Recent brainstorming sessions at SIAI (with participants including Anna, Carl, Jasen, Divia, Will, Amy Willey, and Andrew Critch) have started to produce lists of rationality skills that we could potentially try to teach (at Rationality Boot Camp, at Less Wrong meetups, or similar venues). We've also been trying to break those skills down to the 5-second level (step 2) and come up with ideas for exercises that might teach them (step 3) although we haven't actually composed those exercises yet (step 4, where the actual work takes place).
The bulk of this post will mainly go into the comments, which I'll try to keep to the following format: A top-level comment is a major or minor skill to teach; upvote this comment if you think this skill should get priority in teaching. Sub-level comments describe 5-second subskills that go into this skill, and then third-level comments are ideas for exercises which could potentially train that 5-second skill. If anyone actually went to the work of composing a specific exercise people could run through, that would go to the fourth-level of commenting, I guess. For some major practicable arts with a known standard learning format like "Improv" or "Acting", I'll put the exercise at the top and guesses at which skills it might teach below. (And any plain old replies can go at any level.)
I probably won't be able to get to all of what we brainstormed today, so here's a PNG of the Freemind map that I generated during our session.
I have another suggestion - not with respect to the content of those rationality lessons, but regarding one means of propagating this knowledge: Khan Academy
I'm sure many of you are aware of it by now and I am pretty convinced that Khan Academy is a predecessor of what the future of education will look like. So my suggestion is to get someone charismatic with the skill to explain the skills of rationality in a down-to-earth non-nerdy way and put these explanations up on youtube. If they are good enough and fit the style of Khan Academy lessons, they may have a shot of getting picked up by Khan Academy. (Whether it's the original lessons or an adaptation by Khan wouldn't matter much).
Even if they're not picked up, it would obviously be great to have these lessons up on youtube. But if you could get a foot in the door at KA and make rationality skills an integral part of the many lessons that are available there, it would be an awesome achievement and probably go a long way, considering how fast KA is picking up speed right now. If you want to get serious about teaching rationality skills, the top-level goal must obviously be to get them into the regular school curriculum. KA isn't there yet but give it 5 years time and it may very well be.