ewbrownv comments on Rationality Outreach: A Parable - Less Wrong
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The broad goal, I believe, is raising the sanity waterline in the general public.
The narrow goal, as far as I can tell, is developing a solid local community of strong rationalists, and then to do things with our strengths. (Potentially: invent and test systematic methods for making people and the world more awesome, which may include science, starting businesses, making art, and generally creating things that demonstrate the effectiveness of rationality.)
For the narrow goal, we want to appeal to people who will be unusually good assets. (But not necessarily the usual suspects.) For the broad goal, it would be nice to have pitches for rationality that might nudge anyone, regardless of background, in the right direction.
In that case, I'd propose that if Annie is an adult she’s essentially unreachable. No matter how much effort you expend trying to coach her on basic rational skills she isn’t going to get it, because as a general rule adult humans simply don’t change their basic approach to life that radically. You’d have to replace her entire social milieu with a circle of rationalist associates to have any chance of getting through to her, and even then she’d probably just adopt the surface appearance of rationality as a sort of social-acceptance ritual.
So as a practical matter Barbara, Caroline and Donna are the people who might actually join, contribute to and benifit from a rationalist group, and the question becomes how to balance your appeal to all three instead of restricting yourself to Donnas.