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The Gray Area

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 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.

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Podcasts
What we get wrong about being in loveWhat we get wrong about being in love
Podcast
Podcasts

Carrie Jenkins on what philosophy can teach us about love and heartbreak.

By Sean Illing
Politics
The profound pessimism of Clarence ThomasThe profound pessimism of Clarence Thomas
Podcast
Politics

How “the sense of defeat over the Black freedom struggle” shaped the Supreme Court justice’s thinking.

By Sean Illing
The Marxist scholar who thinks reparations are “a waste of time”
Podcast
Podcasts

Adolph Reed on why talk about reparations is counterproductive.

By Fabiola Cineas
The cost of reparations
Podcast
Podcasts

Economist William “Sandy” Darity and folklorist Kirsten Mullen on how the United States can compensate Black Americans.

By Fabiola Cineas
Want to be happy? Don’t follow your gut.
Podcast
Even Better

A data scientist on what truly makes us happy.

By Sean Illing
Reparations could heal America
Podcast
Podcasts

How the US can create a better future by reconciling the past.

By Vox Staff
Reviving the case for reparations
Podcast
Podcasts

Lawyer and activist Nkechi Taifa explains why reparations is a policy issue “whose time has come.”

By Fabiola Cineas
Even Better
What if your financial future wasn’t stressful?What if your financial future wasn’t stressful?
Podcast
Even Better

Financial planning isn’t only for people who have a lot of money.

By Julia Furlan
Even Better
Setting boundaries is more than just saying “no”Setting boundaries is more than just saying “no”
Podcast
Even Better

Relationships aren’t always easy to preserve. Boundaries can help.

By Julia Furlan
How capitalism ensnared some of its radical critics
Podcast
Podcasts

Postmodernism could’ve been revolutionary. But neoliberalism neutered it.

By Sean Illing
How to define success on your own terms
Podcast
Even Better

Minda Harts and Julia Furlan discuss equity and demanding space for yourself in the workplace.

By Julia Furlan
Politics
How to save democracy from the Supreme CourtHow to save democracy from the Supreme Court
Podcast
Politics

A Harvard law professor on the evolution of the Court and what Congress can do to make it more democratic.

By Sean Illing
New to activism? Here’s where to start.
Podcast
Even Better

A conversation with Brea Baker on starting small and getting involved.

By Julia Furlan
Podcasts
Free speech is essential for democracy. Could it also be democracy’s downfall?Free speech is essential for democracy. Could it also be democracy’s downfall?
Podcast
Podcasts

Margaret Sullivan and I talk about my new book, The Paradox of Democracy.

By Sean Illing
Science
What keeping secrets does to youWhat keeping secrets does to you
Podcast
Science

We can keep a secret — but should we?

By Sean Illing
The Gray Area
“How do you go through the world and not be bitter and angry?”“How do you go through the world and not be bitter and angry?”
Podcast
The Gray Area

Stoicism, explained.

By Sean Illing
Politics
Ukraine and the problem of “futurelessness”Ukraine and the problem of “futurelessness”
Podcast
Politics

Historian Timothy Snyder on the war in Ukraine and the future of democracy.

By Sean Illing
The Gray Area
Being a good father means rethinking masculinityBeing a good father means rethinking masculinity
Podcast
The Gray Area

Michael Ian Black on how to raise better men.

By Sean Illing
The Gray Area
The end of history is historyThe end of history is history
Podcast
The Gray Area

Francis Fukuyama on liberal democracy and its discontents.

By Sean Illing
Podcasts
Cornel West’s pragmatic AmericaCornel West’s pragmatic America
Podcast
Podcasts

Pragmatism is America’s homegrown philosophical tradition. Its lessons are as urgent as ever.

By Sean Illing
Why Anita Hill wants us to take the long view on the Supreme Court
Podcast
Politics

“The Supreme Court is only as good as the people who are on it,” the lawyer and scholar tells Vox.

By Fabiola Cineas
The Gray Area
Why Americans aren’t happy with their sex livesWhy Americans aren’t happy with their sex lives
Podcast
The Gray Area

A new book examines the downsides of sex positivity — and explores the alternatives to our unhappy sexual culture.

