How do you know when you're 'ready' for the big

Infinite Jest is pretty accessible. I'd recommend reading some easier literature, get to know your high school core and read some other, tougher stuff. Then you're probably ready. Also, you don't need to read all of the high school core books.

>>8313358
IJ isn't difficult, so you're ready.

JR is easy if you didn't struggle with any of the ambiguity of sudden dialogue in IJ and was able to keep track of the characters.

You can read Ulysses after reading Dubliners and Portrait.

Skip GR, it's trash.

>>8313372
GR is equal to if not better than Ulysses.

You can read any of those books at any point in time, except for Infinite Jest, which is shit.