I find it very difficult to reason rigorously about this topic, and none of the below is rigorous. But in terms of sources of hypotheses or proto-models of what if anything is up here, some of my favorite books:
Atlas Shrugged (a fictional portrayal of societal decay that has been increasingly reminding me of current events, particularly since 2016 or 2020)
Zen and the Art of Motorcycle Maintenance (an argument that the West was, since ~Aristotle, built on an almost-coherent philosophy whose incoherence has been becoming more visible across time, and a theory of what the gap is. Pays some rent IMO).
Moral Mazes (similar content to Atlas Shrugged, and not as deep I think, but maybe easier to read because based in current observations instead of fiction)
The above are my favorites. Others that seem less good but still helpful to me:
Possibly Pink Floyd’s movie “The Wall”, which shows societal programming since WW1 as a set of increasingly out of sync software programs being echoed and richocheted by a bunch of overwhelmed/traumatized people and processes
Maybe Venkatesh Rao
The Tao Te Ching — it’s pretty abstract but it has a fair bit to say about what happens when Goodhart’s Law hits mass human behavior
Chapter 1 of Vol. 1 of Hayek’s book “Law, Legislation, and Liberty” (the introduction was too hard, and I didn’t make it much past the first chapter, but I got a lot from that chapter)
Possibly “Century of the Self” (a 4-hour propaganda film about the impact of marketing/psychology/self-help on the contemporary world; possibly a must for anyone as involved in trying to develop self-help or “rationality” techniques as you are), and/or the more recent movie sequence that I am partway through by the same person, “Can’t get you out of my head”. Both by Adam Curtis.
Possibly Vervaeke’s 50-hour history of Western Civilization called “Awakening from the meaning crisis”, on themes similar to Pirsig’s “Zen and the Art of Motorcycle Maintenance”
Possibly Eric Weinstein’s model of “embedded growth obligations”, as a theory of how society in general accidentally overpromised and then headed toward lies/unsustainability rather than rethink itself, kinda like a Ponzi scheme.
I find most relevant Michael Vassar, Ben Hoffman, Jessica Taylor, and Zvi on the same topics; I’d have listed them toward the top except that you (Eli) already know them, and I’m afraid of setting off peoples’ “politicized topic” detectors. I’d be pretty interested to try exploring why/how their writing sets this off in people, and what it indicates about them/us, if anyone wants to.
"The Collapse of Complex Societies" by Joseph Tainter (1988) is a good place to start for a historical perspective. To put in relation with the Club de Rome report "Limits to Growth" (1974).
Dirt: The Erosion of Civilizations by David Montgomery. Makes the case many civilization collapses are attributable to poor agricultural practices
John Michael Greer is (I think) very good on societal decay in general. I read him because he’s a good writer, and he challenges my assumptions in an interesting way, which is to say that his foundational beliefs are very very different from mine (and most people here, I would guess). But his writings on modern society and peak oil make a lot of sense. You can start here - https://www.ecosophia.net/ - and there may be a link there to his older blog, which was more collapsonomic-related.
I got a lot out of reading Peter Turchin's "Historical Dynamics: Why States Rise and Fall", and I'm going to read more of his works soon. He makes elegant mathematical arguments about the intertwining effects of population, technology, and social cohesion on growth and collapse of societies.
There's a recent post on Astral Codex Ten, Etirabys' review of Tainter's "Collapse of Complex Societies", which seems like the sort of thing you're looking for: https://astralcodexten.substack.com/p/your-book-review-the-collapse-of
I've often heard rationalist and EAs talk about civilizational collapse, or civilizational decay: the set of trends whereby society seems to be becoming increasingly less functional, and might at some point fail entirely.
Note that I'm not confident that all of these people are talking about precisely the same phenomenon. In fact, I'm pretty sure that they're not, but they are all looking in a similar direction.
I'd like to get more orientation on how to thinking about these, and related ideas, including read whatever analyses, or speculations, that currently exist on this topic or cluster of topics.
Does anyone have suggestions?