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JoshuaFox comments on Checklist of Rationality Habits - Less Wrong
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I realized that what bothers me is the neglect of utility-function differences in the counterfactual world.
Should you start using heroin? Let's try to reframe it in a way that will reduce, or at least switch around, the biases that might be influencing your decision. If you were a heroin addict, and had lost everything, and heroin were your only friend and consolation, would you want to stop? Maybe not. So go ahead, shoot up.
If, despite your deep desire to go into classical music as a career (which in real life you did, to your great satisfaction), you had followed the money into the financial sector, and after years of 80-hours weeks, had sunk into cynicism and no longer cared for anything but making more money to support your extravagant spending habits, would you then want to leave the financial industry for a life of music and a modest income? Probably not, so go ahead, follow the money, burn out your soul, and buy yourself a Porsche.
I have trouble believing that in those situations, I'd actually prefer to be that sort of rock-bottom, burnt-out person rather than thinking "I wish I'd made difference choices when I was 20, oh foolish foolish me."
Having been in some rather bad situations, I've never once thought "Gosh, this is so much better than if I'd had a successful, high-paying, yet enjoyable career!"
This method of reducing bias only works for rational decisions using your current utility. Otherwise you will be prone to circular decisions like those you describe (decisions that feed themselves).