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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: Detach from sunk costs.
Material for exercises: Requires a case where the person has sunk costs and the option of continuing or not continuing. Might want to choose cases slightly less fraught than a marriage or a PhD program - you want to work up to those gradually.
Exercise A: For a case where sunk costs exist, imagine that you are a new person who was just now teleported into this person's life. Variant: Imagine you were just teleported into this person's life, and everyone else knows this, and they all expect you to execute sudden changes of course. See what this changes about your thinking, regardless of whether it changes your decision.
Exercise B: For whatever sunk costs you're in the middle of expending, look at the same scenario and rephrase it as a sunk benefit, the purchased option to finish a task more quickly than before. E.g., if you already paid $100 on a $150 item, change from "I paid $100" to "I now have the option of purchasing this item for $50". Again, the stated objective of the exercise will be, "Notice the difference in your thinking", not, "try to change your decision".
Exercise C: As above, but imagine that you bought the option for a penny on eBay. E.g. if you're one year into a four-year PhD program, imagine that you paid a penny on eBay to purchase an option to get a PhD in three years rather than the usual four years. Would you exercise that option if you paid a penny for it?
That last exercise seems to run afoul of some value-related heuristics. Price is so common a proxy for utility that imagining that you paid a penny for the option on eBay might irrationally devalue whatever you're looking at.
Of course, looking at the contrast might still give you some useful insights -- provided you can untangle them.