
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.
Latest episodes

110 snips
Apr 14, 2025 • 58min
Whatever this is, it isn’t liberalism
In a thought-provoking conversation, political philosopher John Gray, author of The New Leviathans: Thoughts After Liberalism, challenges the long-held beliefs about the dominance of liberal democracy. He discusses the decline of liberalism, highlighting failures across nations like Russia and China. Gray also explores the complexities of political identity, the fragility of societal order, and the impacts of the 'woke movement.' Amidst a legitimacy crisis in America, he urges a deeper understanding of the historical forces shaping current political landscapes.

Apr 11, 2025 • 1min
A new way to listen
This episode highlights the exciting perks of becoming a Vox member. Listeners can enjoy ad-free access to a treasure trove of exclusive content and newsletters. It emphasizes the importance of community support in producing quality podcasts. Plus, members unlock unlimited reading capabilities on the Vox website, transforming their experience into a more enriching one.

158 snips
Apr 7, 2025 • 50min
The beliefs AI is built on
Julia Longoria, Vox host and editorial director, dives deep into the complex world of artificial intelligence. She discusses the dichotomy of AI’s benefits versus its existential threats, influenced by industry leaders' ideologies. Longoria highlights the ethical concerns surrounding biased datasets and the philosophical dilemmas of AI development. The conversation also grapples with whether AI should be viewed as a tool or a god-like entity, emphasizing the importance of aligning technology with human values and maintaining a critical perspective on AI's role in society.

66 snips
Mar 31, 2025 • 56min
Stop comparing yourself to AI
Jaron Lanier, a computer scientist, artist, and writer known for his insights on virtual reality and Silicon Valley, argues we should stop comparing AI to humans. He emphasizes that AI should be seen as a collaborative tool rather than a competitor. The conversation navigates the importance of ethical technology usage and encourages reframing AI's role for human benefit. Lanier also explores the dual nature of AI, touching on its addictive aspects and its potential to enhance creativity, while urging a humanistic perspective in our digital interactions.

60 snips
Mar 24, 2025 • 55min
Democrats need to do something
Ezra Klein, co-founder of Vox and host of The Ezra Klein Show, offers sharp insights on the sluggishness in American governance, particularly among Democrats. He critiques the inefficiencies in their response to rapid changes under the Trump administration. Klein argues for a pivot towards embracing technology and resources to better address essential needs like housing and healthcare. He emphasizes the urgency of reform to better engage with working-class voters and imagines a future where innovation drives political narratives in a more inclusive direction.

42 snips
Mar 17, 2025 • 53min
How to live in uncertain times
Maggie Jackson, a writer and journalist and author of "Uncertain: The Wisdom and Wonder of Being Unsure," shares her insights on the unexpected benefits of embracing uncertainty. She discusses how accepting ambiguity can enhance creativity, problem-solving, and mental well-being. Maggie highlights the importance of adaptability and resilience in navigating life's challenges, while also addressing the dangers of closed-mindedness in a polarized society. Her perspective encourages listeners to see uncertainty not as a barrier, but as a unique opportunity for growth and personal development.

38 snips
Mar 10, 2025 • 51min
How to sink into silence
Pico Iyer, an esteemed essayist and travel writer, discusses the transformative power of silence. He shares personal experiences from living in a Catholic monastery after losing his home, emphasizing how silence can rejuvenate amid life's chaos. Iyer explores the interplay between inner peace and nature, advocating for self-emptying practices over ego-driven distractions. He highlights the spiritual freedom found in solitude and community, offering insights on how to incorporate stillness into our busy lives for deeper fulfillment.

108 snips
Mar 3, 2025 • 43min
How to change your personality
Olga Khazan, a staff writer at The Atlantic and author of "Me, But Better," dives into the fascinating realm of personality change. She shares insights from her journey exploring whether personality traits are fixed or can be transformed. The discussion unveils the intricate balance between genetics and life experiences, emphasizing mindfulness and self-awareness as keys to personal growth. Khazan also challenges the notion of inherent traits by revealing how intentional changes can lead to meaningful transformations.

84 snips
Feb 17, 2025 • 38min
Is ignorance truly bliss?
Mark Lilla, a Professor of Humanities at Columbia University and author of "Ignorance and Bliss: On Wanting Not to Know," dives into the tug-of-war between knowledge and ignorance. He discusses when ignorance might serve us better, referencing Plato's allegory of the cave. Lilla explores how the comfort of not knowing can sometimes shield us from societal pressures and personal anxieties. The conversation reflects on the balance between curiosity and denial, revealing the psychological complexity of wanting both enlightenment and the bliss of ignorance.

163 snips
Feb 10, 2025 • 54min
Is America broken?
Alana Newhouse, founder and editor-in-chief of Tablet Magazine, offers keen insights into America’s institutional divides. She introduces the concept of 'Brokenism,' exploring the clash between those wanting to repair institutions versus those pushing for their dismantlement. Newhouse highlights the emotional impact of systemic failures on individuals and critiques the increasing political polarization. The conversation encourages a deeper understanding of historical contexts and challenges everyone to engage constructively in the evolving political landscape.
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