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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

Why is it so hard for America to build things?

Bridges take years to construct. Housing costs are soaring. Transit systems are crumbling. And we’re struggling to update our infrastructure to prepare for the climate crisis. Even when there’s broad agreement that something needs to be done, collective action feels impossible. Why is that?

Today’s guest is Marc Dunkelman, author of Why Nothing Works, a book about the modern American experience of watching government fail. He argues that by giving too many people the power to say “no,” we’ve stymied our collective progress.

Marc and Sean discuss an inherent tension in American politics: the need for effective, centralized power and a deep fear of its abuse. They trace how that tension has played out across American history, from the clashes between Jefferson and Hamilton, through the New Deal’s Tennessee Valley Authority, to the backlash against figures like Robert Moses. Marc argues that our current system — born out of a reaction to too much top-down authority during the late 20th century — has produced paralysis, dysfunction, and a deep distrust of government.

Host: Sean Illing (@SeanIlling)

Guest: Guest: Marc Dunkelman (@MarcDunkelman), author of Why Nothing Works: Who Killed Progress — and How to Bring It Back.

We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.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

This episode was supported by a grant from Arnold Ventures. Vox had full discretion over the content of this reporting.
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How we built a government that can’t build anything

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 honor the emotions we usually try to outrun. It’s not a celebration of sadness, but Alessandri calls bullshit on the culture of toxic positivity and the idea that happiness is something we’re supposed to choose on command.

Sean and Mariana talk about why Americans are addicted to the light, why “cheering people up” often backfires, how Stoicism shaped our emotional habits, and what it looks like to sit with grief instead of shaming ourselves for feeling it.

Host: Sean Illing (@SeanIlling)

Guest: Mariana Alessandri (@mariana.alessandri), associate professor of philosophy at the University of Texas-Rio Grande Valley and author of Night Vision: Seeing Ourselves Through Dark Moods.

We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.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. This holiday season, your membership goes further: when you join Vox as an annual Member, we’ll gift a free membership to a reader who can’t afford it. By joining today, you’ll get 30% off for an annual membership, and we’ll match your membership. And if you can’t afford it, visit that same link to apply for a free membership through our gift program.
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It’s okay to not be okay

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 us wrong. She’s not against forgiveness — that would be weird — but she says we ought to be more intentional about why we do it, more aware that the expectation to practice forgiveness often lands on the most vulnerable people, and more concerned about what gets lost when we treat forgiveness as the only path to healing. 

Sean and Myisha discuss the 2015 Charleston church shooting, the legacy of slavery, and the real difference between accountability, reconciliation, and simply moving on.

Host: Sean Illing (@SeanIlling)

Guest: Myisha Cherry (@myishacherry), associate professor of philosophy at the University of California Riverside, and author of Failures of Forgiveness: What We Get Wrong and How to Do Better.

This episode was made in partnership with Vox's Future Perfect team. Vox had full discretion over the content of this reporting.

We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.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. This holiday season, your membership goes further: when you join Vox as an annual Member, we’ll gift a free membership to a reader who can’t afford it. By joining today, you’ll get 30% off for an annual membership, and we’ll match your membership. And if you can’t afford it, visit that same link to apply for a free membership through our gift program.
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Forgiveness is optional

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: Daniel Kolitz, author of The Goon Squad

We would love to hear from you. To tell us what you thought of this episode, email thegrayarea@vox.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. 

This holiday season, your membership goes further: when you join Vox as an annual Member, we’ll gift a free membership to a reader who can’t afford it. By joining today, you’ll get 30% off for an annual membership, and we’ll match your membership. And if you can’t afford it, visit that same link to apply for a free membership through our gift program.
Learn more about your ad choices. Visit podcastchoices.com/adchoices

The pornification of everything

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 American politics falters, and what smart policy could do for the people left behind by technological change.

Host: Sean Illing (@SeanIlling)

Guest: J. Bradford DeLong, economic historian and author of Slouching Towards Utopia

We would love to hear from you. To tell us what we thought of this episode, email us at thegrayarea@vox.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

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 counts as progress?

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

How to survive awkward encounters

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

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

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

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

As a non-believer, Devin Moss never thought he would become a chaplain or a spiritual adviser, much less one who counsels hospital patients with terminal illnesses and inmates on death row. Devin joins Sean to talk about his improbable journey, the death penalty, and the role of religion in an increasingly secular society.

Host: Sean Illing (@seanilling), host, The Gray Area
Guest: Devin Moss. His podcast is The Adventures of Memento Mori. 
Enjoyed this episode? Rate The Gray Area ⭐⭐⭐⭐⭐ and leave a review on Apple Podcasts.
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This episode was made by: 

Producer: Jon Ehrens 

Engineer: Patrick Boyd

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The chaplain who doesn't believe in God

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