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timtyler comments on Rationality is Systematized Winning - Less Wrong
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see http://www.overcomingbias.com/2008/10/trying-to-try.html
It's really easy to convince yourself that you've truly, sincerely tried - trying to try is not nearly as effective as trying to win.
As for the "Trying-to-try" page - an argument from Yoda and the Force? It reads like something out of a self-help manual!
Sure: if you are trying to inspire confidence in yourself in order to improve your performance, then you might under some circumstances want to think only of winning - and ignore the possibility of trying and failing. But let's not get our subjects in a muddle, here - the topic is the definition of instrumental rationality, not how some new-age self-help manual might be written.