Why emphasize the connection between rationality and winning? Well... that is what decision theory is for. But also to place a Go stone to block becoming a whining-based community.
Let's be fair to Ayn Rand: There were legitimate messages in Atlas Shrugged that many readers had never heard before, and this lent the book a part of its compelling power over them. The message that it's all right to excel—that it's okay to be, not just good, but better than others—of this the Competitive Conspiracy would approve.
But this is only part of Rand's message, and the other part is the poison pill, a deadlier appeal: It's those looters who don't approve of excellence who are keeping you down. Surely you would be rich and famous and high-status like you deserve if not for them, those unappreciative bastards and their conspiracy of mediocrity.
If you consider the reasonableness-based conception of rationality rather than the winning-based conception of rationality—well, you can easily imagine some community of people congratulating themselves on how reasonable they were, while blaming the surrounding unreasonable society for keeping them down. Wrapping themselves up in their own bitterness for reality refusing to comply with the greatness they thought they should have.
But this is not how decision theory works—the "rational" strategy adapts to the other players' strategies, it does not depend on the other players being rational. If a rational agent believes the other players are irrational then it takes that expectation into account in maximizing expected utility. Van Vogt got this one right: his rationalist protagonists are formidable from accepting reality swiftly and adapting to it swiftly, without reluctance or attachment.
Self-handicapping (hat-tip Yvain) is when people who have been made aware of their own incompetence or probable future failure, deliberately impose handicaps on themselves—on the standard model, in order to give themselves an excuse for failure. To make sure they had an excuse, subjects reduced preparation times for athletic events, studied less, exerted less effort, gave opponents an advantage, lowered their own expectations, even took a drug they had been told was performance-inhibiting...
So you can see how much people value having an excuse—how much they'll pay to make sure they have something outside themselves to blame, in case of failure. And this is a need which many belief systems fill—they provide an excuse.
It's the government's fault, that taxes you and suppresses the economy—if it weren't for that, you would be a great entrepreneur. It's the fault of those less competent who envy your excellence and slander you—if not for that, the whole world would pilgrimage to admire you. It's racism, or sexism, that keeps you down—if it weren't for that, you would have gotten so much further in life with the same effort. Your rival Bob got the promotion by bootlicking. Those you call sinners may be much wealthier than you, but that's because God set up the system to reward the good deeds of the wicked in this world and punish them for their sins in the next, vice versa for the virtuous: "A boor cannot know, nor can a fool understand this: when the wicked bloom like grass and all the doers of iniquity blossom—it is to destroy them till eternity."
And maybe it's all true. The government does impose taxes and barriers to new businesses. There is racism and sexism. Scientists don't run out and embrace new ideas without huge amounts of work to evangelize them. Loyalty is a huge factor in promotions and flattery does signify loyalty. I can't back religions on that divine plan thing, but still, those wealthier than you may have gotten there by means more vile than you care to use...
And so what? In other countries there are those with far greater obstacles and less opportunity than you. There are those born with Down's Syndrome. There's not a one of us in this world, even the luckiest, whose path is entirely straight and without obstacles. In this unfair world, the test of your existence is how well you do in this unfair world.
I earlier suggested that we view our parents and environment and genes as having determined which person makes a decision—plucking you out of Platonic person-space to agonize in front of the burning orphanage, rather than someone else—but you determine what that particular person decides. If, counterfactually, your genes or environment had been different, then it would not so much change your decision as determine that someone else would make that decision.
In the same sense, I would suggest that a baby with your genes, born into a universe entirely fair, would by now be such a different person that as to be nowhere close to "you", your point in Platonic person-space. You are defined by the particular unfair challenges that you face; and the test of your existence is how well you do with them.
And in that unfair challenge, the art of rationality (if you can find it) is there to help you deal with the horrible unfair challenge and by golly win anyway, not to provide fellow bitter losers to hang out with. Even if the government does tax you and people do slander you and racists do discriminate against you and others smarm their way to success while you keep your ethics... still, this whole business of rationality is there to help you win anyway, if you can find the art you need. Find the art together, win together, if we can. And if we can't win, it means we weren't such good rationalists as we thought, and ought to try something different the next time around. (If it's one of those challenges where you get more than one try.)
From within that project—what good does a sense of violated entitlement do? At all? Ever? What good does it do to tell ourselves that we did everything right and deserved better, and that someone or something else is to blame? Is that the key thing we need to change, to do better next time?
Immediate adaptation to the realities of the situation! Followed by winning!
That is how I would cast down the gauntlet, just to make really, really sure we don't go down the utterly, completely, pointlessly unhelpful, surprisingly common path of mutual bitterness and consolation.
Part of the sequence The Craft and the Community
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