This is a similar list from Robert Anton Wilson's Prometheus Rising (there is a list of lists of such exercises through the book, 12 or 15 total but this may be the best one).
Exercises
1.) If you are a liberal, subscribe to the National Review, the country's most intelligent (and witty) conservative magazine, for a year. Each month try to enter their reality tunnel for a few hours while reading their articles.
2.) If you are a conservative, subscribe to the New York Review of Books for a year and try to get into their head-space for a few hours a month.
3.) If you are a rationalist, subscribe to Fate magazine for a year.
4.) If you are an occultist, join the Committee for the Scientific Investigation of Claims of the Paranormal and read their journal, The Skeptical Inquirer, for a year.
5.) Buy a copy of the Scientific American and read any article in it. Ask the following questions: Why do they sound so sure? Does the data support dogmatism at this point, or is dogma a primate habit (defending head-space)? Will these theories still be believed in 2011*? In 2593?
[* - my copy from 2001]
6.) Get into a discussion of philosophy with an educated Marxist, an intelligent Muslim, and a Japanese businessman at the first opportunity.
7.) Buy some ZOOM or LIFT (two names for the same caffeine-high stimulant) at a health food store. (This gives a close approximation of the effects of illegal cocaine). When you are zooming or lifting and your mind is racing, find a victim and explain the universe to them until they are able to escape you. What you experience in this speed rap is what the head of the compulsive rationalist is always like. This is the verbal circuit gone wild and totally oblivious to information coming in on any other circuit. It explains why most people cannot stand rationalists. Speed drugs apparently trigger neurotransmitters characteristic of the verbal centers of the left cortex.
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.