Earl Swift was a reporter for The Virginia Pilot and has contributed to Outside. He’s been nominated for a Pulitzer eight times. Among other books, he wrote Chesapeake Requiem, a New York Times bestseller that chronicles a year in the life of Tangier Island, located 12 miles out in the middle of Virginia’s Chesapeake Bay. There, a dozen miles from shore, residents live a life with “one foot in the twenty-first century and another in times long passed,” he writes.

Swift spoke with Brendan O’Meara, host of The Creative Nonfiction Podcast, about reporting and writing his new book, Up on Cove Mountain: Adventure, Tragedy, and a Quest for Meaning on the Appalachian Trail. Swift hiked the 2,000-mile trail twice, 30 years apart, in order to write the book. He talks with O’Meara about story structure, getting close to the truth, and why it’s important to remove the speedbumps that might cause a reader to abandon your story before the end. 

This conversation has been edited for pacing and flow. 

—Krista Stevens

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Brendan: Much has been written about the Appalachian Trail, and you’ve brought a different kind of sensibility to it. How do you make your book fresh and immediate and yet able to sit alongside all the other titles about the trail?

Earl: I’m lucky, in the sense that probably the two best books about trail hikes were written by people who didn’t finish them. Bill Bryson was one and Cheryl Strayed was the other. Most trail accounts are self-published and unedited, written by folks with relatively little writing experience. Not to sound highfalutin, but it shows. I also knew I had a story to tell with Molly and Jeff and what had happened there. [Ed: to say more about Molly and Jeff here would spoil the plot of Swift’s book.] I felt I was pretty well-suited to tell that story. The opportunity was to be that one rare book about a trail journey that stands apart, and I figured it was worth the risk to try to write that book.

Brendan: As you hiked south, getting into Georgia, you started to experience congestion, more people. You noticed a generational divide at Low Gap and other campsites. Younger hikers seem predisposed to tenting, no matter what. Even in the middle of a downpour, they’ll choose their individual shelter over the communal. You also noticed isolation and phones, something you wouldn’t see 30 years ago.

Earl: You didn’t see it 30 years ago because there were no phones. We forget that the smartphone didn’t come along until 2007, a full 17 years after I did that first hike. It was a very different environment back then. This was eight years before Bill Bryson wrote A Walk in the Woods. The trail did not occupy a spot in the collective consciousness. It was not part of American culture the way it has become since, and so you were dealing with people who were drawn from a much narrower band of society. There were people who were already outdoorsy, and that’s not necessarily the case now. All walks [of life] attempt a thru hike these days, but back then it tended to be people who were already part of the fraternity. If you wanted to make a call, you hitchhiked to the nearest town and went to a payphone. There was no other option. If you wanted a pizza, you had to hitch into town. Now you have people who will get on their phones when they’re two miles from the nearest road crossing, and they’ll arrange for a pizza joint to deliver a pie at the road crossing when they arrive, which would have been science fiction. 

Brendan: There’s a balance in what to include, so that it doesn’t feel repetitive. You need to pick high intensity moments, be it the physical experience of a gnarly section of trail, or the three siblings from Kentucky who are assholes with no etiquette. You pick these moments so it’s not front-loaded or middle-loaded or back-loaded. There is a delicacy in how you deploy various elements throughout.

Earl: For any storyteller, proportionality is the key ingredient. You must figure out how much of each piece you share with the reader. If there’s one fatal flaw in most trail chronicles, it’s that writers don’t make enough of a distinction between telling moments and untelling moments. They just throw everything at you, and it gets boring. 

There are relatively few classic books about the Appalachian Trail, but one of them came in the late ’70s. It’s this two-volume, 1,000-page book called Hiking the Appalachian Trail. It gives you first-person accounts of the first 50 or so thru hikes. By 100 pages into the first volume, you’ve gone numb because every story is exactly the same. Part of the problem is that the whole tenor of the story is This happened, and then this happened. There’s never a moment’s pause to reflect on what it means and why I should care as a reader. Everything’s treated as equally important, and therefore nothing is important.

