Olivia: Jackson, what’s the standard advice for dealing with a broken heart? Jackson: Uh, retreat? Go somewhere quiet? Eat an unreasonable amount of ice cream and avoid all human contact for the foreseeable future? Olivia: Exactly. You cocoon yourself. But the book we’re talking about today flips that entirely. It suggests the best cure for profound grief and insomnia is to throw yourself into the most chaotic, sleepless, and overwhelming city on Earth. Jackson: That sounds like fighting fire with a bigger, louder, more expensive fire. I'm intrigued. Olivia: It's the central, beautiful paradox in "Insomniac City: New York, Oliver, and Me" by Bill Hayes. And what's so compelling is that Hayes, who is a Guggenheim fellow, actually did this. He moved to New York at age 48 after the sudden, tragic death of his long-term partner, arriving with just a one-way ticket and no real plan. Jackson: Wow. So this isn't a thought experiment; he lived it. That completely changes the stakes. So how does that even work? How does a loud, dirty city possibly heal you?

Olivia: Well, that's the first major idea in the book. The city doesn't just distract him; it becomes a mirror for his own internal state. He’s an insomniac, grieving and restless, and he moves to a city that is also insomniac and restless. He says if New York were a patient, it would be diagnosed with a rare condition called 'agrypnia excitata'—chronic insomnia and nervous energy. He found a kindred spirit in the city itself. Jackson: I can see the poetry in that, but I'm still stuck on the practicals. The noise, the crowds... that sounds like my personal nightmare when I'm feeling down. Olivia: But he finds beauty in the most 'unbeautiful' ways. There's this one incredible story. Not long after he moves there, he's standing on Sixth Avenue on a Sunday morning, thinking New York isn't a place you come to for beauty. Suddenly, he hears a rumble. The street is taken over by hundreds of skateboarders, whooping and hollering, waving their shirts in the air. He describes it as 'the anarchy of pure joy.' Jackson: That sounds amazing. A flash mob of pure energy. Olivia: Exactly. And all the bystanders, himself included, just stand there, open-mouthed, and start clapping spontaneously. The moment is over in a flash, and he texts his friend a simple, perfect line: "Beauty stops traffic." He realizes that in New York, beauty isn't in a pristine sunset; it's in these raw, fleeting, human moments. Jackson: That's a great moment, but it's fleeting. What about the day-to-day grind? The loneliness that can feel even more intense when you're surrounded by millions of people? Olivia: He goes there, too. He doesn't shy away from the 'lowlife' routes, the dirty, deserted streets. And that's where he finds an even deeper kind of connection. He tells this powerful story about a homeless street poet named Wolf Song. He'd met him once before, and two and a half years later, he runs into him again by chance. Jackson: And the guy remembers him? In a city of millions? Olivia: Remembers him instantly. Wolf Song wants to write a poem for him, but they don't have any paper. So Hayes buys him a pen and a beer, and the poet finds a scrap of newspaper—a 'Sky Watch' column with a map of the constellations. He sees it as fate. He painstakingly writes this poem right over the stars, a line that just guts you: "Sky why So Much Pain is The Rain Drops eyes To Your Story." Jackson: Whoa. That's... heavy. And beautiful. Olivia: And they both just stand there and cry together. It feels like he's finding this magic where most people would just see poverty or chaos. Jackson: I guess that's the point, isn't it? The book is arguing that the city's soul isn't in its landmarks, but in these raw, human moments, if you're willing to look for them. Olivia: Exactly! It’s a city that’s constantly generating stories. And this openness to the city's raw humanity is what prepared him for the most unexpected connection of all—with a man who was, in his own way, a universe unto himself.

