Episode 014 Transcript

Learning in Stories with Jake Halpern (7/23/18)

KRISTEN LEE: Hi. This is Kristen Lee, Managing Editor of the New York Daily News, and reluctant sister-in-law of Peter Horn. You’re listening to the Point of Learning podcast.

PETER HORN [voiceover]: On today's show, Pulitzer Prize-winning journalist Jake Halpern …

JAKE HALPERN: It's all story. It's how do you tell a story, how do you find a character that people will care about? How do you create a challenge that has to be overcome? What are the plot points that are going to get you through it …

[VO]: We talked some about the learning his work regularly requires.

JAKE: To report a story is to be a student of something new, to learn how that world works, whether it's Freegans, or debt collection, or refugee resettlement, or searching for gold in the mountains of Poland …

[VO]: And about finding the value in rejection.

JAKE: My YA [young adult] book that became a best seller: we were rejected, I think, by about almost every publisher except the one that published it, and then it succeeded—but there's a lot of rejection.

[VO]: I’m excited to share highlights of my conversation with Jake Halpern, a Pulitzer Prize-winning journalist who has told and reported stories for a spectrum of publications, from GQ, and Sports Illustrated, and Outside magazine to The Atlantic Monthly, the New Yorker and the non-failing New York Times. On the radio—a favorite medium for this podcaster—Jake has contributed features to All Things Considered and The New Yorker Radio Hour. His story “Switched at Birth” for This American Life is on their Top 10 list for best shows ever. Jake has also written critically acclaimed full-length works of fiction as well as nonfiction—eight books altogether. He and co-creator Michael Sloan won a Pulitzer prize earlier this spring for the New York Times comic “Welcome to the New World,” the true story of Syrians arriving in the United States on the day after Donald Trump’s election. [Correction: the Syrian brothers and their families arrive on the day of the 2016 election.] His catalog of journalism and fiction storytelling is so wide-ranging, I’ll direct you to his website jakehalpern.com to get a fuller sense of the scope of it. Plus, I promised him I’d keep my intro brief! I first met Jake in 1986, when we were sixth-graders at City Honors, a magnet school for students in grades 5 through 12 in Buffalo, New York. I want to highlight just two strong aspects of his personality that were fully in play when we were kids. First, he’s always been an amazing storyteller. His friends used to joke about what we sometimes called “Jake’s fables,” entertaining stories Jake would relate on just about any subject under the sun. Second, he’s always loved to wander and explore. The extensive international and domestic travel he has since undertaken was foreshadowed by infamous meanderings throughout the City of Buffalo, when I liked to say he was in “urban drift mode.” We refer to both these phenomena at different points in our conversation, but they’re also appropriate touchstones to introduce this remarkable journalist and author. If I had to put the intersection of his personal and professional trajectory in a nutshell, it would be wandering, sometimes getting lost, learning interesting stuff along the way, and telling stories about it afterwards. Jake and his wife Kasia are raising two sons in New Haven, CT. 

PETER: I like to ask guests at the start, because this is a show about what and how and why we learn, do you recall a teacher who was particularly influential for you?

JAKE: Yeah, I mean multiple teachers, really. I remember at City Honors [school in Buffalo, NY] where we went, Mr. Toy was our European history teacher, and he really lectured like a college professor. And you know, we were young in that class. We were like sophomores in high school, but there was a kind of seriousness about the way that he taught that class that, I don't know, that was just very inspiring and kind of instilled a real—I mean, it's so funny, there's stuff I can't remember that happened like, you know, a year ago or six months ago, but I can remember him telling us a story about the Defenestration of Prague. I remember Mr. Fitz with his, just kind of like his really great, kind of like plainspoken.

PETER: This is Mike Fitzpatrick, history teacher.

