Heather Havrilesky writes the Ask Polly and Ask Molly newsletters. Her latest book is Foreverland: On the Divine Tedium of Marriage.

“It’s not a good story when you're bullshitting people. I didn't want this book to feel like bullshit…. I wanted to show enough that you could feel reassured that it's normal to feel conflicted about your life and the people in it. It's normal to feel anxious about how much people love you. And it's normal to feel avoidant about how much people love you. It's normal to feel like a failure in the face of trying to stay with someone over the course of your entire life.”

Caitlin Dickerson is a staff writer for The Atlantic covering immigration. Her latest article, on the secret history of U.S. government’s family-separation policy, is ”An American Catastrophe.”

“I think the line that gets drawn around immigration coverage — which, a lot of times you're just talking about a business story or an education story or a national security story — but when you call it an immigration story, it does feel like it is about this other thing, about other people who aren't us.”

Ira Glass is the host and executive producer of This American Life.

“You can only have so many questions about feelings, I think. At some point people are just like alright, enough with the feelings.”

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Madeleine Baran is an investigative reporter for APM Reports and the host and lead reporter of the podcast In the Dark.

“We’re always thinking about first not so much the narrative, but first what did we find out and how is it important? And how can we construct a story that’s going to take people along on that and they’re going to care about it and be able to follow it. That’s a challenge in any kind of serialized podcast or film where you have one narrative arc from start to finish in a season, but you also have all these individual episodes with narrative arcs. And because we’re not novelists, we don’t get to change the facts, sometimes there are these facts you do not like cause they’re really confusing and you wish they were not that way. We spend a lot of time in storyboarding and edits and group edits and sound edits. We bring in people who don’t know what we’re doing and have them listen for mostly for clarity and confusion.”

Thanks to MailChimp, Screen Dive podcast, Skagen, Squarespace, and Pitt Writers for sponsoring this week's episode.

Jessica Bruder is a journalist and author of the book Nomadland.

“I don’t do a hard sell. I’ll tell people what my MO is, but I don’t push people to talk with me. I want to go deep with people. I want to be able to have the time to just sit with them and to say, ‘start at the beginning.’ Sometimes going chronologically will just take you to these places that wouldn’t have come up if I’ve just done a very guided interview. So I hung out. I’m not relentless. I don’t wear people down. But I stick around. If people just want me to fuck off, I fuck off, and I talk to other people..”

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Robert Kolker is the author of Lost Girls and a contributing editor at New York.

"For better or for worse, my heart's not in the mystery. I want [the killer] to be caught—he's obviously a predator and he's unstable. But they all are. They're all messed up people who victimize other people and they all look normal. The art and science of catching serial killers has become more than slightly overblown in our society. And you know, I love Silence of the Lambs … but I'm not entirely sure that our obsession with who the serial killer is and why a serial killer does it is in proportion with how interesting they end up being."

Thanks to TinyLetter for sponsoring this week's episode.

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Evan Wright, a two-time National Magazine Award winner, is the author of Generation Kill.

"When people were killed, civilians especially, I realized I was the only person there who would write it down. I was frantic about getting names, and in the book there are a few Arabic names, some of the victims. Not that anyone cares. But I thought, 'At least somewhere there's a record of this.'"

Thanks to this week’s sponsors: TinyLetter and HostGator.

Nicholas Carlson writes for Business Insider. His book Marissa Mayer and the Fight to Save Yahoo! came out this week.

“To me people are what’s really interesting. Marissa Mayer is a once in a lifetime subject. She’s full of contradictions. … There are a million business stories, but if you don’t have that character at the center then you’re lost.”

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Alexey Kovalev is a Moscow-based journalist and the author of the recent article, “A Message to My Doomed Colleagues in the American Media."

“It’s really disheartening to see how little it takes for people to start believing in something that directly contradicts the empirical facts that they are directly confronting. The Russian TV channel tells you that the pill is red, but the pill in front of you is blue. It completely alters the perception of reality. You don’t know what’s real anymore.”

Thanks to MailChimp and Penn State World Campus.

Kurt Andersen is the co-founder of Spy Magazine, the author of several books, and the host of Studio 360.

“As a young person, I never thought of myself as a risk-taker. Then I did this risky thing that shouldn't have succeeded, I started this magazine. And it did encourage me to think, ‘Eh, how bad can it be if it fails? Sometimes these long shots work. So fuck it, try it.’”

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David Grann is a staff writer at The New Yorker. His new book is Killers of the Flower Moon: The Osage Murders and the Birth of the FBI.

“The more stories I reported over time, the more I just realized there are parts of the story I can’t always get to. You know, unless this is a reality show and there’s 18 cameras in every room, and people [talk] before they sleep, and maybe you have some mind-bug in their brain for their unconscious, there are just parts you’re just not gonna know. You get as close as you can. And so the struggle to me is to get as close as I can, to peel it back as close as I can, but understanding that there will be elements, there will be pieces, that will remain lingering doubts.”

