In one devastating Infinite Jest chapter, the reader is introduced to things you might experience if "by the virtue of charity or the circumstance of desperation, you ever chance to spend a little time around a Substance-recovery halfway facility"—and among those things:
That the cliche "I don't know who I am" unfortunately turns out to be more than a cliché… .
That other people can often see things about you that you yourself cannot see, even if those people are stupid … .
That cockroaches can, up to a certain point, be lived with … .
That perversely, it is often more fun to want something than to have it … .
That it is permissible to want.
That everybody is identical in their secret unspoken belief that way deep down they are different from everyone else. That this isn't necessarily perverse.
That there might not be angels, but there are people who might as well be angels.
That God—unless you're Charlton Heston, or unhinged, or both—speaks and acts entirely through the vehicle of human beings, if there is a God.
That God might regard the issue of whether you believe there's a God or not as fairly low on his/her/its list of things s/he/it's interested in re you.
Then there is The Pale King, reconstructed by his editor after his death, the "Long Thing" (as he called it) that some people think may have led him to his final despair. The book in some ways is a natural outgrowth of Infinite Jest, which posits that it is the daily grind of ritual that grows us into mature humans—against the easy way to live, which is to wallow in mindless, addictive entertainment. Infinite Jest has two main locations: the recovery halfway facility, Ennet House, and the Enfield Tennis Academy, and the passages on them explore how practice makes the man.
So it's only natural that the practice of boredom and middle-condition mindlessness of The Pale King's IRS is contrasted with the narrators' hyper-attention to individual people's lives. If the good life, as outlined in "This Is Water," is one in which we make myriad unsexy choices to be kind to those around us (who are struggling through their own banalities), then it is through the practice of attentiveness that we reach fullness.
The Pale King champions "minute attentiveness to detail as a way of reconnecting to a life that's been battered by the routines of modernity," as Lee Konstantinou wrote in 2011 in the Los Angeles Review of Books. "It becomes the central insight of what amounts to the novel's spiritual ethic, a compassionate concentration on the details of minute-to-minute experience that's perhaps best limned by Simone Weil's famous line: 'Attention is the highest form of prayer'—studious awareness as the penetration of Being." And that same sense of formation through ritual and attentiveness is all over Wallace's nonfiction, from the cruise ship that entices you into dissatisfaction onward to the conclusion, in the seventeenth footnote (you must always be paying attention to footnotes, in Wallace's work), of his essay "Federer Both Flesh and Not," in which Wallace—who was a nationally ranked tennis player as a teenager—watches Roger Federer play:
It's hard to describe—it's like a thought that's also a feeling. One wouldn't want to make too much of it, or to pretend that it's any sort of equitable balance; that would be grotesque. But the truth is that whatever deity, entity, energy, or random genetic flux produces sick children also produced Roger Federer, and just look at him down there. Look at that.
That practice of attentiveness as an antidote to the narcissism that leads to addiction, I think, is what pushed Wallace into his lifelong pursuit to connect with the reader. In the best interview he ever gave, published in 1993 in The Review of Contemporary Fiction, he told Larry McCaffery that "we all suffer alone in the real world; true empathy's impossible. But if a piece of fiction can allow us imaginatively to identify with a character's pain, we might then also more easily conceive of others identifying with our own."
That need to connect—to bridge the divide between reader and writer, between me and you, between me and everyone—is there from the first. In Wallace's first novel, The Broom of the System (which also started life as an undergraduate thesis: he was double major, in philosophy and English), one man is so scared of loneliness that he intends to eat until his body fills the entire world, so he won't be alone anymore. The novel betrays a clever author very pleased with his own cleverness, but you can forgive a 21-year-old the narcissism when you realize the question at the book's core—can we ever really connect with other people?—was an obsession for Wallace, even as his style matured from a theory-based sophomoric snickering to an empathetic, impassioned searching.