Both in therapy, they spent a lot of their time discussing their painful pasts and how they had come to be the way they were — a catalog of ex-lovers and family, with Wallace focused on Karr and his mother. They talked about wanting community and children. Kymberly was astonished at the intense way Wallace listened. He had become interested in Buddhism through a woman he met in Syracuse and gave Kymberly works on the religion that had been suggested to him, plus the Big Book. One day Victoria Harris found them deep in conversation on the couch in the Harrises’ living room. “Stop talking about your relationship and start having it!” she admonished them.
Michael Pietsch read the portion of Infinite Jest that Wallace sent as soon as he got it in May 1993. He made his way through the 750 pages Wallace had mailed off and responded just as Wallace was getting ready to leave Syracuse. His letter was remarkably insightful, given how little time he’d been able to spend thinking about the partial manuscript of a very complicated book:
You ask what I think it’s about. Since it’s not all here my answer to that (and all my suggestions) will have to be tentative…. It’s a novel made up out of shards, almost as if the story were something broken that someone is picking up the pieces of. This fits with the broken lives the novel’s about; also as a way of recreating two worlds, the halfway house and the tennis academy….[O]ccasionally there surfaces through the stories an “I” who may be the one trying to put everything together.
Pietsch wrote Wallace that he was “seriously loving being inside” the “huge roiling story about addiction and recovery, their culture and language and characters, the hidden world that’s revealed when people come in and tell their stories.” But he also saw a major problem on the horizon: length. Good as it was, the book was on its way to being too long. Wallace had tried to trick him with narrow margins and a tiny font in sending the first 400,000 words, but Pietsch had pulled out a calculator and tallied that if what he had on his desk was two-thirds of the finished book, Infinite Jest would be twelve hundred pages, at the least. He doubted the marketability of such a tome. “This should not,” he lectured Wallace, “be a $30 novel so thick readers feel they have to clear their calendars for a month before they buy it.” He urged Wallace to “try cutting now,” even while he finished his story. His other major editorial worry related to the physics of reading. The fragmentary structure of the book — three plot strands that seemed to come to the fore and then recede without pattern — was a lot. A little structural innovation was enriching, but too much and you lost the reader entirely. This was a harder problem for Wallace to solve, because the book consistently confounded the reader’s expectations on purpose. If reality was fragmented, his book should be too. It was also in keeping with Wallace’s insistence that the story not be so amusing that it re-create the disease he was diagnosing. It must not hook readers too easily, must not allow them to fall into the literary equivalent of “spectation.” Infinite Jest had to be, as he subtitled it, “a failed entertainment.” To the extent the novel was addictive, it should be self-consciously addictive. That was one reason he’d structured the story like a Sierpinski gasket, a geometrical figure that can be subdivided into an infinite number of identical geometrical figures. The shape of the book — following Wallace’s natural cast of mind — was recursive, nested. Big things—Infinite Jest, a novel you keep having to reread to understand — find their counterpart in smaller things: “Infinite Jest,” the video cartridge, which itself plays in an endless loop. One character fears she is blind, so she never opens her eyes. Another has an answering machine message that is like one of those infinite man-holding-a-book-whose-cover-is-the-man-holding-a-book visual regressions: “This is Mike Pemulis’s answering machine’s answering machine.” The effect is to emphasize the characters’ isolation, their lives in a funhouse that isn’t all that fun. As in Broom, the apparent casualness of the structure was intensely thought through.
What Pietsch found most off-putting was the political overlay Wallace had given the book centering on the attempts by Quebecois terrorist groups to wrest back their province from O.N.A.N. “Almost everything that matters emotionally works without reference to the time frame or the interAmerican huggermugger,” Pietsch noted, wondering about the necessity of what he called “the ornately bizarre-to-goofy superstructure” of the book. He warned, “the dog is awfully shaggy already.” The letter left Wallace upset and unsatisfied. “He seemed to agree with most of it, glumly,” Pietsch scribbled on a copy of the letter he later sent to Nadell.
Wallace had not been waiting for Pietsch’s response to resume writing. By the time he left for Illinois in July 1993, as he later told an interviewer, he had reached the scene in which Gately is shot protecting his charges at Ennet House, nearly three-quarters of the way through the story. Likely Wallace had more in rougher form. But the combination of the memo and the move to Illinois deflated him. He was home in Illinois again, or nearly, and near home he often found his momentum dissipating. He spent many summer days staring at the ceiling of his new home. He asked a friend from Syracuse to call him every night to make sure he had written, hoping that guilt would spur him to productivity, but the trick did not work.
Wallace had been stumped in a similar way when he moved to Syracuse, and he drew again on the patience and endurance he had learned in recovery to try to get past the roadblock. But as he was settling down to get back to work, a distracting nonfiction project came his way. The editors at Harper’s were longtime fans of his writing. In 1991, they had published “Tennis, Trigonometry, Tornadoes,” his fanciful remembrance of his high school sports life, and, a year later, an adept parody of John Updike’s Rabbit books called “Rabbit Resurrected.” Updike had been an early love of Wallace’s, before he had awoken to literature, and even now he was stunned by the grace and ease with which Updike wrote. But as he’d changed his attitude toward his own work he had reconceived of Updike as part of the American problem, and of Rabbit Angstrom, his principal character, as symptomatic of the prison of self-absorption and egoism that afflicted so many Americans. There was nothing outside his priapic neediness. Rabbit had died in the fourth installment in the series, Rabbit at Rest, published in 1990. Wallace imagined the next chapter in the pages of Harper’s, resurrecting Rabbit into “a solipsist’s heaven, full of his own dead perceptions.” Rabbit asks, “Would there be vaginas, where he was going, vaginas finally freed from the shrill silly vessels around them, bodiless, pungent, and rubicund, swaddled in angelic linen…the odd breast or two, detached, obliging?”
Despite not having taken his television essay, the Harper’s editors were again on the lookout for assignments to give Wallace. So, soon after they learned he was returning to the Midwest, they asked him if he wanted to go to the state fair. The fair was a massive event, with thousands of booths and tens of thousands of visitors attending its 4H shows, dance competitions, and junior boxing tournaments. Wallace hesitated. He worried that he had never done reporting — to his mind the failed pornography piece no longer counted. But he was intrigued too, eager to make some money, and happy for the chance to escape his own head and see a different side of his native region.