
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

72 snips
Jun 16, 2025 • 53min
Is Trump winning?
Zack Beauchamp, a senior correspondent at Vox and writer of the On the Right newsletter, dives deep into the implications of Donald Trump's second term. They explore how Trump consolidates power and the resulting challenges to American democracy. Discussions include the appeal of Trumpism's narrative, legal battles surrounding his policies, and the troubling allure of authoritarian models. Beauchamp emphasizes the need for a robust counter-narrative from the left to engage younger voters and asserts that the future of democracy remains uncertain and malleable.

154 snips
Jun 9, 2025 • 1h 8min
A right-wing economist makes his case
Oren Cass, founder of American Compass and editor of The New Conservatives, challenges traditional economic policies on the right, advocating for a pro-worker approach. He believes in revitalizing American manufacturing while critiquing the overemphasis on consumption as a measure of success. Cass discusses the tension between libertarianism and traditional values, and the need for effective industrial policy. He explores the complexities of navigating economic policy in a polarized society, emphasizing the importance of aligning profit motives with public interest.

14 snips
Jun 2, 2025 • 56min
What "near death" feels like
Sebastian Junger, a veteran reporter and author of 'In My Time of Dying', shares his transformative near-death experience caused by an undiagnosed aneurysm. He reflects on the profound questions about consciousness and existence that emerged from this encounter with mortality. The conversation dives into the emotional ties that linger after death, the scientific exploration of near-death phenomena, and how facing mortality reshapes our life choices. Junger's insights challenge listeners to rethink their beliefs about life, death, and the afterlife.

106 snips
May 26, 2025 • 52min
Machiavelli on how democracies die
Erica Benner, a political philosopher and author of 'Be Like the Fox,' dives into Machiavelli’s enduring relevance nearly 500 years after his death. She discusses the complexities of Machiavelli’s character, his nuanced views on democracy, and how modern politics, particularly the Trump administration, align with his thoughts. The conversation reveals how his insights on power and morality can critique contemporary authoritarianism and the decline of democratic values. Listeners gain a deeper understanding of Machiavelli's legacy and its implications today.

111 snips
May 12, 2025 • 1h 1min
Do you have moral ambition?
Rutger Bregman, a historian and author of 'Moral Ambition,' believes in prioritizing moral achievements over traditional success metrics. He discusses the disillusionment many feel when personal ambition doesn't align with societal good. Bregman suggests that making moral ambition fashionable can lead to meaningful change. He emphasizes embracing impactful causes, like climate change, and critiques the narrow views of moral progress. The conversation is a compelling invitation to redefine success through a lens of ethical responsibility and collective well-being.

106 snips
May 5, 2025 • 56min
The science of ideology
Leor Zmigrod, a political psychologist and neuroscientist, discusses the fascinating interplay between our biology, psychology, and political beliefs. She explores the challenges of confronting ideologies when faced with contradictory evidence. Zmigrod delves into rigid versus flexible thinking, emphasizing the importance of cognitive flexibility in navigating moral complexities. The conversation highlights how genetic and environmental factors shape our ideological rigidity and calls for an adaptable mindset to foster understanding across the political spectrum.

28 snips
Apr 28, 2025 • 51min
A new analysis of the pandemic
Frances E. Lee, a politics professor at Princeton and co-author of In COVID's Wake: How Our Politics Failed Us, dives into the pandemic's political ramifications. She discusses how political decisions directly influenced public health outcomes and exacerbated inequalities. Lee critiques the partisanship that affected vaccine distribution and decision-making transparency. Highlighting lessons from the pandemic, she emphasizes the need for accountability and honesty among policymakers to rebuild public trust as we navigate future crises.

102 snips
Apr 21, 2025 • 55min
Halfway there: a philosopher’s guide to midlife crises
In this engaging conversation, Kieran Setiya, an MIT professor and author, delves into how philosophy can ease the struggles of midlife crises. He explores the intersection of self-help and ethical living, arguing that reflection can navigate life's complexities. The discussion touches on the malaise of midlife, the weight of regret, and the quest for meaning. Setiya also critiques the focus on happiness, advocating for embracing life's challenges and shared experiences over mere self-love. His insights offer a philosophical roadmap for a fulfilling life.

145 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.