Job one, for anybody writing a book—for anybody writing a story of any kind, of any length—is to get the reader to that last word. If you don’t do that, it doesn’t matter which pretty words you drop in the middle of the story.

Brendan: You’re the tour guide and you’re going to point to what matters. That degree of authorial authority is integral to any narrative, especially something like this, because otherwise it would just be so rote and boring. You have to imbue it with a pulse.

Earl: Job one, for anybody writing a book—for anybody writing a story of any kind, of any length—is to get the reader to that last word. If you don’t do that, it doesn’t matter which pretty words you drop in the middle of the story. It doesn’t matter how brilliantly conceived it is. The story has failed because you have failed to get the reader to the end, to the finish line. 

The whole process of structuring a story, and strategizing about a story comes down to, How do I remove all the speed bumps that will encourage the reader to set this aside? If you can do that effectively, then you win, you get the reader to finish the story. The reader can badmouth the story after the fact. If the reader’s reached the end, you as the writer have achieved what you set out to do. All you can ask is for them to finish the story. You can’t ask them to like it. That’s up to them. But you can get them to finish it if you do it right.

We make decisions about what we include and what we leave out. We decide where we start a story, which is not always at the beginning. We decide where we’re going to end it, which is not always at the ending. You hope that in making those decisions, you get the reader to the truth, or pretty damn close to it, as close as you can, given the facts that you’re working with. But it is a construct, and it is your responsibility. Structure your story in such a way that the story will achieve what it sets out to do. That it will succeed in terms of incorporating enough propulsion to get the reader to the end. 

I probably spent three months doing nothing but cutting. Most of the writing of this book was cutting. I wrote a journal while I was hiking, and then I did nothing but cut when it came to writing the book. 

Brendan: In what ways did the hike change you?

Earl: In 1990, the big takeaway for me was that I could do anything. It boosted my confidence to the point where I’m sure I was pretty obnoxious in the months immediately after. God knows I must have been difficult to deal with. I could do anything! It made me Superman. Part of that was seeing something demonstrated daily that my dad had been saying to me for years. He was always big on saying, “How do you eat the elephant? One bite at a time.” It had just been “dad talk” to me until this hike, when I realized part of being able to do anything is knowing how to bust it up into its components, and then bust those components up into their individual ingredients. How to take each little bite-sized fragment in sequence, and pretty soon you’ve accomplished the whole thing. 

That dictated my approach to big assignments at the paper and in magazines, and certainly it has informed every book effort. It’s a stupid amount of work to write a book. I wouldn’t recommend this line of work to anybody. It’s a ridiculous way to try to make a living. So uncertain, so filled with terror, and so potentially without reward of any kind. But breaking the 2,200 miles into daily doses of 14 to 17 miles describes perfectly how I go about writing a book now. You don’t sit down to write 105,000 words. You sit down to write 1,200 words a day. That’s my daily quota. Do that over enough days, and pretty soon you have the 105,000 words.

Brendan: How did you settle on 1,200?

Earl: Early on, with my first couple of books, it was 2,000, and I just whacked it down. My first hike, I had no trouble banging out 17 to 20 miles a day. Now, 14 miles feels like a pretty tough day at the office, a long day. 

It’s the same with writing. Twelve hundred words takes as much out of me now as 2,000 used to. I’ll probably drop it down to 1,100, maybe even 1,000 with the next book. I’d like to think that the words are better than they used to be. I still find that I spend the first hour or two every morning, in the middle of a book project, going back through what I thought were perfect words laid down the day before. Invariably, when I wake up, I find that they weren’t so perfect after all. In fact, they need a lot of fixing and so I do repair for the first couple of hours, and then try to make something out of the rest of the day with new stuff. 

Listen to the full conversation below.

At one time, Rachel Hartigan edited The Washington Post’s Book World. During a 12-year stint as a writer, reporter, and editor with National Geographic, she covered everything from the genetics of persimmon trees to the long road to women’s suffrage. 

