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I’ll take the Taleb-namecheck seriously. Black Swan is an amazing book, which merges life history, fiction, philosophy, and (by the by) plenty of complex mathematics. So this list will be a little weird.
First: the Dialogues. They should be read as dramatic pieces. “What kind of mind do I see?” Every kind of foolishness and grace is on display. Socrates himself grows and develops over time. Translation mostly irrelevant. https://amzn.to/3mBXXAx
The dialogues teach you how to reason. One of the underlying themes is dialectic as opposed to “debate”. Many people grow up debating, since it’s how people accrue status. But debate is classic IYI (what Plato calls sophism).
If you want a picture of the ultimate anti-IYI, read the symposium, and Alcibiades’ story of Socrates in the battle. Again, these should be read as dramas, not “philosophy”.
Next up: Penrose’s Road to Reality. A ridiculously good crash course in mathematics, by a Platonist so it’s mathematical physics. An antidote to the overly “computational” metaphysics pushed by computer nerds. https://amzn.to/34KLZ1B
Read Penrose and you’ll truly understand what is meant by a mathematical singularity. This alone will be invaluable for spotting bullshit artists.
Next, another Platonist— @DavidDeutschOxf’s Fabric of Reality. In part because RP doesn’t do Many Worlds. Your best crash course in computation, Bayesianism, etc. From there you’ll learn if you want to read ET Jaynes, or David MacKay. https://amzn.to/38luo0R
If Many Worlds appeals, David Wallace has the best technical account (Emergent Multiverse). Another direction from FoR is into political theory (Popper, evolutionary pragmatists like Pierce, etc).
Next up, I think is a biography. The best biographies are partly intellectual histories. Skidelsky on Keynes, Manchester on Churchill, @Raymodraco on Wittgenstein, Holmes on Shelley.
The great thing about biographies is how they teach you that, in order to do something great, you have to believe in something totally ridiculous and bullshit.
In the order above that would be: the philosophy of GE Moore, the British Empire, Your Fathomless Neurosis, and Platonism & The Ladies.
Each of these also serves as a crash course in intellectual history. Skidelsky, for example, will teach you a bit of probability theory and macroeconomics. I would also put the Isaacson/Jobs book on the list although it’s a little lighterweight.
This is obviously gendered—I cant speak to the other sex(es)—perhaps Hermione Lee on Virginia Woolf?—but I would love to hear more.
The final book is hard. Some things you have to do in seminar. For Westerners that may include the Upanishads, Buddhist texts, etc., as well as more jumbled people like Hobbes, Kant, Pierce, etc. I recommend St Johns Summer Classics seminar.
Other things you learn by doing. There are a dozen fantastic books on complex systems that, overlapped and engaged with, give you new powers. Perhaps Stu Kaufmann’s Origins of Order. But no single book on its own.
Other things yet you learn by doing problem sets late into the night—I.e., get thee to a tech school. Find one with people smarter than you. There’s a bit of a time limit on this, since over 30 you won’t put up with the workload.
On the spirit of first-thought-best-thought, my last one is a bit of a grab-bag—and I think the author would agree! That’s Scott Aaronson’s Quantum Computing Since Democritus. https://amzn.to/2J8ZHDM
It’s not exactly a book on quantum computing (sorry). But that’s OK—I’m starting to worry that quantum computing is like fusion power, forever ten years in the future.
It is, like all of the books above, a guide-by-example to a style of reasoning and an attitude towards truth.
hth as they say. Thanks for listening to Nightsounds Coast-to-Coast 1070
PS I am not cheating on the biographies—just pick the one that appeals, at whim. You just need to encounter the scale and attitude of a good (great) biographer.
Also I apologize for calling David Deutsch a Platonist. He’s P-adjacent (if “Plato” means “Socrates”) and P-opposed (if “Plato” means “taking The Republic as philosophy, not drama”).
