"Rationality is systematized winning" is a slogan that was adopted to patch a bug in human cognition. Namely our endless capacity to delude ourselves about how we did in an attempt to save face. The concept seems to have been absorbed, but I'm skeptical it's translated into more effective action. Certainly it produced many essays on why winning isn't happening. But the fact that we've been publishing essentially the same essay for a decade now implies something fairly fundamental is wrong. This slogan was chosen because it patches the bug, but I fear at the cost of neutering our ability to focus.
I mean, isn't the answer to that, as laid out in the Sequences, that Rationality really doesn't have anything to offer them? Tsuyoku Naritai, Something to Protect, etc. - Eliezer made the Sequences because he needed people to be considering the evidence that AI was dangerous and was gonna kill everyone by default, so short-term give money to MIRI and/or long-term join up as a researcher. "No one truly searches for the Way until their parents have failed them, their Gods are dead and their tools have shattered in their hands." I think it's fair that the majority of people don't have problems with that sort of magnitude of impact in their lives; and in any case, anyone who cared that much would already have gone off to join an EA project. I'm not sure that Eliezer-style rationality needs to struggle for some way to justify its existence when the explicit goal of its existence has already largely been fulfilled. Most people don't have one or two questions in their life that they absolutely, pass-or-die need to get right, and the answer is nontrivial. The societal default is a time-tested satisficing path.
When you are struggling to explain why something is true, make sure that it actually is true.
I agree that it's useful in realizing that the default path is likely to be insufficient. I'm not sure that it's particularly useful in helping figure out what to do instead, though. I feel like there have been times when LW rationality has even been a handicap to me, in that it has left me with an understanding of how every available option is somehow inadequate, but failed to suggest anything that would be adequate. The result has been paralysis, when "screw it, I'll just do something" would probably have produced a better result.