In 2009, I began seeing copies of Infinite Jest in unexpected places: on the shelves of non-literary friends’ apartments, in the hands of well-dressed commuters on trains, in the lounges of backpacker hostels in China and Southeast Asia. David Foster Wallace’s suicide had received just enough mainstream media attention to suggest the loss of not just a novelist but an important cultural icon; it makes sense that his most celebrated work would gain popularity after his death. Still, I was surprised, and it struck me that I had underestimated Wallace’s influence. Having once lived with a roommate who was an avid fan of “DFW” (as he was known in our apartment), I had learned how to talk about him, but it wasn’t until years later that I read the thousand-page novel that made him a literary celebrity. I remember admiring his essays—there was something inimitable about the way he could hold an idea aloft in a reader’s mind even as he piled modifier upon caveat upon anxious sub-clause.

But when it came to fiction, I associated Wallace with Thomas Pynchon and John Barth, and I had already made up my mind that if it were between the minimalists and the postmodernists, I would take the minimalists. At least they were trying to tell me a story; if I had wanted to learn about Wittgenstein, I would have taken that seminar when it was offered. What did a philosophical treatise on a linguistic form of solipsism have to do with the way people actually lived their lives? I wanted to read literature about spiritual crises, not intellectual ones. I turned to Dostoevsky, Kierkegaard, and Beckett. I read Marilyn Robinson and Flannery O’Connor. I used to argue to friends that certain authors (Gore Vidal was a favorite example) simply had too much ego: they weren’t willing to disperse themselves into characters or plots or points of view that might carry something other than their own intellectual force. I put Wallace in this group without really giving him a chance. Once, a friend showed me a comment her professor had written on a poem she’d submitted in class: “You knew what you were doing,” it said. I liked that. Wallace knew what he was doing, I thought, and that was the problem.

Reading Wallace’s biography just four years after his death, I was surprised to discover how deep and universal his ambivalence towards literature was. I don’t just mean his uncertainty about whether he was a philosopher or a writer. I mean the kind of inner conflict that led him to call Infinite Jest a “failed entertainment” (his editors, understandably, forbade him from using this as a subtitle), or the kind that drove him to include the “Dave Wallace” character in sections of his posthumous novel The Pale King, despite his ability in other sections to sublimate that well-known authorial self-consciousness. There are ways to intellectualize such ambivalence, which Wallace spent many years doing, but it is ultimately not an intellectual problem. Basically, the problem is this: we feel chronically unfulfilled because we want literature to do more for us than our culture’s attitude towards it will allow. We want to read a novel that does the impossible—that captures something essential about the daily struggle of contemporary life (which means finding the symbolic cross-section between cultural absurdities and private indignities), and at the same time offers us joy in believable ways (which means, as Wallace once put it in an interview, applying “CPR to those elements of what’s human and magical that still live and glow despite the times’ darkness.”) Most novels are only able to do the former—including Wallace’s first attempt, The Broom of the System, which is filled with the kind of metaphysical riffs he would later describe as “gratuitous titty-pinching.” At the end of his life, he still struggled to answer both needs: the compulsive, omniscient cultural observer was always in conflict with the writer who sought to “make heads throb heart-like,” a recurring phrase in his biography. But Wallace was consistent when it came to his exalted expectations for fiction:

Fiction is one of the few experiences where loneliness can be both confronted and relieved. Drugs, movies where stuff blows up, loud parties—all these chase away loneliness by making me forget my name’s Dave and I live in a one-by-one box of bone no other party can penetrate or know. Fiction, poetry, music, really deep serious sex, and, in various ways, religion—these are the places (for me) where loneliness is countenanced, stared down, transfigured, treated.

In Every Love Story is a Ghost Story: A Life of David Foster Wallace, D.T. Max chronicles Wallace’s attempts to treat his loneliness and self-alienation with a series of false cures (language philosophy, postmodern hijinks, iconoclasm and celebrity) before discovering the value of embracing community—through teaching, group therapy, religious retreats, or a regular correspondence with novelist-friends like Jonathan Franzen and Don Delillo. The story has a sad ending, of course, and Max makes sure to leave it as such—overall, his biography offers a clear-eyed account of Wallace’s self-destruction. He does, however, make one noteworthy claim. Writing in The New Yorker about Wallace’s decision to go off the anti-depressant he’d been taking for decades because it kept him from finishing The Pale King, Max calls Wallace “a martyr for literature.”

