Is there ever real progress in philosophy? What about literature, sociology, economics — don’t all the “soft sciences” have the same problem? I think a lot of it hinges on the question of if we think progress is possible without certainty. Personally, I mostly think certainty is impossible, but we can still garner confidence, and not all confidence is equal (some is better than others).
I do think we can be confident that Isaiah Berlin’s distinction between “positive freedom” and “negative freedom” is an advancement, that Karl Popper’s “falsification” puts us in a better epistemological position than we were a hundred years ago, and that we are sharper thanks to the debate between Rawls and Nozick. Can we be certain that we are? No, and philosophical regression is indeed possible, but I’m confident I’d rather live in a world after Aristotle, Arendt, Deleuze, etc. than before them.
But that still leaves another question hanging: Is it the case that the general public is more philosophically erudite today than they were a hundred years ago? That’s a different question, and this highlights why technology has a unique advantage. The general public doesn’t have to read manuals on how a computer works internally in order to use it, and a person’s computer won’t “vanish” if they don’t read the manual. And yet there’s a sense in which philosophical ideas do “fail to be present” (and “invisible”) if people don’t read up on them. While by virtue of being born people basically inherit the technology of the day, there is no guarantee people will inherit the current state of philosophical, literary, etc. debate. People must choose to work on philosophy, and if the social order doesn’t value philosophy, that probably won’t happen, suggesting regression.
That said, I don’t deny the ideas of a book like To Change the World by Dr. Hunter, which generally claims the ideas of academia eventually do reach the public and influence people (often without them realizing it). Hunter acknowledges though that these ideas are usually decades behind the academic conversation (2020 catches the “secondhand smoke” of 1990, per se) — academic ideas “trickle down” slowly, per se — and furthermore what the public inherits tends to be the general versions of these ideas (not the sophisticated systems), which can be problematic. So, indeed, there is a public evolution of philosophical debate, but it’s slower, unrecognized, and less nuanced.
In conclusion, philosophical progress is possible if certainty isn’t required, and the manifestation of that progress across the general public tends to be a few decades behind the current state of the discussion. But I believe it can and does happen — though often it doesn’t feel like it.