JAKE: Yeah. His South Buffalo kind of demeanor. Just the way that he broke everything in history down to a kind of commonsense street smarts. It was kind of thrilling, I mean the stories he would tell, like the story of his friend that would steal the police cars—but he would tie it in. I remember he would also—I mean, it's weird, but I remember him telling the story of—and I don't even have an especially good memory, but I remember him telling the story for the Missouri Compromise and how Thomas Jefferson said that the fight over it woke him like a fire bell in the night. And then he went into this whole bit about what a fire bell in the night meant in 1820 … Anyway, we could go on and on, but Fitz and just like one other guy, that was Mr. Duggan. There was just a general sense of someone that cared about you other than your parents. There's actually a cool little story when I found out that I had won the Pulitzer, I got a call from my editor at the New York Times. He had told me that [the awards would be] announced on Monday, but they told me, “You'll know by the end of business on Friday.” So 5 pm came and we were actually going to Spain. It was a long-planned vacation with Kasia and the boys, and 5 came and it didn't happen. I was like, “Well, whatever.” I didn't really think that was gonna happen. But then at 5:15 the call came. And when I saw it pop up, I didn't say anything to Kasia. I just said, “I gotta take this call.” And the editor said—he was a very casual about it. It was like you're waiting to find out whether you got cancer and he's telling you about your cholesterol. He was like, “Oh, how’s your day? Is your flight taking off on time?” And I'm like, Okay dude. And he was like—eventually he just said, “Hey man, I have some really extraordinary news, you just won the Pulitzer Prize.” And I got really emotional and kind of choked up and Kasia was like, “What's wrong?” She thought like one of our parents died, probably. And then I told her and then we had this—like the boys hugged me and people were trying to get past us. They're like, “Buddy, I got to get me a seat on the plane!” They didn’t care. Anyway, they said, “Look, you can't tell anyone because it's not official until Monday.” Ok look, you're going to tell your parents, right? Which I did, but there was just a moment on that Monday, like about two hours before the [official] announcement. I had my phone on me and I had service and I called James Duggan, and I was like—I hadn't talked to him in years, but it was like an impulse, a genuine impulse (and sometimes you just gotta act on that). And I called him up and I just said, “I'm calling from Spain.” And he was like, “Oh, it's great to hear from you!” And I just said, “Hey, listen, in two hours this is going to happen. I'm going to get this award. I just want to let you know, I'm thinking of you. You’re in my thoughts right now.” And it was genuine. And so it's funny, I remember the things, I remember the things that like specific things that were taught in history classes but I also just remember a few occasions of talking to him in quieter moments and just him listening and feeling that it was really important to have someone that wasn't your parent that listened to you. I don't know. I was thinking of him at that time and I was so glad I called them. It was funny afterwards, there was, you know, just this kind of craziness of social media and all the people from Facebook. And it kind of all became a blur, but I had this really nice little moment with him on the phone. So I think that, yeah, it's a long answer to your question, but I think that really, you know, the teachers that we know when we're that age affect us more than we may realize.

PETER: Well, and especially the ones who you feel know you. Yeah. I mean, that feels so poignant to me.

JAKE: Yeah, I think it was interesting. It was shortly after college I had a gig where I taught at an American International School for year at a high school. I wasn't really qualified to be—

PETER: Was that in Tel Aviv or—?

JAKE: Yeah, that was in Israel. Yeah, it was one of these international schools where people who were diplomats and people who were stationed in the service and companies that have to send their employees abroad send their kids. So it was quite international, and what was interesting about it was that I was not that far out of high school myself. I must've been like a year or two out of college. I mean, I'm sure you relate to this too—

PETER: Absolutely!

JAKE: It was interesting because you're actually not that far removed from high school at that point in time. Like the high school memories are still fresh in your memory. And I just remember thinking it actually was really helpful because it gave me perspective on high school that I didn't have at the time, which is just that we all just feel kind of very—I shouldn’t say “all,” but speaking for myself, I should say, I felt very alone and you know, kind of isolated, and keeping all your fears and insecurities and everything in. And then this is to your point that if there's someone that you can talk to that you feel not judged by, or you feel some amount of genuine care for, it's hugely rare and valuable.

