The Gray Area with Sean Illing

It’s easy to forgive other people because you don’t have to live inside their head. Forgiving yourself is different and much, much harder. Sean Illing is joined by philosopher Myisha Cherry to talk about what it actually means to forgive yourself without letting yourself off the hook. They discuss the difference between guilt and shame (one can push you to repair, while the other just makes you want to hide), why even small screwups can leave a lingering moral aftertaste, and how regret can either trap you in self-reproach or become fuel for doing better. Host: Sean Illing (@SeanIlling) Guest: Myisha Cherry (@myishacherry) We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday. Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Kalle Lasn has been trying to jam consumer culture for decades. Now he thinks that was only the beginning. Sean talks with the Adbusters founder about advertising, culture jamming, meme warfare, surveillance capitalism, and why he believes the old left-right political script is dead. Lasn argues that consumer culture is not just shallow or manipulative but part of a system pushing us toward collapse. His answer is bigger than protest and weirder than reform. He wants a cultural revolution that starts with new ideas, new language, and maybe an entirely new politics. Host: Sean Illing (@seanilling)  Guest: Kalle Lasn (@KalleLasn) We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday. Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. Learn more about your ad choices. Visit podcastchoices.com/adchoices

The Gray Area is taking a short break this week — but we’ve got something special for you. We’re dropping an episode from one of our favorite podcasts, Unexplainable. In it, host Emily Siner explores deceptively simple questions: What is a musical note? And how did something as fundamental as the note A become standardized across the world? It’s a story about science, history, and the hidden complexity behind the sounds we listen to every day.We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.And you can watch new episodes of The Gray Area on YouTube. Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why do humans have this deep need to feel like we matter?  Sean Illing talks with the philosopher Rebecca Goldstein about why “mattering” is not the same thing as being important, how the hunger for validation can go really, really badly, and the different ways we try to justify our lives to ourselves. Love. God. Winning. Greatness. Service.  Host: Sean Illing (@SeanIlling) Guest: Rebecca Goldstein, author of The Mattering Instinct We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday.Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Something is definitely happening in the AI world, but how seriously should we take it? Is this another hype cycle or a genuine inflection point? Sean Illing talks with journalist Kelsey Piper (formerly of Vox, now at The Argument) about what’s changed, why AI “agents” are a different beast than yesterday’s chatbots, and why the debate is stuck between two lazy positions: total panic or total shrug. They get into the incentives driving the labs, what “alignment” even means, and why the real fear isn’t Terminator-style robots, but powerful systems sliding into everything before we’re ready. Host: Sean Illing (@SeanIlling) Guest: Kelsey Piper (@KelseyTuoc) We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday.Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What is consciousness, really? We don’t know. Scientists aren’t sure. Philosophers can’t agree. All we have is the fact that it feels like something to be you right now. Beyond that, human consciousness remains a complete mystery. Sean talks with Michael Pollan about his new book, A World Appears, which is about what we do and don’t know about consciousness and why it continues to be one of the great miracles of nature. They get into why consciousness has proven so hard to define, whether the self is real or just a useful fiction, what psychedelics and meditation reveal about the mind, and why even serious neuroscientists are starting to question strict materialism. Along the way, they wander into plant intelligence, AI psychosis, ego death, and the unsettling possibility that not knowing might actually be the right place to land. Host: Sean Illing (@SeanIlling) Guest: Michael Pollan, author of A World Appears (@michaelpollan) We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com, or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday.Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Venezuela. Greenland. Iran. Things have been moving so quickly that we weren't even at war with Iran when we recorded this episode of The Gray Area with Sean Illing. It’s only March, but it’s been a long year.  The war in Iran is only the latest sign that something deep is shifting in our global politics.  Alliances fraying. Norms weakening. Democracies wobbling. So what exactly is happening? Is the liberal international order slowly eroding? Is it just going through a particularly turbulent chapter? Or are we watching it all collapse? Sean talks with Zack Beauchamp, author of Vox’s On the Right newsletter, about the global democratic backslide and whether the American-led liberal order is slipping, imploding, or just going through a rough patch. Their conversation, which was recorded before the conflict in Iran, digs into the Greenland saga, alliance politics, and why democratic decay can be both obvious and hard to see at the same time.  Host: Sean Illing (@SeanIlling) Guest: Zack Beauchamp (@zackbeauchamp) We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.  And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday.Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Addiction is one of those words that seems obvious until you try to explain it. We tend to fall back on two simple stories. Either addiction is a moral failure or it’s a brain disease that robs people of agency entirely. But neither of those stories feels complete. Today’s guest is philosopher Hanna Pickard, author of What Would You Do Alone in a Cage With Nothing But Cocaine? Pickard argues that it’s a harmful mistake to treat addiction as either sin or sickness. Instead, it’s a form of behavior that’s shaped by trauma, isolation, identity, social conditions, and often deep psychological pain. Sean and Hanna talk about her theory of addiction and why our society has built the cage that so many people are trying to escape. Host: Sean Illing (@SeanIlling) Guest: Hanna Pickard, author of What Would You Do Alone in a Cage With Nothing But Cocaine? We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday. Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What the hell just happened in Iran? The US launched an attack last weekend, and within hours, the explanations were already shifting. Is this regime change? Will it be a few days? A few months? Several years? By the time you’re listening to this, the situation may have moved again. So this is a quick, emergency TGAF about where things currently stand. Sean calls up Wall Street Journal national security reporter Alex Ward to walk through what we actually know, what we don’t, and what could come next. They talk about the risk of regional escalation, the “break it and walk away” strategy, and why the range of possible outcomes right now is…uncomfortably wide. Host: Sean Illing (@SeanIlling) Guest: Alexander Ward (@alexbward) We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.  And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday.Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. Learn more about your ad choices. Visit podcastchoices.com/adchoices

