uselessheuristic comments on The Shadow Question - Less Wrong
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There's also "All-in", aka "Go for broke", which picks high utility OR high disutility, with a distribution of probability that is less extreme than in the case of a lottery ticket (though not necessarily fifty-fifty chances). For instance "with all the hype and all the expectations I have formed, Watchmen-the-movie is either going to be a joyride or a horrible disappointment."
Assuming I understand what you're aiming at... These four don't quite seem to answer the question itself, but rather how you evaluate the possible answers to the question.
This seems to leave open the real issue, which is how you enumerate possible answers to the question.
To take a concrete example, suppose I am fed up with my job, so fed up that I'd take "something, anything, other than that". That's not literally true - it just feels that way. I'm not going to inquire at the nearest McDonald's, for instance.
In this particular case, which should count as a "problem" by your previous definition, I don't believe I would carve up the search space first in terms of approaches such as the four you offer in this post, i.e. asking what would be a big gain, or how do I guarantee no huge loss, etc.. My very first question would be something like "what are the things I would be trading off against one another ?"
My first pass at this, by the availability heuristic, might yield things that are salient properties of the current job (salary, location, etc.). Obviously because that's the most available thing of all, my first pass will include the reason I'm unhappy about the current job: that might be annoying coworkers, a horrible boss, etc.
One of the key skills in problem solving is to also include the less obvious attributes that (possibly) have an even greater weight in my utility function. So my second pass would be "what exactly am I trying to achieve here ?" This may start to yield non-obvious insights, such as why I need a job in the first place, and what acceptable substitutes may be.
I might even say that it's better to explore as much of the problem's causal underpinnings as a first pass.
As a budding design engineer, one of the things that has been hammered into me is first to understand the problem in its wider context. Oftentimes just identifying a PROBLEM as opposed to a TASK is not enough: you need to understand the system that enabled the problem to exist. What aspect of the system is directly detrimental? Why is it detrimental? What features of the system influence that detrimental aspect? Why do those features exist in the first place? Can their core function be satisfied through a different principle of operation, or by restructuring the functions and flows of the system, or even by redefining your requirements?
Only once you understand the system holistically and identify functional requirements, causal structure, and your available tools can you really begin to accurately evaluate your options.