This piece is about a strategy for reading books, with a good starter definition of "book" being a treatment of a subject that goes over 100 pages. If you want a discussion of shorter works, perhaps see my comments on the Searcher's Internet or The Best of Free Internet.
Part 1 Read what I am supposed to have read.
I at first considered putting supposed in quotes (like this: "supposed") but I think we have more of a common understanding what that means than you'd think from our default relativism and rush-from-judgment ways. I think there it would be relatively easy to construct an algorithm for a person feels they should have read if you followed someone around and listened to all of their conversations. The combination of data from a cell phone and Alexa would work nicely for many so-cool cutting-edge modern Americans. I don't mean to state I know how to do the job of the masters of our tiny universe, and almost certainly this will never be what they use their surveillance for, but I imagine the algorithm would either be based on how many times a book or author was mentioned, or perhaps we would need a weighting based on who mentioned the book, opinion leaders being something else I feel it would be easy enough to model. Either way, once the data was established, I think an X percent could be established for how likely we are to state we wish we had read it a book.
I try to read all of those books that form that set for me. Since I was in elementary school I have been able to adopt the tactic of getting through difficult, not super fun books by reading at 10 pages a day until they are done. I don't know why reading needs to be more difficult than this.
Part 2. Read what what "no one" has read.
This time I am using quote marks, because obviously it can't literary be true that no one has read these books. If nothing else, the author had to read it. But really, I just mean read things no one else in my social circle has read.
One benefit of reading what no reads is that I have things to bring up in conversation, different stories, statistics, and anecdotes than anyone else. I remember one time I had read a book from over a hundred years ago about mechanical and electrical tinkering. That evening at a meal with my wife's family I mentioned how funny I thought it was that the took for granted the uses of asbestos. The adults had a laugh and my nephew and the girl he was with did that slight little freeze up thing when you have no idea what someone is talking about. I made light of this, and we all had another little laugh. I may not be world-class weird, but I sure am weird to a small group of people whom I care about.
Another great thing about reading these kinds of obscure books is that it allows me to get practice seeing completely with my own eyes. Since the coming of the printing press, one of the most important arguments for reading has been its ability to transport the reader to other places, thus freeing them from the parochial and mundane. However, when you move past books people should have read to the books people claim to have read (note: experience has taught me to not believe most people when they say they have), you run into the baggage of interpretations and expectations (even if they are lying about having read the work in question). When you read a book no one else knows anything about, you have no choice but to think for yourself.
Ideally, that skill would transfer to other domains, but that a rare thing indeed. However, if nothing else, all this book reading takes you away from advertisements, (lazy) fools, and narcissists. To make a turn on a point Camus made about wealth, the time spent reading can only earn you a reprieve. But a reprieve is always worth taking.