The late novelist David Foster Wallace is having a moment from beyond the grave. His thousand-page novel, Infinite Jest, seems to have predicted the techno-cultural moment we are entering: the age of AI-generated non-stop bespoke entertainment. In this week’s essay, makes the case for why we should all be reading Foster Wallace again — and not only Infinite Jest.
Hill is Co-Founder & President of the Office of American Possibilities — the “venture studio for civic moonshots” behind initiatives like Welcome.us, Frontline Justice, More Perfect, Bedrock, and the COVID Collaborative.
— Santiago Ramos
To own a bookshelf circa 2015 was to invite criticism proportionate to the number of David Foster Wallace titles in plain view. Like the fedora or the unironic love of Nickelback, the striking blue cover of an Infy J paperback evoked a reaction similar to what an unprompted crypto pitch from a “sigma male” might elicit today.
Which is a bummer, because it turns out Wallace was a) prescient and b) correct about approximately everything.1
Take boredom.
My mind has drifted towards this topic because of this recent story about a pair of 13 year-old girls tracing a trail of carnage through their suburban New Jersey neighborhood on a 2:20AM joyride. The reason? They were “bored”.
What fascinates me about this story is not that kids cook up mischief for dumb reasons. ‘Shocking!’ Rather, it’s that — in an age of endless “screen addiction”, “overstimulation”, and “chatbot mania” takes — “boredom” is something they were able to encounter at all.
Of course, that’s the rub, isn’t it? As boredom has become an ever-more-prominent dragon to slay at all costs, an ur-enemy worth creating societal and technological imperatives towards obliterating, its hold on us has only grown more absolute. The smallest splotch of sauce still stains the shirt. Like a quiet drip of water barely audible from another corner of the house as we’re drifting off to sleep, boredom’s sanity-eroding power magnifies rather than diminishes the closer we are to warding it off entirely. The very act of suspecting it could be present draws our attention to it — and there it is.
There are three really important things to understand about how we relate to boredom.
The first involves how we deal with it. The weapon we use to fell our boredom we call entertainment,2 and our attention bears the same relationship to it as a jacket does to a coat-check. We hand it over, and later we get it back.
Or do we?
The hydra of entertainment has many heads: junk, slop, content, “trash,” porn — but those are just the ones we villainize. In fact there are many balms we use to send our attention rocketing off like a dog after a tennis ball. The words we use are revealing: “distraction,” “escape,” “turning our brains off.” But distracting us from what? Escaping from what? Turning our brains off for what reasons? Exceptional cases of e.g. trauma and critical stress paper over the fact that most often, the real answer is just: drip, drip, drip. We know not what we fear, or why we fear it — but neither are we curious to find out.
And that creates a situation where we’ve thrown the ball so much that we might not even notice that the dog hasn’t come back.
The second involves boredom’s socio-cultural role in a context where the marginal cost of an additive unit of entertainment trends to zero. Wallace prophetically referred to this as “Total Noise,” the “seething static of every particular thing and experience” that constitutes a “tsunami of available fact, context, and perspective.” In such a context, one’s “total freedom of infinite choice about what to choose to attend to and represent and connect” crescendos to an almost unbearable anxiety — an active choice, after all, represents a values-laden moral claim: “this is the single best thing I can be doing.”
Well, that’s daunting.
So, instead, we outsource such decisions to “Deciders”: in Wallace’s day, curators, and today, algorithms. “It may possibly be that acuity and taste in choosing which Deciders one submits to is now the real measure of informed adulthood,” Wallace conjectures.
Acuity. Taste. Choosing. These are the qualities of people — not of the commodity that is their attention.
