The Gray Area with Sean Illing - podcast cover

The Gray Area with Sean Illing

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.

Episodes

What’s scary isn’t Trump’s illiberalism but America's acceptance of it

Yascha Mounk is a lecturer at Harvard, a columnist at Slate, and the host of The Good Fight podcast. He’s also an expert on how democracies backslide into illiberalism — which was the topic of our first conversation on this podcast. But when Mounk and I last spoke, fears of Trump’s illiberal instincts seemed to have been overblown. This was an administration too incompetent to be authoritarian. But Mounk made a prediction then that has, I think, been borne out: Trump’s illiberal instincts would ...

Aug 01, 20171 hr 8 minEp. 85

Julia Galef on how to argue better and change your mind more

At least in politics, this is an era of awful arguments. Arguments made in bad faith. Arguments in which no one, on either side, is willing to change their mind. Arguments where the points being made do not describe, or influence, the positions being held. Arguments that leave everyone dumber, angrier, sadder. Which is why I wanted to talk to Julia Galef this week. Julia is the host of the Rationally Speaking podcast, a co-founder of the Center for Applied Rationality, and the creator of the Upd...

Jul 25, 20171 hr 34 minEp. 84

Dr. Nneka Jones Tapia, the first psychologist to run a jail

Cook County Sheriff Thomas Dart calls the 8,000-person Cook County Jail the largest mental health institution in the country. Thirty percent of its inmates have diagnosed mental health issues, and the number with undiagnosed conditions is thought to push the true percentage much higher. So perhaps it’s not surprising that Dart chose Dr. Nneka Jones Tapia, a psychologist, to run it. What is surprising is that Jones Tapia is the first mental health profession to run a jail. In this conversation, w...

Jul 18, 20171 hr 11 minEp. 83

Eddie Izzard on World War I, cake or death, and marathoning

Now that I've gotten Eddie Izzard to re-derive his famed "cake or death?" routine in real time, I'm ending this podcast. Always good to go out on top. Okay, maybe I won't actually end it. But this episode was a thrill to do. Eddie Izzard has long been one of my favorite comics. I've watched his specials more times than I can count. And this conversation was a real pleasure. Izzard — whose new memoir, Believe Me, is now on shelves — thinks fast, and not always linearly, so we covered a lot of gro...

Jul 11, 20171 hr 11 minEp. 82

Avik Roy and Ezra debate the Senate GOP's health bill

According to the Congressional Budget Office, the Senate GOP’s health care bill — officially known as the Better Care Reconciliation Act — will lead to 22 million fewer people with health insurance and plans with such high deductibles that low-income people won’t be able to afford them. On the bright side? Massive tax cuts for the rich. It’s not a widely popular vision — the bill is struggling to attract Republican support, and is polling between 12 and 17 percent. But it does have defenders. Ch...

Jul 03, 20171 hr 29 minEp. 81

danah boyd on why fake news is so easy to believe

danah boyd is an anthropologist and computer scientist who studies the way people actually use technology. Not the way we wish we used technology, or the way we hope we will use technology, but the way we actually use it.“Technology,” she says, "is made by people. In a society. And it has a tendency to mirror and magnify the issues that affect everyday life.”boyd is a principal researcher at Microsoft Research, the founder of Data & Society, a visiting professor at New York University, and a...

Jun 27, 20171 hr 30 minEp. 80

Al Franken on learning to be a politician

Sen. Al Franken’s new book, Al Franken, Giant of the Senate, is the rare politician memoir that’s actually interesting. And note that I said interesting, not funny (though it is also funny).Most books by politicians are about how they’re not really politicians — they’re authentic, they’re honest, they shoot from the hip, they still remember what it was like growing up in a mill town raised by feral dogs and subsisting on nothing but hay.Franken’s book is the opposite: It’s the story of how he le...

