Plan My Week iPhone App - schedules your tasks for a week, depending on duration, urgency, and importance. - I developed the app because I was suffering analysis paralysis trying to develop the perfect plan. See this LessWrong post for a better description. My goals for the project are two fold - 1) Use automation to cure my planning analysis paralysis (success); 2) Release the app and turn it into a commercial product. (In progress)

Chess Machine Learning - Trying to teach a neural network how to play chess. I've written a couple of bog standard tree search programs, but I wondered if you could teach a NN to recognize and generate legal moves given a position. The eventual goal is to get it to play interesting, non computer chess; it doesn't have to be strong. Probably not novel or groundbreaking, but ideas kept popping into my head so I just started coding :)

Becoming too task oriented as well is a bit of trap. As you tick off lots of unimportant tasks, you pat yourself on the back on how effective you are. You risk adding more and more tasks without considering how they fit in with your goals. (This might be what unconsciously goes in the mind of students and writers when they spring clean their houses instead of writing or studying.) Having said that, having a plan that you then act on (and not ignore) is better than not accomplishing anything at all.

I'm not sure how easy a "Plan B" is. If you can anticipate the ways in which your plan fails, why not just incorporate them into "Plan A"? Alternatively I would suggest adding a little flexibility. Evaluating the outcome of your plans should help also. But I really like the "Granularize" and "Quantifying Results". I wish you had written this three months ago. It explains why I'm having so much trouble accomplishing a task. (Develop a marketing plan for an app to be specific.)

Additionally, I especially suffered analysis paralysis by chasing perfection. I'd spend hours shifting tasks around and feel guilty that I spent so much time not getting stuff done. It was for this reason that I built an app to automate my planning process. (Shamful Plug . Currently free for all LessWrong readers.) As a time saving device it's been ok, but it's real benefit is in knowing that I've committed to accomplishing certain tasks and being able to refer to the plan when I get behind or ahead. There's also nothing better than being able to add tasks at odd moments when they pop into your head, instead of sitting down later and thinking "what did I have to do again?".

So I'll finished then on an obvious note: Whatever process or tool you use, you need to record it and not rely on your memory. Because you're more likely to only remember the urgent tasks and delay the important ones.

How long you've been using this system? Has it been tested by a decently-sized period where you had a large workload? Intuitively, needing to always be in a block feels like a considerable amount of bloat in the system -- maintenance work that you're imposing on yourself without sufficiently large gains. However, I don't currently use anything like Pomodoros to prevent procrastination, so I'm likely missing something.

I'm also thinking that it would be tiresome to try to divide everything into 25-minute chunks. If I'm trying to learn something, I don't want to take a break in 25 minutes when I've already loaded stuff into my brain. Maybe more variable length work blocks would be better here? (Or maybe you already use them to a greater extent that I thought when reading your post?)

reports on time usage and a system to help me calibrate my expectations for the amount of time a task is likely to take

Given my own habits, I wouldn't even try to implement something like this unless I'd managed to reduce the maintenance work to almost nil. Both of these seem to involve all task start and end times, which would be a significant pain (for me.)

ETA: Also, upvoted. I like reading things like this -- it helps me get a feel for systems that I personally haven't set up without having to go to the trouble of actually doing so.