Bikura comments on How do humans assign utilities to world states? - Less Wrong Discussion
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Humans don't. "Utility" is part of the map, not part of the territory. We make choices, but utility theory is only a modeling language used to describe choice-making processes.
One are of research you may want to investigate is "Revealed Preference", a concept developed primarily by Paul Samuelson.
"Revealed Preference" has issues, because of things like circular preferences - although it's a mistake to conclude that circular preferences are proof that humans are irrational. Rather, it demonstrates that utility theory in general is just a model, and an incomplete one.
The fundamental issue is that utility, as a model, attempts to compress a topography of many dimensions - human preferences - into a topography of exactly one - a utility value for each potential choice. Impossible Objects - "contradictions", such as circular preferences - are to be expected in the abbreviated topography.
Why is self-reference expected when reducing the dimensions? Is it because these dimensions might influence each other in a circular way?
Circles are valid two-dimensional objects. What mapping do you use to represent a circle in one dimension?