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When faced with dilemmas, I always felt I had no solid ground that'd justify my decision. Say I'm considering becoming a lawyer. But I obviously don't know what being lawyer is like. I can ask my friend (let's say Jim), who is a lawyer how it's like to be a lawyer. But all I will know is what's it's like for Jim to be a lawyer, not this hypothetical version of me working as a lawyer. Let's say that one of my priorities when looking for a job is what the coworkers are like and if my boss is fair. I won't know any of that unless I work there for some time, so the choice of me choosing a job would seem like a guess - perhaps educated guess (I'd try to gather as much information about the firm etc), but a guess nonetheless. So if somebody would ask me "would you like to work there" the only answer seems to be "I don't know, there is too much hidden data to make a decision in one way or the other" which is silly. Of course, that applies to basically any area of life, private or professional alike. Making decision seems very hard and justification of it seems shaky at best. We seem to have very limited knowledge of future implications of our actions. I think I actually read some philosopher arguing in similar fashion, which I'd find cool since I'm not the only one who thinks along these lines. But I don't remember the details - perhaps philosophers here could guide me to literature concerning this topic. I'd appreciate any input on this matter.

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  • There is an entire subfield at the intersection of philosophy and mathematics concerned with justifying decisions, it is called Decision Theory. And yes, justifying present decisions in the face of future uncertainty is a big part of its complexity. It is dealt with by using utilities, probability and expected values, quantified when possible, qualitative when not.
    – Conifold
    Commented Jan 8, 2022 at 0:11

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You should try searching this site on a topic you are interested in. I found:

were on the first page.

Choosing a career is so complex that chaos theory has been applied to it.

I would argue that our senses of being a willed agent with a character, are exactly heuristics for making decisions with incomplete data: Constraints on free will

The deepest aspect is being able to live with being the kind of person that made a given decision. Otherwise, yes, informed guesswork. Usually with abundant cognitive biases and post hoc reasoning. I argue here wisdom can be understood as our dilemma-solving faculty: Wisdom and John Vervaeke's awakening from the meaning crises?

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  • As a sidenote, F. Nietzsche had often claimed in his works that people should affirm their lives through their choices. In the final analysis, they should be content with deciding such and such and living such and such..
    – Nikos M.
    Commented Jan 7, 2022 at 19:46

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