Uploaded July 2025 | Updated September 2026, 2 weeks ago
How to read difficult books: A complete guide...
Okay on a serious note, in our modern lives we have an unending stream of information available to us. For readers, this can be a wonderful way to connect with other readers, find out about new and interesting books, and of course, do deep dives on critical analysis.
Almost every "classic" from the Greeks to the 21st century now has a mountain of peripheral writing and education to go along with it.
There's no doubt that reading guides, lectures, podcasts, and the like have made these works more accessible and understandable for many readers.
HOWEVER...
A trend I've seen popping up over and over again is paralysis by analysis. Folks who spend a lot of time investigating which works they should read before the book they actually want to read, or searching obsessing over the best translations, or committing hours to reading reviews of guides to assess which is the best one, or sometimes, simply just being too intimidated by a book to pick it up.
But consider for a moment that when challenging books like James Joyce's Ulysses, or Thomas Pynchon's Gravity's Rainbow were published, there was no internet.
Most people simply walked into a store, saw these books sitting on a shelf, thought they sounded interesting, and took them home to read.
I'm not saying that you shouldn't use reading guides, or do any leg work, but you should at least take care to not let these things get in the way of your reading, and to accept the fact that you might not understand most of what you read on the first pass.
Most great books are meant to be read more than once anyway.
How to read difficult books: A complete guide...
Okay on a serious note, in our modern lives we have an unending stream of information available to us. For readers, this can be a wonderful way to connect with other readers, find out about new and interesting books, and of course, do deep dives on critical analysis.
Almost every "classic" from the Greeks to the 21st century now has a mountain of peripheral writing and education to go along with it.
There's no doubt that reading guides, lectures, podcasts, and the like have made these works more accessible and understandable for many readers.
HOWEVER...
A trend I've seen popping up over and over again is paralysis by analysis. Folks who spend a lot of time investigating which works they should read before the book they actually want to read, or searching obsessing over the best translations, or committing hours to reading reviews of guides to assess which is the best one, or sometimes, simply just being too intimidated by a book to pick it up.
But consider for a moment that when challenging books like James Joyce's Ulysses, or Thomas Pynchon's Gravity's Rainbow were published, there was no internet.
Most people simply walked into a store, saw these books sitting on a shelf, thought they sounded interesting, and took them home to read.
I'm not saying that you shouldn't use reading guides, or do any leg work, but you should at least take care to not let these things get in the way of your reading, and to accept the fact that you might not understand most of what you read on the first pass.
Most great books are meant to be read more than once anyway.
