The Gray Area with Sean Illing

In today's episode, Vox senior reporter and producer Miles Bryan talks with writer Daniel Kolitz about his piece for The Baffler, "Paid Phones." Kolitz explains what it felt like to be among the first wave of workers displaced by generative AI. The two of them talked about how fintech payday loan apps use hidden fees and subscriptions to profit off of desperate borrowers, and how an online community on Reddit is organizing a quiet resistance against predatory lenders.

Guest Host: Miles Bryan, Vox Senior Producer and Reporter

Guest: Daniel Kolitz, author of Paid Phones .

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What should a college teach? How to think? How to find a career? How to be a good citizen? What about how to acquire money, influence, and power?

In today’s episode, guest host Bryan Walsh speaks to journalist and writer Theo Baker about his investigation into Stanford University, where Baker was an undergrad student at the time. He entered the school as a bright-eye freshman, eager to build a career in tech. He left disillusioned by the school’s culture. His book reveals an insidious relationship between Silicon Valley and Stanford, where power, money, and success are prized higher than ethics, education, and the wellbeing of students.

Guest Host: Bryan Walsh, Senior writer, Coefficient Giving

Guest: Theo Baker, author of How to Rule the World: An Education in Power at Stanford University

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.

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Why does it feel so hard to start a family today? How much of that is truly a personal choice?

In this episode of The Gray Area, guest host Christine Emba sits down with journalist Anna Louie Sussman to discuss her new book, Inconceivable: The Impossibility of Family in an Age of Uncertainty. Together, they look past the surface-level "cost of living" arguments to explore how economic volatility, climate anxiety, and the commodification of reproduction are reshaping the way millennials and Gen Z think about parenthood.

Guest Host Christine Emba, columnist and author

Guest: Anna Luise Sussman, author Inconceivable: The Impossibility of Family in an Age of Uncertainty

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.

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Is "adulthood" a moving target? For millennials, hitting the milestones of the past — homeownership, secure careers, and financial independence — feels tougher than ever. We aren't just having our individual midlife crises; we are simultaneously navigating economic, cultural, and existential crises too.

Guest host Jonquilyn Hill sits down with Amil Niazi, columnist at The Cut, to explore why this stage of life feels so precarious. From the domino effect of the 2008 financial crisis and the collapse of the traditional career path, to the pressures of the "sandwich generation" — caretaking for both children and aging parents — we break down why the millennial experience is fundamentally different from generations past.

Host: Jonquilyn Hill, host of Explain It To Me

Guest: Amil Niazi, columnist The Cut

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.

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If you could change anything about your personality, anything at all, what would it be? And why would you want to change it?

Writer Olga Khazan spent a year trying to answer those questions, and documented the experience in her new book Me, But Better: The Science and Promise of Personality Change.

In this episode, which originally aired in March of 2025, Sean speaks with Olga about the science of personality change, the work it takes to change yourself, and what makes up a personality, anyway.

Host: Sean Illing (@SeanIlling)

Guest: Olga Khazan, author of Me, But Better: The Science and Promise of Personality Change.

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.

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