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 ...
Humans hate uncertainty. It makes us feel unsafe and uneasy. We often organize our lives to avoid it. When it's foisted upon us, we don’t always know how to act.
But writer and journalist Maggie Jackson argues that uncertainty can actually be good for us, and that we’re doing ourselves a disservice by avoiding it.
She tells Sean that embracing uncertainty can spark creativity, improve problem solving skills, and help us lead better, more hopeful lives.
This episode originally aired in January 2024.
Host: Sean Illing (@SeanIlling)
Guest: Maggie Jackson, author of Uncertain: The Wisdom and Wonder of Being Unsure
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52:40
How to sink into silence
How often do you find silence? And do you know what to do with it when you do?
Today’s guest is essayist and travel writer Pico Iyer. His latest book is Aflame: Learning From Silence, which recounts his experiences living at a Catholic monastery in California after losing his home in a fire.
He speaks with Sean about the restorative power of silence, and how being quiet can prepare us for a busy and overstimulated world.
Host: Sean Illing (@SeanIlling)
Guest: Pico Iyer, writer and author of Aflame: Learning From Silence
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50:45
How to change your personality
If you could change anything about your personality, anything at all, what would it be?
And why would you want to change it?Writer Olga Khazan spent a year trying to answer those questions, and documented the experience in her new book Me, But Better: The Science and Promise of Personality Change.
In this episode Sean speaks with Olga about the science of personality change, the work it takes to change yourself, and what makes up a personality, anyway.
Host: Sean Illing (@SeanIlling)
Guest: Olga Khazan, author of Me, But Better: The Science and Promise of Personality Change.
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43:11
Is ignorance truly bliss?
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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38:15
Is America broken?
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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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.
USA