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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.

The Gray Area with Sean Illing

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 fear of discomfort often keeps us from saying what really matters.

This episode originally aired in November of 2024.

Host: Sean Illing (@SeanIlling)

Guest: Alexandra Plakias, associate professor of philosophy and author of Awkwardness: A Theory

We would love to hear from you. To tell us what you thought of this episode, email us at tga@voxmail.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.And you can watch new episodes of The Gray Area on YouTube.

Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members
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You’re not awkward — the world is.

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 and persecution in Spain, and why 1984 and Animal Farm only capture part of his project. 

Host: Sean Illing (@SeanIlling)

Guest: Laura Beers, historian and author of Orwell’s Ghosts

We would love to hear from you. To tell us what you thought of this episode, email us at tga@voxmail.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.

And you can watch new episodes of The Gray Area on YouTube.

Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members
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Truth in an age of doublethink

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 reframe the way we think about meritocracy, blame, punishment, and even hatred.

This episode originally aired in November of 2023.

Host: Sean Illing (@SeanIlling)

Guest: Robert Sapolsky, biologist and neuroscientist at Stanford University and author of ⁠Determined: A Science of Life Without Free Will⁠.

We’d love to hear from you. Tell us what you thought of this episode by emailing thegrayarea@vox.com or leaving us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.

And you can watch new episodes of ⁠The Gray Area on YouTube⁠.

Listen to The Gray Area ad-free by becoming a Vox Member: ⁠vox.com/members⁠
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The case against free will

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 distorted, why despair can be as dangerous as denial, and what a truly energy-abundant, livable future could look like.

Host: Sean Illing (@seanilling)

Guest: Hannah Ritchie, author of Clearing the Air

We’d love to hear from you. Tell us what you thought of this episode at thegrayarea@vox.com or leave a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.

And you can watch new episodes of The Gray Area on YouTube.

Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members

This episode was supported by a grant from Arnold Ventures. Vox had full discretion over the content of this reporting.
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What the climate story gets wrong

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 Suddenly Got Worse and What to Do About It. They discuss how the web became enshittified, why monopolies are the true engine behind our digital decay, and what it would mean to build a freer, fairer, and more human internet.

Host: Sean Illing (@seanilling)

Guest: Cory Doctorow (https://x.com/doctorow), author of Enshittification: Why Everything Suddenly Got Worse and What to Do About It.

We’d love to hear from you. Tell us what you thought of this episode at tga@voxmail.com or leave a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.

And you can watch new episodes of The Gray Area on YouTube.

Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members
Learn more about your ad choices. Visit podcastchoices.com/adchoices

The Great Enshittening

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 what an American civil war might look like in the 21st century, the social and informational dynamics that accelerate breakdown, and whether America still has a path away from the brink.

Host: Sean Illing (@SeanIlling)

Guest: Barbara Walter, professor at UC San Diego and author of How Civil Wars Start

We would love to hear from you. To tell us what you thought of this episode, email us at tga@voxmail.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.

And you can watch new episodes of The Gray Area on YouTube.

Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members
Learn more about your ad choices. Visit podcastchoices.com/adchoices

America chose violence. Now what?

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: Sean Illing (@SeanIlling)

Guest: Charan Ranganath, neuroscientist and author of Why We Remember

We would love to hear from you. To tell us what we thought of this episode, email us at tga@voxmail.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.

And you can watch new episodes of The Gray Area on YouTube.Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members
Learn more about your ad choices. Visit podcastchoices.com/adchoices

What's worth remembering?

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 (@SeanIlling)

Guest: Emily Baker-White, reporter and author of Every Screen on the Planet: The War Over TikTok

The Gray Area has been nominated for a Signal Listener’s Choice Award. Vote for The Gray Area here: https://vote.signalaward.com/PublicVoting#/2025/shows/genre/thought-leadership

We’d love to hear from you. Email us at tga@voxmail.com or leave a voicemail at 1-800-214-5749. Your questions and feedback help us make a better show.

Watch full episodes of The Gray Area on YouTube.

Listen ad-free by becoming a Vox Member: vox.com/members
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Why TikTok matters

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 catastrophe, why each fraction of a degree of warming matters, and how the fossil fuel industry is fighting a desperate last stand. They also discuss the politics of energy in the age of Trump, why Texas and Utah may hold surprising lessons, and how cheap, abundant power could transform not just the climate fight but democracy itself.

Host: Sean Illing (@SeanIlling)

Guest: Bill McKibben, climate activist and author of Here Comes the Sun

We’d love to hear from you. Email us at tga@voxmail.com or leave a voicemail at 1-800-214-5749. Your questions and feedback help us make a better show.

⁠⁠This episode was made in partnership with Vox's Future Perfect team.

Watch full episodes of The Gray Area on YouTube.

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The sun will save us

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 platforms in a global media environment.

Host: Sean Illing (@SeanIlling)

Guest: Fara Dabhoiwala, historian and author of What Is Free Speech?

We’d love to hear from you. Email us at tga@voxmail.com or leave a voicemail at 1-800-214-5749. Your questions and feedback help us make a better show.

Watch full episodes of The Gray Area on YouTube.

Listen ad-free by becoming a Vox Member: http://vox.com/members
Learn more about your ad choices. Visit podcastchoices.com/adchoices

How much free speech is too much?

What happens when you apply the Socratic method to personal relationships? Philosopher Agnes Callard joins Sean Illing to discuss how Socrates inspires her public philosophy project —including the decision to share the details of her love life and how these pursuits have created a more thoughtful and meaningful life.
Host: Sean Illing (@seanilling), host, The Gray Area
Guest: Agnes Callard, (@agnescallard), philosopher, University of Chicago
References: 

“Agnes Callard’s Marriage Of The Minds” by Rachel Aviv (Mar. 2023, The New Yorker)

”Everyone Desires the Good: Socrates' Protreptic Theory of Desire” by Agnes Callard (June 2017, The Review of Metaphysics)

“A Philosopher Gets Fed Up With Profundity” by Agnes Callard (Mar. 2023, The Atlantic)

Plato, Gorgias

Plato, Symposium

Plato, Meno

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This episode was made by: 

Engineer: Patrick Boyd

Editorial Director, Vox Talk: A.M. Hall

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The project of Socratic love with Agnes Callard

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