We use the word “anxiety” to describe stress, dread, worry, panic, even vibes. Which just goes to show: We really don’t know what anxiety is, or where it comes from, or what we’re supposed to do with it. Today’s guest is philosopher Samir Chopra, author of Anxiety: A Philosophical Guide. Chopra argues that anxiety is a permanent feature of being human and the price of being a free, self-conscious creature in an uncertain world. Sean and Samir talk about the difference between fear and anxiety, why modern life seems engineered to keep us on edge, and what Buddhism, existentialism, and Freud can teach us about the anxious mind. Host: Sean Illing (@SeanIlling) Guest: Samir Chopra, author of Anxiety: A Philosophical Guide We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.  And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday.Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. Learn more about your ad choices. Visit podcastchoices.com/adchoices

A lot of Gen Z men sound surprisingly excited about fatherhood. A lot of Gen Z women…do not.  And that divide — and the national handwringing about it — says a lot about the changing status of men and women in this country, and the uncomfortable realization that for American policymakers, not all children are created equal.  Today’s guest is Vox reporter and bestselling novelist Anna North, who covers kids, parenting, and American family life. She writes the Vox newsletter Kids Today, and her latest chart-topping novel is Bog Queen. She recently reported on the gap between young men and young women on parenthood and what that might tell us about gender roles, relationships, and the future of family formation in a politically polarized country. Host: Sean Illing (@SeanIlling) Guest: Anna North  We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday. Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Mindfulness is everywhere now, which is kind of weird. What started as a countercultural practice has become a productivity hack and a billion-dollar app ecosystem. On one level, it’s great that more people are meditating. But somewhere along the way, the whole thing got flattened. When mindfulness is mainly about optimizing your output, we’ve probably missed the point. Today’s guest is Jon Kabat-Zinn, pioneer of the American mindfulness movement and author of the mega-bestseller Wherever You Go, There You Are. Jon’s work helped bring meditation into medicine, schools, sports, and everyday life. He’s also spent decades reminding people that mindfulness isn’t about escape, self-improvement, or becoming some perfectly serene version of yourself. Sean and Jon talk about what mindfulness actually is, why being present is so damn hard, and what happens when industry turns meditation into another tool for self-optimization. This episode originally aired in December of 2023. Host: Sean Illing (@SeanIlling) Guest: Jon Kabat-Zinn, author of Wherever You Go, There You Are: Mindfulness Meditation in Everyday Life. We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday. If you enjoy our reporting and want to hear more from Vox journalists, sign up for our Patreon at patreon.com/vox. Each month, our members get access to exclusive videos, livestreams, and chats with our newsroom. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Sean talks to Atlantic writer Tyler Austin Harper about the killing of Alex Pretti in Minneapolis, and why liberals are missing the point about American gun culture and the right to bear arms.  Beyond that, Tyler asks an important question: If you really believe we’re sliding toward authoritarianism, how can you argue that the public should disarm?  Host: Sean Illing (@SeanIlling) Guest: Tyler Austin Harper (@Tyler_A_Harper) We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday. If you enjoy our reporting and want to hear more from Vox journalists, sign up for our Patreon at patreon.com/vox. Each month, our members get access to exclusive videos, livestreams, and chats with our newsroom. Learn more about your ad choices. Visit podcastchoices.com/adchoices

