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NicoleTedesco comments on Extreme Rationality: It's Not That Great - Less Wrong
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Imagine a world where the only way to become really rich is to win the lottery (and everybody is either risk averse or at least risk neutral). With an expected return of less than $1 per $1 spent on tickets, rational people don't buy lottery tickets. Only irrational people do that. As a result, all the really rich people in this world must be irrational.
In other words, it is possible to have situations where being rational increases your expected performance, but at the same time reduces your changes of being a super achiever. Thus, the claim that "rationalists should win" is not necessarily true, even in theory, if "winning" is taken to mean being among the top performers. A more accurate statement would be, "In a world with both rational and irrational agents, the rational agents should perform better on average than the population average."
It can be rational to accept the responsibility of high risk/high reward behavior, on specific occasions and under specific circumstances. The trick is recognizing those occasions and circumstances and also recognizing when your mind is fooling you into believing "THIS TIME IS DIFFERENT".
A rational agent is Warren Buffet. An irrational agent is Ralph Cramden. Both accept high risk/high reward situations. One is rational about that responsibility. The other is not.
Also, in a world of both rational and irrational agents, in a world where the rational agent must depend upon the irrational, it is sometimes rational to think irrationally!