Hard for me to make sense of this. What philosophical questions do you think you'll get clarity on by doing this? What are some examples of people successfully doing this in the past?

The fact you ask this question is interesting to me, because in my view the opposite question is the more natural one to ask:  What kind of questions can you make progress on without constant grounding and dialogue with reality? This is the default of how we humans build knowledge and solve hard new questions, the places where we do best and get the least drawn astray is exactly those areas where we can have as much feedback from reality in as tight loops as possible, and so if we are trying to tackle ever more lofty problems, it becomes ever more important to get exactly that feedback wherever we can get it! From my point of view, this is the default of successful human epistemology, and the exception should be viewed with suspicion.

And for what it's worth, acting in the real world, building a company, raising money, debating people live, building technology, making friends (and enemies), absolutely helped me become far, far less confused, and far more capable of tackling confusing problems! Actually testing my epistemology and rationality against reality, and failing (a lot), has been far more helpful for deconfusing everything from practical decision making skills to my own values than reading/thinking could have ever been in the same time span. There is value in reading and thinking, of course, but I was in a severe "thinking overhang", and I needed to act in the world to keep learning and improving. I think most people (especially on LW) are in an "action underhang."

"Why do people do things?" is an empirical question, it's a thing that exists in external reality, and you need to interact with it to learn more about it. And if you want to tackle even higher level problems, you need to have even more refined feedback. When a physicist wants to understand the fundamentals of reality, they need to set up insane crazy particle accelerators and space telescopes and supercomputers and what not to squeeze bits of evidence out of reality and actually ground whatever theoretical musings they may have been thinking about. So if you want to understand the fundamentals of philosophy and the human condition, by default I expect you are going to need to do the equivalent kind of "squeezing bits out of reality", by doing hard things such as creating institutions, building novel technology, persuading people, etc. "Building a company" is just one common example of a task that forces you to interact a lot with reality to be good.

Fundamentally, I believe that good philosophy should make you stronger and allow you to make the world better, otherwise, why are you bothering? If you actually "solve metaphilosophy", I think the way this should end up looking is that you can now do crazy things. You can figure out new forms of science crazy fast, you can persuade billionaires to support you, you can build monumental organizations that last for generations. Or, in reverse, I expect that if you develop methods to do such impressive feats, you will necessarily have to learn deep truths about reality and the human condition, and acquire the skills you will need to tackle a task as heroic as "solving metaphilosophy."

Everyone dying isn't the worst thing that could happen. I think from a selfish perspective, I'm personally a bit more scared of surviving into a dystopia powered by ASI that is aligned in some narrow technical sense. Less sure from an altruistic/impartial perspective, but it seems at least plausible that building an aligned AI without making sure that the future human-AI civilization is "safe" is a not good thing to do.

I think this grounds out into object level disagreements about how we expect the future to go, probably. I think s-risks are extremely unlikely at the moment, and when I look at how best to avoid them, most such timelines don't go through "figure out something like metaphilosophy", but more likely through "just apply bog standard decent humanist deontological values and it's good enough." A lot of the s-risk in my view comes from the penchant for maximizing "good" that utilitarianism tends to promote, if we instead aim for "good enough" (which is what most people tend to instinctively favor), that cuts off most of the s-risk (though not all).

To get to the really good timelines, that route through "solve metaphilosophy", there are mandatory previous nodes such as "don't go extinct in 5 years." Buying ourselves more time is powerful optionality, not just for concrete technical work, but also for improving philosophy, human epistemology/rationality, etc.

I don't think I see a short path to communicating the parts of my model that would be most persuasive to you here (if you're up for a call or irl discussion sometime lmk), but in short I think of policy, coordination, civilizational epistemology, institution building and metaphilosophy as closely linked and tractable problems, if only it wasn't the case that there was a small handful of AI labs (largely supported/initiated by EA/LW-types) that are deadset on burning the commons as fast as humanly possible. If we had a few more years/decades, I think we could actually make tangible and compounding progress on these problems.

I would say that better philosophy/arguments around questions like this is a bottleneck. One reason for my interest in metaphilosophy that I didn't mention in the OP is that studying it seems least likely to cause harm or make things worse, compared to any other AI related topics I can work on. (I started thinking this as early as 2012.) Given how much harm people have done in the name of good, maybe we should all take "first do no harm" much more seriously?

I actually respect this reasoning. I disagree strategically, but I think this is a very morally defensible position to hold, unlike the mental acrobatics necessary to work at the x-risk factories because you want to be "in the room".

Which also represents an opportunity...

It does! If I was you, and I wanted to push forward work like this, the first thing I would do is build a company/institution! It will both test your mettle against reality and allow you to build a compounding force.

Is it actually that weird? Do you have any stories of trying to talk about it with someone and having that backfire on you?

