I have a very literarily inclined friend who, when I told I was rereading Infinite Jest this year, told me to keep him abreast of my thoughts. He was curious how it held up in one's thirties, so much of the novel seems connected to his twenties. I shared a lot of these concerns going into the book for the second time.
That said, the first time I read the book, about 10 years ago, I remember it made an impact. I was in my mid-twenties then; I had just started a career and was navigating post-college adulthood. But I also remember Infinite Jest being almost too ridiculous, and I didn't resonate as much with the themes of addiction or social isolation. My introduction to DFW was actually the Pale King, which I would actually argue is better suited for that stage of your life, even as incomplete as it is (so is your life in your mid-twenties).
Having re-read the book now at 35 I can say that The Infinite Jest is not only the perfect book to read in your thirties, it's actually the perfect book to read in the ridiculousness of now.
At 35 I feel the power of technology has largely been focused on ravaging my attention span and social battery life. My family and I are beset by a constant barrage of hedonism: food designed to be overly addictive, portable screens designed to be maximumally engaged with, a market economy built around, as Bo Burnham once astutely put it; "colonizing your attention span and every second of your life".
Inifinite Jest is set in a not-so-distant future and focuses on a couple of congruent plot lines that revolve around the aftermath of an estranged Tennis Academy owning filmmaker creating an Entertainment Cartridge so entertaining that it renders the viewer (literally) terminally addicted to viewing it. The novel explores both the mico/personal/familial level and the macro/geopolitical level of such a creation. This might seem like a hamfisted comment on technology, and it is, but the more dystopian your society gets, the more obvious dystopian literature becomes.
David Foster Wallace could not, in 1996 when he wrote Infinite Jest, predict the age of big data or smartphones or Instagram Reels. It's impossible to stress how little it matters that he got the exact technologies correct and how unbelievably impressive it is that he was able to capture what it's capable of.
Instead of predicting streaming, the world of Infinite Jest has entertainment cartridges that people plug into their massive telephone screens to port in a broadcast. It's remarkably similar to streaming on a smartphone for something written in 1996.
The Entertainment is the name of the cartridge that forcibly addicts its viewers. I think the reason DFW gets away with the thematic obviousness is that the book loves to fuck with you in its form. Like the fact that it's 1100 pages long and has 200 pages of footnotes that make you flip away from the main text on a side quest. DFW knows the reader is a distracted animal. Sometimes, he likes to punish you with a highly technical, chemistry term heavy history of DMT, other times, he likes to bash you in the head with an obvious truth like you're seven years old. All of these things make finishing the book an accomplishment.
There are other modern things it's worth noting only for the fun of it. Telephone calls in the world of Infinite Jest have been replaced by video calls, leading to people with sickening self-consciousness all the time. Sounds familiar? There is a footnote on grocery delivery services where you order groceries off your phone. There is a passage about a counter-culture to standing and bearing live witness to things. Again, the overall capture from the technology here is the effects on people, but it is funny when he gets the actual existence of the technology right as well.
In the midst of reading, I would come across things like this video of a teacher talking about how all the kids in her class "behave like addicts" because they're given a neverending feed of dopamine from their cellphones and then go through withdrawals in school: https://www.instagram.com/teachermisery/reel/DHwe2f8SeLL/
These things really hit home after DFW hits you with the real societal ramifications to overstimulation, to isolating large swaths of the (if not the entire) population in their "customized screens...a floating no-space world of personal spectation". 10 years ago I remember feeling the macro-societal plot in the Infinite Jest too cartoonish, but a decade later, our former-reality star president is threatening to buy Greenland and to annex Canada - which is a literal plot point in this book! There is a new organization run by a billionaire and named after a cryptocurrency scam that is gutting the public sector with reckless abandon right now. Suddenly, Infinite Jest's fictional government department of "Unspecificed Services" is no longer ridiculous.
It could be that our infinite distractibility drives isolation; it's easier to be in front of your little viewing monitor perfectly calibrated to cater to the chemistry in your brain than to deal with people, even loved ones. This feeling should be immeasurably recognizable in anyone who comes home after a long day at work and reaches for their smartphone or video game controller rather than interacting with their family.
It is then that the intense isolation brings the dark irony to life. The more isolated we become the less we care about the people around us and what happens to them. We are living in the societal implication of all of this, which is why Infinite Jest feels so important now. All of this is In The Book.
DFW does offer an answer too, but as is usually the case with great fiction authors (see my review on Ministry for the Future), it misses the mark. Weaved throughout Inifinite Jest is "a community spiel"; whether it's the Tennis Academy boys and their tight friendships getting them through the grueling sports and academia regimen or the addicts in the book's halfway house finding community and getting clean through AA. The only way to seemingly beat back the hedonistic onslaught is to ground yourself in the people around you despite how difficult and arduous it is.
Do not get me wrong; this is a beautiful message and one that everyone should take seriously and try to emulate. This is important. But there is a distinct lack of villains in Infinite Jest. Things like hyper-powerful drugs, addictive technologies and foods seem just immutable, like they just exist in the world from out of nowhere. Outside the book, the villains abound. Capitalism and the profit-seekers the system breeds are the ones who are unleashing these things. Social media companies employ some of the greatest scientific minds to figure out how to attract your eyes to the screen; scientists at huge food and drug conglomerates are figuring out how to make you maximally addicted to their product. Even now that weed is legal, its potency and desirability are being worked on. Vapes, porn, junk food, social media, energy drinks, the addictiveness of these things is visited upon us for a profit and it is truly ruining our lives, planet, culture, and probably the fabric of society.
Not only does DFW explicitly leave these things out of a book that would seem to have plenty of room for them, but he also gives several explications as to why he is doing so explicitly. The most forward is when several characters attend an AA meeting and someone speaking tries to give an explanation as to why they are an addict, why they have the "disease";
"the talk's tone of self pity itself is less offensive than the subcurrent of explanation, an appeal to exterior Cause that can slide, in the addictive mind, so insidiously into Excuse that any causattribution is in Boston AA feared, shunned, punished by empathetic distress. The Why of the disease is a labyrinth it is strongly suggested all boycott the Boston AA in here that protects against a return to Out There is not about explaining what caused your disease. It's about a goofily simple practical recipe for how to remember you've got the disease day by day and how to treat the disease day by day, how to keep the seductive ghost of a bliss long absconded from baiting you and hooking you."
This is repeatedly implied, but the other favorite is the group that protagonist Hal stumbles upon thinking he is going to an AA meeting; the group is really one that entirely focuses on the reasons for one's afflictions. I would spoil the portrayal of the people in this meeting, but let's just say DFW is not kind to this idea and what it does to a person.
There is almost a Petersonian, Rules-to-Life aspect to that belief. That it doesn't actually matter where any of our problems come from and only matters how you get through it. This doesn't necessarily diminish the importance of DFW's work; I would give the advice inherent in this book to anyone freely, and in fact, try to live it in my own life. However, I think it is important to both understand where these afflictions derive and take an activist approach to dismantling the forces that are raining them down. Even if it is only in artistic expression.
So in the end, yes, if you're in your thirties and alive right now, Inifinite Jest holds up. In fact you would be doing yourself a favor by forcing yourself to read it. I feel like DFW wrote this book knowing every person who finished it is a victory over The Entertainment as it exists in the real world. That's two wins for me.
For pure DFW philosophical literary magic, turn to Page 203.
