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Getting Things Done in Email

Back in December of last year, I passed along a new technique I developed for handling email in Eudora. It relied on Eudora’s long-standing capability to create "saved searches," which are essentially the same idea as the new "smart mailboxes" in the version of Apple Mail included with Mac OS X 10.4 Tiger. In either case, you define a set of criteria, and all messages that meet your criteria – no matter where they may be filed – appear in the search mailbox. The key to the technique I outlined back in that article is that I pay the most attention to unread mail (which isn’t necessarily ideal, but it’s the way my brain works), so I created a saved search that pulled unread mail from 33 different mailboxes, each of which held filtered messages from individuals (mailing lists are handled separately). When I couldn’t or didn’t feel like dealing with a new message right away, I’d mark it with a label, and my saved search also displayed messages with that label.


It was a good start, and it worked well for a while, but eventually, I ended up with so many labeled messages that they started to disappear off the top of my Unread Mail saved search window. As it’s an unfortunate fact about me that I tend to ignore messages that are out of sight, the end result was that I once again started to fall behind in replying to messages, usually the important ones that didn’t have easy responses for one reason or another.

The First Refinement — About this time, Tonya and I started reading David Allen’s excellent book "Getting Things Done," in which he suggests making four buckets for incoming information, whether email or not. (See "A Shiny New NoteBook" in TidBITS-777 for how I implement other aspects of the Getting Things Done model in Circus Ponies Software’s NoteBook.) First is the bucket of items you haven’t yet seen – Unread. Next is an Act On bucket, which contains those items you cannot deal with in just a few minutes. Then there’s a Waiting For bucket for items that you need to keep active until someone else gets back to you about the topic in question. Last, you need a Read & Review bucket for items that have little time pressure, but which you need to read at some point.


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I was on a similar track, since my Unread Mail saved search displayed everything new, and in theory, I was creating an Act On bucket by labeling messages I couldn’t deal with right away. But since I had too many labeled messages, they were being lost in the crush of the hundreds of unread messages that arrive daily.

So the first refinement I made to my system was to create a second saved search, called Act On, that contained just messages in the 33 relevant mailboxes with the Act On label. I did the same for the Waiting For and Read & Review buckets, making labels that I could assign to appropriate messages and then collecting those messages with saved searches.

This refinement worked well at first, since it enabled me to clear out my Unread Mail saved search regularly – there are never too many messages to work through in any given mail check. To assign labels quickly, I created toolbar buttons in Eudora (Command-click an empty spot in the toolbar and choose the desired menu item or press a key combination) for each label, and I used Script Software’s iKey to cause Command-1 through 3 to open the Unread Mail, Act On, and Waiting For saved searches.


Unfortunately, as with nearly ever other tracking system that I create, I fell behind. The problem (and it’s not clear that the Getting Things Done model has an answer to this) is that I simply have too much to do in the time available, and a number of the things I have to do occupy many hours at a stretch such that they block getting to other items that might not take as long. So my Act On mailbox grew ever larger, despite occasional attempts to beat it down, and the larger it got, the more psychologically difficult it became to open. Similarly, Waiting For became a never-never land that I seldom, if ever, opened, making for an awkward situation a few weeks ago when I completely forgot about a message that I’d marked as Waiting For, even after I received the necessary reply. And Read & Review has become a total graveyard; I don’t think I’ve opened it more than once since setting it up.

A key aspect of the Getting Things Done model is the Weekly Review, a task you’re supposed to perform early every Friday afternoon. During the Weekly Review, you’re supposed to check through all your Waiting For items, and generally review all your current projects. Then, you can push various to-do items off to other people before the weekend, enabling you to take some time off from work without constantly thinking about all your open projects. It’s a great idea, and it has worked well when I’ve been able to accomplish it, but all too often life intervenes (in the form of unexpected visitors or phone calls, or a server crisis), or the Weekly Review falls prey to more important work, such as finishing an article for TidBITS or working on a Take Control ebook. And once I missed a couple of Weekly Reviews, I forgot all about it even during weeks when I had the time.

Refining the Refinement — By now I’m sure it’s clear that I don’t have all the answers yet; I’m still trying to find the best combination of methods that will fit with my working style and schedule. It’s a constant effort, or, more accurately, it’s an effort that undergoes fits and spurts of activity as I realize a new problem and attempt to resolve it. Here are my latest attempts.

Most important, I need a way to prevent the Act On and Waiting For saved searches from becoming black holes that inhale important messages, never to be seen again. Since I’ve learned that pure mental fortitude isn’t sufficient – I’ll always find some subconscious method of ignoring these saved searches – I’m planning to enlist iKey as my conscience. Twice per day, once in the morning before I get up, and once toward the end of the day, I’ve set iKey to open those saved searches automatically. My hope is that if I’m presented with them on a regular basis, I’ll be able to muster the courage to deal with some of the stickier messages that I’ve had trouble handling in the past.

Read & Review is a different problem. I have an essentially infinite amount of real work that I need to accomplish, so I don’t have quantities of time to spend reading long articles or email messages, no matter how interesting or relevant. There’s always something more pressing clamoring for my attention. However, I find that I sometimes use my PowerBook at night to do Web browsing or other Internet tasks that aren’t work-related, which pointed me toward a strategy that’s been working well in the short while I’ve used it.

My main email account is a POP account, since I like to have local access to all of the gigabytes of email I’ve received and saved. But since Web Crossing, our integrated server software, supports IMAP just fine, I created a new IMAP email account (which no one but me will ever use directly). Then I copied every message marked Read & Review into a folder in that IMAP account, and created a Eudora toolbar button to make it easy to copy new things to that account. Now, whenever I have something that I know will take some time to read, I can easily pop it into my IMAP Read & Review folder, and read it later on my PowerBook using any IMAP client I like (at the moment, I’m trying Apple Mail, though my years of Eudora usage make Mail’s interface seem awkward).

Once I set up my private IMAP account, I had another revelation, which is that it can sometimes be too easy to become caught up in interesting discussions on mailing lists that aren’t work-related, and like everyone else, I get plenty of joke mail, or forwarded political screeds. Rather than spend valuable work time during the day reading and responding to such mail, I modified the filters that move mailing list messages into particular folders to place a copy of each list message on my IMAP account. Another toolbar button simplified the process of copying other random joke or personal messages to my IMAP account for evening reading on the PowerBook as well.

As I said, I haven’t been doing this for all that long, but it has been a relief to regain some of the time I spent reading email during the day, and it’s nice to sit on the couch with Tonya (for whom we set up the same system) and our laptops, reading mail from friends and family, or talking about some discussion that’s come up in a mailing list.

I do want to note two subtleties to what I’ve done. First, I initially thought to redirect messages from mailing lists to the IMAP account, but that turned out to be a bad idea, even after I twiddled x-eudora-setting:273 to turn off Eudora’s built-in protection against redirecting list messages (in order to prevent mail loops). Redirecting eliminated some of the original headers in incoming messages, making them harder to filter in the IMAP account, added (by way of…) to every message, put a copy of every message in my Out box, and most important, in some cases changed the order of messages in a thread. All those problems disappeared by making my Eudora filters copy the mailing list messages to the IMAP account using a copy action rather than a redirect action. Second, because I like to keep all my mail in once place, I’m intentionally copying, rather than moving, each message. That way I can delete anything from the IMAP account after reading without worrying about my main archive.

I’ll report more on how these refinements work for me after I’ve had more time to live with them – my gut feeling is that some will prove highly effective and will survive, whereas others won’t and will require replacement with new ideas.

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