

The Gray Area with Sean Illing
Vox
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.
Episodes
Mentioned books

22 snips
Dec 22, 2025 • 59min
It’s okay to not be okay
Mariana Alessandri, a philosophy professor and author, challenges the cultural obsession with positivity and re-evaluates how we view dark moods. She argues that sadness and grief aren’t failures, but integral parts of the human experience. The conversation explores why societal pressure to 'cheer up' often backfires and critiques Stoic and Aristotle’s approaches to emotions. Mariana emphasizes the importance of sitting with grief and providing emotional honesty, particularly in parenting, and calls for a shift away from shame toward acceptance.

51 snips
Dec 15, 2025 • 1h 4min
Forgiveness is optional
Myisha Cherry, a philosopher and associate professor at UC Riverside, tackles the complexities of forgiveness in this engaging conversation. She critiques the cultural pressure to forgive, especially on vulnerable victims, and questions whether it's always beneficial. Highlighting the 2015 Charleston church shooting, she explores the dangers of idolizing forgiveness as a remedy. Cherry emphasizes that anger can be a moral tool, advocating for intentionality in forgiveness and recognizing that some harms require more than just forgiving to heal.

52 snips
Dec 8, 2025 • 56min
The pornification of everything
Daniel Kolitz, a writer for Harper's Magazine, dives into the intriguing world of 'gooning,' a subculture blending prolonged pleasure with community dynamics. He explores how hyperkinetic media is reshaping our patience and attention spans, framing gooning as a reflection of broader societal changes. Kolitz reveals that many participants are regular young adults, complicating stereotypes around this behavior. The discussion also touches on how this phenomenon mirrors an emerging pornosexuality and the cultural ramifications of living primarily in a screen-dominated reality.

121 snips
Dec 1, 2025 • 41min
What counts as progress?
J. Bradford DeLong, an economic historian and UC Berkeley professor, dives into the perplexing paradox of wealth versus true well-being. He explores how technology impacts our lives, with AI promising both productivity and distraction. DeLong discusses the importance of stable politics in addressing rapid changes, noting a growing divide in the workforce as creative destruction affects even white-collar jobs. He argues the 21st century will hinge on attention management amidst information overload and highlights the crucial need for effective policies to support displaced workers.

86 snips
Nov 17, 2025 • 57min
How to survive awkward encounters
Alexandra Plakias, an associate professor of philosophy and author of Awkwardness: A Theory, explores the social roots of awkwardness. She argues that it's not a personal flaw but a reflection of broken social scripts. The conversation highlights how power dynamics influence who feels awkward and how anxiety can stifle important conversations. Plakias shares practical tips for navigating awkward moments and emphasizes the collective responsibility to reframe our understanding of social discomfort.

97 snips
Nov 10, 2025 • 52min
Truth in an age of doublethink
Laura Beers, a historian and author of "Orwell's Ghosts," discusses George Orwell's enduring relevance in today's world of surveillance and misinformation. They explore Orwell's defense of truth over ideology, his critique of euphemism, and the importance of intellectual honesty. Beers also examines Orwell's insights on language, totalitarianism, and his blind spots regarding gender. The conversation emphasizes the crucial need to uphold truthful speech as a safeguard against disinformation, making Orwell's lessons more pertinent than ever.

138 snips
Nov 3, 2025 • 59min
The case against free will
Robert Sapolsky, a renowned biologist and neuroscientist from Stanford University, discusses his provocative stance that free will is an illusion. He explains how our choices are intricately linked to genetics, environment, and history, challenging the traditional views on meritocracy and blame. Sapolsky explores the implications of a deterministic worldview, emphasizing that behaviors often arise from biological and cultural influences rather than individual volition. He argues for a shift in societal responses, advocating for prevention over punitive measures in understanding human behavior.

34 snips
Oct 27, 2025 • 49min
What the climate story gets wrong
Hannah Ritchie, a data scientist and Deputy Editor at Our World in Data, dives into the often distorted narratives around climate change. She reveals that emissions are peaking and clean energy is scaling faster than expected, challenging the doom-and-gloom mindset. Ritchie emphasizes the importance of both individual actions and systemic change. She also highlights how public opinion is stronger than we think, the potential for renewables in red states, and the transformative power of plant-based diets. A hopeful vision for a decarbonized future emerges throughout their conversation.

185 snips
Oct 20, 2025 • 48min
The Great Enshittening
Cory Doctorow, a journalist and science fiction author known for his work on digital rights, dives deep into the concept of enshittification—the decline of online platforms. He unpacks how this decay happens, starting with Google's 2019 changes and extending to how other industries are affected. Doctorow discusses the reasons users stick with subpar platforms, the implications of monopolies, and the importance of potential reforms in policy and collective action. He poses an intriguing question: can we ever reverse this trend?

73 snips
Oct 13, 2025 • 58min
America chose violence. Now what?
Barbara Walter, a political scientist from UC San Diego and author of 'How Civil Wars Start,' shares insights on America's rising political violence. She highlights the dangers of partisan rhetoric and how domestic terror is largely driven by far-right actors. Walter discusses the modern patterns of insurgency and the growing public acceptance of political violence. She warns that the U.S. is in a precarious state for potential civil conflict, stressing the importance of grassroots efforts to uphold democratic norms.