Jun 20, 201758 minEp. 79

Zephyr Teachout on suing Trump, fighting corruption, and breaking monopolies

Zephyr Teachout is a law professor at Fordham University, the author of Corruption in America, one of the lead lawyers in the emoluments case that’s been brought against Donald Trump, and a former gubernatorial and congressional candidate. Which is all to say that Teachout is someone who knows a lot about political corruption, and so we dive deep into that topic in this podcast.We talk about how political corruption was defined by the Founding Fathers, and why, during the Constitutional Conventi...

Jun 13, 20171 hr 35 minEp. 78

Masha Gessen offers a plausible Trump-Russia theory

Masha Gessen is a Russian-American journalist and the author of, among other books, The Man Without a Face: The Unlikely Rise of Vladimir Putin. Since the election, she has been analyzing Donald Trump through the lens of Russian politics and personalities in a series of viral essays in the New York Review of Books. But as the Trump campaign's relationship with Russia has evolved into a dominant storyline of his presidency, Gessen has grown skeptical. She thinks the left has been overwhelmed by c...

Jun 06, 20171 hr 9 minEp. 77

Kwame Anthony Appiah on cosmopolitanism

Few words are as reviled in American politics as “cosmopolitan.” The term invokes sneering, urban, elite condescension. It’s those smug cosmopolitans who led to Donald Trump’s election. It’s those rootless cosmopolitans who’re shipping jobs overseas with no thought for their home communities. Cosmopolitans. Ick. Kwame Anthony Appiah is a British-born Ghanaian-American philosopher at New York University, as well the writer of the New York Times Magazine’s “Ethicist” column. He’s also the author o...

May 30, 20171 hr 9 minEp. 76

Yascha Mounk: Is Trump’s incompetence saving us from his illiberalism?

Yascha Mounk is a Lecturer on Government at Harvard University, a Fellow in the Political Reform Program at New America, and host of the podcast, The Good Fight. He’s also the author of some of the scariest political science research I’ve seen in a long time.What Mounk found is that the consensus we thought existed on behalf of democracy and democratic norms is weakening. The percentage of Americans who think it’s important to live in a democracy has been plummeting in recent decades. The percen...

May 23, 20171 hr 37 minEp. 75

Bryan Stevenson on why the opposite of poverty isn’t wealth, but justice

Bryan Stevenson is the founder and executive director of the Equal Justice Initiative. He and his staff have won reversals, relief, or release for more than 115 wrongly convicted prisoners on death row. He’s the author of the power book Just Mercy, and a winner of a MacArthur “Genius” grant. There are only a few people I’d say this about, but he’s a genuine American hero.This conversation begins with one of Stevenson’s most provocative arguments. “The opposite of poverty isn’t wealth,” he says. ...

May 16, 20171 hr 35 minEp. 74

Death, Sex, and Money’s Anna Sale on bringing empathy to politics

There’s much talk of “empathy” in today’s politics, but it’s a cramped, weaponized form of empathy — an empathy designed to force us to grudgingly tolerate each other, or an empathy used to explain away the reasons we hurt each other.You can glimpse something better in the space Anna Sale creates on the WNYC podcast Death, Sex, and Money. Her show is, in this moment, powerful; the empathy she extends to her guests feels real and deep; the conversations she holds are bracingly difficult while sti...

May 09, 201756 minEp. 73

Cory Booker returns, live, to talk trust, Trump, and basic incomes

Senator Cory Booker is back! In this special live episode of The Ezra Klein Show — taped at Vox Conversations — Booker and I dig into America’s crisis of trust. Faith in both political figures and political institutions has plummeted in recent decades, and the product is, among other things, Trump’s presidency. So what does Booker think can be done about it?We also talk about: Whether Democrats need to be angry to fight Trump The $400,000 President Barack Obama recently accepted for a speech to ...

May 04, 20171 hr 13 minEp. 72

VC Bill Gurley on transforming health care

Washington has been gripped of late by the world’s most depressing, least imaginative, debate over health care. The question, as it stands, is whether Obamacare will survive (while being mildly, but persistently, sabotaged by the Trump administration), or whether it will be rolled back and replaced with a system that covers 24 million fewer people in order to fund tax cuts for the richest Americans. Huzzah!But a better conversation awaits. Bill Gurley is a partner at Benchmark Capital, and an ea...

