Presumably you consider "winning" a self-directed act, so not everybody who is wealthy, happy and has good friends is necessarily a winner, they can also get lucky or be favoured in a rigged game. Furthermore, the majority of people, even the ones who have lived arguably self-directed lives, did not do so in the methodical way we're proposing to do so. Living a good life is, typically, a non-transferrable skill. "Winning", as I interpret it, is about creating a transferrable skill for achieving such goals. It's about identifying the things you or somebody like you need do to achieve such goals in a systematic way. What you, as a rationalist, would do in order to win is not necessarily the same as what those people you hold as exemplars of the state you hope to achieve have done. People who live good lives aren't maligned, that's true, but people who pursue goals in a systematic, transferable way are maligned.

I agree that ultimately the outcome should be to be wealthy, happy, socially successful, etc. I simply disagree on how easy that is. If somebody came to me and told me they've made great strides in rationality, I wouldn't expect them to be rich and happy and to have the best of friends. I wouldn't expect them to have made great scientific breakthroughs. I'd expect them to have something to show for it but I'd expect that it would be a modest accomplishment and likely only recognised by their peers. I suspect if we took a poll on Less Wrong - if we could agree on who are the best rationalists and tallied up their achievements - those achievements would be in line with my expectations.

Why is this? Because most success in our society is much more like, say, becoming a successful politician than becoming a successful athlete. One might suppose that I can become a successful athlete, given the right genes, simply by training hard and being acknowledged for my skill. But to become a successful politician I'd have to pretend to be somebody I'm not almost every waking moment of my life. That's what I mean by committing subterfuge in a rigged game. Many rationalists appear to think everything in life is like becoming a successful athlete - I can just look at what other people do and do that or do it better - but I think that's wrong. Almost everything is like becoming a successful politician. I need to look at what other people do, figure out what is salient in their behaviour and then find a way to exploit it to my own ends in an environment where rationality (i.e. systemic, transferable pursuit of a goal) is maligned or even punished, and that's a hard problem. That's a problem that involves considerably more advanced knowledge of human psychology than we have now.