PETER: As part of my preparation for interviews, I like to watch whatever I can find about my guests on YouTube. Recently I spent 45 minutes of my morning tramp on the elliptical watching your address to the American Bankruptcy Institute—you remember this?—following the release of your 2014 nonfiction book Bad Paper, about an unholy alliance between a former banking exec and a former bank robber who team up in your compelling exposé of the debt collection business. I was smiling to watch you hold forth up there without notes, telling literally incredible stories about your adventures while reporting the book. Judging from the audible reactions, you had the crowd in the palm of your hand, as well as me, there on the exercise machine—the elliptical might as well have been in your hand is what I’m saying—and I wondered, is this the through line for you? I’ve been engaged by your storytelling since sixth grade—comfortably more than 30 years now.

JAKE: The only problem is the stories now has to be fact-checked!

PETER: [Laughing] But I wondered if this is the through line because as I’ve thought about all the different kinds of stories that you've written and researched and told for NPR and the New Yorker and the and the thriving, non-failing New York Times and the Atlantic as well as the fantasy novels and full-length nonfiction books. Is it enjoying, appreciating, reveling in, and ultimately wanting to tell great stories that you would describe as your major passion and professional life project? Or is there another—

JAKE: Yeah, no, that's it. And it's funny because I don't think it really even fully occurred to me that that was the common thread. Maybe I knew, but I think at times because I've done a lot of different things … I've done radio and magazine and then I have these young adult fantasy novels about, you know, iceberg fortresses and haunted forests … At times it's felt like, “Jesus, what is this all add up to? This feels pretty ADD, like, just not focusing on doing one thing. Why can't I have a niche like other journalists? But I think that at some point I—

PETER: Because it's been travel, you know, it's been family stuff. You've taken on teen fame, you've been exploring debt collection … I mean, it's really a diverse portfolio of things that you've taken up, let alone the stuff that you've taken on in the fantasy realm—

JAKE: Well, I learned a lot from the fantasy stuff too. I mean in the sense of—it's all story. The commonality is absolutely story. It's how do you tell a story, how do you find a character that people will care about? How do you create a challenge that has to be overcome? What are the plot points that are going to get you through it? And it's weird. It's funny, you would think that it would be all intuitive, but actually, good storytelling is—I don't know. It's harder to do and define than you'd think, but that is the through line for sure.

PETER: Well, how is it different—because you've got these different genres. One of the truly impressive things, as somebody who's known you for a long time, part of what I marvel at is that you delve into these different regions. So how would you say it's different working with an idea for a novel, as opposed to something you're going to put in an in an op-ed piece in the Wall Street Journal, as opposed to what you hope will become a full length nonfiction book or a radio piece or more recently, a graphic tale? Is it the itch to work with an idea or set of ideas? Is that what comes first? Or are they the constraints that are based on the genre? Or is it different every time?

JAKE: With the nonfiction, there's a magic to it. I mean, the funny thing is as you would think that like the magic would be in fantasy, which to some extent it is, but to me actually nonfiction is almost more magical because you're delving into these worlds like debt collectors or Freegans … You’re looking around in there and you're thinking, “This is an interesting world!” but it took me a lot of years to realize that an interesting world doesn't necessarily make a story. Even an important idea doesn't necessarily make a story. The story needs a character and it needs a conflict. It needs narrative tension, and it has to have these points in an arc. And that took many years to kind of—I don’t know, it seems, it sounds so simple. One example that I like about this is that I was living in India for a bit and I was writing a story for the New Yorker about a temple where they found I think $20 billion worth of treasure, or something incredible like that. And it was a super complicated story. It had all these crazy twists: that the treasury of the temple belonged to the Deity of the temple. But because the Deity can't or doesn't speak, the old Maharaja of the province was head custodian of the Deity. And therefore the Maharaja really controlled the wealth, but some people, the devotees to the temple thought that the Maharaja was doing a bad job … It was really complicated and really interesting. But I was also lost as to how to tell the story—which is a very common and also not a great feeling of just like Oh my god, there's so much here! How do you tell this? And we were driving by the temple with my then five-year-old in the back of the car and he was like, “Dad, isn't that the temple that’s in your story?” And I was like, “Yeah.” He's like, “What's the story?” And I was like, I can’t even figure out what the story is, how am I going to tell him? He's five! How's he going to understand the story? And I was like, “Ah, it's complicated.” And he's like, “Dad, I asked you, what's the story?” It was just like, you know, he wanted to know. So I was like, alright, you got it—

