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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

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 in January 2024

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

You can watch new episodes of ⁠⁠The Gray Area on YouTube⁠⁠.

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Imagine there's no billionaires

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 America’s "lawyerly society," and what China and America must learn from each other.

Host: Sean Illing (@SeanIlling)

Guest: Dan Wang, author of Breakneck: China's Quest to Engineer the Future

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

We would love to hear from you. To tell us what you thought! Email us at tga@voxmail.com or leave us a voicemail at 1-800-214-5749. We read and listen to everything, and might use your comments and questions in future episodes.

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America's lawyers vs. China's engineers

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 cataloging the wild world of far-right thinking for her book Furious Minds: The Making of the MAGA New Right. 

She speaks with guest host Zack Beauchamp, author of Vox newsletter On The Right, about why ordinary Americans should really, definitely, and absolutely care what a handful of thinkers are putting out on obscure Substacks and YouTube channels.

Host: Zack Beauchamp

Guest: Laura Field

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.

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So, what exactly is the “New Right?”

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 is won and lost on them.

Today’s guest is Jonathan D. Cohen, author of Losing Big: America's Reckless Bet on Sports Gambling. He and Sean discuss the rise of sports betting, why the industry targets young men in their advertising, the social costs of frictionless sports gambling, and how the industry could be improved.

Host: Sean Illing (@SeanIlling)

Guest: Jonathan D. Cohen, writer and author of Losing Big: America's Reckless Bet on Sports Gambling

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

America is losing big on sports betting

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 take to build something different. Along the way, they talk about the loss of weirdness, the logic of capitalism, the dangers of scale, and the difference between systems thinking and systems feeling. They also reflect on whether it’s still possible to use technology to foster a more connected and communal life.

Host: Sean Illing (@SeanIlling)

Guest: Douglas Rushkoff, media theorist and host of Team Human

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.

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It’s time to get weird

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 philosophical roots of climate change, the dangers of individualism, the false promise of techno-utopianism, and what it might mean to shift from seeing ourselves as isolated egos to members of a vast, interdependent web. They talk about AI, death, Hegel, Descartes, hope, and why ideas matter.

Host: Sean Illing (@SeanIlling)

Guest: Mark C. Taylor, philosopher and author of After the Human: A Philosophy for the Future.

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.

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What if humans went extinct next Friday?

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 guest is Michael Roth, president of Wesleyan University. He’s a vocal defender of higher education. But he’s also honest about where things have gone wrong and what needs to change. Michael and Sean discuss the Trump administration’s efforts to change universities and colleges, the potential societal effects of that effort, political biases on campus, the dangers of ideological conformity, and the value of a college education (what is even the point of going to college any more?).

Host: Sean Illing (@SeanIlling)Guest: Michael Roth, president of Wesleyan University and author of numerous books including Beyond the University: Why Liberal Education Matters and The Student: A Short History.

Mentioned in this episode: Host Sean Illing’s interview with reporter James Walsh about AI on campuses.

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.

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

And you can watch new episodes of The Gray Area on YouTube.
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Can college survive Trump?

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 episode, Sean interviews philosopher Mara van der Lugt about her new book Hopeful Pessimism. The two talk about how to sustain hope when you’re feeling pessimistic, the pitfalls of blind hope, and what the climate movement can teach us about staying motivated when success is unlikely.

Host: Sean Illing (@SeanIlling)Guest: Mara van der Lugt, lecturer in philosophy at the University of St Andrews and author of Hopeful Pessimism.

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Hopeful pessimism

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 College." The two discuss how students are using AI to finish their assignments, how colleges are (and aren’t) responding to these challenges, and whether you can learn to think when something else does the thinking for you.

Host: Sean Illing (@SeanIlling)

Guest: James Walsh, features writer for New York magazine's Intelligencer.

Read James’s article: "Everyone is Cheating Their Way Through College."

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If AI can do your classwork, why go to college?

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 appeals to his supporters, and how the left can respond to the Trump administration.

Host: Sean Illing (@SeanIlling)

Guest: Zack Beauchamp, Vox senior correspondent and the author of the On the Right newsletter. Sign up for the newsletter here.

Listen to Sean’s previous interview with Zack about the state of right-wing politics here.

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

Is Trump winning?

Every time I do an episode on polarization, I get a few emails asking: What about deliberative democracy? Couldn’t that be an answer?
Deliberative democracy, if you’re not familiar, refers to a broad set of approaches in which citizens get together, with or without their representatives, to deliberate on political questions. Not just vote, or donate money, but actually work through hard questions, in a structured process, together.
Jane Mansbridge is the Charles F. Adams professor of political leadership and democratic values at Harvard’s Kennedy School of Government, a past president of the American Political Science Association, and co-editor of the book, Deliberative Systems: Deliberative Democracy at the Large Scale. So she’s not just a pioneering theorist on deliberative democracy, she’s specifically studied the question where I’m most skeptical: Can it scale?
Book recommendations:
Politics with the People: Building a Directly Representative Democracy by Michael A. Neblo
Democracy When the People Are Thinking: Revitalizing Our Politics Through Public Deliberation by James S. Fishkin
Insecure Majorities: Congress and the Perpetual Campaign by Frances E. Lee
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What deliberative democracy can, and can’t, do (with Jane Mansbridge)

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