For me, part of moving onto a new job has always been getting electronically settled-in — getting my new email address, figuring out how to connect to my centralized file shares (and asking which of them get backed up regularly!), and learning what other network resources are available for me to use. In my new job, I’ve picked up that keeping my calendar on the central Exchange server is going to be more than a little bit useful… and that it’s probably time for me to figure out once and for all how to make the mishmash of calendars and schedules in my life work together in a way that’s actually usable.

At this very moment, I have bona-fide calendars living in too many different places — on the aforementioned Exchange server at work, within Google Calendar, and on my PalmPilot. Each lives where it does for a reason; the Exchange server is obvious, the Google calendars were started by Shannon and me when we realized that we were desperate for a way to coordinate our lives, and my PalmPilot calendar is my original life planner, with information going all the way back to August 10th, 1998. I also have a few different interfaces for the calendars, like Outlook, Google Calendar, and iCal. Since iCal is the repository for the Palm information (thanks to The Missing Sync) and can pull in the Google Calendar data, it’s as close to a complete picture as I can get in one app… but since it can only read from Google Calendar, and can’t write back to the service, I still have to switch to a web browser a million times a day to add and update that information. As a whole, the situation is as suboptimal as things can get, and I’ve spent the past few weeks trying to figure out a solution that might help me bring everything together in as seamless a way as possible. (Given that I’ll have an additional tool added into the mix in the next week or two, I’m anxious to solve this!)

My ultimate dream setup would be to have my work calendar live on the Exchange server and synchronize to Google, to have my personal calendar living at Google, and to have the ability to use any of the interfaces — Outlook (and Outlook Web Access), GCal, iCal, the BlackBerry — to view and update any of them. Right now, this is hampered by Outlook not natively doing the GCal thing, by iCal only being able to subscribe in a read-only way to GCal, and by me not having the BlackBerry yet (so not knowing what the heck it can do). Something like Remote Calendars might help me on the Outlook/GCal side of things, but it looks like it’d require a Windows machine running Outlook 24/7 in order to make it work the way I want. As for a two-way link between iCal and GCal, there seem to be a lot of stupid hacks out there, but nothing close to prime-time (which is surprising given that the Mac has an extensible synchronization app, iSync, to use as a foundation). I’m not sure that I’ll ever be able to make all these apps play well together, but I’ll fill in the blanks as I try to figure it out.