Critical Thinking Books [Trenchant Edges]

It's another softball day for me but there's a bunch here you wouldn't expect

Welcome back my friends, this is the Trenchant Edges, a Newsletter about plumbing the depths of fringe culture.

We’ve got an odd version today, following up on the UFO and Critical thinking book idea. One of my favorite research tricks is surveying the audience I’ve built up because I absolutely never see their responses coming and it’s GREAT.

So I reached out to a few people and asking their favorite books on the subject and got just a weird mess, and that’s not even going into my own weird list on the same subject. I think the variety here is very important.

As I commented, the hard thing about defining boundaries on a discussion on thinking better is every well-written book will have much to teach about thinking (there’s my print-bias at work :-D )

So here’s the list loosely organized by my familiarity with it:

The Suggested Books I’ve Read

Carl Sagan’s The Demon-Haunted World; Not gonna lie, I don’t like Carl Sagan, as anyone willing to play general expert for the media inevitably says a bunch of worse than useless crap. This is a good book though but I’m ultimately on the side of the demons and haunting over the rationalist project of the enlightenment so…

Robert Anton Wilson’s Prometheus Rising; It’s probably the most enduring of the books that came out of the 60s counterculture and the only one anyone mentioned for good reasons. Just the idea of reality tunnels and creating some kind of map (even a bad one) of different levels of thinking/experience is valuable.

Marcus Aurelius’ Meditations; Everyone bags on how Romans didn’t innovate much in stoic philosophy, but I’ve always found Aurelius’ perspective as a literal goddamn emperor contending with his own ideals while also ruling a profoundly unidealistic empire makes stoicism far more vivid, real, and understandable. I consider it invaluable as a tool for seeing how you might contend with the practical application of any theory you might have.

Dr Seuss’ One Fish, Two Fish, Red Fish, Blue fish; I don’t remember anything about this book, lol.

Daniel Kahneman’s Thinking Fast and Slow; A great book, which I admittedly mostly say because it gave me a lot of scientific language & facts to back institutions I developed while going crazy before it was published. I’m a rabid enemy of the rational actor model of human behavior.

Don Miguel Ruiz’s The Four Agreements; A classic of the higher grade of new age treacle. The four agreements themselves are fine but I don’t remember the rest of the book as being super worth reading.

Agreement 1: Be Impeccable With Your Word.
Agreement 2: Don't Take Anything Personally.
Agreement 3: Don't Make Assumptions.
Agreement 4: Always Do Your Best.

I tend to think of these as the approach any esotericist or occultist who hasn’t committed to a monstrous path will end up approaching.

Malcolm Gladwell’s Blink; Baby’s first Thinking Fast and Slow. A good book, but not one I’d recommend anymore. Probably Gladwell’s most solid book.

I Ching; A book I’d recommend anyone too enmeshed in the “western”/print linear/rationalist thinking style to limber things up.

Margret Wise Brown’s Goodnight Moon; This one got a surprising amount of recommendations. Another children’s book I have lots of fond feelings towards and no memory of, lol.

Dan Ariely’s Predictably Irrational; Anything that knocks down the myth of primary rationality is hella good in my book.

Descartes’ Discourse on Method; A classic for a reason. We’ve gone beyond him but it’s important to go back and poke around in these fundamental books to really get a sense of the fundamentals of both method and the development of the rationalist project.

Paulo Freire’s Pedagogy of the Oppressed; Another must-read to unpack the way culture convinces people to work against their own desires and interests. Kind of the foundational text of decolonization, IMO.

R Pirsig’s Zen and the Art of Motorcycle Maintenance; This is one of those books that feels like it was probably revolutionary at some point but has hat all its vital juices sucked away by a culture digesting it.

Dr Seuss’ Horton Hears a Who; See Goodnight Moon. I’m sure there’s good stuff here but I do not remember it.

Robert Heinlien’s Stranger in a Strange Land; Become an edgy cutting edge thinker for the 1960s. Didn’t age as well as The Moon is a Harsh Mistress.

OK, so I was going to continue with the ones I haven't read but this has taken a ton more time than I thought it would to collect my thoughts and the multiple sources for this.

My Top 5 books on Critical Thinking

Presented in no particular order and probably missing several books I’ll find myself really embarrassed for missing later:

Plato’s Republic; Once you recognize that Socrates is actually the villain of the Plato Cinematic Universe and the vast majority of his dialogues are about bringing up and problematizing all the obvious views to force deeper thinking and skepticism in his students, Plato goes from a third rate dogmatist to, “Oh, yeah, that’s why he’s fuckin Plato.” It’s also the most taught book in USAian Ivy League schools, probably just for the rigid caste structure where they’re either guardians or philosopher-kings and the noble lie.

It’s a fantastic book and it keeps getting better as you do.

Aristotle’s Rhetoric; Oh shit, I’m doubling down on greek classics. Look, the Ethos/Logos/Pathos model is still pretty much the best way I know to break down the content of an argument. It’s real fucking good. Technically there’s a bunch of Aristotle you should read first but it’s good enough on its own.

Eihei Dōgen’s Shobogenzo; Dogen is my favorite Buddhist and Shobogenzo my favorite Buddhist text. I could compliment it all day, but it’s probably the most thorough single text for deconstructing the self and one’s perceptions I’ve ever read.

It’s focused, grounded, and tied into a broad history of Buddhist thought.

Alvin Toffler’s Future Shock; This one is more idiosyncratic and a factor of when I read it (in 2003 when I was in high school). The idea of an onrushing future crushing the present blew my little mind at the time and has shaped my perspective ever since. Just the way Toffler presented futurism as a skillset was really useful.

Nassim Nicholas Taleb’s Incerto series; The modern contrarian’s contrarian, Taleb is a man I rarely agree with but got a lot out of wrestling with his ideas. Sometimes he goofs on himself really hard, but his works are at least provocative and fun to read and reread.

Alright, instead of a quick thing this has turned into an hour of thinking and writing I shouldn’t have spent on it, whoops.

I want to leave you with a definition and a couple questions.

Mortimer J Adler once defined great books as books written with sufficient elevation that almost no matter how much you develop and grow that they still have much to teach you. His How to Read a Book was on my shortlist for top 5.

  1. What books have you reread and found to be great with this definition?

  2. What books on critical thinking have most influenced you?