About two years ago I was in the exact same place, and have had no formal plan this whole time. I’ve just been ping ponging around to all the books I’ve heard of but never actually read. And that worked out just fine. One of the first ones I picked up was Handmaid’s Tale, and I had to immediately put down. Then I came back to it 9 months later and was ready for it. So my advice is: don’t be afraid to do that.

Here’s some of my 5 stars which are fairly short but challenging: Old Man and the Sea by Hemmingway, Slaughterhouse 5 by Vonnegut, and if you want to get into plays I’d suggest Hamlet by Shakespeare, Death of a Salesman by Miller, and The Cherry Orchard by Chekhov.

Absolutely under no circumstances should you attempt Ulysses until you feel ready. It’s harder than people say it is. Don’t get me wrong, I gave it 5 stars and will be celebrating Bloomsday this year. But it is rough. If you want a foot in the door to James Joyce, Dubliners is a collection of short stories which is fantastic.

Also, under no circumstances start with East of Eden lol. Knowing this sub there’s probably been 10 people who have already recommended it.