Checking In

James Pogue on Making It as a Roving Dirtbag Reporter

James Pogue, a gallivanting contributor to Harper’s, The New Yorker, and The New York Times Magazine, among many others, was a couple of drinks gone, wandering around Jackson, Wyoming — “I’m not in Wyoming, I’m in Jackson” — when The Fine Print called. Nothing had gone as planned. “All my shit got stolen a couple days ago, so I don’t have an I.D. and I’m not sure if Liz Cheney has Secret Service protection. If she does, a three-dollar-a-word, unlimited expenses story built around Liz Cheney in Wyoming is not going to work because I’m not going to get into her event. So I’m just in Jackson, totally unsure about whether this huge story is gonna fucking play out,” he said. “For whatever reason, they won’t tell me if I’m going to be able to get in without an I.D. So right now, I’m just wasting Vanity Fair’s money, eating buffalo tartar and drinking beer and just waiting to see what happens tomorrow.”

From the outside, it can seem like Pogue is living a freelance writer’s dream. He published his first piece in The New Yorker in 2012. “I had a New Yorker print clip at 22 or something,” he said, “and I was like, ‘I’m going to be fucking set.’” For his first book Chosen Country, which he admits “wasn’t super successful” on the level of sales, he gained an astonishing amount of access to the leaders of the Bundy occupation in Oregon. In recent months, his Twitter feed has been crowded with shots of freshly caught fish, geological finds, and his dog dwarfed by endless landscapes. The reality, inevitably, is more complex than that wandering imagery. “I have a rule, that I literally never ever follow, that is: When you take breaks, take breaks really hard and be offline and go fishing and do that, and when you report, report really hard. It’s almost impossible to actually maintain that now because you have to be responsive to editors and sources at such a quick turnaround,” he said. “You get little snatches and breaks, but actually the hectic thing is the constant experience.”

The last few months had been particularly frenzied. He’d sublet his $1,500 a month apartment in Los Angeles to spend eight months living in a trailer park in Siskiyou County, Northern California, trying to work on a novel and a non-fiction book. But after Vanity Fair published his story on the new right in April, that plan went off the rails. “After the Vanity Fair piece blew up, I did basically three months of free fuckin’ labor, just going on podcasts and TV and radio every single fucking day and not getting any of my own work done,” he said. “I was like, ‘I have to throw a hard stop to this and get my literal physical health back.’” So he retreated back to L.A., “just because I have a little bit of a structure there that’s built-in. I have a gym and a local bar and stuff like that, that I just actually needed really badly.”

Two weeks later, he was on the road again to report another story. “I got Covid while I was on the road,” he said, “so I was stuck in a motel for two weeks dealing with that.” After, he touched base in L.A. for just two days. “My girlfriend [whose name he asked not to include in this piece] and I literally wanted to just have one home-cooked meal, and in those two days, she got called by The New Yorker to go to Alaska, and I got called by VF to go to Montana and Wyoming,” he said. “Neither of us saw the interior of our apartment for more than 16 hours, and we were back on the fucking road. Both of us are losing our minds. And it’s cool because it’s literally the dream. I’m getting paid three dollars a word, but you also have no control over your physical environment, and it feels absolutely insane. Both of us are like, ‘There’s no way to make this work longterm.’”

Now, it was all teetering again. “Even in the position where I’m at, where I’m pretty okay, like if I have a story I want to do, I tend to think it’s probably going to go somewhere,” he said. “Once that story is assigned, if it doesn’t work, I’m still fucked. So, I have no control over that reality, and it’s very frustrating.” What if the Liz Cheney story were to fall through? “How real do we want to get?” he said. “I live off of savings from stuff I’ve already done and then I put everything on a credit card. So, if this story fell through, then I’m selling my life savings at a massive loss to fund the credit card debt that I’ve incurred while reporting this story and any small dream I have of owning a house or having a normal life would be evaporated in the space of an hour.”

The risk and uncertainty weighed on him, though they weren’t anything new. He’d dropped out of McGill to hop trains but landed a gig working as a handyman at a camp first. “I really wanted to train hop,” he said, “but I didn’t know how to do it because I was scared to do it alone.” A girl he met at the camp who went by Rabbit decided to show him the ropes. “She very kindly sent me a 40-page handwritten booklet on how to do it with super, super detailed stuff, like diagrams of grainers, how to catch a grainer on the fly, where to hide, super, super detailed stuff, just hand-drawn,” he said. “I was like, ‘Well, fuck, this is cosmic, I have to do it.’ And so I went directly from there to Cincinnati, saw my parents for a bit, told them what I was gonna do. They were oddly very supportive.” They knew they couldn’t stop him.

