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scientism comments on Rationality and Winning - Less Wrong
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Another thing that's pretty crucial here is that rationality is only aimed at expected winning.
Suppose we live on Lottery Planet, where nearly everyone has a miserable life, but you can buy a lottery ticket for a chance of $BIGNUM dollars. Nonetheless, the chances of winning the lottery are so small that the expected value of buying a ticket is negative. So the rational recommendation is to refrain from buying lottery tickets.
Nonetheless, the agents who would be "smiling down from their huge piles of utility" could only be the ones who "irrationally" bought lottery tickets. (Credit for this example goes to someone else, but I can't remember who...)
You shouldn't expect rationality to help you win absolutely. Some people will just get lucky. You should expect it to help you do better than average, however. The rationalist on lottery planet is certainly likely to be doing better than the average lottery-ticket buyer.
On a similar note: rationally succeeding and simply succeeding might involve two entirely different approaches. For example, if success is largely a result of other successful people conferring success on you because they see you displaying certain signals, it doesn't follow that gaming the system will be as easy as naturally producing those signals. Signalling often relies on displays that are difficult to fake. The cognitive resources needed to fake it are often vastly disproportionate to the resources used in sincere signalling and, regardless, in many cases we may not even know what the signals are or how to fake them. The rational road to, say, political success might involve a multibillion dollar research program in social neuroscience whereas the natural road simply involves being born into the right family, going to the right schools, etc, and naturally acquiring all the signalling associated with that.