The Gray Area with Sean Illing

Sean Decatur is the president of Kenyon College and the first African-American to hold that job. He’s also one of the most thoughtful voices in the debate over free speech and political correctness on campus."Colleges and universities have been charged from their very origins to advance civility, and this has meant regulating student behavior on campus,” he says. "If anything, the approach taken earlier in history was far stricter than anything that 21st-century critics of higher education see as a product of 'political correctness.’” Decatur manages these conflicts as a college president, looks at them as a historian, and brings a perspective that’s unusually alert to the larger social context. As such, this is a conversation that begins in the fights over speech but quickly dives into more fundamental questions, like what kind of learnings we value, whose definitions of civility matter, what we ask colleges to teach, and what the role of the student has become.This debate often plays out with far less nuance than it deserves. Decatur's perspective is an antidote to that.Book Recommendations:Demographics and the Demand for Higher Education by Nathan D. GraweThe Lies That Bind: Rethinking Identity by Kwame Anthony AppiahLab Girl by Hope Jahren Learn more about your ad choices. Visit podcastchoices.com/adchoices

Cal Newport suspects you’re a digital maximalist — someone who believes that any potential for benefit is reason enough to start using a new technology. Don’t feel bad. That’s how most of us are. That’s how society teaches us to be.Newport wants us to become digital minimalists. He defines digital minimalism as “a philosophy of technology use in which you focus your online time on a small number of carefully selected activities … that strongly support things you value, and then happily miss out on everything else.”Newport is making a bid to be the Marie Kondo of technology: someone with an actual plan for helping you realize the digital pursuits that do, and don’t, spark joy and bring value to your life. This is a conversation about becoming a digital minimalist: why to do it, how to do it, and what it might get you. Whether you want to try Newport’s whole plan or just pick and choose some good ideas from his buffet, there’s a lot in here that will help you find a healthier, more intentional approach to technology.Book Recommendations:The Technological Society by Jacques EllulMedieval Technology and Social Change by Lynn White Learn more about your ad choices. Visit podcastchoices.com/adchoices

Eric Holder was attorney general during the first six years of Barack Obama’s presidency, and there are days when it feels like he’s the attorney general of Obama’s post-presidency, too. Holder chairs the National Democratic Redistricting Committee, a cause close enough to Obama’s heart that the ex-president recently folded his Organizing for America operation into it. Holder calls the project “a partisan effort for good government,” a line rich with both the promise and problems of Obamaism. The NDRC doesn’t want to build a redistricting operation to match the GOP’s machine, they want to take redistricting out of the hands of politicians altogether. But critics worry that their organizing will work in blue states, fail in red states, and lead to Democrats unilaterally disarming in the redistricting wars. In this conversation, Holder lays out his strategy to end redistricting and answers his critics. We discuss whether there’s still the possibility of a Supreme Court ruling on the subject, and what tools Democrats have in red states. We also revisit Holder’s famous “nation of cowards” speech on race, and discuss whether more bankers should’ve been sent to jail during the financial crisis. Enjoy! Book Recommendations: An Unfinished Life: John F. Kennedy, 1917 - 1963 by Robert Dallek The Collected Poems of Langston Hughes by Langston Hughes 1944: FDR and the Year That Changed History by Jay Winik  Learn more about your ad choices. Visit podcastchoices.com/adchoices

“Marc Andreessen famously said that ‘software is eating the world,’ but it’s far more accurate to say that the neoliberal values of software tycoons are eating the world,” wrote Anil Dash. Dash’s argument caught my eye. But then, a lot of Dash’s arguments catch my eye. He’s one of the most perceptive interpreters and critics of the tech industry around these days. That’s in part because Dash is part of the world he’s describing: He’s the CEO of Glitch, the host of the excellent tech podcast Function, and a longtime developer and blogger. In this conversation, Dash and I discuss his excellent list of the 12 things everyone should know about technology. This episode left me with an idea I didn’t have going in: What if the problem with a lot of the social technologies we use — and, lately, lament — isn’t the ethics of their creators or the revenue models they’re built on, but the sheer scale they’ve achieved? What if products like Facebook and Twitter and Google have just gotten too big and too powerful for anyone to truly understand, much less manage? You know the topics that obsess me on this podcast. Polarization. Identity. Attention. I’ve come to believe that all of them are downstream from the technologies on which they rest. If you feel like society has gone a bit wrong, it’s likely because the internet has gone a bit wrong. And Dash’s arguments help explain why. Book Recommendations: Respect: The Life of Aretha Franklin by David Ritz Prince and the Purple Rain Era Studio Sessions: 1983 and 1984 by Duane Tudahl  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jill Lepore is a Harvard historian, a New Yorker contributor, and the author of These Truths, a dazzling one-volume synthesis of American history. She’s the kind of history teacher everyone wishes they’d had, able to effortlessly connect the events and themes of American history to make sense of our past and clarify our present. “The American Revolution did not begin in 1775 and it didn’t end when the war was over,” Lepore writes. This is a conversation about those revolutions. But more than that, it’s a conversation about who we are as a country, and how that self-definition is always contested and constantly in flux. And beyond all that, Lepore is just damn fun to talk to. Every answer she gives has something worth chewing over for weeks. You’ll enjoy this one. Recommended books: Fear Itself by Ira Katznelson A Godly Hero by Michael Kazin The Warmth of Other Sons by Isabel Wilkerson Learn more about your ad choices. Visit podcastchoices.com/adchoices