The Gray Area with Sean Illing is now twice a week! Look for new episodes every Monday and Friday, here in your ears and at Youtube.com/vox for your eyes.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Games are fun. Aren’t they? When we play games — board games, video games, any kind of game — something magical happens. Games allow us to explore, to create little worlds where we can be different versions of ourselves. But when we turn life into a game — where we have to get the best grade, or the most money, or the most “likes” — then games stop being fun. Why is that? This week Sean speaks with philosopher C. Thi Nguyen about what a game really is, the difference between playing for enjoyment and playing to win, and why games lose their magic when the stakes become real. Thi argues that the things we value in life are increasingly captured by grades and likes and downloads and step counts and a thousand other metrics that quietly rewrite what we want and what we think makes us happy. Host: Sean Illing (@SeanIlling) Guest: C. Thi Nguyen, author of The Score We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why do we love football so much? Why does this sport dominate American culture in a way nothing else can? Why does it feel essential even to people who barely like sports? And what does it say about us that we keep watching, even as the risks and contradictions become harder to ignore? Today’s guest is Chuck Klosterman, cultural critic and bestselling author, whose new book Football tries to explain the game at the height of its power. Sean and Chuck talk about how football became the defining spectacle of modern America, why it’s easily the best television show we’ve ever seen, and why it presents a ton of moral dilemmas we can’t really solve.  Host: Sean Illing (@SeanIlling) Guest: Chuck Klosterman, author of Football We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.And you can watch new episodes of The Gray Area on YouTube. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why is it so hard for America to build things? Bridges take years to construct. Housing costs are soaring. Transit systems are crumbling. And we’re struggling to update our infrastructure to prepare for the climate crisis. Even when there’s broad agreement that something needs to be done, collective action feels impossible. Why is that? Today’s guest is Marc Dunkelman, author of Why Nothing Works, a book about the modern American experience of watching government fail. He argues that by giving too many people the power to say “no,” we’ve stymied our collective progress. Marc and Sean discuss an inherent tension in American politics: the need for effective, centralized power and a deep fear of its abuse. They trace how that tension has played out across American history, from the clashes between Jefferson and Hamilton, through the New Deal’s Tennessee Valley Authority, to the backlash against figures like Robert Moses. Marc argues that our current system — born out of a reaction to too much top-down authority during the late 20th century — has produced paralysis, dysfunction, and a deep distrust of government. Host: Sean Illing (@SeanIlling) Guest: Guest: Marc Dunkelman (@MarcDunkelman), author of Why Nothing Works: Who Killed Progress — and How to Bring It Back. We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube.Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members This episode was supported by a grant from Arnold Ventures. Vox had full discretion over the content of this reporting. Learn more about your ad choices. Visit podcastchoices.com/adchoices

