It has been a long arduous journey, almost two years in the making. I almost began to think that I would never have an empty inbox. I got close a few times. Over long weekends, if I gave up my freedom, I could get down to under 100 messages. I just knew there had to be a better way, so I started my journey in earnest…

I started looking for a way to quickly handle and file the 75-100 emails I received each day. I was (and am) stuck with Outlook 2003, so my solutions centered around things that were compatible with Outlook. I had a beautiful intricate hierarchy of folders organized by project, sub-project, sub-sub-sub-project, and well, you get the picture. Once the emails were filed, I could effortlessly browse my way to any email I needed to find. The problem was that most of the emails were not sitting in those pretty little folders. They were sitting in my inbox! Why? Because the chore of filing hundreds of emails each day was loathsome! I would read an email, reply to it, and then just close it. I’d tell myself that there are too many emails to get through, so I can worry about filing later. This ended up being the downfall of my whole system. By the way, if you’ve read David Allen’s Getting Things Done, he spends a great deal of time trying to make the filing system as easy as possible. If it’s hard to file stuff, you just won’t do it and you’ll end up with a mess. At first, my method was dragging emails to the various folders. This was a pain because, most of the time, the folder I needed would be off screen or buried three levels deep. Next, I discovered the “Move to Folder” dialog in Outlook, which was okay. It tended to remember where I was, and could be launched quickly using CTRL-SHIFT-V. That still was too much of a pain, so I needed something better.

From there, I discovered a wonderful utility named SpeedFiler. I downloaded the trial version, and the thing worked great. I could bring up the dialog box with a shortcut key, type just a few characters from the Outlook folder name I had in mind, and presto! A short list of candidates appeared and I could send the email on its way. The trial period ran out, and well, I’m cheap. Very cheap. Just ask my wife. As a matter of fact, a theme you’ll probably see running through my productivity posts is how to do stuff for free or nearly free. At the time I think it was $29.95 or maybe even $39.95 for a license. I balked. I may have bought the tool, but I wasn’t going to shell out any cash without first re-surveying the landscape of available tools. That search led me to my next tool…

Outclass – This is a handy and free utility that integrates the popular open-source tool PopFile into Microsoft Outlook. Wow! This system had two big advantages over SpeedFiler: (1) It was free, (2) It *automatically* categorized emails and moved them into my folders. That was fantastic! Outclass used PopFile’s self-learning Bayesian engine to build a corpus of data and classify incoming messages. It was trainable and reasonably fast. There was a brief second when a message hit the inbox where Outlook would pause. It was a noticeable pause, but not bothersome. The message would get categorized and you’d be on your way. Outclass could monitor a number of incoming folders, and take different actions (such as moving a message) for each folder it was monitoring. After training on about 1000 messages, it got to be pretty darn accurate. I’d estimate that 9/10 messages were put in the right “bucket”. Life was almost good… So what was the issue? Well, for one, Outclass was a bit unstable. It tended to crash Outlook quite a bit (maybe once a day), and sometimes starting Outlook took several tries. Also, it seemed to be a dead tool. While PopFile has an active community, the developer working on Outclass seemed to have stop working on it. The forums on the site were always down, and now it even seems that the whole site is down (link). Sadly, I knew this wasn’t the permanent solution. Aside: If anyone is interested in picking up the Outclass banner, I’m sure there would be a lot of interested users! So, my search for the perfect filing method continued.

BTW, after typing all of this, I think I’m starting to sound a bit like Mike Myers’ character in So I Married an Axe Murderer. Just to jog your memory, here’s the dialog that comes to mind:

Charlie Mackenzie: That’s not true. I broke up with those girls for very good reasons. Tony Giardino: Oh really? Charlie Mackenzie: Yes. Tony Giardino: Oh really? What about Jill? Charlie Mackenzie: She was in the mafia. Tony Giardino: What about Pam? Charlie Mackenzie: She smelled like soup.

So anyway, I broke it off with those other tools for very good reasons. Oh really? Yes.

Through reading numerous productivity blogs, I came across my next candidate: Taglocity. I’ve been using Taglocity for almost six months now, and haven’t looked back. So far it’s a great tool. It maintains all of the advantages of the above tools (automatic AI engine for filing, integration with Outlook, etc.) and adds a few more… For one, the paradigm is tagging instead of filing. One of the worries in the back of my head whenever I filed a message was whether or not this folder was the best choice. Many messages had contained multiple topics, and I sometimes found myself making copies of messages just so I could file it in two places. This added to my aversion for filing and subtly encouraged me to avoid clearing my inbox. With tagging, I could quickly add as many tag as appropriate and not worry about it. Some of the other nice features are the user interface (QuickTag, Tag Cloud, etc), the different search/filter options, and the ability to embed the tags in outgoing messages.

Okay, so that’s enough for now. I’ll publish some more posts on how I’m using Taglocity, along with some tips and tricks. Oh, and is my inbox empty? Not quite, but it is well below 100. You can see the actual number if you check out the first screen shot in this later post on Taglocity found here.