
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. From the Vox Media Podcast Network.
Latest episodes

29 snips
Jul 14, 2025 • 56min
Hopeful pessimism
Philosopher Mara van der Lugt, a lecturer at the University of St Andrews and author of 'Hopeful Pessimism,' dives into the complexities of balancing hope and despair. She discusses how blind hope can lead to disappointment and advocates for a more realistic, nuanced mindset. The conversation covers the emotional intricacies of climate activism, highlighting Greta Thunberg's unique blend of hope and realism. Van der Lugt emphasizes that acknowledging darker emotions like anger and grief can inspire authentic change in a troubled world.

287 snips
Jun 30, 2025 • 59min
If AI can do your classwork, why go to college?
James Walsh, a features writer for New York Magazine's Intelligencer and author of 'Everyone is Cheating Their Way Through College,' dives into the troubling trend of AI in academia. He discusses how students are leveraging AI tools to handle their assignments, leading to concerns about academic integrity. Walsh explores whether traditional colleges can adapt to this new reality, the ethical dilemmas of using AI, and its impact on critical thinking. The conversation highlights a broader rethinking of the purpose of college in an AI-driven world.

79 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.