I think you basically can't go wrong trying to understand your desires, as long as you also understand that they're not all necessarily stable & it's possible to be wrong about them. This is true of your destination & path, too, but there are additional risks there...
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For my part I have managed to internalize the psychology of "there is only a certain set of lives I'm interested in living and if that doesn't work and I starve and die and I'm OK with that". This is suboptimal in all sorts of ways and incompatible with many lifestyles though.
There’s definitely something to figuring out what reduced circumstances you can live with in order to avoid winding up trapped in a labor exchange situation you hate. I was willing to live out of my car for a while, though fortunately it hasn’t ever come to that
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"winding up trapped in a labor exchange situation you hate" - I feel like this really is a trap. There are all kinds of negative feedback loops associated with that kind of a situation that make it difficult for people to escape once in it.
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I think they’re super difficult to avoid even if you see them coming — for example, people very typically take on new recurring expenses when they start making more money. It’s super easy to become a servant indentured to yourself while believing your quality of life is improving
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