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Overhauling My GTD System Under Windows

As you may know, I’m a reluctant switcher from Mac to Windows. I am also a fan of GTD. I had been using Jello Dashboard (JD) to implement GTD under Outlook. JD is a very nice system, the developer is friendly and responsive, and I had even written several patches to adapt it to my way of working. I was even in the process of drafting a series of blog posts titled “My GTD under Outlook setup”.

However, a couple of months ago JD stopped working for me. Not in the technical sense, mind you, but in the GTD sense. I stopped processing my Inbox, I stopped updating my lists, and of course I stopped checking them for getting my next actions. It didn’t happen all at once, but over time I stopped having confidence in my system.

What happened?

I have come to the conclusion that the main reason I stopped using and trusting JD was what David Allen calls “friction”. A system that has a lot of friction, Allen says, will eventually become unused and untrusted (I am paraphrasing, but the message is there in his books and articles). JD, as nice as it is, requires you to switch to a different “mode” within Outlook to use it, since it is essentially a web application that runs inside Outlook (it is all written in Javascript). This means that as I am processing my mailbox, for example, and encounter an actionable email, I cannot simply create an actionable task at that point. I have to (1) switch to JD, (2) find the email in JD’s view of my Inbox, which is different than the one in Outlook Mail, (3) mark it as actionable, tag it and file it, and (4) go back to my Outlook Inbox to continue processing it. Friction.

What is supposed to happen, I guess, is that you do all the processing from inside JD. But JD’s mail viewer is not nearly as nice as the native Outlook one (for example, it shows all messages as plain text), it is slower, and does not have a threaded message view, among many other differences. The result was that my mode of operation, while I was still using JD, was to read my mail in Outlook, archive or delete non-actionable messages, and then switch to JD just to file the remaining ones as actions. Of course, as my workload increased, I stopped doing the switch as frequently, due to the mental friction of having to deal with the “not as nice” environment and losing time and momentum in the process.

And slowly, over time, I fell back into old bad habits: keeping things in my Inbox because I would need them later, and working off it. As a years-old GTD practitioner, I can tell you that the difference was noticeable. I started missing commitments and forgetting things, I became crankier and more stressed, and both my personal and professional lives suffered.

But the nice thing about GTD is that it is very forgiving. If you “fall off the wagon”, all you have to do is do a good mind sweep and review, start recapturing stuff, and be on your way.

But first, I had to overhaul my system. I was sure that if I started capturing stuff into JD again, I would eventually encounter the same problem. So I went back to the basics: I signed up for a free GTD Connect trial (GTD Connect is an amazing resource, too bad I cannot at the moment spend USD$50-a-month on it), downloaded the “GTD and Outlook 2007” guide and the Outlook 2010 supplement, and got to work. Followed the instructions, removed all my categories (JD uses categories for projects as well and for all its tags, so I had over a hundred of them), set it up with the minimum recommended set, and got to work on processing all my accumulated stuff.

I am not done yet, mind you, since I have literally hundreds of old tasks and emails, but I am making steady progress. I feel calmer than I was only a few days ago, because I am again slowly capturing all my stuff in a system that I hope can become trusted. For the first time in months I am decreasing my pile instead of increasing it constantly. The amount of things to do remains the same, but the pile of amorphous “stuff” that is there giving me the creeps has decreased. Eventually I need to get to the point where I can continue maintaining my system in cruise control, keeping things under control. I will blog more details about my specific setup later.

My conclusion is this: if you fall off the GTD wagon, just get back in! And don’t be afraid to throw away your old system if you realize it is not working for you. The beauty of GTD is that it is not tied to a specific toolset, and if the tools you use do not support your good habits, you can easily switch them for others that do.

Reduce the friction, and it will improve your life.