Breaking the Cycle

One of the recurring themes in my quest to be organized is that of todo list staleness. Inevitably, the cycle looks like this: I sit down, and in a burst of creative energy I create a beautifully crafted, perfectly organized todo list. It’s a thing to behold. Everything is broken down into nice orderly projects, each with a clearly identified next action. There are contexts assigned to everything: this one is an errand, this one needs to be done online, this one needs to be done in the kitchen. It is, without a doubt, the epitome of organization. And this time, it’s going to stick. I’m going to review it daily, weekly, monthly to make sure that everything is current. This todo list will give me productivity superpowers.

This generally lasts less than a week.

Fairly quickly, I stop reviewing the todo list. For reasons unknown, I’ve never been able to develop the habit of reviewing my lists on a daily basis. Once I stop reviewing the list, I stop putting things into it consistently. Often, I will write them down on paper (or in a text file, or perhaps in Evernote), and then do them without ever entering them into whatever tool I’m using. Once this happens, I end up using the simpler tool as my whole todo list. I stop organizing things in projects, I just write things down, and then do them.

The next stop on this train is that I stop reviewing things weekly. This inevitably creates a bit of anxiety. I know that there are things in there that I should be doing, but I’m not. I’m focused on the things on my little todo list. It’s a paradox, because on the one hand I feel productive checking things off of my little list. On the other hand, I know that this means I’m not making the best use of my time. It means that my todo list is skewed towards the most recent things that I’ve put on it, rather than things on the larger list that might have more strategic value. To borrow a phrase from Stephen Covey, it’s the urgent, not the important.

In the end, the list atrophies. It’s not updated anymore, and starts to resemble a decaying building that’s been left to sit for decades. It’s a mix of things that have already been completed but never checked off, projects that are long-past relavant but still sitting on the list, and poorly worded tasks, the context of which have long been forgotten. It’s Exhibit A in the argument for the Broken Windows Theory. I could go through and get everything up to date again, but I don’t. Mostly, I suspect, it’s just too overwhelming. There’s lots of stuff there and my eyes just glaze over when I look at it.

Inevitably, in a fit of productive frustration, the cycle begins again. Sometimes it’s a restart with the same tool, purging the old and busted, and replacing it with the new hotness. Quite frequently, however, it’s with a new tool altogether (I think I’m on my sixth or seventh system by now).

In the most recent cycle, I switched tools again. This time from Evernote (which is an awesome notetaking tool, but a very poor todo list manager, at least for people with more than a handful of things going on) to Omnifocus. I’ve watched Omnifocus for years and always viewed it with quite a bit of interest. I’m a GTD advocate (even if I frequently fall off the wagon) and it was designed from the ground up to work well with GTD. It’s got great mobile apps, and a top notch desktop experience as well. The reason I hadn’t used it before now is that I spend a good portion of my day using Windows. Not by choice, mind you, but it pays the bills. Without a solid cross platform experience, I didn’t really think I could be productive. But now that I work from home, and have easy and constant access to not only my iOS devices, but my Mac as well, it becomes a little more practical. So I plunked down my cash on the counter and bought into the entire ecosystem.

So far, Omnifocus has been great. But predictably, there are signs of the cycle repeating. I’ve gone days or weeks without even looking at it. I’ve got a small, hand-written list on an index card (the amazing Frictionless Capture Cards). There are things in Omnifocus that are certainly out of date, and there are projects that I’m working on that aren’t in there at all. The first window is shattered.

There’s hope though. Omnifocus has one thing that I have yet to see anywhere else, which is a review mode. It exists in the desktop app, but it really shines in the iPad application. It works like this: you tap Review, and Omnifocus takes you through every single project in your list, and presents it to you one at a time. You can look it over, check things off that have been completed, and add things that might be needed. Then you mark it as reviewed, and Omnifocus gives you the next item. It’s brilliant. You only see one project at a time, so it’s much less overwhelming (at least to me). Once I’m done with the review, everything is current and I feel much more relaxed. It doesn’t matter how long it’s been since the last review, in less than an hour I can be completely current.

So after decades of using tools that never stuck for long, I feel like I’ve finally found the one that works the way my brain does. And while it’s not perfect, it suits me well.

The cycle is broken (for now).