The following is adapted from "A Head That Throbbed Heartlike: The Philosophical Mind of David Foster Wallace," an introduction to Wallace's undergraduate honor thesis in philosophy, which has just been published by Columbia University Press as Fate, Time, and Language: An Essay on Free Will.
I. "A special sort of buzz"
When the future novelist David Foster Wallace was about 14 years old, he asked his father, the University of Illinois philosophy professor James D. Wallace, to explain to him what philosophy is, so that when people would ask him exactly what it was that his father did, he could give them an answer. James had the two of them read Plato's Phaedo dialogue together, an experience that turned out to be pivotal in his understanding of his son. "I had never had an undergraduate student who caught on so quickly or who responded with such maturity and sophistication," James recalls. "This was this first time I realized what a phenomenal mind David had."
The experience seems to have made an impression on David as well. Not long after he arrived at Amherst College in the early 1980s, he developed a reputation among his professors as a rare philosophical talent, an exceptional student who combined raw analytical horsepower with an indefatigable work ethic. He was thought, by himself and by others, to be headed toward a career as a professor of philosophy. Even after he began writing fiction, a pursuit he undertook midway through college, philosophy remained the source of his academic identity. "I knew him as a philosopher with a fiction hobby," Jay Garfield, a professor now at Smith College who worked with Wallace at the time, remembers. "I didn't realize he was one of the great fiction writers of his generation with a philosophy hobby."
For most of college, Wallace's main philosophical interests were in the more technical branches of the subject, such as mathematical logic and the philosophy of language. One semester, he took a seminar on the philosophy of Ludwig Wittgenstein, whose early work grapples with the writings of Gottlob Frege and Bertrand Russell, two of the founders of modern logic. As Wallace recollected in 1992 in a letter to the novelist Lance Olsen, he was "deeply taken" in the seminar with Wittgenstein's first book, Tractatus Logico-Philosophicus (1921). Along with its controversial arguments about the nature and limits of language, the Tractatus introduced some indisputable formal innovations, including a method of analyzing the propositions of modern logic by way of "truth tables." To some, the book might have seemed forbiddingly spare and exacting; Wallace remembered being moved by its "cold formal beauty." When the seminar moved on to Wittgenstein's so-called late philosophy, in which he repudiates the ideas and austere methodology of the Tractatus in favor of new assumptions and a looser, less mathematical style, Wallace was not immediately impressed. He wrote to Olsen that at first he found Philosophical Investigations, the crowning statement of the late philosophy, to be "silly."
Wallace would later identify his attraction to technical philosophy in aesthetic terms: It was, he suggested, a craving for a certain kind of beauty, for the variety of imaginative experience characteristic of formal systems like mathematics and chess. In an interview with the literary critic Larry McCaffery published in 1993, Wallace explained that as a philosophy student he had been "chasing a special sort of buzz," a flash of feeling whose nature he didn't comprehend at first. "One teacher called these moments 'mathematical experiences,' " he recalled. "What I didn't know then was that a mathematical experience was aesthetic in nature, an epiphany in Joyce's original sense. These moments appeared in proof-completions, or maybe algorithms. Or like a gorgeously simple solution you suddenly see after filling half a notebook with gnarly attempted solutions. It was really an experience of what I think Yeats called 'the click of a well-made box.' The word I always think of it as is 'click.' "
For his honors thesis in philosophy, Wallace continued to chase the click, writing a highly specialized, 76-page work on the metaphysical doctrine of fatalism (which holds, quite radically, that human actions and decisions have no influence on the future). Brace yourself for a sample sentence: "Let Φ (a physical possibility structure) be a set of distinct but intersecting paths ji – jn, each of which is a set of functions, L's, on ordered pairs <t, w> (<time, world situation>), such that for any Ln, Lm in some ji, Ln R Lm, where R is a primitive accessibility relation corresponding to physical possibility understood in terms of diachronic physical compatibility." There are reasons that he is better known for an essay about a cruise ship.
II. An "artistic and religious crisis"
One of the many impressive aspects of Wallace's work on the thesis was that he was able to sustain his philosophical focus long after having begun a countervailing transformation: from budding philosopher to burgeoning novelist. The transition was set in motion toward the end of his sophomore year, when a bout of severe depression overcame him. He left school early and took off the following term. Wallace would suffer from depression for much of his life, and he tended to avoid public discussion of it. On a rare occasion in which he did allude publicly to his hiatus from Amherst, in his interview with McCaffery about a decade later, he described the episode as a crisis of identity precipitated by mounting ambivalence about his future as a philosopher. "I was just awfully good at technical philosophy," he said, "and it was the first thing I'd ever been really good at, and so everybody, including me, anticipated I'd make it a career. But it sort of emptied out for me somewhere around age twenty."