What does it mean to be a martyr for literature? It’s difficult to say. Literature has always been a shadowy project, and one that is perpetually under siege—from within as much as from without. In fact, the four years between Wallace’s death and the publication of his biography have been marked by another crisis of confidence in the relevance of literary fiction. In his book Reality Hunger, David Shields made the case that traditional forms of literary artifice were failing to satisfy a deeper need in a culture dominated by cable news, advertising, and an inexhaustible fascination with celebrity. In her 2010 book of essays, Changing my Mind, Zadie Smith suggested that she and her colleagues now found themselves marooned somewhere between the example of Joseph O’Neill’s Netherland (lyrical and well-behaved) and that of Tom McCarthy’s Remainder (“a kind of anti-literature hoax”). (Smith’s new novel, NW, reads like an attempt to bridge the gap: it is formally adventurous yet still concerns basic, commonsense, middle-class themes of friendship and family and aging and belonging.)

And then came Sheila Heti’s How Should A Person Be?: A Novel from Life, which uses transcribed conversations, real emails, and is, according to the publisher, “part literary novel, part self-help manual, part bawdy confessional.” If Wallace struggled to give his readers a new kind of Realism by acknowledging how fragmented and perversely stimulated the average American’s experience really was, Heti’s goal is to move beyond Realism. It seems clear that the “Sheila” in her novel is meant to represent the “real” Sheila in a more straightforward way than the authorial “Dave” of The Pale King is meant to represent Wallace, but then one encounters a passage like this and has to reconsider:

When I strip away my dreams, what I imagine to be my potential, all the things I haven’t said, what I imagine I feel for other people in the absence of my expressing it, all the rules I’ve made for myself that I don’t follow—I see that I’ve done as little as anyone else in this world to deserve the grand moniker I. In fact, apart from being the only person living in this apartment, I’m not sure what distinguishes me.

In How Should a Person Be?, Heti’s voice sometimes resembles Wallace’s non-fiction persona not in terms of style, but in its mock-casual attitude towards difficult moral and aesthetic questions. The difference is that as Wallace developed, he began to push the paradoxes and struggles of artistic creation explicitly into the moral realm. He saw that writers, just like people, want to be truthful and likeable at the same time; the only solution in both cases is to activate “the part of you that loves, not the part of you that wants to be loved.” The problem of creating a fictional character from scratch is unique to the novelist, but Wallace understood that to live a good life one sometimes needs to call upon similarly heroic reserves of empathy and attentiveness. Heti’s rejection of traditional Realism seems to have more to do with her own frustration over the creative process itself, whereas Wallace, at least in his later fiction, seemed equally concerned with the reader’s experience. It was part of what inflamed his sense of failure.

Heti seems to have a healthier, quirkier artistic self-consciousness (“Better to have a good imagination than a good grilled cheese sandwich.”), but this may be because she is more concerned with authenticity than morality. How Should A Person Be? chronicles the idiosyncratically messy lives of artists in Toronto; its main sources of tension are Sheila’s failure to write a play that she fears will be insincere and her complicated relationship with Margaux, a painter-friend she admires and envies. One major plotline involves a competition to see who can create the ugliest painting, which leads Margaux to muse about the difficulty of explaining her taste:

Well, everything I like is ugly-beautiful. For me, what’s truly ugly is, like, tight blue jeans with cowboy boots and a lot of makeup—restrained things. That’s realy ugly—or like a really detailed drawing of a rocking horse. I think anything tight is truly ugly for me. Not ugly for the world—people love that—but it just looks awful to me. It looks like death.

In other words, Heti’s “novel from life” is really a novel about the lives of artists. This is important to recognize, because communities of artists have their own special dynamic: each member of the community spends most of his or her time trying to decide who is genuine and who is full of shit, and the rest of it suspecting oneself of being on the wrong side of this divide. In some ways Heti’s book is more honest (it is hard to imagine Wallace being so open about the camaraderie and competitiveness in his relationships with Franzen and Delillo), but it is also more restricting, because a non-artist reader has to work harder to conceive of this particular world. Wallace might not have agreed with the way Heti goes about answering the question her title asks, but he would have acknowledged the importance of asking the question in the first place, and he certainly saw the novel as our culture’s best chance to tackle it, irony notwithstanding.