“The first ride was Cincinnati to Atlanta. I couldn’t really figure out the yard, so I hitched out of Atlanta, and ended up with a guy whose full time job was to run drugs from the valley in Texas up to Atlanta,” he said. “In Alabama, it was like everybody was paid off. In Mississippi, they weren’t and so they were hunting us, and I was hiding like Anne Frank in the back of the truck. We got arrested, there were no drugs in the truck because he was coming back, but we got arrested for an open container because there was a six-pack of Guinness that was missing one bottle. And so they put us in cuffs and lined us up against the truck and shoved our heads and searched everything. And then he went to jail, because he was smoking crack the whole time and he was on papers, so he went back to jail the minute he got back to Texas. It was super fucked up, and he was sleeping with prostitutes in the truck under me. Anyway, that was my first train hopping experience. It got very real very quick.”

That’s not necessarily a typical hitchhike. What was he putting out there that attracted that kind of ride? “I paid a crackhead a dollar to find me a ride at a truck stop, and he was the first guy who came back. But I think there’s a certain kind of personality that would be like, ‘Okay, this is a bad vibe.’ I just don’t have that personality. I have the personality of like, ‘This is a bad vibe, I will stay.’ And that does serve you well in journalism,” he said. “My girlfriend’s the same way. My girlfriend will see the creepiest looking people in the creepiest looking bar and just be like, ‘We have to stop at the bar.’ And it’s bad because, between the two of us, we can’t drive anywhere without something fucking insane happening.”

He train-hopped his way through the South for months, ending up in L.A. “I got a call from a friend’s mom, being like, ‘I run this resource exploration company, I feel like you could do this job,’” he recalled. “I flew from L.A. to West Africa. I never even went home. I just had a backpack.” So he ran logistics for a mining company in the Sahara. “I was like 20 years old, 21 years old, sleeping with a block of $40,000 in local currency under my pillow. I had a driver, I had a staff of 15 people who answered directly to me,” he said. “It was crazy.”

When he got back, he transferred into The New School. “The n+1 dudes who were teaching at Lang at the time were kind of interested in my stories,” he recalled. “They were like, ‘You should become a writer.’ And so, they got me the Harper’s internship.” That was his first taste of New York media. “I stayed in New York, and I fucking hated it. I was really, really unhappy, but I was like, ‘Well, this is what you have to do in order to be a writer,’” he said. “A lot of the problem with New York media is there’s a shrinking pot of money and an ever constant influx of people who want to be part of it, and it turns people against each other in ways that I found really unpleasant and not fun to be a part of.”

It’s been a long process of trying to break away, but he finally feels out of orbit. “I haven’t had coffee with a magazine editor in five years, but you’re incentivized to spend your time trying to make stuff work, for real make stuff work, because if it doesn’t, you disappear, you just fully disappear from the whole world. It’s a very alienating, scary experience,” he said. “I spent a lot of that time not doing good work and not getting stuff done and being forgotten about. And then every once in a while, something really hits, and it hits in part because you’re out in the world, you’re seeing stuff that people in New York think is fake.”

His first escape attempt came immediately after the internship. “My friend Wes [Enzinna] got a job with the Oxford American down in Little Rock, and I was like, ‘I gotta get the fuck out of here.’ And he was like, ‘Well, if you move in and be my roommate, the rent is $175 bucks,’” Pogue recalled. “I just loaded up a car and went to Little Rock, sight unseen.” After a year, he came back to New York to start fact-checking at GQ, met a girl, and asked her to move to New Orleans, “again sight unseen.” From there, he packed up his pickup and drove west, trying to find somewhere that felt right. “It’s the very classic L.A. story where you’re driving west, you keep thinking you’re gonna find somewhere that’s the perfect place, and then you run out of continent, and you’re just in L.A., and you’re like, ‘Okay, I guess I’m here, there’s nowhere else to go,’” he said. “So I ended up in L.A. before everyone moved to L.A.” It was still relatively cheap to live there, so he could leave town and travel around the West for months at a time, soaking in milieus away from the coasts.

“I kind of discovered that I could hang with a certain kind of guy who now has become a major American political figure. At the time, it was just guys with guns and beards who hung out in bars. I could talk to them and they would think that I was funny, but also think that I was down, because I could fish and go out shooting with them. And so, not to be cynical, but that turned out to be a thing you can traffic in,” he said. “It turned out that we were headed towards an American moment where everybody at the highest levels of American power wanted to know what was going on in the places where I just hung out because it seemed normal to hang out in. And so it became kind of a schtick. Not intrinsically hating or being suspicious of the people that I was talking to made me sort of unique in that regard, where it was just like, you can send all these Vox reporters to like Idaho, and they’re gonna come back with the dark heart of America in Idaho, all these guys are evil and scary. I was just doing a different thing. And so that became a little bit of a career path, and it was weird, because actually, all I wanted to do was fish and yet, every time you went fishing, you discovered the threat to the Republic. And so you kind of just ended up being like, ‘Okay, this is my job now.’”