PETER: You know, I'm thinking of that scene from Philadelphia where Denzel Washington is like, “Explain this to me like I'm five …”

JAKE: Yeah, totally! That was it! And so I had to break it down. That was right. That was it. I had to. I was like, “Well …” And when I broke it down to him like he was five, which he was five. Yeah. I had this weird—like, Holy shit, that's the story! You know, because like I feel like that's the thing. You should be able to explain any story to a five-year-old. It should be really simple, but we make it unnecessarily complicated. So that’s what having kids taught me and also writing for young adults taught me, which is that I'm just trying to think of the story and several beats and keep it simple. So that is definitely a through line with all these things. It was true with the comic. It was true with all these things. “What's the story?” Yep.

PETER: I want to ask about collaboration. So let me underscore first that you’ve authored dozens of pieces for print and radio as a solo reporter, which is the way that we normally think about authorship—one creator gets an idea or a lead, pursues it, then develops it into some kind of piece. But you also have extensive experience working as a collaborator. You’ve co-authored three fantasy novels—the Dormia trilogy, Nightfall, and most recently Edgeland—with Peter Kujawinski, and the project for which you just won a Pulitzer, a nonfiction graphic tale about a Syrian refugee family who arrive in the US on Election Day 2016 called “Welcome to the New World” and published in installments in the NYT. That was a collaboration with illustrator Michael Sloan. What are the blessings and challenges of collaboration, and how have you figured out ways to make it work?

JAKE: My longest time collaborator is Peter Kujawinski. I’ve written five books with him and that actually also goes back to that school that I was teaching at, the international school, he was still in Israel. He was stationed there was a diplomat, so we became friends.

PETER: Is that right?

JAKE: Yeah, that's when we met. We had a friendship before we collaborated, and in fact I visited him in Paris and we went out one night with our wives—yes, I think we were married then—with our wives and we had a lot to drink, and you know, at one point I was like, “Oh yeah, I have an idea for a kid's book.” And he was like, “Well, me too!” And I was like, “We should do this together!” in a moment of … expansiveness. And then the next morning he was like, “So when do we get started?” And I was like, “Oh shit, he's serious about this!” And you know, I was like, “All right …”

PETER: Wow! I had one of those lights too. It was in Philadelphia, but I have yet to make that happen! Wow, it’s cool that that came out of a Let's do this! And then somebody was like, “All right, let's hold ourselves to this!” That’s inspiring!

JAKE: Right. And it was probably one of the best decisions I ever made. (I should say I've had impulses that were—I've seen it go the other way, too.) But with Peter [Kujawinski], we started working on this and I remember thinking to myself very distinctly, Okay, we're friends, but now we're going in basically like going into business together, and aren't you never supposed to go into business with your friend or your brother, or whatever? And then all of a sudden, you know, every time I talk to him on the phone, it's going to be like work, and the relationship … And that all seemed quite reasonable at the time and felt like a legitimate concern. What I didn't anticipate was that the work would actually create an infrastructure for the friendship. And I think that like, you know, especially as you enter our—we're the same age, you know—I mean I don't know how it is for you, but it's, it's harder to maintain friendships. It's like you can have friendships, but you know, life is busy, there's work and there's your wife and there's kids and there's, there's just a million things and, and so. But I had to talk to Peter because we're working on this. We had to talk sometimes every day, sometimes multiple times a day and we had to problem-solve like these bizarre problems of like, “Okay, there's a forest where you—”

PETER: I will observe that this is the longest you and I have talked for years.

JAKE: Totally. You know, but that's actually kind of relevant. You could think like, Oh, this is work! but this is like a small collaboration—

PETER: You know, this isn’t going on the air, dude. This is just like a ruse to get you to talk to me.

JAKE: Well done! I don't know. It's weird. I don't know. It's a weird thing about middle age where it's like we've got one friend in neighborhood who like drops over unannounced and it's like “He's the guy that drops in!” and you're like, When did I become this old codger that doesn't like people dropping by unannounced? It's just like, it's crazy. So I think this is all part of this isolating—

PETER: Dude, you used to drop by unannounced.