She spoke with Brendan O’Meara, host of The Creative Nonfiction Podcast, about being a self-taught writer, how being open to opportunity can change your career, and how editing others can help you improve your own writing.

Hartigan’s first book, Lost: Amelia Earhart’s Three Mysterious Deaths and One Extraordinary Life, both a biography of the aviator’s life and a survey of the leading theories surrounding her death and disappearance, is now available. 

This conversation has been edited for pacing and flow. 

—Krista Stevens

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Brendan: What did your career look like in your head at the start, and how did that change?

Rachel: I was not a kid with a clear version of what I wanted to do. I really like to read, to write, and to learn things. My parents were quite aggravated with me because they had spent a lot of money to educate me. I tried being a paralegal at a legal publishing company and then at the Nevada State Legislature. I was probably lounging on the sofa when my dad came in and slapped a Harper’s Magazine on me and said, “There are internships there. You should apply to that.” OK, it’s in New York. I have friends in New York, so that’s what I did, and somehow I got it. My career has not been a straight path; it’s been a lot of happenstance where I somehow get a job and figure out how to do it once I’m there. People come to me with plans and say, “I’m going to do this, this, and this,” but that’s not my mindset. I wish I was more like that. My career is always a surprise to me.

Brendan: With pursuing something a bit squishy, like writing, how did you deal with the pressure of expectation and the burden to prove yourself to your peers and your parents?

Rachel: My parents weren’t too bad; I was harder on myself because I never went to journalism school. I have always felt like an apprentice, like I’m still figuring it out. It’s only recently that I feel like I know how to do this. I know how to structure something. I know how to get a reader going, but I never felt like I had the right credentials. One reason I’ve gone back and forth with writing and editing—and I feel like each one has helped the other—is because it’s much easier to spot the weaknesses in somebody else’s draft than in mine. Sometimes it’s harder to do with your own prose.

Brendan: An apt metaphor, be it someone else’s work or your own, is looking under the hood like a mechanic to see how things are working, whether everything’s moving as it should. How do you revisit text or analyze work that inspires you, so you can learn from it and apply it to your own work?

Rachel: I have a copy of David Grann’s The Lost City of Z where I wrote down what each paragraph was doing, and what each chapter was doing, trying to figure out how he balanced telling a historical tale—the story of those who were looking for Percy Fawcett—as well as his own story. I used to do that with features I liked, or if I was assigned a feature and I had no idea how to go about it, I would look at similar ones, whether from my colleagues or from other publications, and break down the structure. It gets you over the hump of the blank page because you don’t have to worry about how you start your masterpiece. You’re just like, nope, this is what this paragraph has to do.

Brendan: How have you cultivated that sense of voice over your writing career? 

Rachel: I’ve been a journalist for a very long time. Clarity has always been a priority, especially at National Geographic. When I was writing scientific stories, some of them had to be really, really short. It’s front-of-book for the magazine, and it’s almost like writing poetry because every word has to count. If you’re doing something complicated, you have to think about how the reader is taking it in. Is this clear to the reader? Is the reader going to want to read the next paragraph? Where is the momentum? I’m thinking about that a lot. I’m trying to remember that I’m in partnership with a reader, and they need to understand what I’m writing about.

Brendan: How do you approach interviewing as a skill and as a craft?

Rachel: I always have my questions, but I’m not an aggressive interviewer. I like to let people talk, and I like to use people’s own words in my writing. I like to hear people’s voices, so I am probably a minimalist interviewer, though I wouldn’t say a minimalist reporter. But for instance, when I went on expeditions to Nikumaroro—an island where some think Amelia Earhart died as a castaway—I felt like I was a spy and an eavesdropper. I would interview people and ask them what they were doing, but mostly I was trying to watch and listen and see how people were doing, and I hoped they would forget I’m there. 

