The Gray Area with Sean Illing

Vox
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Jan 12, 2026 • 46min

How we built a government that can’t build anything

In this discussion, Marc Dunkelman, an author and political commentator, dives deep into why the U.S. struggles to build infrastructure. He explores the historical tension between centralized authority and individual liberty, tracing back to Jefferson and Hamilton. Marc argues that procedural reforms intended to prevent abuse have instead caused government paralysis, leading to current crises in housing and infrastructure. He advocates for a balance of decision-making that fosters progress while maintaining community input, providing a cautious glimpse of hope for rebuilding public trust.
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132 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.
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64 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.
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62 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.
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130 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.
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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.
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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.
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179 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.
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35 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.
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186 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?

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