JAKE: Totally. I know it's a thing.

PETER: If you were in “drift mode,” remember that? That was “urban drift mode.”

JAKE: Man. I remember that. I feel like those, like, yeah, that, and my stories, “Jake's fables”—I mean I tell you, man, when I had to start fact-checking here, that really cramped my style! My point was that I realized that it kept a friend in my life and it gave me a reason to call him and talk to him. And actually, it wasn't a problem that the personal and the interpersonal bled into one another. There was camaraderie. That was what it is. It's like, you know, when you're younger and you're, you're on a sports team together or you're in a class together, you're dealing with a teacher or—even for all of our shit that we put each other through in school, just being pains in the asses to one another. There was a camaraderie. There was a sense of a kind of connectedness and of being in this together. And I think that is so much stripped away at this point in our life. And I think I realized especially with Peter, how deeply I hungered for that anyway. Just one other cool thing. I remember one time, Peter and I went to an English teacher's conference up in Saratoga Springs, New York, because this is part of the thing they have you do to promote your book. It’s a logical audience. And one of these teachers said to us, “Who is the audience that you write for when you write? Who is your audience?” And Peter went to answer the question first. And he said, “Oh, that's easy. My audience is Jake.” It was such a beautiful thing to say. And it was true. I think that the first draft he wrote with me in mind to see if like I could get him excited or if I saw problems with that. And I quickly realized, Yeah, I guess that’s right. I'm writing for Peter. And writing is such a solitary thing to be able to say something like that— It was really profound, and it kind of spoke to what a collaboration could be at its best.

PETER: And did you guys—forgive me, I think I did know this at one point, but did you trade chapters, or did you, like he would do a portion of the story and then you would take in feedback and work from there, or did you both come at like what was your rhythm?

JAKE: The truth is is that it's changed a lot over the years, but generally what we try to do is we spend lot of time talking on the phone, sketching out the story. In fact, there's times where we talk so much it's like, This is ridiculous. When are we going to start writing? But the talking is kind of how you hash out the story and the characters. But we have alternated chapters and our voices have merged a little bit more over the years. Sometimes I read it and I can't remember who wrote that. Was that him or me? And that's actually true for a lot of it.

PETER: So for example, in your most recent collaboration, when you were in the heat of writing it, would you guys be talking like a once a week, a couple times a week, once every other week?

JAKE: That book was insane! We had been writing these books at a very, very sleepy pace for years where there was not a huge sense of urgency, where we’d talk once a day maybe. What happened with Edgeland was that the previous book, Nightfall was bought by Penguin, which is a much bigger machine. And the book was briefly on the bestseller list and so the editor basically told us You need to turn this book around in nine months. And it was just crazy. Looking back, we should have been like, “No!” But it was conveyed to us that if we wanted the full might of their support that we needed to do this quickly, So this is how crazy that got: We were on the phone like five times a day and we were working on it as a Google Doc, and Peter would be working on one section and I’d be working on another and then we'd hand it to the editor, but we couldn't do it fast enough. In a traditional draft process, you write the draft and you send it to the editor and the editor sends it back to you with comments—but that wasn't fast enough. So we were writing—I was writing Chapter, say, Four, he was reworking Chapter Six and the editor was behind us on Chapter Three and you could see her cursor on the Google Doc, like basically she was kind of chasing you—

PETER: Like Pac-Man.

JAKE: It was totally like Pac-Man! And then we finished the book. I remember finishing a draft of the book and usually like, you finish the book, you like take a week off, you go out and have a dinner … I literally remember looking back and seeing Pac-Man behind me! I was going down getting a glass of water and came back up and then just immediately starting back on the introduction again like five minutes later because Pac-Man was moving through the conclusion, and we had to just immediately start the next round because she had already put fresh edits there. It was just incredible. It was not fun. I mean we did it and at the end we're just like, We're never doing that again. On some level it did beat a bit of the joy out of the whole thing. And the joy is important to having some sort of spark to it. But yes, so that was like three people simultaneously all working on the same document and you could just see where we were. Yeah, it's crazy. That was—I've never seen that.

