Having read through the Sequences, Methods of Rationality, related blogs and books and so on, and having changed my mind a few times on at least a few ideas that I'd been fairly sure about... I feel that I finally have enough of a grasp of the basics of LessWrong-style rationality to start trying to introduce it to other people. And while the Sequences form a good set of basics, getting someone interested enough in rationality to start reading them is a step of its own... and, as best as I can tell, one that needs to be custom-tailored to a particular audience.
For my first attempt, I've focused on two online subcultures which I'm at least somewhat familiar with: furries and a certain subset of libertarians. For example, a large number of furry fans are fairly easy to please - give them a short comic to read involving a cute anthropomorphic animal, throw in a bit of sex appeal and maybe a message that's compatible with tolerance of all people, and that comic will be happily read by a lot of them. Trying to avoid "politics is the mind-killer" derailment, the community of libertarians I'm aiming for tend to have their own quirks about what attracts their attention.
The result I came up with was the creation of Rationality Matters, a couple of comics pages that introduce some LW-type thoughts in an audience-compatible fashion without beating the readers' heads with them. I've already received some positive feedback from members of both target groups, indicating that I've accomplished my goal with at least a few individuals... so now I'm posting the link here, for whatever feedback I can get that could improve the existing pages (mainly for the text, since re-doing the art at this stage is impractical), and to make any future pages (should I decide to create them) better than I would have made them without such help.
(And yes, I try to follow Crocker's Rules.)
"Never attribute to malice what can adequately be explained by incompetence"
Another issue is that while they may have done whatever out of self-interest, they aren't necessarily trying to do damage to you.
What's probably much much more common in bad outcomes is people doing something and not knowing its impact on other things, not thinking about it at all, or just thinking that it was in fact a good idea in the first place.
Every revolutionary thinks that they're right, and most people in power think that they're exercising it for the good of the people, and act in ways that they think will actually help.