Getting Things Done with Outlook 2007, revisited

A while ago I posted a few things that I found about implementing the GTD methodology with Outlook. Since I recently changed jobs, I’ve had an opportunity to carry some of the best practices forward as well as start from ground zero (a true Inbox Zero!) in some other areas. Here’s a quick roundup of what I did on my brand new inbox to facilitate maximum productivity.

The very first thing I did was to download and install Taglocity, which has saved my bacon so many times. I don’t know why people who design software to manage large volumes of information don’t get this, so I’ll just say why I find this so superior to the built-in Categories feature: it is much much faster to type in multiple tags for an inbound email than it is to make multiple mouse movements to pick multiple categories from a list. It’s fundamentally the same principle as why Keyword Assistant is absolutely necessary with iPhoto (at least, pre-2008). Email may be full text searchable, but from an actionability standpoint it’s just as opaque as photos until you give it context through tags. And the more tags, frankly, the better. All the UIs that assume that you’ll only be assigning one or two categories or tags are fundamentally broken because they don’t help solve the problem of how to find something later.

The second thing I did was to create exactly one sub-folder in my Inbox, called _archive. The underscore is a habit; it’s left over from when I had a billion subfolders and wanted to be sure my Archive folder bubbled to the top of the list.

The third piece was adopting the discipline that I’ve learned from practicing a little (a very little) GTD:

  1. Scan each mail for actionability.
  2. If it’s calendar related, triage it (right now that means “accept it” but a more complex triage process is required as my calendar actually gets full).
  3. If it’s a task, do it quickly (< 2 min) or tag it and add it to the task list.
  4. If it’s useful reference, tag it and add it into the archive.
  5. If it’s none of those things, delete it.

Lastly, I set up a few smart folders: Tag folders (smart folders that look at categorized items across all my mailboxes, created through Taglocity) for all my projects; a smart mailbox for Unread Mail and for Unread or For Follow Up items. Today, I added one other smart mailbox—items in my inbox that weren’t flagged, meaning that they hadn’t been processed or moved to the task list. I also set up a custom Shortcut bar and added task age to my To Do list view. The last three items were based on the helpful advice from David Ornstein in this blog post.

Some stuff I might try to do in the future: custom button bars based on the posts by Simon Guest (and again) and Omar Shahine, and maybe tweak some of my task creation settings based on the advice by Melissa Macbeth.

And what has fallen by the wayside? The Hipster PDA was cool for about five minutes. I’ve graduated, on those occasions where I don’t have my laptop, to a little Moleskine notebook. But increasingly everything goes directly into Outlook. Likewise, I’m not bothering with the customized Project form hack mentioned in the same old post; it never worked well enough under Outlook XP for me to try bringing it forward into Office 2007.

And I’m on the edge about Google Desktop; while I was hooked on it before, I’m starting to think critically about the tradeoff between security and functionality that it provides, and I’m not sure I like the conclusions I’m drawing. More later.

Boston gets philosophy again

As Dave Winer would say, it’s philosophy time for Patriots Nation. What a heartbreaker of a game last night. But it was that rare Superbowl, one that was exciting to watch from beginning to end, and for that I thank both the Patriots and the Giants.

Yeah, I thank the Giants. Now maybe Brady can get his feet back on the ground and his head back to the game. I think the last two weeks of preemptive crowning of the team in the media were not good for the play last night.

I’m really grateful to the Pats, too, who gave us an amazing ride all season long. I don’t expect to see this kind of season again, but now I’ll always hope.