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Introduction: searching for the perfect digital calendar solution

I always aspire to lead an organized life. Whether I actually am or not at any given point in time is really another story. (I am lucky enough to have a photographic memory and be able to put my hands on things that I need in my office or my apartment pretty easily!) I can be pretty anal retentive about digital things like the way my Google Reader feeds are organized in their folders, the things on my Firefox toolbar, or my del.icio.us bookmarks even when my car is a mess and the clothes in my closet are more on the floor or in a never-ending laundry basket than they are on hangers.

However, in my work life, I can’t help but be as organized as I can. I rely heavily on email, because often times it drives my daily tasks as well as provides a clear documented line of communication between me and my clients. I think it’s that way at almost every company in the modern age–live and die by email. I also use the Outlook Calendar a lot for scheduling client meetings, internal kickoffs, and more.

We have a documented project process that we follow for every client project, and I have the elements in place on my computer at work to get those things set up and completed. However, I am forever writing new to-do lists in the margins of my Levenger Circa notebook (my best analog tool at the office!) and I really hate trying to keep a paper datebook because my timelines for projects tend to be very fluid when there are delays, hiccups, or changes in scope. I also hate having to change all my Outlook calendar entries when a project’s timeline changes, because somehow it never seems to sync up right to my PDA phone or iCal on my Mac at home.

I know I’m not the only one who has sat down with their various daily driver gadgets and thought, “Surely there has to be a way to make it all talk to each other!” There doesn’t seem to be one outstanding solution that will handle all needs for all platforms–yet. I think it’s coming, I HOPE it’s coming soon, but I can’t wait for it to arrive. I need a solution NOW.

I use the following devices every day:

Windows Mobile Pocket PC phone running WM 5.0

PC at work running Windows XP

Power PC Mac at home running Leopard

eeePC running Ubuntu Hardy Heron 8.04

I think I am slowly but surely figuring out the way that I can get everything to connect and sync together without trying to sync the PDA phone with any computer (a nightmare on Mac and Linux, annoying even on Windows) and across the multiple software platforms.

I have the first three “phases” of my calendaring setup completed and working, which I’ll document in more depth tomorrow. So far, I have the eeePC, the work PC, and the Windows Mobile phone all communicating to the same central hub that I have set up in Google Calendars.

Up next, part one–tweaking out Thunderbird on the eeePC to be a robust calendar and task solution!

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