Recommend Organizing Electronic Documents GTD-Style? (Email)

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Over at Lifehack.Community user anithri asks "How do I organize a large and growing collection of Electronic documents?":
I have a collection of 200+ PDF's, Word docs, text files...It's easy to find one if I know the name of what I'm looking for already, but opening a large number of them looking for what I'm currently interested in is getting very old very quickly.

What I'd ideally like is an application that allows me to "tag" my files ala del.icio.us or flickr.com and then allow me to pull up lists of all files with a particular tag.
This is a big problem that's near and dear to my heart, and one that hasn't been adequately addressed yet. It's a huge topic (the British Computer Society recently called "Memories for life" one of the Grand Challenges in Computing), but I wanted to briefly: a) observe that current techniques are missing the point (relationships), and 2) ask if a GTD-style A-Z reference system apply to the digital realm.


Current Filing Techniques Aren't Relational

The two suggestions given in response to the Lifehack article ("use Spotlight as the tagging system", and "look into Google Desktop") are based on an IR-style index-and-search approach, also discussed in The Death of Folders? and The File Manager Is Dead. Long Live the Lifeblog. However, I think these approaches are missing one of the fundamental concepts about our information: It is connected. Among other things, documents relate to:
  • people (e.g., about them (incl. photos), received from them, or sent to them),
  • events (e.g., prepared for, or received during), or
  • projects (e.g., supporting information or output artifact)
In fact, it's hard for me to think of any document that simply exists by itself; i.e., context provides much greater meaning for documents. The recent move towards tagging tries to leverage connections in an ad hoc manner - by providing support for arbitrary keywords, a form of linking in which connections are expressed via sharing the same keyword(s). However, this impoverished form of linking has limitations, including not supporting attributes on the links themselves. More on this later, but you might want to leave you with some related links.
A simple alpha filing system for electronic documents?

The other idea this question stimulated is applying David Allen's GTD filing system to the digital realm. I'm currently testing this for email, and it has worked pretty well so far. Briefly, in addition to @action and @waiting-for, I have a top-level email directory for each letter of the alphabet, each of which contains email archive files (mbox files on my unix machine) for each project (e.g., n/nsf-site-visit-2005, p/personal-information-web). Finally, each of those latter files contains the relevant messages. Here's the conceptual map (vertical dimension is 'containment', with the outer-most container at the top):

paperemail
filing cabinetemail system
A-Z dividera-z top-level directory
file foldermbox email file
piece of paperemail message

This works OK - Filing is pretty fast, for the same reasons as with the analog GTD version: Quick to dream up a name, only a few places I might have put it, etc. However, due to the email client I use (pine), textual search is pretty difficult. (Side note: When will someone write a simple lucene Java app to index mbox files? JavaMail has been around forever!) What I'd like to know is how well an analogous system would apply to documents. Maybe I'll give it a try, at least for new ones. However, compared to most people my electronic document needs are pretty basic - I seem to rely mostly on email, printed documents, Manila folders, and letter size paper. (Yes, it's about as low tech as possible.)

As always, comments are welcome.


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