PETER: That stresses me out. Even like on a BlueJeans conference call, you know, when there's three other people looking at the same Google Doc and we're not even doing that much, but just being there at the same time. I know it can add a little anxiety! Remarkable. So tell me a little bit—I've read there was a piece in the Times explaining how they decided to pair you up with Michael Sloan to take on this project. You know, for a paper that famously had no kind of comic presence—

JAKE: The way that it happened was I actually pitched an idea which the Times rejected—which is very common, and most of my ideas are actually rejected, which is important, and worth saying. But I pitched this idea, they said no, but it was a story about a refugee kid. And they're like, “But there is someone who's interested in doing a project with refugee kids. You’ve got to talk to this guy, Bruce Hedlam,” who was the editor. It was Bruce’s idea. He said, “I want to do a comic. I want to do a true comic about a family who are recent immigrants.” He said, “Would you be interested?” and I immediately was intrigued by the idea. I just thought it was different and in a way that really appealed to me. And so then I found Michael and then so Michael was kind of on board and then Bruce was like, “Well, now you just gotta find the family.” So I reached out to this guy that runs IRIS, which is the local resettlement agency in Connecticut, and he said, “Hey, I got an idea for you. What if you follow a family from the day they arrive like when they basically touch down in the US?” And he said, “You have to circle back to them and get their approval and if they don't want to do it then we'll find you another family, but doing it this way.” And I'm like, “Oh, that's cool! I like it.” And I sent it to Bruce, and Bruce is like, “Great.” And then—

PETER: Your editor. Bruce is the editor.

JAKE: Exactly. Bruce is like, “This is cool.” And then the resettlement agency was like, “Ooh, we have two brothers coming on election day,” which seemed kind of cool, but no one, you know, everyone thought Hillary was gonna win, so it doesn't matter.

PETER: An interesting idea beforehand.

JAKE: Yeah. No. And then of course what happens is that they arrive, I meet them, and then I get home and Trump wins, and all of a sudden I remember thinking to myself, This family landed in one country and they're gonna wake up the next morning in another country.

PETER: “Welcome to the new world!”

JAKE: Yeah. And then I was just like—that was electric for me because first of all, that was just electric for me. I just, I have to say, at that moment I felt this could be a very dynamic story and this could be an important story. And sometimes you don't feel that. That was one time where I was like—but we had to convince the Times. The Times initially was reluctant because— People think that they're a liberal organization, but they're actually conservative in the sense that they are an old institution that is used to doing things a certain way. And so I think it took some convincing that this was worth doing, and there was a two month period in between when they arrived before the Times actually ran the thing and it was very unclear during that time whether or not they were going to do it and we weren't really being paid. I should add that we didn't get paid hardly anything for this entire series. We got—I mean, it's not public, but I don't have any problem with saying it was a 20-part series in the New York Times that took the better part of a work year to do. And I got paid about 14 grand. So that's just not a lot of money for how much work it was. So Michael and I were kind of in this, and neither of us is making a lot of money. The Times is also not making us any promises on how long they're going to run this. They refused. We kept on pushing them and saying, “Give us how long. It will help us story-wise. How many episodes will you run of this comic?” And they wouldn't tell us. And Bruce finally said, “They’ll run it as long as they feel it's good,” which added like another layer of stress, which is like We might get canceled.

PETER: Yeah, how do you plan the arc if you don't know how many seasons your show's gonna run, right? And you don't know what's going to happen because you're not—

JAKE: Then things happened. The most dramatic thing that happened was that the one family received a death threat, which the FBI investigated and then eventually the family ended up having to leave the town where they were and it was really hard for them. I mean, it was like one of these conflicting moments as a journalist because it was terrible for the family, which I can be care about, but of course I'm not dumb. I understood as a journalist that it was really powerful for the story. So it was one of these hard conflicts. But so Michael and I had bonded through this because we didn't know how long the Times was going to run it and neither of us was making a lot of money, and we kind of felt like as it was going on and as the Times kept on running it and people—particularly in our neighborhood because it was a Connecticut story—started following it. And then we kind of felt like, All right, we did this, man, like, This is this crazy thing that we're doing together. And it was really great working with him and it shared the— Again, it was like the other thing in the other project I described. It shared the loneliness of the whole endeavor because we were in it together.

