I find stuff like this fascinating: HOW WE DECIDE: mind-blowing neuroscience of decision-making
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The answer to this is meta-cognition: think about what you're thinking. Think about what you're feeling. Think about your circumstances and what happened the last time you were here.
But don't think too much. There are classes of problems -- ones in which there are more variables than the conscious mind can juggle -- where thinking overwhelms your brain's ability to synthesize all these variables into a good conclusion. Timothy Wilson, a U Virginia psychologist, asked two groups of female college students to choose and keep their favorite art print from a selection containing a Monet, a van Gogh, and some inspirational kitten posters. A control group was asked to rate each poster from 1 to 9 and keep their top one. The experimental group was asked to fill in questionnaires about what they liked about each poster.
The controls overwhelmingly picked the fine art. Follow-up questions established that they were still happy with their decisions weeks later.
But the experimental group -- the group that had to explain what they liked about each poster -- chose the kittens. And when they were followed up, they were disappointed with their decision.
Wilson explains that the failure arises because the good things about fine art are difficult to describe: they are intangible aesthetic elements. We like them, but most of us can't explain why. On the other hand, the virtues of a kitten-picture are easy to enumerate. When asked to explain, rationally, which one is best, kittens win every time. But it is this very superficiality that causes us to quickly tire of the kittens and wish for a Monet.
Of course, it's not just kittens. Ap Dijksterhuis at the Dutch Radbout University has shown that the same failure plagues house-buyers. When given the choice of a modest house in the city near work and amenities and a huge McMansion in the suburbs, introspection favors the McMansion. It has easy-to-enumerate virtues: we can have big dinners there, the family can come to stay, and so on. But we only have a few big dinner parties and houseguests a year, and the rest of the year we're stuck with long commutes and no night-life.
I like kittens....