Yup, absolutely. If you take even a microstep outside of the EA/rat-sphere, these kind of topics quickly become utterly alien to anyone. Try explaining to a politician worried about job loss, or a middle aged housewife worried about her future pension, or a young high school dropout unable to afford housing, that actually we should be worried about whether we are doing metaphilosophy correctly to ensure that future immortal superintelligence reason correctly about acausal alien gods from math-space so they don't cause them to torture trillions of simulated souls! This is exaggerated for comedic effect, but this is really what even relatively intro level LW philosophy by default often sounds like to many people! 

As the saying goes, "Grub first, then ethics." (though I would go further and say that people's instinctive rejection of what I would less charitably call "galaxy brain thinking" is actually often well calibrated)

What if I’m mainly interested in how philosophical reasoning ideally ought to work?

My view would suggest: develop a philosophical view of normativity and apply that view to the practice of philosophy itself. For example, if it is in general unethical to lie, then it is also unethical to lie about philosophy. Philosophical practice being normative would lead to some outcomes being favored over others. (It seems like a problem if you need philosophy to have a theory of normativity and a theory of normativity to do meta-philosophy and meta-philosophy to do better philosophy, but earlier versions of each theory can be used to make later versions of them, in a bootstrapping process like with compilers)

I mean normativity to include ethics, aesthetics, teleology, etc. Developing a theory of teleology in general would allow applying that theory to philosophy (taken as a system/practice/etc). It would be strange to have a distinct normative theory for philosophical practice than for other practices, since philosophical practice is a subset of practice in general; philosophical normativity is a specified variant of general normativity, analogous to normativity about other areas of study. The normative theory is mostly derived from cases other than cases of normative philosophizing, since most activity that normativity could apply to is not philosophizing.

How would you flesh out the non-foundationalist view?

That seems like describing my views about things in general, which would take a long time. The original comment was meant to indicate what is non-foundationalist about this view.

I don’t understand this sentence at all. Please explain more?

Imagine a subjective credit system. A bunch of people think other people are helpful/unhelpful to them. Maybe they help support helpful people and so people who are more helpful to helpful people (etc) succeed more. It's subjective, there's no foundation where there's some terminal goal and other things are instrumental to that.

An intersubjective credit system would be the outcome of something like Pareto optimal bargaining between the people, which would lead to a unified utility function, which would imply some terminal goals and other goals being instrumental.

Speculatively, it's possible to create an intersubjective credit system (implying a common currency) given a subjective credit system.

This might apply at multiple levels. Perhaps individual agents seem to have terminal goals because different parts of their mind create subjective credit systems and then they get transformed into an objective credit system in a way that prevents money pumps etc (usual consequences of not being a VNM agent).

I'm speculating that a certain kind of circular-seeming discourse, where area A is explained in terms of area B and vice versa, might be in some way analogous to a subjective credit network, and there might be some transformation of it that puts foundations on everything, analogous to founding an intersubjective credit network in terminal goals. Some things that look like circular reasoning can be made valid and others can't. The cases I'm considering are like, cases where your theory of normativity depends on your theory of philosophy and your theory of philosophy depends on your theory of meta-philosophy and your theory of meta-philosophy depends on your theory of normativity, which seems kind of like a subjective credit system.

Sorry if this is confusing (it's confusing to me too).

Yep that's probably part of it. Standard human epistemic vices. Also maybe publish-or-perish has something to do with it? idk. I definitely noticed incentives to double-down / be dogmatic in order to seem impressive on the job market. Oh also, iirc one professor had a cynical theory that if you find an interesting flaw in your own theory/argument, you shouldn't mention it in your paper, because then the reviewers will independently notice the flaw and think 'aha, this paper has an interesting flaw, if it gets published I could easily and quickly write my own paper pointing out the flaw' and then they'll be more inclined to recommend publication. It's also a great way to get citations.

Note also that I said "a few hundred a year" not "ten thousand a year" which is roughly how many people become philosophy grad students. I was more selective because in my experience most philosophy grad students don't have as much... epistemic ambition? as you or me. Sorta like the Hamming Question thing -- some, but definitely a minority, of grad students can say "I am working on it actually, here's my current plan..." to the question "what's the most important problem in your field and why aren't you working on it?" (to be clear epistemic ambition is a spectrum not a binary)

Here's another bullet point to add to the list:
 

• It is generally understood now that ethics is subjective, in the following technical sense: 'what final goals you have' is a ~free parameter in powerful-mind-space, such that if you make a powerful mind without specifically having a mechanism for getting it to have only the goals you want, it'll probably end up with goals you don't want. What if ethics isn't the only such free parameter? Indeed, philosophers tell us that in the bayesian framework your priors are subjective in this sense, and also that your decision theory is subjective in this sense maybe. Perhaps, therefore, what we consider "doing good/wise philosophy" is going to involve at least a few subjective elements, where what we want is for our AGIs to do philosophy (with respect to those elements) in the same way that we would want and not in various other ways, and that won't happen by default, we need to have some mechanism to make it happen.