May 02, 20171 hr 15 minEp. 71

Elizabeth Warren on what Barack Obama got wrong

Elizabeth Warren is the founder of the Consumer Financial Protection Bureau, the senior senator from Massachusetts, and the author of the new book, “This Fight Is Our Fight: The Battle to Save America's Middle Class.”You might have heard of her.Warren is also one of the Democrats most capable of defining the Democratic Party’s soul and message in a post-Trump era. In her book, she says she had at least one big disagreement with President Obama — a disagreement that speaks to the direction she wa...

Apr 25, 201749 minEp. 70

Cal Newport on doing Deep Work and escaping social media

I was asked recently to name a book that changed my life. The book I chose was Cal Newport’s “Deep Work,” and for the most literal of reasons: it’s changed how I lived my life. Particularly, it’s led me to stop scheduling morning meetings, and to preserve that time for more sustained, creative work.Which is all to say that I’m a bit obsessed with Newport’s work right now, and especially his account of how the digital environment we inhabit is training us out of concentration and into distraction...

Apr 18, 20171 hr 26 minEp. 69

G. Willow Wilson on religion, comics, and modern myths

This is a podcast about topics we don’t always cover on this show. Religion. Spirituality. Gender roles. Traditionalist societies. Comic books.G. Willow Wilson is the author of The Butterfly Mosque, Alif the Unseen, and the Hugo award winning comic book, Ms. Marvel. She’s also lived a fascinating, unusual life: she’s an American who converted to Islam and then moved to Egypt, where she met her now-husband. The hallmark of her work is an empathy and appreciation for societies that are often caric...

Apr 11, 20171 hr 18 minEp. 68

Chris Hayes on the crisis of elites and the politics of order

I could describe this podcast, and I will. But the tl;dr is this is one of my favorite conversations so far, and you’re going to enjoy it. So just go listen. Chris Hayes is, of course, the host of the MSNBC primetime show, “All In.” He’s also the author of the new book “Colony in a Nation,” as well as (the extremely prescient) Twilight of the Elites. But beyond the bio, Chris is a crazily smart and insightful thinker on US politics and society, and he's in rare form here. Among our topics:• The ...

Apr 04, 20171 hr 45 minEp. 67

Tyler Cowen explains it all

I have never come across a mind quite like Tyler Cowen’s. The George Mason economist, and Marginal Revolution blogger, has an interesting opinion on, well, everything. He’s a genuine polymath who can talk knowledgeably about more subjects than I even know exist.So coming in to this interview, I had a simple plan: ask Cowen for his thoughts on as many topics as possible. And I think it worked out pretty well. We discuss everything from New Jersey to high school sports to finding love to smoked tr...

Mar 28, 20171 hr 37 minEp. 66

Molly Ball on whether facts matter in politics

You may remember the Atlantic's Molly Ball from the fantastic pre-election conversation we had on this podcast. She's back this week to talk about an issue I've become more and more obsessed with — does factual argument matter in American politics? Or is it just a contest of identity activation?In the most recent Atlantic, Ball profiles Kellyanne Conway, whose television appearances and "alternative facts" offer an unusually clear window into this debate. We talk about that, as well as:- What's ...

Mar 21, 20171 hr 19 minEp. 65

Denis McDonough on how to run the White House

How do you actually run a White House? What is the president’s actual job? What is the chief of staff’s role? What happens if you screw up? These are questions I’ve been reflecting on rather a lot lately, for obvious reasons. And so I asked Denis McDonough on the podcast to talk about them.McDonough served as President Barack Obama’s chief of staff from 2013 to 2017 — a position in which he earned the nickname “Obama’s Obama.” This is his first lengthy interview since leaving the White House, an...

Mar 14, 20171 hr 24 minEp. 64

Cecile Richards on Planned Parenthood, labor organizing, and the Supreme Court

Before Cecile Richards was president of Planned Parenthood, she was a labor organizer working with garment workers in El Paso, Texas. The experience taught her a key principle of political change: people do things for their reasons, not your reasons.In this conversation, we talk about her organizing background, and how it's informing her work as she tries to protect her the institution she leads. Defunding Planned Parenthood is a core Republican promise. It is also, as she explains, a more punit...

