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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

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
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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.

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

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 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.
Learn more about your ad choices. Visit podcastchoices.com/adchoices

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.

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

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

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 it is.

In today’s episode, the founder of the think tank America Compass speaks to Sean about right-wing economic populism. The two discuss a conservative, pro-worker approach to economic policy, Cass’s plan to bring manufacturing back to the US, and what types of behavior economic policy should incentivize.

Host: Sean Illing (@SeanIlling)Guest: Oren Cass, chief economist and founder of American Compass. Editor of The New Conservatives: Restoring America's Commitment to Family, Community, and Industry.

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

Help us plan for the future of The Gray Area by filling out a brief survey: ⁠voxmedia.com/survey⁠. Thank you!

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A right-wing economist makes his case

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 joins Sean to talk about what it’s like to almost die and what quantum physics can tell us about the afterlife.

Host: Sean Illing (⁠⁠@SeanIlling⁠⁠)

Guest: Sebastian Junger, journalist and author of ⁠⁠In My Time of Dying: How I Came Face to Face With the Idea of an Afterlife⁠

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

Help us plan for the future of The Gray Area by filling out a brief survey: ⁠voxmedia.com/survey⁠. Thank you!
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What "near death" feels like

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 on democracy, and what he might say about the Trump administration were he alive today.

Host: Sean Illing (@SeanIlling)Guest: Erica Benner, political philosopher, historian, and author of Be Like the Fox

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

Help us plan for the future of The Gray Area by filling out a brief survey: voxmedia.com/survey. Thank you!

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Machiavelli on how democracies die

Arthur Brooks is the president of the American Enterprise Institute, one of Washington’s most respected and powerful conservative think tanks. He’s also launching a new podcast, The Arthur Brooks Show, with Vox Media on the art and practice of disagreement. I’ve known Brooks for a while. And I disagree with him on, well, a lot — at least when it comes to American politics. And yet, those disagreements haven’t ended a years-long conversation between us on everything from management to spirituality to policy. I can say from experience: Brooks really is good at disagreeing. In this podcast, Brooks — a Seattle native with a liberal family and a background as a traveling musician — reveals what he’s learned on how to disagree better, why civility shouldn’t be the goal in conversation, and why it’s healthy to have a lot of arguments. We talk about why he’s stepping down from his position at AEI, why I stepped down from management at Vox, and why anger is a healthy emotion and contempt isn’t. This is one of those conversations I’ve thought about daily since having it. The anger versus contempt rubric has been particularly useful for me, and I think it will be for you. Enjoy! Recommended books: Zen and the Art of Archery by Eugen Herrigel The Unpersuadables by Will Storr The Consolations of Mortality by Andrew Stark
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How to disagree better

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