1. Constant self-questioning while reading - "Is this obvious? did I already know this?"
2. Lots of examples or stories
3. Try to turn a simple metaphor/slogan into a complete philosophy for life - i.e "skin in the game"
And like the other commenter said, there is a huge difference between reading something, understanding that something, applying that understanding, and finally mastering that application.
When it comes to self-help / philosophy in general, I've found that application is very different from knowing. I believe, selling yourself completely an idea/routine/process (however obvious or well-known to oneself) & build that natural instinct / capability in applying it (when the situation warrants), as if it was second nature, is the point of these books.
> Lots of examples or stories
Some books could be blog posts (btw, LLMs are great for questions like "summarize <widely reviewed book name> chapter by chapter" and follow up questions like "highlight key arguments, counter-intuitive points, novel ideas outlined in <chapter>") and some have just the worst kind of filibustering to bloat the page count; but the many stories / narratives are so one can identify self in at least one among it & consequently build a strong recall to its morals / conclusions.
> ... simple metaphor/slogan into a complete philosophy for life ...
We mustn't fault books for having apt titles? (:
Starting with Taleb at a young age was helpful for me, as he introduced me to the Narrative Fallacy. I.e, the easiest way to convince anyone of anything is to posit a causal chain with some neat story, and 95% of the population will absorb it uncritically (including me, at the time).
I'm asked if I read Cal Newport a lot, and I can't stand him because he makes some good points, some trite points, then relies on the examples and stories. There's a place for them, but he does it in a way that I don't find compelling.
I'm a bit sad that I didn't think of those three bullet points as I was writing this piece, as that's a great short list. It's also super funny that "Skin In The Game" is explicitly one of Taleb's books, the same author who inoculated me from the rest of the list, hah. Not that I think Skin In The Game is bad or anything, just a funny example.
(I don't do that - my writing is all abstract arguments. I should use concrete examples, but have trouble thinking of them. That's why I'm writing critical comments in Internet forums and not blogging.)
I get what you mean about how storytelling is sometimes a contrary indicator, though. When there is too much storytelling and the stories are too simple, it comes across as fake.
I think the best writers want to tell stories with additional complexity even when it doesn't entirely fit the point they're trying to make, because the world isn't really story-shaped. Stories are better when they're not too polished and the author isn't afraid to include contrary evidence.
I'll have to check out more taleb, I didn't know about the narrative fallacy.
There's always one or two good ideas that you get early in the book, and then the rest is repetition and filler.
Because this issue is so common, I think that it actually is okay to just listen to a youtube video summary of most of these books.
My other trick is to always get the first edition version of the book; they tend to be shorter and clearer.