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The Gray Area

Resist certainty, embrace ambiguity. The Gray Area is a philosophical take on culture, politics, and everything in between with host Sean Illing. We don’t pretend to have the answers, but we do offer a space for real dialogue. Get some cool takes on a very hot world. New episodes drop every Monday. Transcripts of the show are available here.

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Why we fear uncertainty — and why we shouldn’t

Why work is so miserable in America

How mindfulness went mainstream

The philosophy of anarchism, explained

What our brain chemistry says about free will

The author Michael Lewis on the lessons of Sam Bankman-Fried

David Brooks thinks Americans are getting meaner

Naomi Klein on her doppelganger (and yours)

Stuart Russell wrote the textbook on AI safety. He explains how to keep it from spiraling out of control.

Democracy is the antidote to capitalism

Is the populist right’s future ... democratic socialism?

The case for reimagining the nuclear family

The new crisis of masculinity

How to raise kids in the face of climate change

When you can’t separate art from artist

How “enlightened selfishness” can lead to a more fulfilling marriage

Are you a good listener? The answer may surprise you.

Katie Porter thinks Democrats have a confidence problem

The media wants the audience’s trust. But is it being earned?

How Palo Alto created capitalism as we know it

Neil deGrasse Tyson gets political

A GOP insider on the Republicans who knew Trump was dangerous — and went MAGA anyway

What we get wrong about being in love

The profound pessimism of Clarence Thomas

The Marxist scholar who thinks reparations are “a waste of time”

The cost of reparations

Want to be happy? Don’t follow your gut.

Reparations could heal America

Reviving the case for reparations

What if your financial future wasn’t stressful? 

Setting boundaries is more than just saying “no”

How capitalism ensnared some of its radical critics

How to define success on your own terms

How to save democracy from the Supreme Court

New to activism? Here’s where to start.

Free speech is essential for democracy. Could it also be democracy’s downfall?

What keeping secrets does to you

“How do you go through the world and not be bitter and angry?”

Ukraine and the problem of “futurelessness”

Being a good father means rethinking masculinity

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