#2 Infinite Jest in a San Francisco Alley

When I step through the back gate onto Jessie Street from my office's back door, I can’t help but think of David Foster Wallace’s book Infinite Jest. The parallels are uncanny. Both the alley and the novel are filled with people trapped in loops they can’t escape, locked in cycles of addiction, survival, and the quiet erosion of time. On Jessie Street, as in Wallace’s world, everyone is moving but no one is going anywhere.

It is a narrow, grimy stretch that has become its own ecosystem. Tents line one wall, cars with cracked windows and sagging tires cluster on the other, and in between, people shuffle through the day, performing the same grim routines. A man in a torn jacket fiddles with a lighter behind a dumpster. A woman with a cart full of tangled belongings mutters to herself. The smell of ammonia and burnt plastic hangs in the air like an unwanted guest.

In Wallace’s Infinite Jest, the residents of Ennet House, a halfway home for addicts, live in similar loops. They are haunted by the same cycles of need and self-destruction that shape life on Jessie Street. The novel captures the claustrophobia of addiction, the way it narrows the world to a series of desperate, immediate choices. On Jessie Street, this narrowing is visible in every movement, every glance. The people here aren’t just surviving; they’re surviving in the most constrained sense of the word, where each day is a repetition of the last, and the future is an abstraction that doesn’t apply.

In Infinite Jest, the systems meant to help—rehab programs, therapy, the vague promises of AA—are portrayed as incomplete, their efficacy limited by the enormity of the problems they’re trying to address. Jessie Street is its own kind of Ennet House, with the city of San Francisco playing the role of the well-meaning but ineffectual support system. The Mayor’s Office likes to talk about its plans—five-year strategies to reduce homelessness, ten-year plans to combat addiction—but Jessie Street doesn’t have five or ten years to wait.

The Mayor’s Office sends sweeps to clear the tents, police to scatter the dealers, and social workers to connect people to services. These efforts are the municipal equivalent of Wallace’s AA meetings: structured, repetitive, and capable of providing small, temporary reprieves. But they don’t address the deeper cycles at play. The tents come back, the dealers regroup, and the people who were displaced simply find another spot to occupy.

Much like the halfway house residents in Infinite Jest, the people on Jessie Street aren’t failures. They are products of a system that has failed to offer them meaningful exits. The Mayor’s Office plays a role that Wallace would have recognized: an institution caught in its own loop of well-intentioned but inadequate action, moving paper around while the real problems remain stubbornly in place.

Wallace’s novel is also a meditation on time—how addiction and despair distort it, compress it, make it unbearable. Time works differently on Jessie Street, too. Days stretch endlessly, filled with small, immediate tasks: find food, stay warm, avoid conflict. But from the outside, it looks like nothing changes. The people here seem frozen, locked in place.

The Mayor’s Office, on the other hand, operates on a faster timeline. Progress is measured in meetings, grant applications, and press releases. The office declares victories that Jessie Street never feels. It’s a kind of performative progress, the same way Ennet House offers its residents the promise of redemption while leaving most of them in the same cycle.

Every day I spend time on Jessie Street, I see these parallels more clearly. The street is a novel in itself (this is a really cheesy thing to write, right? See my footnote), filled with characters who are complex, flawed, and deeply human. The man who always sits near the fire hydrant, his face lined with years of exhaustion but still capable of a quick, biting joke. The woman who drags a cart full of mismatched objects, muttering about conspiracies but smiling when someone offers her a cigarette.

The real tragedy of Jessie Street, much like the tragedy of Infinite Jest, is that the people aren’t the problem. The systems are. The cycles of addiction, poverty, and displacement are bigger than the individuals caught in them. The city’s response—short-term plans and shallow interventions—feels as incomplete as the half-hearted therapies in Wallace’s novel.

And yet, both the book and the alley leave room for a kind of reluctant hope. In Infinite Jest, the characters who survive don’t do so because the system saves them but because they find ways to navigate it, to persist in spite of it. Here, survival is its own kind of resistance. The people endure in ways that are both heartbreaking and awe-inspiring.

David Foster Wallace’s suicide hangs over Infinite Jest like a storm cloud that never quite breaks. The novel’s deep dive into addiction, despair, and the crushing weight of modernity feels less like fiction and more like autobiography in hindsight. Wallace understood something terrifying about the world we’ve created: that it often fails to provide meaning or relief, and that even survival can feel unbearable under the wrong conditions. Jessie Street feels like an extension of that understanding—a place where modernity’s sharp edges have carved out lives too fragile to withstand them. The alley is a monument to how easily people can slip through the cracks, to how progress can leave so many behind.

It’s easy to blame the Mayor’s Office, or the city, or the system at large, but the truth is more complex. Just as Wallace struggled with the weight of his own brilliance, the people trying to address Jessie Street struggle under the enormity of their task. The city is fighting problems that feel insurmountable, problems made worse by decades of neglect and systems too tangled to untie. There’s something profoundly human in both stories: Wallace’s inability to keep going despite his genius, and the Mayor’s Office stumbling in its efforts to solve a problem too big to solve quickly. Both deserve sympathy, not derision. And yet, the loops remain. Jessie Street endures, much like Infinite Jest, as a stark reminder that modernity is as overwhelming as it is inescapable, and that the solutions, if they exist, will take more time than any of us want to admit.

This is part of an ongoing series. This series explores the hidden lives and stark realities of a single alley in San Francisco—a microcosm of the city’s housing crisis and societal failures. Through personal reflections and broader cultural parallels, the essays tackle themes of displacement, addiction, mental illness, and systemic neglect. Each piece pulls back the curtain on the promises we make as a society and the people we leave behind, challenging us to rethink what progress means and who it serves. These aren’t just stories about a place; they’re stories about resilience, humanity, and the urgent need for change.