By Sean Illing
The Gray Area
The philosopher who warned us about loneliness and totalitarianismThe philosopher who warned us about loneliness and totalitarianism
Podcast
The Gray Area

Revisiting Hannah Arendt’s ideas about social isolation and mass resentment.

By Sean Illing
The Gray Area
Michael Lewis on why Americans don’t trust expertsMichael Lewis on why Americans don’t trust experts
Podcast
The Gray Area

How a society that is so good at creating knowledge can be so bad at applying it.

By Sean Illing
The Gray Area
The case for regretThe case for regret
Podcast
The Gray Area

Regrets, I’ve had a few, and they’re good actually.

By Sean Illing
The Gray Area
The wisdom of childrenThe wisdom of children
Podcast
The Gray Area

An old book makes an interesting case for parenting as a spiritual practice.

By Sean Illing
The limits of forgiveness
Podcast
The Gray Area

A philosopher on the complicated role of forgiveness in a polarized society.

By Sean Illing
The Gray Area
Standup comedy and the myth of cancel cultureStandup comedy and the myth of cancel culture
Podcast
The Gray Area

David Cross on political humor, how standup has changed, and why complaints about cancellation are “bullshit.”

By Sean Illing
The Gray Area
The conversation about guns we’re not havingThe conversation about guns we’re not having
Podcast
The Gray Area

A Q&A with a pro-gun journalist about guns and tribalism, the blind spots on both sides, and where the debate might go from here.

By Sean Illing
Russia-Ukraine war
Russia’s war with Ukraine — and realityRussia’s war with Ukraine — and reality
Podcast
Russia-Ukraine war

Peter Pomerantsev on whether Putin’s ability to manufacture reality may have reached its limits in Ukraine.

By Sean Illing
The Gray Area
The real story of “Don’t Look Up”The real story of “Don’t Look Up”
Podcast
The Gray Area

Co-writer (and Academy Award nominee) David Sirota on what the movie is really about.

By Sean Illing
The Gray Area
Why you (probably) won’t finish reading this storyWhy you (probably) won’t finish reading this story
Podcast
The Gray Area

We live in the most distracted time in human history. Can we reclaim our attention spans?

By Sean Illing
The Gray Area
Why good messaging won’t save DemocratsWhy good messaging won’t save Democrats
Podcast
The Gray Area

Dan Pfeiffer on the Democratic brand and how to revive it.

By Sean Illing
The Gray Area
Virtual reality is reality, tooVirtual reality is reality, too
Podcast
The Gray Area

Philosopher David Chalmers on the significance of digital worlds and why we’re maybe living in a simulation.

By Sean Illing
Future Perfect
“When everything looks hopeless, you’re the hope”“When everything looks hopeless, you’re the hope”
Podcast
Future Perfect

Jamie Raskin lost his son. He didn’t want to lose American democracy too.

By Dylan Matthews
The Gray Area
The GOP’s masculinity panicThe GOP’s masculinity panic
Podcast
The Gray Area

David French on the cult of toughness on the Trumpist right.

By Sean Illing
The Gray Area
Here are the 9 most interesting conversations I had in 2021Here are the 9 most interesting conversations I had in 2021
Podcast
The Gray Area

The conversations that challenged me the most and got me thinking about a difficult problem or provocative idea.

By Sean Illing
The Gray Area
A good life is painfulA good life is painful
Podcast
The Gray Area

Psychologist Paul Bloom on the importance of suffering, the shortcomings of hedonism, and why he would never plug into the Matrix.

By Sean Illing
Climate
The father of environmental justice, on whether we’re all doomedThe father of environmental justice, on whether we’re all doomed
Podcast
Climate

Robert Bullard joined Vox Conversations to discuss the global struggle to keep this world safe to live in, and how racism gets in the way.

By Jamil Smith
The Gray Area
Elon Musk’s imaginary worldElon Musk’s imaginary world
Podcast
The Gray Area

Historian Jill Lepore on the strange but familiar appeal of “Muskism.”

By Sean Illing