Jackson: You’re talking about the legendary neurologist, Oliver Sacks. The book is dedicated to him, 'in memory of Oliver.' Their relationship is at the heart of this, isn't it? Olivia: It is. And it's one of the most unconventional and touching love stories I've ever read. It began with a letter. Sacks read one of Hayes's earlier books and wrote to him. They started a correspondence, and eventually, after Hayes moved to New York, they fell in love. Jackson: What's so fascinating, from the background info, is that Sacks was in his seventies and had lived what he called a 'monk-like existence' for over 35 years. He was essentially falling in love for the first time, late in life. Olivia: Yes! And their relationship was built on this incredible intellectual and emotional curiosity. Their dates weren't dinner and a movie. They were long walks in botanical gardens where Oliver would expound on ferns, or trips to the Museum of Natural History to discuss the periodic table. It was a meeting of two brilliant, deeply curious minds. Jackson: It sounds incredibly romantic, but also... a little intimidating? I mean, this is Oliver Sacks. What was their dynamic like? Olivia: It was quirky and deeply endearing. Hayes paints this picture of a man who was a genius but also profoundly disconnected from popular culture. There's this hilarious moment the day after Michael Jackson died. The whole world is mourning, and Oliver turns to Bill and asks, with genuine curiosity, "What is Michael Jackson?" Jackson: (laughing) No way. That's amazing. So this world-famous genius had no idea who the King of Pop was? What was it like to be in a relationship with someone so brilliant but so out of sync with the modern world? Olivia: It was a huge part of the charm. Their love language wasn't shared cultural references; it was shared wonder. They were both insomniacs, both writers, both obsessed with the mechanics of the world and the human mind. Their connection was built on this profound philosophical foundation. Sacks has this incredible quote in the book's epigraph: "I don’t so much fear death as I do wasting life." Jackson: And it feels like his relationship with Hayes was his way of making sure he didn't waste a moment. It’s less about grand romantic gestures and more like finding your perfect intellectual sparring partner who also happens to hold your hand. The meeting of minds is the primary romance. Olivia: That’s a perfect way to put it. And it’s why so many readers and critics, from The New Yorker to Joyce Carol Oates, were so captivated. The book gives us this rare, tender, and deeply human portrait of a man many only knew as a scientific giant. It shows us Oliver Sacks, the man who is learning to love. Jackson: It seems like both his love for the city and his love for Oliver Sacks came from the same place: a willingness to pay incredibly close attention to things.

Olivia: You've hit on the third and perhaps most central theme of the book: what I'd call 'the art of noticing.' Hayes argues that the deepest meaning in life is found not in grand events, but in these small, observed, fleeting moments. Jackson: The 'evanescent, the eavesdropped, the unexpected,' as he puts it. Olivia: Precisely. He has this wonderful philosophy about how to truly 'own' a piece of art. He's at the Metropolitan Museum with his nieces, and one of them says she wishes she could own a Monet. Hayes tells her she can. He says, "Ownership does not come free. One must spend time with it; visit at different times of the day or evening; and bring to it one’s full attention." Jackson: So ownership isn't about possession, it's about attention. I love that. It democratizes the whole experience. You don't need millions of dollars; you just need to be present. Olivia: And he applies that philosophy to everything—to art, to the city, to people. It’s why the book is filled with his own black-and-white photographs of strangers on the street. He’s not just documenting; he’s paying attention. He’s 'owning' the moment. Jackson: This feels like a direct challenge to our current culture. He's talking about deep, slow attention. We're all about quick scrolls and hot takes. Is this book basically a guide to unplugging from the 21st century? Olivia: I think it's more a guide to re-tuning our attention. It’s not about escaping the world, but about engaging with it more deeply. In the final part of the book, as Oliver is facing his terminal illness, this philosophy becomes even more critical. Their time is limited, so every moment—every shared glance, every conversation—is imbued with immense meaning. Jackson: That’s heartbreaking, but also incredibly powerful. It makes the simple act of being present feel like the most important thing in the world. Olivia: It is. And that leads to the book's ultimate conclusion. In the postscript, after all the grief and love and observation, Hayes is wrestling with the question of 'what's the point?' Why go on after so much loss? And he lands on the most simple, profound answer. Jackson: Which is? Olivia: "To be alive." That's it. That's the point. The experience itself is the meaning.

Jackson: Wow. So when you put it all together, it’s a kind of blueprint. The city gives him the chaotic, anonymous space he needs to grieve. The relationship with Oliver Sacks gives him a new anchor and a new way to understand love. And this 'art of noticing' is the actual tool he uses to navigate it all and find meaning. Olivia: That’s it exactly. It's a story about rebuilding a life from fragments. He arrives in New York broken, and he pieces himself back together not by following a plan, but by staying open to the city, to love, and to the beauty of the present moment. It’s a testament to resilience. Jackson: It’s funny, the book was widely acclaimed and named a best book of the year by major outlets, but some readers found it a bit slow or plotless. After this conversation, I feel like that’s the whole point. Life isn't a plot. It's a series of moments, and the beauty is in how you string them together. Olivia: That’s the genius of it. It mirrors the texture of life itself. It’s not a story about what happens; it’s a story about what it feels like to be alive. Jackson: After hearing all this, it makes me wonder: what unexpected beauty have I walked past today just because I wasn't paying attention? A poem on a star chart, the anarchy of pure joy... what did I miss? Olivia: That's the question the book leaves you with, isn't it? And we'd love to hear from our listeners—what's a small, 'Insomniac City' moment you've noticed in your own life? A brief moment of connection or unexpected beauty. Share it with us on our social channels. We'd genuinely love to read them. Jackson: A beautiful thought to end on. Olivia: It really is. This is Aibrary, signing off.