Mar 07, 20171 hr 18 minEp. 63

Tim Ferriss on suffering, psychedelics, and spirituality

Tim Ferriss is the author of the 4-Hour Workweek, as well as the new book, Tools of Titans. He’s also the host of The Tim Ferriss Show, which is one of my favorite podcasts, and an inspiration for this show. Tim is a relentless optimizer, and on his program, he interviews fascinating people to discover how they work, think, and get things done. It’s a show about the secrets of high performers. Here, I ask Tim about basically the reverse of that. How does he think about the parts of his life that...

Mar 02, 20171 hr 54 minEp. 62

Yuval Harari, author of “Sapiens,” on AI, religion, and 60-day meditation retreats

Yuval Noah Harari’s first book, “Sapiens,” was an international sensation. The Israeli historian’s mind-bending tour through the trump of Homo sapiens is a favorite of, among others, Bill Gates, Mark Zuckerberg, and Barack Obama. His new book, Homo Deus, is about what comes next for humanity — and the threat our own intelligence and creative capacity poses to our future. And it, too, is fantastically interesting. I’ve wanted to talk to Harari since reading Sapiens. I’ve had one big question abou...

Feb 28, 20171 hr 13 minEp. 61

Elizabeth Drew covered Watergate. Here's what she thinks of Trump.

Elizabeth Drew is the author of Washington Journal, one of my favorite books about Watergate. Drew covered the story as a reporter for the New Yorker, and the book emerges from the real-time, journalistic diary she kept amidst the chaos. As such, it does something no other Watergate book does: tells the story not as a tidy tale with a clear beginning and inevitable end, but as an experience thick with confusion, rumors, alarm, and half-truths.Of late, I've heard a lot of people comparing the ear...

Feb 21, 20171 hr 14 minEp. 60

Avik Roy on why conservatives need to embrace diversity

Avik Roy advised Mitt Romney’s 2012 campaign on health care, ran the policy shop on Rick Perry’s 2016 campaign, and then worked for Marco Rubio after Perry dropped out. So Roy’s Republican credentials are pretty solid. But he’s aghast at the direction his party has taken in recent years. The question Roy asks of conservatives today is a profound one: what is it you’re seeking to conserve? Under Donald Trump, he fears Republicans are fighting to conserve the idea of America as a fundamentally whi...

Feb 14, 20171 hr 34 minEp. 59

Kara Swisher gives a master class on reporting and interviewing

Before I launched this podcast, I asked Kara Swisher to coffee. Swisher founded the technology news site Recode, hosts the excellent Recode Decode podcast, and runs a legendary conference series. She is among the best interviewers working today. Some of her gets — including the first and only dual interview of Steve Jobs and Bill Gates — have passed nearly into myth. I've used the advice Swisher gave me in every episode of this podcast. But in this conversation, she goes further, offering her ti...

Feb 07, 20171 hr 41 minEp. 58

David Miliband explains the global refugee crisis

Donald Trump's executive order temporarily banning Muslim refugees from Iraq, Iran, Libya, Somalia, Sudan, and Yemen, and indefinitely banning them from Syria, doesn't come in a vacuum. The world is currently experience the worst refugee crisis since World War II — a crisis that has destabilized the Middle East, torn at the fabric of Europe, and left 65 million people displaced.This is what America is turning its back on. And just because we slam our doors, it doesn't mean the crisis eases. It c...

Feb 02, 201752 minEp. 57

Jennifer Lawless on why you — yes, you — should run for office

There are 500,000 elected positions in the United States. I'll say that again: 500,000. And that's no accident. "Our political system is built on the premise that running for office is something that a broad group of citizens should want to do," writes political scientist Jennifer Lawless.But Lawless's research reveals something scary — something that helps explain the political moment we're in. Participating in politics has begun to repulse the average America. 89 percent of high schoolers says...

Jan 31, 20171 hr 7 minEp. 56
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