The Therapeutic Philosophy of David Foster Wallace

In 2008, I found myself in Rome searching for The Savage Detectives by Chilean author Roberto Bolaño. The book was sold out, and the friendly clerk at the bookstore handed me Infinite Jest by David Foster Wallace instead. I bought it, along with a couple of others, and perhaps three or four years later, I finally finished it—and most of Wallace’s other work.

This seemingly serendipitous moment came just months after Wallace’s tragic suicide. Since then, I’ve often thought about writing on the philosophy underpinning his work. Now, I don’t have to. Jon Baskin, writer and journalist, has written a profoundly insightful book titled Ordinary Unhappiness: The Therapeutic Fiction of David Foster Wallace. In it, Baskin examines Wallace’s fiction as an engagement with philosophy, showing how literature and philosophy intertwine to address the human condition.

Let me share some areas of relevance for psychologists.

Philosophy as Therapy

Baskin’s book isn’t the first to analyze Wallace’s work philosophically. Marshall Boswell’s Understanding David Foster Wallace (2003) offered an excellent overview but didn’t cover Wallace’s later work. Baskin, however, focuses exclusively on Wallace’s fiction and highlights how it serves as a kind of literary therapy—a concept deeply rooted in philosophy.

For Baskin, philosophy is not merely a tool for exposing logical fallacies or constructing theoretical arguments. Drawing from Ludwig Wittgenstein, he argues that philosophy can be therapeutic, seeking to dissolve problems by clarifying how we think about them. Wittgenstein famously wrote in Philosophical Investigations: “There is not a philosophical method, though there are indeed methods, like different therapies.” Baskin applies this idea to literature, suggesting that Wallace’s problems aren’t embedded in the text but within ourselves—our ways of thinking and being.

In this framework, criticism becomes therapeutic when it exposes what we have hidden from ourselves rather than uncovering secrets buried in the work. In other words, Wallace’s literary therapy is “aimed at helping us see the senselessness of our questions.” This approach reflects Wallace’s desire to move beyond the binary oppositions that dominate academic and intellectual debates. Instead of pitting one position against another, Wallace encourages readers to confront their assumptions and see the world more clearly.

Wallace’s Ethical Vision

Wallace’s therapeutic approach is strongly connected to ethics. His philosophy isn’t about prescribing moral rules or outlining abstract ideals; it’s about cultivating an ethical way of living grounded in the realities of human experience.

Wallace’s work repeatedly underscores the importance of attention and clarity. Infinite Jest provides one of the most profound literary explorations of addiction and depression, depicting them not as isolated afflictions but as interwoven aspects of contemporary life. Wallace portrays addiction as a failure of attention, a desperate attempt to escape the pain of existence by numbing it. As he writes: “That no single, individual moment is in and of itself unendurable.” (Infinite Jest)

This simple yet devastating insight suggests that addiction and depression often arise not from one catastrophic event but from an accumulation of unexamined, numbed moments. The real suffering lies not in a specific instance of pain but in the inability to be present with reality.

Wallace’s The Pale King further underscores attention’s ethical and existential significance. At one point, he writes: “Almost anything you pay close, direct attention to becomes interesting…” Could it be that a life not worth living is simply an inattentive life? Suppose boredom, addiction, and depression are rooted in a failure to pay attention. In that case, Wallace’s philosophy suggests that learning to attend—entirely and without distraction—might be one of the most vital human skills. Wallace's concept of "attention" is not just about focusing on a task, but about being fully present in the moment, engaging with the world and others, and understanding the interconnectedness of all things.

The Disease of Modern Life

Wallace’s therapeutic project addresses a deep malaise in contemporary life—a “dis-ease,” as he calls it in Infinite Jest. This ailment stems from the separation of mind and body, theory and practice, intellect and emotion. Wallace saw this divide as both a symptom and a cause of the alienation that characterizes modern existence. The "disease of modern life" as Wallace sees it is a pervasive sense of disconnection, a lack of engagement with the world and others, and a focus on individual success at the expense of collective well-being.

Baskin explores how Wallace sought to bridge this gap by blending philosophy and literature. This fusion allows him to diagnose our time’s psychological and social pathologies. Wallace doesn’t provide cures; instead, he offers readers the tools to see the world—and themselves—more clearly. By shifting our perspective, we can begin to address the root causes of our dissatisfaction rather than merely treating its symptoms.

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One striking example comes from Wallace’s unfinished novel, The Pale King, which revisits many of the themes in Infinite Jest, including addiction and the struggle for freedom. Wallace describes addiction as a form of compulsive thinking, a symptom of our unhealthy relationship with our own minds. Overcoming this addiction requires a kind of maturity—a willingness to confront life’s difficulties without succumbing to despair or nihilism.

As Baskin writes, Wallace’s vision of maturity involves “being an uncomplaining adult, who suffers the indignities of life without making too much of them.” This echoes the ethical philosophy of Gilles Deleuze, who defined ethics as “not being unworthy of what happens to us.” Wallace’s work invites us to embrace this ethos, recognizing that life’s problems are not obstacles to be eliminated but opportunities for growth and transformation.

Why Wallace Matters

At its core, Wallace’s fiction is about life and death, about what it means to be human. It challenges us to think deeply, live more consciously, and confront our limitations honestly and humbly.

For those who have yet to read Infinite Jest or The Pale King, no amount of analysis can substitute for the experience of engaging with Wallace’s work directly. Reading Wallace is difficult—frustrating, bewildering, and sometimes even dull. But it is also transformative. As Wittgenstein might say, the world of someone who has read Wallace differs from that of someone who hasn’t.

Wallace’s work diagnoses the ailments of our culture—stress, burnout, anxiety—not as individual failings but as symptoms of a sick social structure. In today's world, where mental health issues are on the rise and people are increasingly feeling disconnected, Wallace's insights are more relevant than ever. Baskin argues that Wallace’s fiction helps us see these problems for what they are: not personal flaws but collective conditions that require a new way of thinking.

Ultimately, Wallace’s legacy lies in his ability to illuminate the ordinary unhappiness of life and show us how to live with it. As Baskin notes, the goal isn’t to eliminate suffering but to transform it—to turn “hysterical misery into ordinary unhappiness,” as Freud once said. In this way, Wallace’s work is both a diagnosis and a call to action, urging us to confront the challenges of modern life with courage, clarity, and compassion.

David Foster Wallace’s fiction is not a user’s guide or a set of instructions for how to live. It invites thinking, feeling, and seeing the world more clearly.