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. New episodes drop every Monday.
Episodes
June 30, 2025 • 59 mins
What’s the point of college if no one’s actually doing the work? It’s not a rhetorical question. In the age of AI, it's incredibly easy for students to offload their assignments. AI tools can write essays, make study guides, and even complete whole assignments.
So what is the point of higher education?
In today’s episode, Sean speaks with journalist James Walsh about his recent article, "Everyone is Cheating Their Way Through C...
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June 16, 2025 • 52 mins
We’re nearly six months into Donald Trump’s second term as president, and a lot of us are still trying to figure out what that actually means. Not just politically. But culturally. What kind of country are we living in? And what kind of future are we heading toward?
In today’s episode, Sean and Vox senior correspondent Zack Beauchamp try to answer these difficult questions. They discuss Trump’s successes and failures, how he app...
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June 9, 2025 • 68 mins
For decades, the American right has stayed on brand: the economy. Low taxes. Free markets. Deregulation. Those have been the buzzwords for more than half a century. But that doctrine is now being challenged by other conservatives who envision a future in which America’s trade deficit is lower, manufacturing returns to the US, and Americans buy more American-made products. Is this future even possible?
Economist Oren Cass thinks ...
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June 2, 2025 • 56 mins
Sebastian Junger came as close as you possibly can to dying. While his doctors struggled to revive him, the veteran reporter and avowed rationalist experienced things that shocked and shook him, leaving him with profound questions and unexpected revelations. In his book, In My Time of Dying, he explores the mysteries and commonalities of people’s near-death experiences.
In this episode, which originally aired in May 2024, he joi...
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May 26, 2025 • 51 mins
Almost nothing stands the test of time. Machiavelli's writings are a rare exception.
Why are we still talking about Machiavelli, nearly 500 years after his death? What is it about his political philosophy that feels so important, prescient, or maybe chilling today?
In this episode, Sean speaks with political philosopher and writer Erica Benner about Niccolo Machiavelli’s legacy. The two discuss The Prince, Machiavelli’s views...
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May 12, 2025 • 60 mins
We’re told from a young age to achieve. Get good grades. Get into a good school. Get a good job. Be ambitious about earning a high salary or a high-status position.
Some of us love this endless climb. But lots of us, at least once in our lives, find ourselves asking, "What’s the point of all this ambition?"Historian and author Rutger Bregman doesn’t think there is a point to that kind of ambition. Instead, he wants us to be mora...
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May 5, 2025 • 55 mins
What do you do when you’re faced with evidence that challenges your ideology? Do you engage with that new information? Are you willing to change your mind about your most deeply held beliefs? Are you pre-disposed to be more rigid or more flexible in your thinking?
That’s what political psychologist and neuroscientist Leor Zmigrod wants to know. In her new book, The Ideological Brain, she examines the connection between our biolo...
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April 28, 2025 • 51 mins
There are lots of stories to tell about the Covid pandemic. Most of them, on some level, are about politics, about decisions that affected people’s lives in different — and very unequal — ways.
Covid hasn’t disappeared, but the crisis has subsided. So do we have enough distance from it to reflect on what we got right, what we got wrong, and what we can do differently when the next crisis strikes?
Professor Frances E. Lee — co...
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April 21, 2025 • 54 mins
Philosophy often feels like a disconnected discipline, obsessed with tedious and abstract problems. But MIT professor Kieran Setiya believes philosophical inquiry has a practical purpose outside the classroom — to help guide us through life’s most challenging circumstances. He joins Sean to talk about self-help, FOMO, and midlife crises.
This episode originally aired in April 2024.
Host: Sean Illing (@SeanIlling)
Guest: Kier...
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April 14, 2025 • 57 mins
What exactly is the basis for democracy?
Arguably Iiberalism, the belief that the government serves the people, is the stone on which modern democracy was founded. That notion is so ingrained in the US that we often forget that America could be governed any other way. But political philosopher John Gray believes that liberalism has been waning for a long, long time.
He joins Sean to discuss the great liberal thinker Thomas Hobbes...
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April 11, 2025 • 1 min
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April 7, 2025 • 50 mins
There’s a lot of uncertainty when it comes to artificial intelligence. Technologists love to talk about all the good these tools can do in the world, all the problems they might solve. Yet, many of those same technologists are also warning us about all the ways AI might upend society, how it might even destroy humanity.
Julia Longoria, Vox host and editorial director, spent a year trying to understand that dichotomy. The result is...
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March 31, 2025 • 55 mins
Why do we keep comparing AI to humans?
Jaron Lanier — virtual reality pioneer, digital philosopher, and the author of several best-selling books on technology — thinks that we should stop. In his view, technology is only valuable if it has beneficiaries. So instead of asking "What can AI do?," we should be asking, "What can AI do for us?"
In today’s episode, Jaron and Sean discuss a humanist approach to AI and how changing our u...
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March 24, 2025 • 54 mins
American government has a speed issue. Both parties are slow to solve problems. Slow to build new things. Slow to make any change at all.
Until now. The Trump administration is pushing through sweeping changes as fast as possible, completely changing the dynamic. And the Democrats? They’ve been slow to respond. Slow to mount a defense. Slow to change tactics. Still.
Ezra Klein — writer, co-founder of Vox, and host of The Ezra Kle...
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March 17, 2025 • 52 mins
Humans hate uncertainty. It makes us feel unsafe and uneasy. We often organize our lives to avoid it. When it's foisted upon us, we don’t always know how to act.
But writer and journalist Maggie Jackson argues that uncertainty can actually be good for us, and that we’re doing ourselves a disservice by avoiding it.
She tells Sean that embracing uncertainty can spark creativity, improve problem solving skills, and help us lead better...
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March 10, 2025 • 50 mins
How often do you find silence? And do you know what to do with it when you do?
Today’s guest is essayist and travel writer Pico Iyer. His latest book is Aflame: Learning From Silence, which recounts his experiences living at a Catholic monastery in California after losing his home in a fire.
He speaks with Sean about the restorative power of silence, and how being quiet can prepare us for a busy and overstimulated world.
Host: Sean...
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March 3, 2025 • 43 mins
If you could change anything about your personality, anything at all, what would it be?
And why would you want to change it?Writer Olga Khazan spent a year trying to answer those questions, and documented the experience in her new book Me, But Better: The Science and Promise of Personality Change.
In this episode Sean speaks with Olga about the science of personality change, the work it takes to change yourself, and what makes up a...
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February 17, 2025 • 38 mins
Are you ever happier not knowing something?
As Aristotle famously claimed, “All human beings want to know.” But denial and avoidance are also human impulses. Sometimes they’re even more powerful than our curiosity.
In this episode Sean speaks with professor Mark Lilla about when we’re better off searching for knowledge and when we’re better off living in the dark. Lilla’s new book is called Ignorance and Bliss: On Wanting Not to ...
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February 10, 2025 • 53 mins
What do you think of America’s institutions?
Alana Newhouse, founder and editor-in-chief of Tablet Magazine, says that may be the most important political question in America.
In an essay published more than two years ago, Newhouse argued that there is a new political divide, one in which your place — and the place of your allies and adversaries — is determined by whether you believe that America’s institutions should be fixed or d...
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February 3, 2025 • 45 mins
Americans are spending an historic amount of time alone, a phenomenon that is often referred to as an "epidemic of loneliness."
But are we actually lonely? Or do we prefer being by ourselves? And if we do, what does that mean for us and our society?
Today’s guest is journalist Derek Thompson, who, in a recent essay for the Atlantic, challenges the conventional wisdom around loneliness. He argues that Americans prefer solitude, and ...
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