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To-do list management is always an issue around here, as I suspect it is for most people. Even the professional organizer we work with has admitted she has problems keeping up with her many things to do.

One of the biggest problems I have with to-do lists is that if you keep your list online, in any form, it tends to silt up with unloved items (things that you really want to have done, but just can’t be bothered to do). On the other hand, if you keep your list on paper, it becomes messy, or it isn’t there when you need it, or you have to recopy it, and things get lost.

I have used a variety of different techniques over the years. One of my favorites is to keep the list on paper and recopy it to a new sheet every day. This gives me a daily opportunity to reprioritize, including dropping items that I’m sick of copying over and over and realize I’m never going to do. But this technique becomes unweildly when the list gets too long.

The list of things I wanted to do right away when we got back from Germany was huge, and I spent much of January unsuccessfully battling it. It was so big that I was actually stymied sometimes — so unable to decide what to do that I did nothing.

In the last week of January I hit upon a way to break this list paralysis. I printed out the list and numbered each item, 0 to 68. These numbers were arbitrary, not in priority order. Then I rolled percentile dice to determine what to do next. There was no cheating allowed — once I had rolled an item, I couldn’t do anything else until I did it. If I rolled a number greater than 68, something I had already done, or something that was impossible at the moment, I rolled again.

Sometimes I rolled a number and, staring at the task, realized that the task simply wasn’t worth the effort it would take to do, and never would be, so I scratched it off. That counts. Sometimes I would notice other items that would dovetail well with the selected item (e.g. running several errands on the same side of town) and do those too.

This technique worked well. In a week I scratched off 41 of the 69 items, and made some kind of progress on several more. Some of the crossed-off items were perennials, like washing the dishes, but it still provided positive feedback to see the list getting shorter.

An important part of the technique was having one physical piece of paper that only ever got tasks crossed off, never added. New tasks that arose during the week were added to the online version of the list for future attention. Anything more urgent than that would be done immediately.

Well, between our trip to Chattanooga and the following trip to Radcon just a few days later, my list got huge again, so I’m going to use the same technique between now and Potlatch. The list has 93 items this time, and several of them have hard deadlines so I’m going to have to find some balance between “do something that’s urgent” and “roll dice to do something you might otherwise put off.” Wish me luck.

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