays and other recurring appointmentson my Outlook calendar, so I sidelined CompanionLink and basicially let GCal wither on the vine.
But no longer! Google themselves came out with an Outlook / GCal sync tool, and so far, I like it a lot. It's a small app that sits in your tray and it snychs up your calendars on a given schedule. (Default is every 120 minutes.)
Whaty's also nice is it allows for one-way sync... so I push my Outlook calendar out to my GCal and my wife knows (within two hours) where I'll be.