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PODCAST

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.

society & culture philosophy

All Episodes

58:35

It’s okay to not be okay

The Gray Area with Sean Illing ·

2025/12/22

It’s not always the most wonderful time of the year.Every December, we’re told to be merry and stay positive. But a lot of us don’t feel that way. And when we don’t, the pressure to be happy makes everything worse. Sadness feels like failure. Grief feels like a personal mistake. Depression becomes something to hide. But what if dark moods aren’t problems to fix? What if they’re part of being human? Today’s guest is philosopher Mariana Alessandri, author of Night Vision, a book about how to

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64:06

Forgiveness is optional

The Gray Area with Sean Illing ·

2025/12/15

You have to forgive people who wrong you…right? The world is filled with injustice and wrongdoing, and to live in the world — to not be consumed by anger — forgiveness is necessary. At least that’s what we’re told over and over again: By forgiving, we can set ourselves free.But is there a cost to forgiveness? Are we forgiving too quickly and too often?Today’s guest is philosopher Myisha Cherry, whose book Failures of Forgiveness critiques our cultural obsession with forgiving those who have done

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56:09

Across the Gooniverse

The Gray Area with Sean Illing ·

2025/12/08

Sean’s guest today is Daniel Kolitz, author of a remarkable Harper’s story on “gooning.” They talk about this emerging subculture and how it reflects back on the larger world, from the economics of attention to the rise of short-form everything. Kolitz explains why the Gooniverse isn’t just about porn, how hyperkinetic media rewires our sense of pleasure and patience, and why this is really a story about how society is changing in ways we might not like. Host: Sean Illing (@SeanIlling) Guest:

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41:06

What counts as progress?

The Gray Area with Sean Illing ·

2025/12/01

We’ve never had more wealth, more data, or more ways to be entertained. So why doesn’t it feel like progress? Sean’s guest today is Brad DeLong, an economic historian at UC Berkeley and author of Slouching Towards Utopia. They talk about the difference between getting richer and living well, and why the real hinge of the 21st century might be attention rather than growth. DeLong explains how AI could make life easier or simply make us more distracted, why the world’s progress continues even as

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56:52

You’re not awkward — the world is.

The Gray Area with Sean Illing ·

2025/11/17

We all know what awkwardness feels like. It's that jolt of discomfort when the social script breaks down, and no one knows what to do next. But what if awkwardness isn’t a flaw to fix but a window into how we live together? Sean’s guest today is Alexandra Plakias, associate professor of philosophy at Hamilton College and author of Awkwardness: A Theory. They talk about why awkwardness isn’t a personal problem but a social one, how power and privilege shape who gets to be awkward, and why our

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52:16

Truth in an age of doublethink

The Gray Area with Sean Illing ·

2025/11/10

We use “Orwellian” to describe everything from campus dust-ups to authoritarian crackdowns. But what did George Orwell actually stand for, what did he get wrong, and what can we learn from him about our age of surveillance capitalism and distraction? Sean’s guest is Laura Beers, historian at American University and author of Orwell’s Ghosts: Wisdom and Warnings for the 21st Century. They dig into Orwell’s defense of truth over ideology, his crusade against euphemism, his experience with propaganda

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58:50

The case against free will

The Gray Area with Sean Illing ·

2025/11/03

We all think of ourselves as authors of our lives. The difference between our happy ending and someone else’s tragic one are the choices we each make. But what if none of that’s true?Sean’s guest today is Robert Sapolsky, a biologist and neuroscientist at Stanford University and author of Determined: A Science of Life Without Free Will. They dig into Sapolsky’s claim that free will is an illusion and discuss what the science says about genes, stress, culture, and how all this research might

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49:06

What the climate story gets wrong

The Gray Area with Sean Illing ·

2025/10/27

The story we tell about climate change is mostly a story about loss. But look to the data, and that story starts to fall apart. Emissions are peaking in key sectors. Clean energy is scaling faster than anyone predicted. Real progress is happening. It’s just not happening in the way we imagine it. Sean’s guest today is Hannah Ritchie, Deputy Editor at Our World in Data and author of Clearing the Air: A Hopeful Guide to Solving Climate Change. They discuss why our picture of the planet is so

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47:31

The Great Enshittening

The Gray Area with Sean Illing ·

2025/10/20

Open a browser and you can feel it instantly: everything online just feels… worse. Search results that look like ads. Social feeds that you don’t control. Streaming platforms that are packed with ads. Services that used to be free, but are now behind paywalls. It’s not your imagination — it’s enshittification, the process by which good platforms turn bad… and it’s starting to happen outside the internet as well.Sean’s guest today is Cory Doctorow, author of Enshittification: Why Everything

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58:23

America chose violence. Now what?

The Gray Area with Sean Illing ·

2025/10/13

Is America at a tipping point?Sean Illing talks with Barbara Walter, one of the world’s leading experts on violent extremism and domestic terror. She’s the author of How Civil Wars Start, about how democracies unravel from within, and a professor at UC San Diego’s School of Global Policy and Strategy. Walter talks to Sean about the warning signs she’s seeing in the US, why polarization and party identity become combustible, and what lessons we can draw from other countries. They also discuss

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58:54

You must remember this?

The Gray Area with Sean Illing ·

2025/10/06

We like to think of memory as a record of the past. But that’s not really what it is. Memory doesn’t keep the past — it can also remake it. It stitches fragments into stories, and those stories — true or not — are what we end up calling our life, and sometimes, our collective history.Sean’s guest today is Charan Ranganath, a neuroscientist and author of a book called Why We Remember. The two discuss the strange alchemy of remembering and how the stories our minds create end up creating us. Host:

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63:38

Why TikTok matters

The Gray Area with Sean Illing ·

2025/09/29

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 ultimately control the app's US-operations. Host: Sean Illing

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47:08

The sun will save us

The Gray Area with Sean Illing ·

2025/09/22

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 the peril and promise of this moment. They explore how close we are to

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54:26

How much free speech is too much?

The Gray Area with Sean Illing ·

2025/09/15

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 heard, the dangers of harmful speech, and the challenges of regulating

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53:51

Imagine there's no billionaires

The Gray Area with Sean Illing ·

2025/09/01

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: ⁠⁠The Case Against Extreme Wealth⁠⁠ This episode originally aired

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51:37

America's lawyers vs. China's engineers

The Gray Area with Sean Illing ·

2025/08/25

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 tackle remarkable feats of engineering, the advantages and drawbacks of

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51:36

So, what exactly is the “New Right?”

The Gray Area with Sean Illing ·

2025/08/18

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 theorist who’s spent a lot of time in the conservative intellectual world

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53:49

America is losing big on sports betting

The Gray Area with Sean Illing ·

2025/08/11

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 arguably fun — the cost of these apps is much higher than the money that

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60:34

It’s time to get weird

The Gray Area with Sean Illing ·

2025/08/04

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 utopian beginnings to its corporate capture, and explore what it would

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59:31

What if humans went extinct next Friday?

The Gray Area with Sean Illing ·

2025/07/28

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 critic, and author of After the Human. Mark and Sean discuss the

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