I’ve been experimenting with a mix of tools for personal organization:

I’m slowly finding a rhythm. I recently found an easy way to update my
Outlook calendar from Web Calendar. When in Web Calendar, I create a new
appointment and include my own caledar as an “invitee,” and it allows me
to “Mail all invitees” (myself). I select the “vCal” option to attach a
vCalendar file.

I’ve set up a special email address for this calendar, which is the
default recipient for the mail message. Then, when Outlook downloads my
mail, a rule sorts messages from the special email address to an
“Appointments” folder. All that’s left to do is open each message and its
accompanying attachment. Then I save the appointment, and voila! The
appointment from my Web Calendar is saved to Outlook and synchronized to
my PocketPC.

Very cool.