PETER: I want to circle back to the idea of you stressed for a second. It's important to emphasize that most of the ideas that you pitch get rejected or have gotten rejected. You want to say some more about that?

JAKE: Yeah. I feel like it's important to say even like, I think Nightfall, my YA [young adult] book that became a bestseller. We were rejected by I think almost every publisher except the one that published it. And then it succeeded! But there's a lot of rejection. I just pitched an op-ed like two days ago to the Times Sunday Review, who I just won a Pulitzer for, and they rejected it. And they were very polite about it, but they rejected it. And then I sent it to the Wall Street Journal and they rejected it, and then I sent it to the New Yorker online and I’m guessing tomorrow they're going to reject it. But the thing is that sometimes they are right. Sometimes your idea is bad, or is not fully developed, or is not good. Yeah, just plain not good. But sometimes they're wrong: sometimes your idea is good and they just don't see it, or they're too risk-averse, and then maybe some of the times you just don't know. You're like, Is this a good idea that they can't see, or is this a bad idea that I should be embarrassed that I sent to them? And you often vacillate between those two ideas. But the only thing you have to do is you just can't stop sending out the ideas because then that's death. Then just nothing happens. And so this is a good example of this: the comic that we've been talking about. I had an idea—remember I said it started off with an idea that was rejected. The idea that was rejected was there was a family, a refugee family from Syria that wanted to settle in Indiana. And then-governor Mike Pence said, “We don't want them.” And Connecticut accepted them and their kids go to the same afterschool program as my kids. And I thought, Oh, that might be something there. So I was at the soccer practice with my 10-year-old and I actually thought this thought: This is a cool little idea. Pitch it right now before you talk yourself out of it and convince yourself that it's a crap idea, because you will convince yourself that it's a crap idea if you sit on it for too long. So right there on the field with my little iPhone, I sent this little pitch to my editor at the Sunday Review and hit SEND. And the minute I said it, I was like, Oh my god, why'd I do that? That was a crap idea! And then she wrote back and she did reject the idea, but then she said, “But hey, you should talk to Bruce.” And that’s what started the comic that ended up winning the Pulitzer. So it started with a rejection. And it also started though with this little dialogue that I had in my own head, which was Send the idea off before your doubt sets in. Often these half-baked ideas are the best ideas. And somehow you have to just get over the fear that they're not going to work out, or accept that many of them are going to be rejected. Yeah, that's probably better. You know, accept it. And I don't know. I've spent about 20 years trying to deal with that mindset of just figuring out how to keep faith.

[VO]: I asked Jake, somewhat cheekily, which of the following honors he found most special—winning a Pulitzer prize, being interviewed on NPR’s Fresh Air, or having John Oliver use a video clip of him talking about the business of debt collection on the HBO smash hit Last Week Tonight. Jake didn’t take the bait.

