Reeves Wiedeman is a reporter at New York Magazine and the author of the new book Billion Dollar Loser.

“You get inside these companies and … you assume everything is running based on models and numbers and then you get inside and it’s just people. And sometimes they have MBAs and sometimes they don’t. … At the end of the day, whether you’re running a media company or an office space company, it’s all people making these decisions and they often do very strange, contradictory, and ultimately unsuccessful things.”

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Tommy Tomlinson, a former newspaper columnist, is the host of Southbound podcast. His new book is The Elephant in the Room: One Fat Man's Quest to Get Smaller in a Growing America.

“The thing that galvanized me was the death of my sister. I signed the contract November 2014, she died Christmas Eve of that year. She had been overweight just like me. She was older than me and died from complications, an infection that was directly connected to her weight. And that more than anything made me think if I don’t deal with this now, I’m not going to be around in 10 years to write this book. So, the book helped certainly. The idea that I was going to put this stuff on paper and expose myself in this way to the world and I didn’t want to be a failure at the end of it. More than that, I didn’t want to be a failure because I didn’t want to be a failure. I don’t want to die.”

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Donovan X. Ramsey is a journalist and author of the new book When Crack Was King: A People’s History of a Misunderstood Era.

“I've only ever wanted to write about Black people—and that includes the elements of our lives that are difficult. I’ve always prided myself on being able to metabolize that information and not really be harmed by it. And this book really taught me that writing and processing is not just something that you do in your head. That the information does go through you as you're trying to make sense of it. And it's not happening to you, right? It's not like a direct form of PTSD that you have, but you do experience some trauma when you open up your imagination in that way.”

Roxanna Asgarian is the law and courts reporter for the Texas Tribune. Her new book is We Were Once a Family: A Story of Love, Death, and Child Removal in America.

“Every once in a while, I'll have someone just freak out at me. And it keeps you honest, in a way, because they don't owe you anything. People don't owe you anything as a journalist. ... But everyone reacts to trauma differently and some people really do want to talk about it. And I think the families in this book really wanted to talk about it and it felt like no one was even paying attention to them.”

Michelle Dean is a journalist and critic. Her new book is Sharp: The Women Who Made an Art of Having an Opinion.

“There isn’t one answer. I wish there was one answer. The answer is: You just have to wing it. And I’m learning that — I’m learning to be okay with the winging it. ... I guess the lesson to me of what went on with a lot of women in the book is: You have to be comfortable with the fact that some days are going to be good, and some days are going to not be good.”

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Ben Smith is the editor-in-chief of BuzzFeed.

“I do think as a reporter in general, most of what we deal in is ephemera. And I love that. I mean that’s the business, and I don’t think there’s anything wrong with that. In fact, I think that’s a plus and something that shapes how you succeed at the job because you realize that this thing you’re writing is about this moment and right now, and about its place in the conversation. It’s not some piece of art to hang on the wall.”

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Latria Graham is a writer living in South Carolina. Her work has appeared in Outside, Garden & Gun, The Guardian, and The New York Times. Her latest essay is "Out There, Nobody Can Hear You Scream."

“My goal as a person—not just as a writer—is to be the adult that I needed when I was younger. That’s why I go and talk to college classes. That’s why I write some of these vulnerable things, to let people that are struggling know that they’re not on their own. … I have to be unmerciful to myself, I think, in order to do it. I really do try to dissect myself and my mistakes. And just kind of say, Here’s the full deck of my life. Take from it what you need. But I’m not holding out on you.”

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Nilay Patel is editor-in-chief of The Verge and hosts the podcast Decoder.

“The instant ability—unmanaged ability—for people to say horrible things to each other because of phones is tearing our culture apart. It just is. And so sometimes, I’m like, Man, I wish our headline had been: ‘iPhone Released. It’s A Mistake.’ … But I think there’s a really important flipside to that … a bunch of teenagers are able to create culture at a scale that has never been possible before. Also, a bunch of marginalized communities are able to speak with coordinated voices and make change very rapidly. And that balance—I don’t think we’ve quite understood.”

