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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.

The Gray Area with Sean Illing

This week, host Sean Illing gets personal when he asks professor and podcast host Scott Galloway: What’s going on with men?
There’s a growing body of evidence that men are falling behind in education, the labor market, and other areas. And when you look at the numbers on drug overdoses and deaths by suicide, it’s pretty bleak.
Sean and Scott — both of whom are raising sons — talk about the struggles men are facing today, how parents can navigate the current moment, and the challenges they each faced as young men.
Host: Sean Illing (@SeanIlling)
Guest: Scott Galloway, professor and podcast host
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Are men okay?

Can you ever really know what’s going on inside the mind of another creature?
In some cases, like other humans, or dogs and cats, we might be able to guess with a bit of confidence. But what about octopuses? Or insects? What about AI systems — will they ever be able to feel anything? And if they do feel anything, what are our ethical obligations toward them?
In today’s episode, Vox staff writer Oshan Jarow brings those questions to philosopher of science Jonathan Birch.
Birch is the principal investigator on the Foundations of Animal Sentience Project at the London School of Economics, and author of the recently released book, The Edge of Sentience: Risk and Precaution in Humans, Other Animals, and AI. Birch also convinced the UK government to consider lobsters, octopuses, and crabs sentient and therefore deserving of legal protection.
This unique perspective earned Jonathan a place on Vox’s Future Perfect 50 list, an annual celebration of the people working to make the future a better place. The list — published last month — includes writers, scientists, thinkers, and activists who are reshaping our world for the better.
In this conversation, Oshan and Jonathan explore everything we know— and don't know — about sentience, and how to make ethical decisions about creatures who may possess it.

Guest host: Oshan Jarow
Guest: Jonathan Birch, Author of The Edge of Sentience: Risk and Precaution in Humans, Other Animals, and AI. Available for free on the Oxford Academic platform.
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What do animals feel?

How can we find happiness? That's an old question. Since the beginning of philosophy people have been wondering what makes us happy and how to get more of it. But if you're a real person living in the real world, you know already that it's not possible to be happy all the time. So what do we do when we’re experiencing depression or grief or a dark mood?
Philosopher Mariana Alessandri thinks that we should stop trying to repress these feelings.
In this conversation, which originally aired in 2023, Sean speaks with Mariana about her book Night Vision: Seeing Ourselves Through Dark Moods and how our obsession with staying positive has produced destructive emotional cycles.

Host, Sean Illing (@seanilling)
Guest: Mariana Alessandri, philosopher and author of Night Vision: Seeing Ourselves Through Dark Moods
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What to do with your sadness, pain, and grief

At the beginning of the new year, many of us make pledges to change ourselves. We want to work out more. Or read more. Or cook more. Within a few months, some of us will have succeeded but many of us will have failed. When we do, we’ll probably tell ourselves to try again, that failure inevitably leads to success.
But is that true? And is failure really such a bad thing?
In this episode, which originally aired in March of 2023, Sean interviews professor Costica Bradatan about his book In Praise of Failure: Four Lessons in Humility. The two explore different kinds of failure and discuss how embracing our limitations can teach us humility and ultimately be good for us.

Host: Sean Illing (@SeanIlling)
Guest: Costica Bradatan, professor and author of In Praise of Failure: Four Lessons in Humility
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The importance of failure

What is the first thing that you touch in the morning? What about the last thing you touch before you go to sleep? For many of us, it’s our phone. Digital devices are with us constantly, often putting a digital layer between us and the world. The benefits of this are enormous: convenience, efficiency, and constant stimulation.
But is there a personal cost to living in a mediated reality?
Today’s guest is Christine Rosen, a senior fellow at the American Enterprise Institute and the author of the new book The Extinction of Experience: Being Human in a Disembodied World. Christine and Sean discuss how the digital revolution is affecting our social skills and our quality of life.
Host: Sean Illing (@seanilling)
Guest: Christine Rosen, senior fellow at the American Enterprise Institute and the author of The Extinction of Experience: Being Human in a Disembodied World.
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The screens between us

What does it take to be happy? Professor of psychology Laurie Santos just might have the answer.

This week The Gray Area takes a break from its regular programming to bring you an episode of another podcast that we love.

In this episode of Stay Tuned With Preet, host Preet Bharara interviews Laurie Santos, a psychology professor at Yale University, about what we all can do to be happier. The two discuss how to maximize your happiness, how to bring meaning to your career, self-care vs. caring for others, and the barriers to happiness that parents face.

Host: Preet Bharara, host of Stay Tuned With Preet
Guest: Laurie Santos, professor of psychology at Yale University, and host of The Happiness Lab
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How to be happy

Where is your attention right now? Where was it a minute ago? A second ago? Where will it be a minute from now?
One of the primary features of this age — the age of the internet and smartphones and algorithmic feeds — is that our attention is everywhere and nowhere at the same time.
This is no accident. Our devices and apps are engineered to constantly alert us to things that are important and to things that are not. That’s because holding our attention is valuable. The time we spend reading, watching, and listening to content on our digital devices has been commodified, and that commodity is fueling the economy of the digital age.
Today’s guest is Chris Hayes, the host of All In with Chris Hayes on MSNBC and author of The Sirens' Call: How Attention Became the World’s Most Endangered Resource. Chris speaks with Sean about how the attention industry is changing our economy, our society, and ourselves.

Host: Sean Illing (@SeanIlling).
Guest: Chris Hayes, host of All In with Chris Hayes on MSNBC and author of The Sirens' Call: How Attention Became the World’s Most Endangered Resource.
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Attention pays (with Chris Hayes)

Americans are spending an historic amount of time alone, a phenomenon that is often referred to as an "epidemic of loneliness."
But are we actually lonely? Or do we prefer being by ourselves? And if we do, what does that mean for us and our society?
Today’s guest is journalist Derek Thompson, who, in a recent essay for the Atlantic, challenges the conventional wisdom around loneliness. He argues that Americans prefer solitude, and that preference presents a wholly different kind of challenge for the country.
Derek and Sean discuss the far-reaching effects of America’s antisocial behavior, including what it means for our society, our politics, and our future.

Host: Sean Illing (@SeanIlling)
Guest: Derek Thompson, staff writer, The Atlantic
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The cost of spending time alone

What do you think of America’s institutions?
Alana Newhouse, founder and editor-in-chief of Tablet Magazine, says that may be the most important political question in America.
In an essay published more than two years ago, Newhouse argued that there is a new political divide, one in which your place — and the place of your allies and adversaries — is determined by whether you believe that America’s institutions should be fixed or destroyed. Her argument feels eerily prescient in light of the Trump administration’s recent efforts to dismantle government programs.
In this episode, which first aired in February of 2023, Alana and Sean debate what that divide means for America’s present and future, and whether it supersedes labels like "left" or "right" and "Democrat" or "Republican."
Host: Sean Illing (@seanilling), host, The Gray Area
Guest: Alana Newhouse (@alananewhouse) editor-in-chief, Tablet and author of "Brokenism."
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Is America broken?

Are you ever happier not knowing something?

As Aristotle famously claimed, “All human beings want to know.” But denial and avoidance are also human impulses. Sometimes they’re even more powerful than our curiosity.

In this episode Sean speaks with professor Mark Lilla about when we’re better off searching for knowledge and when we’re better off living in the dark. Lilla’s new book is called Ignorance and Bliss: On Wanting Not to Know.

﻿Host: Sean Illing (@SeanIlling)
Guest: Mark Lilla, professor of humanities at Columbia University and author of Ignorance and Bliss: On Wanting Not to Know.
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The importance of failure

Lyssna när som helst, var som helst

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