This is the most fun I’ve ever had on a podcast. Nora Jemisin — better known by her pen name, N.K. Jemisin — won the Hugo Award for best novel this year for the third year in a row. No one had ever done that before. Jemisin is also the first author to have every book in a single series — her Broken Earth trilogy — win the Hugo for best novel, and the first black author to win a Hugo for best novel. She’s a badass. But what made this episode such a delight is it isn’t just a conversation. It’s a demonstration. Here, Jemisin takes me through the way she builds new worlds, and in doing, she offers a master class on how to think more rigorously, clearly, and thoroughly about our own world. Don’t miss it. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Bryan Stevenson, founder of the Equal Justice Initiative, discusses topics such as the injustice of wealth and poverty, confronting racial discrimination, the significance of memorial spaces and monuments, shame and the death penalty, bias in criminal justice, addressing trauma and rehabilitation, and the power of leadership and collaboration.

When I decided to start an interview podcast, the first person I went to for advice was Kara Swisher — founder of Recode, host of the Code Conference and the Recode/Decode podcast, and one of the most legendary interviewers in the business. Since then, she’s been a guest on this show, and Vox and Recode have started up a partnership that’s given me the gift of working with her much more closely. Recently, Kara interviewed me in front of a live audience at Manny’s in San Francisco for Recode/Decode. We talked about the future of journalism, the culture of DC, and so much more. One of the secrets to Kara’s success as an interviewer is that even when she’s grilling you, no one is more fun to talk to, and that comes out in this conversation. Enjoy!  Learn more about your ad choices. Visit podcastchoices.com/adchoices

You know TED. Black stage, red accents, wireless mic, one speaker. Billions of views each year. TED is more than a conference now; it’s a meme: “Thanks for coming to my TED talk” closes Tumblr and Twitter posts. Chris Anderson is the guy that took TED from tiny conference to global juggernaut. Today, he’s TED’s chief curator and the host of the TED Interview podcast. But I wanted him on the show for something specific — his success with TED relied on answering two questions this podcast has left me obsessed with: 1. How do you convince an audience, or even yourself, to listen openly to what’s being said? 2. How do you find ideas, research, and activists that the media is otherwise overlooking? In this conversation, Anderson offers a visual I love: "the steel door of skepticism" that can slam down on us when we know we don't want to listen to what we're about to hear. How to get control of that door is a topic worth meditating on, and it's the focus of this podcast.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Katie Porter is the Rep.-elect from California’s 45th District, which happens to be the district I grew up in. She’s part of the brigade of Democrats who turned Orange County blue for the first time since the Great Depression. But that’s not why I asked her on the show. I asked her on the show because she’s one of the most interesting members of the incoming House majority. Porter grew up on an Iowa farm, watching the debt crises of the ’80s devastate her family and her region. At Harvard Law, she took the class of a particularly charismatic professor whom you might have heard of: Elizabeth Warren. That class changed Porter’s life. Porter’s academic work explores how rarely markets work the way they’re supposed to, and how often banks and other lenders play by different rules than the law says they need to. In 2012, then-state Attorney General Kamala Harris appointed Porter to be California’s independent monitor of banks, where she saw the lengths they went to to avoid abiding by the settlements they’d signed. In this conversation, Porter and I talk about how all this informed her path to Congress, why she thinks Americans are losing faith in capitalism, whether the Obama administration failed homeowners in the aftermath of the subprime mortgage collapse, and why lenders are always making you fax them documents (the answer is, honestly, infuriating). I know, I know, interviews with politicians are often a bit bland. Trust me. This isn’t one of those. Recommended books: Evicted by Matthew Desmond Denial by Jessica Stern Lonesome Dove Larry McMurtry Notes from our sponsors:LEGO: In today's show you heard advertising content from The LEGO Store. With LEGO, every gift has a story. Start your story today at https://LEGO.build/EKS-Pop Learn more about your ad choices. Visit podcastchoices.com/adchoices