Brendan: I love what you said at the start of your book, about being bored with your job working on tiny morsels for the magazine, bored with your marriage to another deskbound journalist, and most of all, bored of yourself. Take us to that moment, this middle-age malaise, this boredom.

Rachel: I was in my little cubicle writing and editing for the front-of-book, which was fairly routine. I knew what was happening: This week and the next was writing, and the next week was editing. My son was in school, so there was his school routine, and I just didn’t know what I wanted to do next. The writing and editing for the front-of-book had become pretty easy, and I felt somewhat underemployed. But here I am again at my desk, and literally, one of the editors at Nat Geo, Glenn Oeland, stopped me in the hallway and said, “We have a berth on this ship going out to an island in the Pacific. Do you want to go?” And I said yes, and I really had no idea where I was going.

When I started at Nat Geo, I had been a book review editor at the The Washington Post, which is a very desk-bound job. I had no idea what I was doing, so I said yes to things, which up until that point wasn’t anything hugely dramatic. So this was the biggest yes. I realized it wasn’t just a yes that I had to say, but I also had to get buy-in from my then-husband and my son, who was 12 at the time. I had to think about all the details involved in going to a place like this. I had never been on a ship; I had never been anywhere tropical. But once I got on the ship, I focused on doing the story, and it felt like a huge weight fell off my shoulders, even though I was very seasick at first. But once the preparation is over, you immerse yourself in the story and the people, trying to figure out the dynamics of what you need to find out. It’s such a flow state. 

My career has not been a straight path; it’s been a lot of happenstance where I somehow get a job and figure out how to do it once I’m there.

Brendan: And as you’re reporting and tackling the project at large, it can be overwhelming to think about the scope of it. Thinking: This is going to be a book. How do I even do that? In what way did this book stretch you? 

Rachel: I did two expeditions, one looking for Amelia Earhart’s bones, and the other with Robert Ballard, who is the man who found the Titanic, looking for her plane in the waters around the island. So it was fairly clear what the stories were. But once I got back from the second expedition and started thinking about doing a book on it, I was really struggling. For one thing, we never found anything. We still don’t know what happened to her. So, is there really a book here? And if there is a book, how do I write about all these different things? At least four narratives needed to be tackled. I could have just written a book that theorized what happened to her. I was frustrated when writing news stories because it was mostly about the search for her, not as much about Earhart herself. I didn’t know that much about her beyond what we learn in elementary school: a groundbreaking aviator disappears. I really wanted something that incorporated more of her biography. So that would be one narrative. But then there’s all the theories and the people who pursued them, and it’s all very involved. I had a hard time figuring out how to braid all those strands together.

Brendan: You came up with a three-part structure: captured, castaway, and sank. How did you arrive at three “deaths of Amelia” as the scaffolding to weave these stories around?

Rachel: It was challenging to figure out how to approach each theory, how to lay it out in a way that wouldn’t be utterly baffling to the reader. The first way I tried was utterly baffling to my editor, so I had to have another go. I was trying to do it almost chronologically, which involved all the theories all at once, and it would have been very difficult. So instead, I decided to alternate between the biography chapters and one theory at a time, starting from the least likely to the most likely. I don’t advocate for any one theory in the book, but part of the reason I wanted to start with the least likely is that it’s also the most exciting.

Brendan: You mention that there have been solid biographies written about Earhart. I imagine that as you were looking to sell this book, you were wondering about what can be said that hasn’t already been said? How did you approach selling a new book on Amelia Earhart?

Rachel: In my darkest moments, I’m like, who needs this book? I don’t know. There had been some good biographies, and a lot of the different searchers had written books arguing for what they think happened. There hadn’t really been a book that combined it all, and there hadn’t been a book that contextualized the searches. I think that’s what helped sell the book. 

Brendan: I love the first third of the book or so. You write that she wanted a life of purpose and she couldn’t imagine finding it in a purely domestic existence. What do you think she was so, almost at ease, with bucking societal norms of the time?