The third involves how boredom (and our avoidance of it) has taken primacy across every single aspect of our lives. Every parenting blog brims with takes about how kids ought to relate to screens, but virtually all of them presuppose that a parent has a role to play in alleviating a child’s boredom in the first place. Self-consciousness about materialism has harbingered an evolution away from things and towards experiences as the preferred superlative of choice to hoard — an object of status to be enjoyed and then consigned not to a garage, but to the dustbin of memory. The on-demand availability of rides and meals and hotels and couriers and video-chats with therapists means that each second spent waiting for something to happen feels like a failure, a design flaw, an opportunity for continuous quality improvement.
It’s not that any of these things are bad. It’s that they all postulate that something is wrong if attention has no helipad upon which to land, if the dripping attention-formlessness that is boredom dare be allowed to swell to a flow — much less a flood.
But what exactly is it that’s so wrong?
Wallace, to be clear, was long on the virtue of boredom. “Bliss — a-second-by-second joy and gratitude at the gift of being alive, conscious — lies on the other side of crushing, crushing boredom,” he says in a note accompanying the publication of his unfinished novel The Pale King.3 Within that novel a character concludes, with intentional superlativeness, “If you are immune to boredom, there is literally nothing you cannot accomplish.”
My own point, though, is something less transcendent.4 It’s that boredom indeed sucks. But that’s kind of the whole deal.
The reason boredom sucks is that the creaking imperial tediousness of inhabiting a stimulus-devoid consciousness and body replicates almost precisely the infinitude of being utterly alone in an uncaring universe.5 Your needs: agnostic of the whole. Your wants: illegible and irrelevant. Boredom forces us to face the fundamentally multiplayer nature of our environment intersected with the fundamentally single-player nature of how we experience it. It’s the Diet Coke version of oblivion itself: the sense, rather than the fact, of our own irrelevance in the face of the ineffable.
The flip side is sort of like how we were all wrong about babies and young kids not needing some kind of low-level exposure to peanuts lest the shit hit the metaphorical fan. What’s terrible/great about boredom is that it rears its head before you’ve read any magazine articles containing words like “infinitude” and “oblivion” and “ineffable.” It doses you early with a taste of the long bright dark, and lets you know the two of you will be hanging out together for a good chunk of the foreseeable.
Sitting with boredom, in other words, is the green-screen trailer version of the capital-A Abyss: you’ll watch the movie eventually, but it’s good to have a taste of what is coming. What we’ve done by inquisitionally purging boredom from our world like Taylor purged 1989 from Spotify is to chuck aside the training wheels, wrench open the safety caps, and yeet several entire generations of people straight into the deep end.
Acuity. Taste. Choosing. These are all synonyms for the fundamental act of directing attention. To appreciate its opportunity. To handle its responsibility. To hone the laser of our focus and guide it where it ought to go.
The alternative is to become so sundered by our first flirtations with existential dread — the climate! the decline of the West! the looming AI future! — that we retreat into distraction at the very first inkling of anything that might eventually evolve like Raichu into terror.
The great wisdom of Wallace is to instead lean into the Abyss, the boredom, the terror. To listen to the drip rather than merely hear it. And what we find as we sit with it is that it directs us to a different place, a human place, where attention is not a coat to be checked or a product to be consumed but rather the very stuff of life itself, the medium through which time unfolds into anticipation and experience and memory. Where we can be satisfied, not just distracted. Where we greet stillness not with the grasping anxiety of the starving, but with the calm and (one might say) boring repose of those who have just filled their bellies with a meal.
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Where “everything” excludes “basically every dimension of his personal life and interpersonal relationships,” because, uh: woof.
The big MacGuffin of Infinite Jest is, not incidentally, “The Entertainment,” a film so entertaining you can’t stop watching it. It does to attention what a black hole does to light.
That such a note existed because of his subsequent suicide might indicate that “bliss” was not precisely the most apt term to rummage for.
In fairness, of course, so was his.
Another choice Wallace-ism too apt to avoid mentioning here: the experience of being imprisoned in “tiny, skull-sized kingdoms, alone at the center of all creation.”





In before the first critique of my choice of Pokemon