It’s not always the most wonderful time of the year. Every December, we’re told to be merry and stay positive. But a lot of us don’t feel that way. And when we don’t, the pressure to be happy makes everything worse. Sadness feels like failure. Grief feels like a personal mistake. Depression becomes something to hide. But what if dark moods aren’t problems to fix? What if they’re part of being human? Today’s guest is philosopher Mariana Alessandri, author of Night Vision, a book about how to honor the emotions we usually try to outrun. It’s not a celebration of sadness, but Alessandri calls bullshit on the culture of toxic positivity and the idea that happiness is something we’re supposed to choose on command. Sean and Mariana talk about why Americans are addicted to the light, why “cheering people up” often backfires, how Stoicism shaped our emotional habits, and what it looks like to sit with grief instead of shaming ourselves for feeling it. Host: Sean Illing (@SeanIlling) Guest: Mariana Alessandri (@mariana.alessandri), associate professor of philosophy at the University of Texas-Rio Grande Valley and author of Night Vision: Seeing Ourselves Through Dark Moods. We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. This holiday season, your membership goes further: when you join Vox as an annual Member, we’ll gift a free membership to a reader who can’t afford it. By joining today, you’ll get 30% off for an annual membership, and we’ll match your membership. And if you can’t afford it, visit that same link to apply for a free membership through our gift program. Learn more about your ad choices. Visit podcastchoices.com/adchoices

You have to forgive people who wrong you…right? The world is filled with injustice and wrongdoing, and to live in the world — to not be consumed by anger — forgiveness is necessary. At least that’s what we’re told over and over again: By forgiving, we can set ourselves free.But is there a cost to forgiveness? Are we forgiving too quickly and too often? Today’s guest is philosopher Myisha Cherry, whose book Failures of Forgiveness critiques our cultural obsession with forgiving those who have done us wrong. She’s not against forgiveness — that would be weird — but she says we ought to be more intentional about why we do it, more aware that the expectation to practice forgiveness often lands on the most vulnerable people, and more concerned about what gets lost when we treat forgiveness as the only path to healing.  Sean and Myisha discuss the 2015 Charleston church shooting, the legacy of slavery, and the real difference between accountability, reconciliation, and simply moving on. Host: Sean Illing (@SeanIlling) Guest: Myisha Cherry (@myishacherry), associate professor of philosophy at the University of California Riverside, and author of Failures of Forgiveness: What We Get Wrong and How to Do Better. This episode was made in partnership with Vox's Future Perfect team. Vox had full discretion over the content of this reporting. We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube.Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. This holiday season, your membership goes further: when you join Vox as an annual Member, we’ll gift a free membership to a reader who can’t afford it. By joining today, you’ll get 30% off for an annual membership, and we’ll match your membership. And if you can’t afford it, visit that same link to apply for a free membership through our gift program. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Sean’s guest today is Daniel Kolitz, author of a remarkable Harper’s story on “gooning.”  They talk about this emerging subculture and how it reflects back on the larger world, from the economics of attention to the rise of short-form everything. Kolitz explains why the Gooniverse isn’t just about porn, how hyperkinetic media rewires our sense of pleasure and patience, and why this is really a story about how society is changing in ways we might not like. Host: Sean Illing (@SeanIlling) Guest: Daniel Kolitz, author of The Goon Squad We would love to hear from you. To tell us what you thought of this episode, email thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of ⁠⁠The Gray Area on YouTube⁠⁠.. Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. This holiday season, your membership goes further: when you join Vox as an annual Member, we’ll gift a free membership to a reader who can’t afford it. By joining today, you’ll get 30% off for an annual membership, and we’ll match your membership. And if you can’t afford it, visit that same link to apply for a free membership through our gift program. Learn more about your ad choices. Visit podcastchoices.com/adchoices