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The Gray Area with Sean Illing

The Gray Area with Sean Illing takes a philosophy-minded look at culture, technology, politics, and the world of ideas. Each week, we invite a guest to explore a question or topic that matters. From the the state of democracy, to the struggle with depression and anxiety, to the nature of identity in the digital age, each episode looks for nuance and honesty in the most important conversations of our time. N

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Who ruined your chocolate?
Nov 2026
Why everyone is embracing populism
Nov 2026
How Silicon Valley learned to love war
Nov 2026 · 1 book
Cover of The Imagineers of War: The Untold Story of DARPA, the Pentagon Agency That Changed the World
The Imagineers of War: The Untold Story of DARPA, the Pentagon Agency That Changed the World
Sharon Weinberger
“Her new book is called Valley of Death. how big tech is fueling the future of war”
Is America a gerontocracy?
Oct 2026
Inside the secret race to build artificial intelligence
Oct 2026 · 2 books
Cover of The AGI Chronicles: The Inside Story of the Race to Create an Artificial Superintelligence
The AGI Chronicles: The Inside Story of the Race to Create an Artificial Superintelligence
Kevin Roose
“journalist Kevin Roos. whose new book, The AGI Chronicles, The Inside Story of the Race to Create an Artificial Superintelligence”
Cover of The Making of the Atomic Bomb
The Making of the Atomic Bomb
Richard Rhodes
“Dario Amade in particular is obsessed with this book, The Making of the Atomic Bomb, which is a polter winning history of the Manhattan Project written by Richard Rhodes”
What makes a life good enough?
Oct 2026 · 1 book
Cover of The Art of the Nice Life: How to Elevate the Everyday and Find Joy in What You Have
The Art of the Nice Life: How to Elevate the Everyday and Find Joy in What You Have
Rachel Wilkerson Miller
“we talk about her book, The Nice Life, how to elevate the everyday and find joy in what you have”
Can prediction markets be good for society?
Oct 2026
Our gender divide
Oct 2026 · 3 books
Cover of Generation Uncoupled: A Generation Apart: America's New Gender Divide and the Crisis of Human Connection
Generation Uncoupled: A Generation Apart: America's New Gender Divide and the Crisis of Human Connection
Daniel Cox
“Danielle has just written a new book titled Generation Uncoupled. America's new gender divide and the crisis of human connection”
Cover of Rethinking Sex: A Provocation
Rethinking Sex: A Provocation
Christine Emba
“some of that was drawn from your, you know, truly excellent book, Rethinking Sex, right”
Cover of The Second Coming
The Second Coming
Carter Sherman
“from the journalist Carter Sherman's book. The second coming”
The death row assembly line
Oct 2026 · 1 book
Cover of To Catch a Devil
To Catch a Devil
Pamela Colloff
“she has a new book out called To Catch a Devil”
Is it bad to want to be rich?
Oct 2026 · 3 books
Cover of Why It's Okay to Want to Be Rich
Why It's Okay to Want to Be Rich
Jason Brennan
“author of a book with an unforgettable title. Why it's okay. To want to be rich”
Cover of The Wealth of Nations
The Wealth of Nations
Adam Smith
“Adam Smith wrote this book called The Wealth of Nations in seventeen seventy six”
Cover of Glass Houses: Choosing Grace in a Judgmental World
Glass Houses: Choosing Grace in a Judgmental World
Jason Brennan
“a book coming out in about a month that's called uh Uh glass houses choosing grace in a judgmental world”
Why does killing a bug feel wrong?
Oct 2026
How trauma became a status symbol
Sep 2026 · 4 books
Cover of Traumatized: The New Politics of Public Suffering
Traumatized: The New Politics of Public Suffering
Catherine Liu
“scathing new book. Traumatized. The new politics of public suffering”
Cover of The Making of the English Working Class
The Making of the English Working Class
E. P. Thompson
“E. P. Thompson tries to paint a port. portrait of that in the invention of the English working class”
Cover of Capital
Capital
Karl Marx
“you have to go into E. P. Thompson and Marks To get an account of what it was like to be in In the factories”
Cover of The Cult of Smart: Education and Our Degrading Democracy
The Cult of Smart: Education and Our Degrading Democracy
Freddie deBoer
“I think you're talking about Freddie Deborah's book, I think on um mental illness as identity”
Inside the world of cash advance apps
Sep 2026
This is how you rule the world
Sep 2026 · 1 book
Cover of How to Rule the World: An Education in Power at Stanford University
How to Rule the World: An Education in Power at Stanford University
Theo Baker
“Theew's book is called How to Rule the World, and the title isn't a metaphor”
Is starting a family becoming impossible?
Sep 2026 · 1 book
Cover of Inconceivable: The Impossibility of Family in an Age of Uncertainty
Inconceivable: The Impossibility of Family in an Age of Uncertainty
Anna Louis Sussman
“Her new book, Inconceivable, The Impossibility of Family in an Age of Uncertainty, goes deep, reporting with insight and fantastic stories on the web of factors influencing the new turn away from childbearing”
The millennial midlife crisis
Sep 2026 · 2 books
Cover of But You're Still So Young
But You're Still So Young
Kayleen Schaeffer
“There's this book that I read when I was in my early 30s”
LA
Life After Ambition, a Good Enough Memoir
Emile Niazi
“It's called Life After Ambition, a Good Enough Memoir”
How to be less neurotic
Sep 2026 · 2 books
Cover of Me, But Better: The Science and Promise of Personality Change
Me, But Better: The Science and Promise of Personality Change
Olga Kazan
“author of me. But better. The scientist and promise of personality change”
Cover of 10% Happier
10% Happier
Dan Harris
“one of the books that I read kind of in in reporting out my book is 10% happier”
Your body wasn’t built for a desk
Sep 2026 · 2 books
Cover of Body Electric
Body Electric
Manoush Zomorodi
“A Benoiticious New Book. Body Electric. About what a life of sitting and staring at screens is doing to us”
Cover of The Anxious Generation
The Anxious Generation
Jonathan Haidt
“we know John Height's book, The Anxious Generation, has been on the bestseller list for years now”
Why we want to believe in aliens
Aug 2026 · 1 book
Cover of We Want to Believe: How Aliens Went Mainstream and Why It Matters
We Want to Believe: How Aliens Went Mainstream and Why It Matters
Adam Kirsch
“He's a senior editor at The Atlantic and author of We want to believe. How aliens went mainstream and why it matters”
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