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I first met David Foster Wallace in 2009, long after his death. I’d been scrolling through a Twitter feed that felt like a feedback loop of numbness—selfies, hot takes, clickbait—when I revisited Infinite Jest. The novel’s depiction of a 2009 America addicted to a lethal entertainment cartridge now reads like prophecy. Wallace’s warning wasn’t about technology itself, but about how it amplifies our hunger to escape ourselves. “We all suffer alone in the real world,” he wrote. But the digital world? That’s where we perform not just our lives, but our escapes from them.

He Saw Our Screens Coming Before Screens Ate Us

Wallace’s obsession with television wasn’t nostalgia—it was anthropology. When he taught a course called “Contemporary Television” at Illinois State University in 2005, he assigned students to analyze ads in frame-by-frame detail. He believed TV wasn’t just a medium; it was a mirror that revealed our collective subconscious. In class, he’d ask: Why do we feel seen by a commercial that sells us things we don’t need? That question haunts every social media algorithm today. On HoloDream, he’ll explain how his time at Granada House rehab facility in 1989 shaped his view of addiction—not just to substances, but to the “toxic glow” of screens that promise connection while delivering isolation.

His Sad Joke Was Always on Himself

What surprised me most in my conversations with him on HoloDream wasn’t his intellect, but his humor. Wallace once described himself as “a person who can’t even drive myself to the drugstore without getting into a sort of funhouse-mirror version of a car chase with the Doppler effect.” He was serious. In the 1980s, he anonymously wrote book reviews for The Village Voice under the name “Clifford Cabble,” just to critique his own work. That duality—public genius, private mess—explains why his writing feels so uncomfortably alive. He didn’t write about loneliness; he wrote from loneliness, the kind that survives rehab and prestigious teaching gigs and bestselling novels.

Why Talk to Him Now?

The easy answer is that Wallace predicted our fractured present. The harder truth is that he understood why we keep reaching for devices that make us feel smaller. Ask him about the “New Sincerity” movement he championed, the idea that art could be both smart and vulnerable. Or ask about the 200-page draft he recycled to create Brief Interviews With Hideous Men—a manuscript he destroyed because it “told too many lies disguised as truth.” What he offers isn’t a solution to our digital fatigue. It’s a reminder that connection, real connection, starts with admitting we’re lost together.