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Reeves Wiedeman is a reporter at New York.

“I think the main reason I love the job is reporting. And the fact that you get to go out into situations that you wouldn’t otherwise as your job. I’m someone who gets antsy if I’m just on a vacation sitting around. I’d much rather go somewhere weird and kind of have a purpose. So, just feeling like you can kind of go anywhere and see anything and talk to anyone is a pretty cool way to live your day.”

Thanks to MailChimp, Pitt Writers, Thermacell, and Best Self for sponsoring this week's episode.

Renata Adler is a journalist, critic, and novelist. Her nonfiction collection is After the Tall Timber.

“Unless you're going to be fairly definite, what's the point of writing?”

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Sheelah Kolhatkar is a staff writer at The New Yorker and the author of Black Edge: Inside Information, Dirty Money, and the Quest to Bring Down the Most Wanted Man on Wall Street.

“Suddenly the financial crisis happened and all this stuff that had been hidden from view came out into the open. It was like, ‘Oh, this was actually all kind of a big façade.’ And there was all this fraud and stealing and manipulation and corruption, and all these other things going on underneath the whole shiny rock star surface. And that really also demonstrated to people how connected business stories, or anything to do with money, are to everything else going on. I mean, really almost everything that happens in our world, if you trace it back to its source, it’s money at the root of it.”

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Nancy Jo Sales writes for Vanity Fair and is the author of The Bling Ring.

"I'm a mom now, so my life's a little different. I can't do certain things that I used to do, and I won't, because they're dangerous or ridiculous or keep me out till five in the morning or whatever. But back in those days, I didn't even have a pet. This was everything I did. This was my whole life, this passion to find out these things, and do these things, and see these things, and have these adventures and be able to report about this street life that rarely gets talked about. I just didn't really have a lot of boundaries in those days. I don't think I had any, really. And if you really throw yourself into something, you can get a great story. You can also not have a life of your own."

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Jia Tolentino is the deputy editor of Jezebel.

“Insult itself is an opportunity. I’m glad to be a woman, and I’m glad not to be white. I think it’s made me tougher. I’ve never been able to assume comfort or power. I’m just glad. I’m glad, especially as you watch the great white male woke freak-out meltdown that’s happening right now, I’m glad that it’s good to come from below.”

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Megan Greenwell is the editor-in-chief of Deadspin.

“I’m the first external hire to be the EIC in Deadspin history, so not everybody knew me or knew anything about my work. I don’t think there was resistance to me being hired, but I do think when you’re coming in from outside, there’s a need to say, ‘Hey, no, I can do this.’ Somebody told me about a management adage at one point: Everybody tries to prove that they’re competent when they first start, and what you actually have to prove is you’re trustworthy. That is something that I think about all the time.”

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Bonnie Tsui is a journalist and author of the new book Why We Swim.

“I am a self-motivated person. I really don’t like being told what to do. I’ve thought about this many times over the last 16 years that I’ve been a full-time freelancer... even though I thought my dream was to always and forever be living in New York, working in publishing, working at a magazine, being an editor, writing. When I was an editor, I kind of hated it. I just didn’t like being chained to a desk.”

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Olivia Nuzzi is the White House correspondent for New York.

“I don’t think that, broadly speaking, this a group of redeemable people. … But I do think there is tremendous value, in this first draft of history, trying to understand why the fuck they are like this. … There is value in understanding why these people are like this because they are the reason why we are here in this situation. And I think it’s a [question] that historians will try to answer years from now. … I view my job as providing fodder for that.”

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Sloane Crosley is the author of I Was Told There’d Be Cake and How Did You Get This Number. Her latest essay collection is Look Alive Out There.

“The more extreme things get in reality, the more extreme escapism has to be. It’s like Game of Thrones or bust. But in reality, I think that part of what I’m trying to do with this book — or in anything I write — is to give permission to be mad about little things. Just because there’s all of this, someone still slid their hand down a subway pole and touched you. Or somebody bumped into you. There are still these minor indignities and infractions that occur consistently. And I think there’s some sort of robbing if you tell yourself, Well, I’m not going to be mad about this because of the political landscape that we’re in.”

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Casey Newton writes the Platformer newsletter. Kevin Roose is a technology columnist for The New York Times. Together they co-host the podcast Hard Fork.

CN: “People actually like to be a little bit confused. They like listening to things where people are talking about things they don’t quite understand, which was very counterintuitive to me. I think a lot of editor-types would scoff at, but I’ve come around.”

KR: “We can revisit subjects and we do. We can change our minds. Print pieces feel so permanent, they feel so definitive. Podcasts, we can just sort of say, ‘I don't know what to make of this, ask me again in a month.’”