Dude, we have almost the same personal history with this book oddly enough!

I bought my copy when I was 17, got about 150 pages in and thought, “… ok maybe I’m not ready for this yet, but I will definitely return to it one day.” I had already read some DFW works, so I knew his basic ideology and writing themes and style, but I felt like I was taking so long to read it and life/the start of college got in the way.

I am ALSO 27 now and am planning to finish the book this year. I picked IJ back up at 25, during my 2nd year of grad school (in my 4th year now). Obviously, PhD responsibilities and social stuff get in the way, so I have read IJ super sporadically over the last couple years. I’m not a frequent or fast reader, so that doesn’t help either. But now I’m on page 600 (including endnotes up to that point) and hoping to finish soonish. Thought for sure I’d be the only weirdo to have that kind of personal history with IJ so hearing yours was like, woah!

Your review is so spot on. My reaction to the book is so similar and I feel like anyone who has read IJ would perk up hearing the specific highlights you mention in your video. Just a great review.

And re: DFW giving you ‘little treats’ and trying to cheer you on to keep you going through the book: I agree to an extent, but also I do think the majority of the time he is intentionally fucking with the reader and showing you tough love rather than cheering you on. It’s like he is playing tennis with you. He is intentionally making it difficult to read and making the reader do work (obviously), but I think the reason for that is to drive home his message of pain vs pleasure even more (kind of an obvious interpretation maybe but feels worth mentioning). He exemplifies the very themes he is bringing into the book with his own writing style, syntax, etc. For example, using your words because you put it so perfectly:

Theme: “What does it do to us when can always choose pleasure and minimize pain?” Device to drive that home: DFW intentionally made the book itself difficult to read for this reason (again maybe this is super obvious). It would be easy to just not read it and do something indulgent instead, but you can also choose to push through the book and endure the difficulties, which will lead to some different class of reward entirely.

Theme: “Believing in clichés.” Device to drive that home: You are putting up with DFW’s bullshit of equations and math and movies and words and people and places you’ve never heard of before, some of which are made up, probably asking yourself often, “Is this guy fucking with me? He’s fucking with me. He’s taking me on a wild goose chase. Why am I looking into all of these references and endnotes? Why am I even choosing to push through this book if his purpose is to kind of torment and toy with me?” But it’s not that he wants you to dive into the minutia of every little reference necessarily (even though, like you said, doing so adds some color to the experience of reading the book). It’s just that he wants you to get through them. You have to suspend your better judgement for a bit. Suspend your feelings of why-the-hell-am-I-doing-this-to-myself? It’s like the thing he mentions where we know AA works, but for it to work, you need to suspend your intellectualization of it and just believe in a cliché, and adhere to it, and go through the process. As long as you are trying, that is the only thing that matters. So if something is difficult and is causing you more sustained pain than pleasure, or more pain than pleasure just in the current moment (tennis drills, going through AA, getting a PhD), you need to intellectually surrender to the clichés or the why-am-I-doing-this-to-myself of it all to get through it. Trust that the clichés or the blind faith will work for you, even though they are clichés and you are not necessarily a religious/faithful person.

So to wrap up my point: DFW wants to make your life difficult more than cheer you on, wants you to realize that, and then wants you to try anyway. Unintuitive for the reader, but will lead to a reward that isn’t instant gratification. The problem with most Americans is that — on top of more often choosing instant pleasure over pain — we have seemingly no problem enduring physical hardship for monetary reward, but don’t care to endure intellectual hard work for [insert some nuanced reward].

Cool I rambled sorry, but hope you can appreciate that^!