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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 and Thursday. Transcripts of the show are available here.

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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”