Evolution in personal organization

Over the course of my academic and professional careers, I have been forced, out of the pain of disorganization, to get "organized."

The Amateur Academic Years

In high school and college, this usually meant a trip to the office supply store and a set of new folders or a binder or both. I would resolve to keep better track of my assignments by writing them down in a consistent way, and I would stay on top of them by reviewing it often. But it never stuck.

Paper Goes Prime Time

Shortly after I started my professional career, I learned of the Franklin Planner (now the Franklin Covey Planner) from a colleague. Its impact on my organization habits was compelling. I now had a central place for tracking just about anything, and a method for taking notes and indexing them. The prescribed daily period of "Planning & Solitude" both forced me and enabled me to stay on top of the tasks and notes I had entered into the system. What's more, the consistent form factor (5.5"x8.5" 7-ring paper) allowed me to collect a long-running archive that I could reference at any time. Not that I did it that often, but occasionally, it proved critical in finding contact information or directions I had long since purged from my active set that I carried with me.

Still, it was strictly paper-based, so it had its disadvantages. It had no backup and it required being with you all the time so nothing would slip through the cracks. (Franklin Covey did, however, offer a small notepad version called the Satellite that was about the size of a checkbook and could be carried with you. The paper was punched to fit a classic binder just like the full-size paper, so it easily integrated back into the system.)

The Digital Transition

Eventually I acquired a Palm III and Franklin Covey planner binder that would accommodate both the Palm and the classic paper. I still use this binder today, although I currently fill its PDA slot with a Palm Zire 72s.
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I won't bore you with all of the phases in between other than to say that I tried an iPAQ for a while, I have struggled to keep Outlook in sync with whatever PDA I was currently operating, and now things like
Google Calendar have entered the picture.

More Change on the Horizon

All of this has been to say that, yet again, I feel as though my habits, techniques, and tools for organization is about to change. Along with my more recent adoption of GTD (Getting Things Done) as my planning method, I've been contemplating using Remember The Milk as my primary task manager. (Its lack of Outlook synchronization--until now--has made it a non-starter for me. I must have desktop/PDA synchronization to make it work.)

None of these changes have happened in a vacuum, nor could they. I've even learned some things about the difference between tools and techniques (what you do with or without your tools).

Should I take the Smart Phone Plunge?

In the face of an impending phone upgrade, I'm forced to consider another possible change--do I retire my Palm and go for an advanced phone/PDA with a data plan? I hate the idea of having my PDA be tied to a particular wireless carrier, but having an increased level of integration for my personal information is compelling.

Just as Merlin Mann of 43Folders.com proposed in his post about choosing a new phone, I think I should prepare for the phone (and PDA?) upgrade by making a list of all of the features that it must have to support even my current organization methods. I'll probably post more on that later.

Feedback

Do you have any thoughts on the ups and downs of digital organization? Tell me what you think.

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