Rachel: I think she was interested in what was new, in new experiences, in new technology; having a life where things basically stayed the same just would have been the end of her. I just don’t think she would have been able to handle that. She had an unstable childhood, but her parents did well. They had two girls, and when the girls wanted a BB gun, they got a BB gun. Her mom sewed them rompers so that they could actually play rather than being constricted in dresses. She was raised to be herself, basically, and I think she never learned how to shut that down, which is wonderful. She was always looking for what she could do beyond what was expected of her, you know, how can I be what I want to be when society expects me to be a certain way? It’s a question that we all still struggle with. And she was pretty eloquent about wanting people to be able to do what they wanted.

Listen to the full conversation below.

Pamela Colloff is an award-winning reporter at ProPublica and a staff writer at The New York Times Magazine. 

She spoke with Brendan O’Meara, host of The Creative Nonfiction Podcast, about how she developed as a reporter and writer, using these skills to uncover the failures of the American criminal justice system. Colloff and O’Meara talk about preparing for interviews, how thoughtful reportage can effect real change, and learning from the perspectives of incarcerated and exonerated people.

Colloff’s first book, Catch the Devil, a deep dive into serial con man Paul Skalnik, is now available. 

This conversation has been edited for pacing and flow. 

—Krista Stevens

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Brendan: What do you make of the fact that regardless of how skilled, experienced, and accomplished you become as a writer, it’s still really, really hard? And yet writers put together amazing work that creates change, and if not change, at least true art that makes meaning.

Pamela: Every assignment, at the beginning? I’m sure this is the one that reveals I’m a failure, that I don’t know what I’m doing. This is the one that’s going to break me. There are different stages. There’s the elation after finding a great idea, and then despair because no one’s going to talk to you, and then elation when people talk to you. Then there’s despair because you have this amazing material, but you have no idea how to write it. It’s this endless roller coaster. It’s funny to have been doing this for so long and still have so much self-doubt. 

I remember asking Gary Cartwright [Ed: Cartwright wrote for Texas Monthly from 1975–2010.] about this after a particularly tough close on a story. This was in the late ’90s, early ’00s, and I was really struggling because it felt like every story took so much out of me. It still feels that way, quite honestly. And I sought him out and said something like, “Gosh, this is so hard. Does it get easier?” And he just laughed and he said, “When it gets easier, it’s time to hang it up.” I think what he was saying is that when the work gets boring, when you feel like you really know what you’re doing, then maybe you should move on to something else. I loved that, and it also gave me an appreciation. I think about this a lot now; I feel so lucky at this point in my career to be doing work that is endlessly challenging, like every story is a new Rubik’s Cube to figure out.

Brendan: When it comes to writing, there’s something called the Skip Hollandsworth Method. What is that method, and do you still employ it? 

Pamela: He read a draft of mine. I couldn’t tell you which story. His rewriting instruction was to take all the quotes out, and once I had taken the quotes out, to revise it. And once I had revised it, then decide which quotes to put back in. He said, “You’ve got to do a draft where the only voice that’s there is yours.” It was such good advice because in that particular story (and I think this happens in stories where I’m having more difficulty), I was leaning really hard on quotes. He was telling me to figure out what the story was saying. You have to tell the story, and then thoughtfully choose where you need someone else’s voice and judiciously put that back in. It might also have been referring to Skip’s theory of interviewing. My inclination is to over-research everything before I arrive at the interview, to show the person that I’m knowledgeable. I have to earn their respect. Skip would show up to an interview and say, “Wow, so what’s podcasting? How do you do it?” Just the most broad questions imaginable. He got great material just coming to people totally fresh. He’d done his homework, and if he needed to follow up with something specific, he could. But I think there’s something to that. I’m really working on coming in and trying to leave a lot of space for the person I’m interviewing instead of showing them how much work I’ve done.

Brendan: You need to get them talking and get into their headspace, and it helps to have that baseball card knowledge. But the whole idea is to get them talking.