Wallace’s biography—and the response to it—is a reminder that there is most definitely a hunger out there, but it is not necessarily a hunger for “reality.” It is more likely a hunger for community. I do not feel that I know the “real” Wallace any better after reading about his life, but I do feel more connected to a community of readers. I took pleasure in the knowledge that Wallace once lost a tennis match to the poet Stephen Dunn, and I found it illuminating that he once described Infinite Jest as “an attempt to wash Pynchonian excess in the chilling waters of Don Delillo’s prose and then heat it up again in Dostoevsky’s redemptive fire.” The problem is, not everyone would share this reaction. Those of us who appreciate Wallace (even latecomers such as myself) feel that we exist in a larger, more disparate version of the community Sheila Heti describes. After all, each of us has a kernel of the artist’s impulse. (One of the great accomplishments of Ulysses, another famously difficult novel, is that Joyce’s ostensibly pedestrian Leopold Bloom becomes both a ‘hero’ and an ‘artist’ in his resistance to ideologies ranging from nationalism to fatalism; readers feel affection for Bloom because he symbolizes parts of ourselves we can never find ways to discuss—both the harrowing skeptic and the hopeless sap.) At the same time, not everyone believes that literature can operate at the level of religion or moral philosophy. The fact that Wallace tried to reach both sets of readers helps explain why he found the work so difficult.

And yet he did succeed in important ways. Wallace’s dilemmas turned dictums (“choose carefully what you worship”; “disturb the comfortable and comfort the disturbed”) are memorable partly because they are unexpected; Wallace was offering solace to a generation who had been trained to think that solace was lame—some kind of quasi-religious sentimentality that belonged in a Raymond Carver story. In “Good People,” a section of The Pale King that was published in The New Yorker, he had begun to see that “the good” was as complex and prismatic and exhilarating to chase as “the real.” Wallace seemed to acknowledge that even fragmented realities need to be made comprehensible if literature is to fulfill its promise. Still, he insisted that the reader tolerate a measure of uncertainty. Michael Silverblatt, an L.A. radio host who interviewed Wallace after the publication of Infinite Jest, said the novel’s sadness is “formed by the obligation to have no stable position.” This seems true for The Pale King as well. Wallace never abandoned his search for the real, nor did he overcome the impulse to smuggle his creative anxieties into his fiction. He did, however, make a conscious effort to present his readers with states of being (the self-doubt of a young Christian; the crushing boredom of an IRS employee) that would allow them to experience and “stare down” moral and existential quandries that all of us—not just writers—face.

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For a long time I kept Infinite Jest in the same traveling bag as Fernando Pessoa’s The Book of Disquiet, a “factless autobiography” written under the semi-heteronym Bernardo Soares and published forty-seven years after Pessoa’s death in 1935. There was no reason to be reading these two books at the same time, apart from the fact that Pessoa’s is fragmentary, aphoristic, and filled with “dolorous interludes” that offered temporary relief from the long sections of Infinite Jest. But as I went along, it seemed to me that Bernardo, a lonely bookkeeper in Lisbon with a deep artistic sensibility, is the kind of character Wallace would have been curious about. Interspersed with long mediations on Bernardo’s asceticism are gems like this one: “I can’t be too disappointed about not having become a Roman emperor, but I can sorely regret never once having spoken to the seamstress who at the street corner turns right at about nine o’clock every morning.” Even better are his enigmatic pronouncements on the question of art vs. life, some of which seemed oddly relevant to the task of reading Wallace’s novel. The one that struck me most was this: “Art lies because it is social…We all love each other, and the lie is the kiss we exchange.”

Had Wallace ever read this book? I knew from interviews posted after his death that The Brothers Karamazov had been important to him (in fact, the brothers of Infinite Jest are loosely analogous to Dostoevsky’s), and this opened the possibility for a different interpretation of Wallace, one that saw his fragmented narratives not only as a statement about our experience living in a media-saturated society, but also an attempt to put our hopes, fears, beliefs and doubts in conversation with each other. Wallace worried about being sincere. He talked about loving his reader; he said he wanted to stare into the camera. He was drawn to Catholicism—a religion that, as Walter Pater once put it, asks people to look at their lives as works of art. He was also drawn to Buddhism (In a letter to a practicing Zen Buddhist who had read his commencement speech at Kenyon College and detected Buddhist principles, he wrote: “Is it half-lotus or nothing? If so, why?”). But more than anything he was drawn to the problem of writing. It is as if he could not accept the fact that he was an artist. Or maybe he assumed that by “artist” we mean someone whose moral vision need not be taken seriously, someone who is cloistered, obscure, and unapproachable—in which case perhaps he never wanted to be one.