I think the failure is environmental, not personal. Wallerstein started out his pitch for World Systems Theory by arguing against the empiricism of the null hypothesis: because physics can be A/B tested, physics rose to the top of the science heirarchy and in the rush to reclaim ascendancy, all sorts of disciplines adopted falsifiable hypotheses where there was absolutely no reason to do so. His main whipping boy is anthropology, where uncontacted societies are the gold standard because they lack the impurities of modern culture. Wallerstein's argument was that an uncontacted society is, by definition, a failure because it is so fragile that any contact with another culture causes it to evaporate and that drawing conclusions from the undisputed laggards of the selection set will teach you nothing about its champions.

There's also the broad dissemination of knowledge thanks to literacy, printing and the general availability of education. Only the elite read David Hume when he was alive but now you're likely to get his quotes in a USA Today article. "Philosophy" used to be "knowledge" whereas now it's "knowledge not otherwise specified." That "not otherwise specified" caveat has, in my opinion, left philosophy with slim pickings. A former era would consider Robert Fulghum a philosopher. This era considers him a self-help author. If HL Mencken were alive in Augustinian Rome his bust would be next to Cicero's.

It has been my experience that any discussion of modern philosophy involves staring down not just your own navel, but the navel of someone staring down someone else's navel who is staring down someone else's navel who is mostly standing there arguing where Hegel got it wrong. It has also been my experience that I cannot be compelled to give a shit about Hegel.

Conrad Lorenz, Nazi zoologist, wrote a book called "On Aggression" that was all the rage among psychiatrists and psychologists back in the '70s. Daniel Quinn turned it into a shitty novel about a talking ape twenty years later. Seven years after that, Hollywood turned the ape in to Anthony Hopkins. That, to me, is modern philosophy - misapplication of scientific principles smeared through enough I-want-it filters that the original arguments are virtually unrecognizable, which is probably for the best because they were pure sophistry from the drop. The Qualia of Color could be solved by inspection - why the fuck would we evolve to experience colors differently? - while the Munchausen Trilemma is basically a pretentious-ass way of saying "that's just, like, your opinion maaaaaaaaan" about every other scientific pursuit. Lorenz literally went "when I watch cichlids fight in my fishtank I am learning things about people" and he got a Nobel for it.

I recognize that this reads as me slagging on an entire millennia-old branch of learning. It's not - it's me arguing that anything that wraps itself in the cloak of "philosophy" past, say, Engels is justifying its esotericism through academia. As far as recommendations, I made one in that thread that I still stand by. Tegmark has more recently been wrapped up in the TESCREAL posse but back before the brainrot set in, he did up an amusing little book on the philosophy of quantum physics.