JAKE: External validation is like such a tricky thing because, you know, we all crave it—or I certainly crave it. I think many people do and it feels really good initially, but then it's tricky. Like it leaves you often craving more in a way that feels greedy and not really great. I think that all three of those experiences, in their own little ways relate to that. But I will say the best moment, the moment I'll never forget, is just being at the airport on that Friday before the Pulitzers were announced and getting the phone call from the New York Times and the editor saying, “Jake, I’ve got some extraordinary news. You and Michael just won the Pulitzer Prize.” And then turning to my wife and just saying, “We won,” and her hugging me, and the boys hugging me on the jetway to that airplane. That meant something. That was— And then I called my mom and I thanked her, and I called my dad and then the plane took off and then I was completely cut off for those next seven hours. And it was kind of a beautiful thing because I had shared it with the people that meant the most to me and had this moment of just feeling like— There is so much rejection with this work. And there have been many years where I haven't made very much money and there's been so many times where I've just been filled with doubt. It just really, really, really meant a lot to me to have that moment with Kasia and the boys and, and to kind of just be like, Oh my god, I can't believe that, like, this is amazing! and just enjoy that. And it kind of washed over me. Then when all the, you know, then you get a lot of messages from people on Facebook and Twitter and whatnot and it's all nice. But then it just, it was like It’s too much! you know. But that moment, that moment was personal and real, and one that I treasure. You said the greatest kind of commonality or through line here is story, but I think certainly with the nonfiction, the other through line is just learning. It’s that to report a story is to be a student of something new, to learn how a world works, whether it's Freegans or debt collection, or refugee resettlement, or searching for gold in the mountains of Poland. You know, all things like that, and you learn, and it requires a kind of humility about it like, I don't know how any of this works. I mean, I often hear myself saying, but it's actually somewhat true, I hear myself saying, “Forgive me, this is a really stupid question.” Because all my initial questions seem stupid and I'm grateful that I have a chance to learn these things because, you know, if you stop learning, then it's just, it's over, you're done. There’s just nothing more depressing than not learning new things. So I don't know, I think that like for me in a very small way, every time I start one of these things, it's that same feeling of I don't know what I'm doing. I'm lost here in this complicated world, how am I going to understand it? And feeling kind of a little flustered and like, I'm not an economics writer. I'm not a— you know—I'm not a health writer, how can I even do this? And then it'd be like, All right dude, just chill out and you'll figure it out. And, and even though it's a little stressful, somewhere along the way I’m like, This is cool, I'm learning something new and being forced to learn something new and I'm not bored. So I don't know, that's kind of rambling, but I think it's all to your point about how vital it is that we force ourselves into— We almost have to put ourselves in situations that necessitate learning.

PETER: You always have, man. I mean we were joking earlier about “urban drift mode” and stuff, but from the time I first knew you, you would love wandering, and kind of seeing where you wound up and paying attention to the interesting things along the way, and then telling stories about it afterwards.

JAKE: I know your mom remembers this because I've talked to her about this many times, and she, she definitely remembers it too. But I remember one time just like walking across the city and ending up at your house and you weren't there. Your mom will probably remember the details of it better than I would, but for some reason she had all this food, and there had been some confusion. There was a ham. It was only—like the table was set for like eight people, but there was no one there!

PETER: This is Gretchen, star of podcast number 013. Yeah. Okay, go ahead.

JAKE: Now your mom is like, you know, your mom is just great, just such a sweetheart. And she was just always welcoming and there was always that goodwill, very genuine goodwill. And you know I always had such a soft spot for your mom, and she said, “Well why don't you come in, you have something to eat?” So it was you—no it was me, and you weren't there. You were not there. It was me and your mom having this dinner at the house. And I asked, “What were you going to do with all this food?” And then she just laughed. There was a story that was lost on me. But, but I remember it was cool. I don't remember exactly what we talked about, but we talked and like those moments are so great, you know, like, I would never have been like, “I'm going to walk across the city to have dinner with Gretchen!” because that would just be weird.

PETER: No, she loved it. And I remember hearing about it right afterwards. I said, “Wait, what happened?” And I was like, “Oh, that's pretty cool. It all worked out.”

JAKE: Yeah, we had a good time. Yeah. No, it was good. It was good.

[VO]: That’s it for today! Thanks so much to Jake Halpern spending a few hours with me to record this conversation—again, check out his voluminous portfolio of writing and radio work at jakehalpern.com—and thanks so much to you for listening, subscribing, rating, and sharing this podcast with everyone you know interested in what and how and why we learn. Shayfer James wrote all the music used in today’s program; if you like the grooves, you’ll love the lyrics, so do be sure to visit his site, shayferjames.com. See you next month!  

JAKE: [referring to Mr. Toy’s European History class during our sophomore year of high school] You defenestrated his podium. Although it was only a partial defenestration because it was, it was dangling from—

PETER: Yeah, I think it was the threat of—it was an implied defenestration.

JAKE: Just for clarity, what you did—for those who weren't there—you somehow took his podium and hung it out the second floor window of the school on some sort of rope.

PETER: It wasn't, it wasn't safe or advisable. I think. I mean, I believed it was secure at the time, but probably just going too far.

JAKE: Crazy. Now I have some questions for you. Like, I want to understand like how that happened. But the, um …