The people he was meeting weren’t the sort he’d met train hopping and hitchhiking. “When you hang out hitchhiking, you’re really on the fucking fringes — you’re on the fringes of a very insane and evil class system that spins people out to the margins and leaves them there. Your friends are crackheads and criminals. It’s a different thing,” he said. “There’s a problem with describing America right now, where it’s like 50 percent of any country can’t be a lunatic fringe, right? But 50 percent of the country is regarded by the other 50 percent as a lunatic fringe. That comes from both left and right. So now, the ‘extremists,’ again, from left and right, as seen from across the political chasm, are actually normal. In their own environments, they’re normies. When you’re train hopping, those are people who are truly not normal. Whatever they’re coming from, whatever they did to end up in the positions that they’re at, those are drug dealers, criminals, freaks, and weirdos. And so if you try to describe America through that lens, it works kind of, because this is the country we’re becoming, where everyone is getting cast out to the margins. But they’re not the thing that the Vox reporter goes to find, because they’re not the thing that the Vox reporter goes and thinks is descriptive of the Ruby Red Heart of America.”

Pogue train-hopped for the last time when he was 25. The yardmaster pulled him off a train in Memphis, and he got charged with aggravated trespassing. “I ended up getting sent to a cell. I didn’t get bailed out, I had to go to court. Obviously, of course, the felony got kicked down, but you’re sitting there with a fucking actual felony, Memphis jail, you have nobody within 600 miles of you who could conceivably cover your bail, and you’re just like, ‘Okay, I have to build a life that is not this,’” he said. What made it worse was that he was on deadline for a story. “You do get a little resentful where you’re like, ‘People have pushed me to become a professional writer and in order to fund this story that I care about’ — in that case, I wasn’t even riding trains because I was like, ‘Hell yeah, I’m gonna ride trains.’ It was like, ‘This is the way that I know that I can move across the country in an affordable manner, is riding a freight train,’” he said. “Then you’re in jail getting your story killed. And you’re just like, ‘Wait, this is not worth it. Next time I’m gonna go back to them and say give me more money, or I’m just not going to do this.’”

In the last few years, he’s questioned how much of the chaos that remains in his work is sustainable. “I’ve been semi-nomadic for my entire adult life and something I think about a lot is that the reportorial life, it appeals to people who are instinctively kind of nomadic, kind of capable of dealing with chaos, kind of into that kind of thing. But the people who do it really well and aren’t bothered by it are actually very type A organized boring people,” he said. “Like many people did, I ran to it because I liked the chaos. After 15 years of doing it, you’re like, ‘Okay, wait, this actually doesn’t work.’ I have to prioritize the organization and the home base and stuff like that. And so that only came in the last three years, where I was like, ‘Oh, shit, if I’m gonna do this long term, I gotta figure out some other stuff.’”

He’s also been thinking about how rich people in the profession don’t have to think about any of that. “You can remove a lot of the emotional and physical fatigue that comes with doing this work by just inputting money. You upgrade that hotel, you lose a document, and you get it FedExed, and it’s not a fucking problem, and you don’t think about the 120 bucks that it costs to overnight,” he said. “I’m middle class, I’m not raging about poor James, but it weeds out even people like me.” Still, so far, he’s made it through. “There’s a very specific kind of person who is not rich, who can wade through the incentives to drink away three weeks in a row and run out of money,” he said. “You get a very small set of people who survive past 31 without developing massive depression, or alcohol issues. Those people just imbibe the chaos and can kind of survive, but they’re like me or Wes, they’re living in fucking shacks, doing really crazy shit at a point in your life where you’re like, ‘This maybe shouldn’t be happening.’ And then 90 percent of the other people are just rich enough that they’d never even confront these issues. And you’re competing against them. And that’s crazy. It’s not something I wake up every morning and think about, but if you’re trying to do this stuff, and you think about how much easier it is for people who went to Princeton and can retreat back to their parents second house whenever something goes wrong, it would make you stop doing it immediately.”

“Boomers don’t really get this stuff, because there’s so many really, really good older magazine reporters who are not really a part of this dynamic. They got in under the wire and it wasn’t that hard to transition from like, ‘I was a stringer in Côte d’Ivoire,’ to ‘now I’m a pretty comfortable magazine writer who’s grandfathered into a system that pays me $4 a word, I’m not sure what you’re talking about when you rail about this stuff.’ And I understand that, I’m not trying to take anything away from those people. But that wire got lower and lower and lower at an increasing pace. By the time it was 2015, it was so low that very, very few people I knew made it under.” People who went on a writing and editing track seemed to fare better. “The people whose temperament it is to be like, ‘I’m going to do one big piece every two years, but get a job editing at The Atlantic.’ Those people it often worked out pretty well for. Indeed, those are the people who now have houses upstate,” Pogue said. “The vast majority of people I knew who wanted to do longform writing, it did not work out for,” however cheaply they lived. “The cheapness that they needed to sustain in order to be a writer became their full-time job, for a lot of people. Being the shitbag that you needed to be in order to sustain the writing life, that took over and they became full-time shitbag and non-writer.”

The day after we spoke, Pogue watched a band playing John Prine’s “Paradise” at the Liz Cheney event. “Seems a bit rich but honestly go for it dudes,” he tweeted. Crisis averted, he would live to report another day.