In the podcast between Spencer Greenberg and Buck Shlegeris, Taking pleasure in being wrong, Buck says:
I think that when you are learning subjects something that you should really be taken your eye out for is the simplest question in the field that you don't know the answer to.
I think a lot of the time people try to learn physics or something and their approach is as quickly as possible to answer hard questions about complicated subjects. And I think that's what I thought was cool when I was younger. They delighted at questions that were at the limit of fanciness that they could possibly answer and it feels to me now that it is a lot more productive to seek out questions that are as simple sounding as possible while still being really hard to answer. Or that still demonstrate that there's something you don't understand about the subject.
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It seems like we should be seeking out these most basic questions in the hope of finding holes in the foundation of our knowledge.
If we apply that approach to applied rationality, what questions do you have that seem to be simple but where you don't know the answer?
Who has a life I would want? What proxy measures are least goodharted? Where can I find them and how can I learn from them?
Where can I live that would have the highest quality of life? What data can I gather beyond summary statistics? How are the summary statistics biased?
How can I save money for the future given high uncertainty about socio-political volatility over the next 40 years?
How can I find good data about the vast work life balance deltas between people, sometimes even in the same field?
What sort of people should I pursue for friendships and romance? What factors predict the things I care about in relationship?
Should I consider moving or making other large scale lifestyle adjustments for consideration X? Where is predictive accuracy good and bad here?
Will my preferences change in any easy to predict ways given certain things happening? Can I reach reflective equilibrium faster?
How malleable are my own preferences and values? Where does this warrant caution and opportunity?