Eliezer_Yudkowsky comments on Teachable Rationality Skills - Less Wrong
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Skill: Being strategic. I.e., life-consequentialism, where you actually do things based on their expected future consequences, as opposed to drifting into a PhD program because your friends are doing it.
Exercise materials: We either need to develop efficient probes for getting people to list out major life choices that they could actually remake (are under serious reconsideration) or we need to develop hypothetical life stories and policy decisions to use in exercises.
Subskill: Avoid pitfalls of verbal strategic reasoning.
There are studies showing that people who consider their decisions more make worse decisions. As I understand it, the main explanation for this is that people shift from an intuitive sum of costs and benefits, to seeking verbally justifiable decisions, which in turn might lead them to one-reason-decisionmaking, ignoring some of their costs and benefits which are important to them but seem less "sensible". I also suspect it may exacerbate other biases like scope insensitivity or rare events - thinking about cases which are rare or short in duration.
The classic case being "Let's get a bigger house, further away from work, so it has an extra bedroom in case Grandma comes over", which she does once a year, but the 20 minutes of extra commute time happen every day and are not acclimated-to.
"Let's get a bigger house, further away from work, so it has an extra bedroom in case Grandma comes over"
Not saying this is a bad example, but it COULD be the case that grandma never being able to come over is totally unacceptable. Which is also a pitfall - something can seem trivial until it goes away.
Only if there's really no other way for Grandma to come over - not even for example sleeping in the living room so she can have the sole bedroom.
Exercise A: Give somebody two hypothetical package deals to choose from. First, have them choose quickly and intuitively. Then, have them think about consequences and list out desiderata and alternatives... but at the end of that, have them do the intuitive sum and state a preference, rather than coming up with a verbal reason for the decision.
Exercise B: Have some of the desiderata be rare cases or cases of short duration. Detect these, cross them out with a black marker.