I have been using MS Outlook and some form of a synchronized PDA (Personal Digital Assistant) to manage my calendar for a long time (probably since Office 95 and the original Palm Pilot).  Recently my wife expressed an interest in moving to a digital based calendar.  Since she didn't have a strong preference for what type of software to use, I began exploring a solution that would provide her an easy transition while allowing us both to view each other's calendars.  My exploration led me to here, here, and here.  I eventually arrived at the following setup.  We first setup my wife with Google Calendar.  It provides a very nice, easy to use, Web 2.0 user experience. 

Since I use Outlook to manage my calendar, I needed the ability to view her Google calendar.  Outlook 2007 has very nice support for Internet Calendars.  I used the Internet Calendars tab under Tools/Account Settings to add a subscription to my wife’s Google calendar using the URL provided by Google under Calendar settings/Private Address.  This process is further described here.  Using the ICAL format, Outlook can consume a Google calendar and display it in side by side mode or overlay mode as seen here and here.

The next step was to provide access to my Outlook calendar from within Google calendar.  It appears that only options Outlook provides for sharing calendars are through publishing to Office Online and publishing to a WebDAV server.  Since my current hosting provider doesn’t support WebDAV and I didn’t want to manage my own, I looked at publishing to Office Online.  This seems to be a nice solution for sharing a calendar with other folks on Office Online, or if one wishes to provide public access to their calendar.  Since I only wanted to share my calendar with my wife and preferred a solution that better integrated with Google calendar, I tried Nagarro’s  SyncMyCal product (hint – if you’re installing on Windows Vista, make sure you use the “Run as Administrator” option to avoid the .NET PolicyException).  SyncMyCal uses the Google calendar APIs to provide synchronization services between Outlook Calendar and Google Calendar.  I created a Google calendar for myself and setup SyncMyCal to automatically upload my Outlook calendar to it periodically.  Since my calendar is now in Google, my wife can use the Google sharing features to view our calendars side by side or overlaid (very similar to Outlook’s features).  This seems to work pretty well so far.  Now, my wife can view my calendar side by side with hers using Google calendar and I can view her calendar side by side with mine in Outlook.

As others have noted, I was surprised that, with as much technology that exists today, there is still so much implicit knowledge required to get this solution to work.