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I'm a big fan of rereading the same books that I found super helpful/useful, vs reading a lot

Used to do the 52 books in 52 weeks challenge for multiple years, until I felt I was just padding my stats with books that weren't useful

Then I saw a Naval tweet that was: "I would rather read the best 100 books over and over again until I absorb them rather than read all the books.”

And I adopted that strategy, which has been more useful for me


The hardest part is knowing which 100 books to reread.

I'd like to think there's a period in your youth when you devour everything - even, god forbid, modern books on management. From here you move on to the classics - Dickens, Twain, Tolstoy, Fitzgerald. If a book bores you, drop it. After enough years, inevitably, you reach a point where you're ready for real literature - Dostoevsky, Proust, Molière, Kant - the greats.

Some books can't be summarized (poetry and real literature), some can be compressed to about ten pages and the majority to 0 pages.


Totally agree, feel like it comes down to an exploration vs exploitation optimization.

Don't have an answer unfortunately, still looking for one myself!

I do agree with the method you describe: taking the recommendations of others, and then later navigating toward what you feel is best for yourself


"The hardest part is knowing which 100 books to reread."

Not if you're like me - my total number read is only about that many in my adult life (other than textbooks and reference books).


This is a good insight, and I sometimes worry I am just optimizing for quantity instead of quality.

That said, how would you pick the “best 100 books” to reread?I also tend to reread things that I enjoyed in the past but it seems like there might be a better way to go about this. I do read from a lot of the “Best books of all time” type of lists and I don’t find a markedly higher success rate with that strategy.


I made this comment above, but it fits here too. I totally agree with rereading books.

I can’t remember the source, but I like the saying “if a book isn’t worth reading twice it’s probably not worth reading once”


Seems like a catchy way of saying what needs to happen for you to lose weight: calories in must be lower than calories out


Amazing guy, his challenges and the way he dealt with them, over his lifetime could teach a lot about handling stress and pressure.


Can +1 that, read that book recently on a friend's recommendation. The way he describes how the trees feel is so impressive


Sad to read. Does seem like anxiety and stress is a big factor of the tech world.


If anyone's looking for a good book on psychedelics, How to Change Your Mind by Michael Pollan made me think completely differently on them (the book isn't about changing your mind on psychedelics fyi)


Now that the stoics have become so popular in the self help / psychology niche, it seems people are now covering everything about the stoics, besides they're actual useful philosophy (including Holiday, who was one of the ones that made them mainstream in the first place)


Same, I don't see anything new that the author really adds to the discussion


That's an awesome idea. Looks like the videos they post online of the bridge area great way to get people excited about it as well.


Great article. It is amazing how many "best selling" books you read, end up being terrible. Would agree with Atomic Habits being an exception, got the book thinking it would be another overhyped one, but actually really enjoyed it (from the practical habit building formulas it gives)


His episode on the Rich Roll podcast was excellent, highly recommended.


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