Pamela: I will make my list of questions, which is usually absurdly detailed and many pages long, and I’ll spend a lot of time working on that. I put it away when I get to the interview. Of course the work that went into it is informing the conversation, but I just try to have a normal conversation for as long as I possibly can. And it’s not until we’re going to shift gears and I’m trying to remember the things I haven’t asked that I pull out my notes. I used to be embarrassed about looking at my notes. I don’t know why I used to be so self-conscious about that.

Brendan: I loved that you brought up Skip’s tip on removing the quotes, and then having the confidence with your authority over the material, and then cherry-picking the right ones. You need to take agency and shape the piece in your own voice. 

Pamela: Before I have the confidence to write in the way that I want to write, where I really own the material, I have to spend so much time with people. At the outset, once I outline what it’s going to involve after they say yes to talking to me, I’ll say, “I’m going to be around a lot and you’re going to get sick of me at some point.” To be clear, it’s not always in person. I just finished a story where much was done by phone and Zoom and text, but I was in constant communication with my sources for about six weeks, throughout the day, every day, in various ways. For me it’s spending enough time with people that I feel like I have the right to describe what I’m describing in a story, and to tell their story in a somewhat omniscient way, that their voice comes in when they say something unique in the way that they phrased it, or makes you suck in your breath. 

Brendan: There’s your book, and the long stories you’ve written. There are false starts, stories that don’t get off the ground. Coming up with ideas is paramount. Ideas are your currency. How do you generate the story ideas that you know that you’ll run with, be it for ProPublica, The New York Times, or even a book?

Pamela: When I started at Texas Monthly at 25, again having no idea what I was doing, we had a monthly staff meeting with everyone who worked at the magazine. Before the meeting, each writer had to submit five fully developed story ideas. Not just “Hey, it would be cool if we wrote about this.” You had made some calls, or had done some real research, and you had them fleshed out. It was coming up with five viable ideas, so you had to come up with 20 ideas to get down to five, and then you had to flesh them out, and you had to write them up, and they were put in a packet that was distributed to everyone. You would get called on. If the editor in chief liked an idea on your page, you would get called on to talk about it. To pull that off every month, you’re looking for story ideas every second of every day. There’s nothing that is not fodder. There is no conversation that is not something that might lead to a story idea. I felt like it made me. I was already a curious person, but it made me talk to anyone and everyone and ask them more about their lives. So that was really good training. And it’s an exercise, a muscle you build over time. 

So much of what I write about is dark and intense. The people I get to spend time with to tell these stories? I feel like my life is a lot richer with them in it.

Brendan: In your work for The New York Times, but also in Catch the Devil,  there are men on death row, and they hear guards stomping and keys jingling, and they’re wondering if they’ll be taken to death watch. It’s chilling to hear that and you put us in their headspace. It’s incredibly moving and pulses with a kind of terror that you feel for them, no matter what they may have done.

Pamela: So much of what I write about is dark and intense. The people I get to spend time with to tell these stories? I feel like my life is a lot richer with them in it. I always think about the perspective that I have as someone who spends a lot of time talking to people who are incarcerated or formerly incarcerated, the things they long for, or the things that they savor when they have the chance to get them. I’m thinking in particular of one exoneree who I’ve spent a lot of time with. The way that they described just the most ordinary things. Anthony Graves had been on Texas’s death row and was freed. He talked about what it was like to go into a grocery store after you’ve been in solitary for years, and all the colors and textures and smells and the way light falls on different things. The way he talked about going to the grocery store was like how one of us might talk about going to see the greatest work of art we’ve ever seen. The way these men talk about the food they long for or putting their feet in the grass, things like that. I’m lucky to have that perspective. 

Another thing is the potential for writing to change things. Some stories I’ve written made things happen in the world, and that is the greatest feeling there is. And then there are other stories that haven’t done that, but they have put a light on people who really needed that light on them. They’ve highlighted something important to make readers think more deeply, or maybe focused on people working in the trenches where no one’s paying attention, but what they’re doing is so important.

Listen to the full conversation below.