I debated including Vonnegut. I too devoured them ~15-19. But they don’t fit somehow. They might be a first introduction to vibing/feeling rather than thinking.
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Yeah Daniel Quinn’s Ishmael is at least adjacent. I feel it falls short because it doesn’t supply enough of a complex canvas. It’s more one big idea. Might be a good support for the Pirsig tribe.
A nerd-out metaphysics with lots of fiddle details to it seems like a core feature.
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I'd add that environmental one about the gorilla (...little help?). It also becomes a red flag, but mostly for "nice but not super smart".
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Any votes for Infinite Jest? I tried and quickly abandoned it at age 35 or so. Murakar I seems to be another candidate (never read).
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I kinda feel like infinite jest fits in this trend, but maybe more toward the tail end. Feels more 21 than 18
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Yeah, there’s a bunch of coming-of-age novels that I feel are a separate category. Vonnegut, Great Gatsby, Catcher in the Rye, Catch 22, World According to Garp. They’re more like video games rather than operating systems for the sophomore mind. They occupy but don’t animate. t.co/H8GhPz1pmR
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Murakami a couple of tweets up.
“Totalizing” is it. Hence OS as the metaphor.
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... and the problem (or rather a feature, if we’re using then as red flags) being they’re too self-consistent to raise suspicion and too expansive/vague to be easily cross-checked 
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🤔 I think Taleb and NKS (Wolfram) are unlikely first-consciousness books. I suspect they’re second or third consciousness. Probably for those who are consciously terminal-locking into a hedgehog mindset ~ 25-30. Include in this set: Ivan Illich, C. Alexander, Charlie Munger…
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pleasantly surprised to see GEB in the list btw ) also, NKS and/or Taleb?
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In part because they’re more intellectually demanding and require more life experience to relate to.
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Hmm. Borges is an odd case. In between the thinking and vibing portals. I was introduced to him via GEB like many engineers, but Borges has probably stayed with me much more than Hofstadter himself.
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Crap, yes. Sapiens is in the set now. ~2014 inductee into sophomore portal (also for older techies and VCs who apparently skipped adolescence because they were too busy killing it 🤣)
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Wait, I got it. Sapiens?
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This thread has been your friendly neighborhood tutorial on how to make enemies and alienate people.
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I should reorganize my now-reading page by this logic. Categorize the top-recos column by appropriate age.
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That’s basically it. HHG is (or can be) nihilism 101 and people who are uncritically attached/attracted to the idea of being/doing ‘good’ see HHG fandom as a red flag of moral degeneration or something.
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What do you mean by "a read flag for good people"?
I'd introduce a child to HHGG and GEB because they're good fun and give them language to practice juggling metaphors and abstractions. But would avoid Ayn rand, Pirsig or anything with strong claims on morality and virtue!
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I was wondering if there are Act 2 portal books, for the post mid-life crisis 42+ set, and it struck me that by 42 you’re too fragmented for books to have that big an effect. So the portal is now-or-never activities. If you don’t start now you’ll physically become incapable soon.
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That’s one reason I’m getting into maker shit now. 20y ago there would have been expectations of doing something actually impressive like inventing a significant robot thing.
Otoh If I wait eyesight/dexterity might get too poor to get through learning curve.
Now or never.
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I’ll also guess that beyond a certain age it’s impossible to *write* portal works unless you’ve already started. Without looking I’ll guess that these authors had at least started their major works before they turned 40.
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Can see that. I read Glass Bead Game a few years ago and could tell 19-year-old me would have missed the satire and unironically gone on a yak shave to invent the game. I did read Siddhartha as a teen, but that one’s kinda a weird misfire for Indian readers. Uncanny valley.
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I wonder about Herman Hesse on this list , especially siddharta and steppenwolfe — read them around the time I read the others on this list and I remember them having a similar impact on me
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Moral of the story: Every 19-year-old is unique in the same way, every 42-year-old is a cliche in their own way.
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