The Gray Area with Sean Illing

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. From the Vox Media Podcast Network.

Episodes

Why TikTok matters

September 29, 2025 • 63 mins
This week, Sean talks with Emily Baker-White, author of Every Screen on the Planet, about why TikTok feels uniquely addictive, how it turned social media into a push-not-pull entertainment feed, and what happens when human editors inside the company can override the algorithm. A few days after they spoke, TikTok was in the headlines again. So they jumped on a follow-up call to unpack the latest twists in the saga of who will ult...
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The sun will save us

September 22, 2025 • 47 mins
Bill McKibben has spent four decades warning us about climate change. Much of what he predicted has come true. And yet, his new book Here Comes the Sun is more hopeful than you might expect. That’s because, for the first time, we have a genuine alternative: Solar and wind energy are now the cheapest, fastest-growing sources of power on Earth. The revolution has already begun. This week, Sean is joined by McKibben to talk about t...
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How much free speech is too much?

September 15, 2025 • 54 mins
Free speech is often treated as a timeless and sacred right. But what if it’s more myth than reality? This week, Sean is joined by historian Fara Dabhoiwala, author of What Is Free Speech? They trace the history of free expression from 18th-century pamphleteers, to John Stuart Mill, to the digital platforms that dominate our lives today. They explore why speech is never just “speech,” how context and power shape who gets hear...
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Imagine there's no billionaires

September 1, 2025 • 53 mins
How much money is too much? In today’s episode, political philosopher Ingrid Robeyns tells Sean that we need to cap the amount of wealth a person can accumulate. They talk about how extreme inequality affects democracy, the role of money in politics, and why limiting personal wealth benefits everyone, including the super rich. Host: Sean Illing (⁠⁠@SeanIlling⁠⁠) Guest: Ingrid Robeyns, ⁠⁠professor⁠⁠ and author of Limitarianism:...
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America's lawyers vs. China's engineers

August 25, 2025 • 51 mins
America has a hard time building stuff. Roads. Trains. Bridges. Housing. Everything takes seemingly forever. Meanwhile, China seems to have no trouble at all: high-speed rails, solar panels, electric cars, bridges, ports, all churned out at breakneck speed. Why is that? Sean's guest is Dan Wang, author of the new book Breakneck: China’s Quest to Engineer the Future. They discuss the policies and mindset that allow China to tack...
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So, what exactly is the “New Right?”

August 18, 2025 • 51 mins
A loose movement of radical intellectuals is driving American politics.  They’re called the “New Right,” and they share a basic hostility to American liberal democracy, a real desire to fundamentally overhaul it, and real influence in the White House. But why do they think that? How much influence do they really have? And what would a response to their rising prominence look like? Today’s guest is Laura Field, a political theori...
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America is losing big on sports betting

August 11, 2025 • 53 mins
Almost every tech platform is designed to grab and hold your attention, to keep you clicking, scrolling, and buying for as long as possible. Sports gambling has become one of the clearest examples of this. The industry has created frictionless apps on your phone that let you bet on everything from March Madness to a pregame coin toss to who wins a minor league British dart tournament. While betting has become easier — and arg...
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It’s time to get weird

August 4, 2025 • 60 mins
The internet was supposed to set us free. But somewhere along the way, it became a tool for surveillance, extraction, and control. What happened? And is there still time to reclaim the weird, untapped potential of the digital world? This week, Sean is joined by Douglas Rushkoff. He’s a media theorist, author of Survival of the Richest and Team Human, and host of the Team Human podcast. They trace the arc of the internet from its u...
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What if humans went extinct next Friday?

July 28, 2025 • 59 mins
What comes after the human? We’re living through multiple crises — ecological, technological, political. But beneath all of that is something even deeper: a crisis of the self. Who are we, really? How did we come to see ourselves as separate from the world, from each other, from the systems that sustain us? And what if that way of thinking is what got us into this mess? Today’s guest is Mark C. Taylor, philosopher, cultural c...
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Can college survive Trump?

July 21, 2025 • 57 mins
American higher education is under attack. Project 2025 laid out the battle plan pretty clearly: Get rid of the Department of Education, shut off federal funding, take control of the accreditation system, and take down diversity, equity, and inclusion programs. And in the end, change what students are encouraged to study and what professors are allowed to teach. The questions we’re left with is why? And is it working? Today’s...
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Hopeful pessimism

July 14, 2025 • 51 mins
We live in a culture obsessed with hope. We are trained to believe that being hopeful is the key to success. Stay positive. The sun will come out tomorrow. Keep the faith. But maintaining that kind of blind hope is hard. When our hopes are dashed, we often feel defeated. In a world that’s filled with lots of dark clouds and very few silver linings, perhaps we need a better way to balance our hope and our pessimism. In today’s e...
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If AI can do your classwork, why go to college?

June 30, 2025 • 55 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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Is Trump winning?

June 16, 2025 • 48 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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A right-wing economist makes his case

June 9, 2025 • 64 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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What "near death" feels like

June 2, 2025 • 52 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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Machiavelli on how democracies die

May 26, 2025 • 47 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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Do you have moral ambition?

May 12, 2025 • 56 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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The science of ideology

May 5, 2025 • 51 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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A new analysis of the pandemic

April 28, 2025 • 47 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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Halfway there: a philosopher’s guide to midlife crises

April 21, 2025 • 50 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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