Last weekend, I had an incredibly productive burst of disorganization (so much so that it took a week to get organized enough to post about it). Quite simply, I ignored my two courses and played with a new research idea all weekend. It was simultaneously invigorating and frustrating. Frustrating in that even after two days, I couldn't point to any "solved" piece of the puzzle (the "cross it off the list" mentality), but invigorating because the repeated failures to tie up the loose ends illustrated the subtleties that will make this project interesting and worth doing. I couldn't have asked for a better outcome from a "get disorganized" moment.
This weekend, in contrast, has been solidly organized. The difference lay in the to-do list. While my "get disorganized" crusade is about not being a slave to the list, abolishing the list isn't the right approach. Last weekend, all the list items were about getting ahead for the following week (so I'd have more unstructured creative time). This weekend, the list items reflect hard deadlines for stuff due on Monday. My victory from last week was deciding to grab the creative time at the moment, rather than to work off the list so I could (hopefully) avail of the moment later. That seems a learnable behavior.
In the end, it's about prioritizing unstructured time relative to hard deadlines. If my todo list is about tracking and making priorities, perhaps the unstructured activity should go on the list, especially since I sometimes struggle to "remember" to make that unstructured time. But part of the point of the list is to be able to scratch things off, so that doesn't work so well for an ongoing effort. I do know that ditching the list entirely isn't the answer (as noted in a comment on my original post on this effort). It's about keeping the list in perspective while getting on with the things that are too big to warrant being written down.