Strong advice but I feel it's much harder nowadays to go down that route when there are distractions like YouTube videos that are easy to watch and make you feel you're learning when really it's scratching a superficial curiosity itch with no depth.
That said, to answer OP's question, I got Mortimer's book called "Great Treasury of Western Thought" that has compiled quotes from Western classics into key themes (the human condition, love, religions, etc), and it provided the missing link between getting meaty samples of key concepts, versus actually reading ALL the classics (the book started as the the index or 'syntopicon' of the 'Great Books of the Western World', a full compilation of Western works)
When I read the Wiki for Stoner years ago I saw this line, "Bryan Appleyard's review quotes critic D.G. Myers saying that the novel was a good book for beginners in the world of "serious literature"". I looked up D.G. Myers and to see if he had a list of serious literature or a twitter where I could ask about such a list only to find he passed away in 2014.
Does anyone know of such a list? Googling provides results but nothing... conclusive.
Anyway, Bloom's list: http://sonic.net/~rteeter/grtbloom.html
Adler's: https://en.wikipedia.org/wiki/Great_Books_of_the_Western_Wor...
Stoner isn't on either one of them lists, FWIIW. Neither are other favorites of mine, such as The Bjorndal Saga.
I also usually search HN for threads like these when I'm looking for things to read. I'm fairly certain that's how I came across Seveneves.
I did a little searching this morning and did find D.G. Myers old blog where he posts a few of his favorite novels, including Stoner. Link here: https://dgmyers.blogspot.com/2012/12/my-favorite-martians.ht...
I guess if I had any advice to offer to someone wanting to achieve that (if it's an achievement) it'd be to try older popular literature (try King Solomon's Mines, it's amazing, then work your way to even older stuff) to get used to older English (nb not Old English, which is another thing entirely and you're not likely to encounter much of it in anything but an extremely deep reading of English lit) and to read short, relatively easy "literary" works that are more recent. Vonnegut's way at the easy end. Maybe try Fitzgerald's The Great Gatsby or his short stories? Salinger's Nine Stories? I'm not sure—at this point I have trouble judging what's approachable. I'd make a terrible teacher of literature.
Lots of things kinda work this way. Jazz and "classical" music usually take some work on the listener's part, to personally learn and develop, before they yield their greatest fruits. Most folks have trouble enjoying silent films, but there are some damn good ones out there. Just takes effort and time.
I'll just add that the sweet spot for learning is rarely as far out as your younger self found it to be (much to the credit of your youthful determination). Too easy, and one's engaging in little more than practice. Too hard, and one lacks the conceptual framework onto which extend one's understanding.
However, I do definitely agree with your advice not to fear the uncomfortable feeling of being at the hard end of the spectrum. With time and determination, we're often capable of longer grasps than we realize.
I agree 100%. The hardest general books are probably in the area of philosophy. My recent fav: The Logic of Scientific Discovery by Karl Popper.