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Alexis C. Madrigal is an editor-at-large for Fusion, where he’s producing the upcoming podcast, Containers.

“Sometimes you think like, 'Man the media business is the worst. This is so hard.' When you spend time with all these other business people, you probably are going to say, ‘Capitalism is the worst. This is hard.’ Competition that’s linked to global things is so hard because global companies are locked in this incredible efficiency battle that just drives all of the slack out of the system. Like media, there’s no slack left, and I don’t know where things go after that.”

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May Jeong is a magazine writer and investigative reporter.

“I don’t have kids, I don’t have an expensive drug habit. Everything that I do right now at this moment in my life is to serve the story. That means that sometimes I’m not the best partner. I’m not the best friend. I’m a really terrible daughter probably. If my parents had a satisfaction survey, I don’t think I’d rank really high. I have friends who are buying houses and stuff. I’m very far away from that. What else have I sacrificed? I don’t know. Sometimes I let my body atrophy because I’m on the road all the time. I think I can do it for five more years. I’m 30, so things will have to change.”

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Andrea Elliott is an investigative reporter for The New York Times. Her recent book, Invisible Child: Poverty, Survival & Hope in An American City, won a Pulitzer Prize.

”I don’t see reporting as a one-way street. ... I think that people need to know as much as they can about you. And yes, there are boundaries ... but at the same time, the fact of the boundaries is something to talk about with the people you’re writing about. Isn’t it weird that this is my job to be reporting on your life when we can laugh and we can break bread together and I spend all these hours with you and you know about my kids? ... And at the same time, I’m also here to write a book. ... And those two facts I learned to just allow to coexist within me. But it was not easy.”

Rukmini Callimachi covers ISIS for The New York Times. Part 1 of this episode is available here.

“Ever since I started in journalism, I feel like I'm perpetually winded. Like I'm just running as hard as I can to stay ahead of this train that's crashing. The caboose is falling off the back and I'm trying to run faster than the train to get to this very limited pool of amazing jobs. Once I got overseas I would say a prayer every night for the amazing life I was finally able to lead.”

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Katherine Eban is an investigative journalist and contributing writer at Fortune Magazine. Her new book is Bottle of Lies: The Inside Story of the Generic Drug Boom.

“I am not known for my optimism. I think it’s hard to do this work and retain a sunny view of humankind. I hate to say that. On the other hand, I do believe there will always be whistleblowers. And it’s interesting to me that even in the darkest spaces, even when it looks like everything is arrayed against them, there are people who will say: ‘This just isn’t right, and I must do something.’ Which is kind of extraordinary.”

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Vinson Cunningham is a staff writer for The New Yorker.

“I think the job is just paying a bunch of attention. If you're a person like me, where thoughts and worries are intruding on your consciousness all the time, it is a great relief to have something to just over-describe and over-pay-attention to—and kind of just give all of your latent, usually anxious attention to this one thing. That, to me, is a great joy.”

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Raquel Willis, the former executive editor of Out, is an activist, journalist, and writer.

Guest host Patrice Peck is a freelance journalist and writes the Coronavirus News for Black Folks newsletter.

“To my peers, I would just say that we have to rethink our idea of leadership. Rethink our idea of storytelling. As the media, we shouldn’t be seeing ourselves as the owners and the gatekeepers of people’s stories. We actually need to be democratizing this experience—sharing the tools of storytelling with other folks. Folks are hungry to tell their own stories and may not always have the tools.”

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Ashley C. Ford is a writer and host of the podcast Fortune Favors the Bold. Her memoir, Somebody's Daughter, is forthcoming from Flatiron Books.

“For the first time I felt like I had so many more choices in my life than I originally thought I had. That was my first realization that I did not just have to react to the world, that I could be intentional in the world, and just curious about what came back to me.”

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