I've heard other people mention this approvingly, but I don't know if the actually did it. It's on my list of things to try at some point, though.
This is probably what you meant, but it might be more productive (and slightly less Hard Mode) to be able to choose "do immediately, do never, or break up into subtasks" while you're actually going through the list.
Also, there are some tasks that I actually do want to postpone because they're not my comparative advantage (for example, it's raining right now, so I want to postpone errands until later tonight when it stops). That's prone to rationalization, so I'm not sure how a system could handle that, but it's something to think about.
See also: Boring Advice Repository, Solved Problems Repository, Grad Student Advice Repository, Useful Concepts Repository, Bad Concepts Repository
I just got back from the July CFAR workshop, where I was a guest instructor. One useful piece of rationality I started paying more attention to as a result of the workshop is the idea of useful questions to ask in various situations, particularly because I had been introduced to a new one:
"What skill am I actually training?"
This is a question that can be asked whenever you're practicing something, but more generally it can also be asked whenever you're doing something you do frequently, and it can help you notice when you're practicing a skill you weren't intending to train. Some examples of when to use this question:
Many of the lessons of the sequences can also be packaged as useful questions, like "what do I believe and why do I believe it?" and "what would I expect to see if this were true?"
I'd like to invite people to post other examples of useful questions in the comments, hopefully together with an explanation of why they're useful and some examples of when to use them. As usual, one useful question per comment for voting purposes.