Ted Conover is one of the leading participatory journalists working today. He was still in college when he did the research (read: did the real thing) for his first book, Rolling Nowhere: Riding the Rails with America’s Hoboes (1984). His second and third books quickly followed: Coyotes: A Journey Across Borders with America’s Illegal Migrants (1987) and Whiteout: Lost in Aspen (1991). His most well-known undercover feat is rendered in his fourth book, Newjack: Guarding Sing Sing (2000), for which he trained and worked as a rookie correction officer in a maximum security prison— all covertly, without the state’s knowledge. Newjack won the 2000 National Book Critics Circle Award in General Nonfiction and was a finalist for the Pulitzer Prize. In a New York Times review of Conover’s most recent book, The Routes of Man: How Roads Are Changing the World and the Way We Live Today (2010), William T. Vollmann writes, “Here is a man who cares about people everywhere, not merely that convenient abstraction, humanity, but people in particular.”
Conover’s work has appeared in The New York Times Magazine, The New Yorker, The Atlantic Monthly, and National Geographic Magazine, among others. He earned his B.A. from Amherst College and was awarded a Marshall Scholarship to study English literature and Latin American studies at Cambridge University. He currently teaches at New York University’s Carter Journalism Institute, in the graduate program in Literary Reportage.
Considering the stress he puts on inserting himself into his subject matter, it is deeply satisfying to find that Conover in person closely resembles Conover on the page: humorous, precise, inviting.
When did you first start writing?
Third grade is when I first got praised for creative writing. I wrote an essay titled “Pork McBean” that used all of our spelling words—my teacher showed it to the principal. She was a wonderful teacher who read out loud to us and gave lots of creative assignments. I liked making people laugh.
I worked at a couple of school newspapers in junior and senior high school with the same idea— that this doesn’t all have to be straight news, we can have some fun. When I got to high school we did theme issues–- a sex and violence issue, a National Enquirer parody, etc. “Liberated Girls Make Advances,” was one headline. Also in high school I got my first job at a real newspaper, at a chain of suburban weeklies around Denver, which was not very creative but it was fun. I liked the license the job gave me to speak to strangers and ask them things. I was fascinated by the role of the reporter in getting people to share things they know.
Did you have an idea of what it meant to be a “writer?”
I remember reading the phrase “freelance writer” in an airline magazine and thinking it sounds chivalric, it sounds like Don Quixote, it sounds exciting and vaguely martial. I liked the idea of the kind of job where you weren’t limited by much more than your ability. In the public schools I attended I’d been bored a lot of the time. It seemed to me that if I were involved in a writing project, there’d be no excuse for producing something boring, that a good writer should find something interesting in any subject.
But I was thinking along those lines just in terms of school. It seemed unlikely that I could actually become a freelance writer. I thought, if I got lucky, I’d get a job at a magazine, and if I didn’t, I might go to law school. That was truly my fallback position. I thought, “Maybe there is a way to combine law and journalism.”
Liberal arts plus career uncertainty just seemed to point to law school.
Where did the idea of taking an unconventional slant to a story come from?
I think being in a conventional environment spurs me to be funny, or to try to be subversive. To poke fun at things or to see if I can get away with things. I had a couple of friends who were like-minded and we gained control of our high school paper during our junior year.
That sounds vaguely martial as well!
Well, it was more like there was a vacuum and we stepped into it. I think if I actually had to work hard in academics during high school, I may not have ended up at this point because I wouldn’t have had time. We were, truly, killing time and trying not to be bored.
Do you remember an early story you wrote?
I remember a long editorial about the inadequacy of sex ed in our school, how clinical and remote from real life it all seemed to be. It got a lot of attention, and at first I thought I was going to get in trouble for it. But it was in a period of time when student journalists were being encouraged to be a bit unconventional.
You were an anthropology major at Amherst college. Tell me about that.
First I thought I would be an English major. But then I tried an intro anthropology class. Literature offered a peek into the minds of some interesting writers, but in anthropology you could look into the minds of whole cultures, whole other ways of looking at the sunrise and the sunset and the entirely non-imaginary ways that people had organized their worlds. To me, that was really, really fascinating and as I learned about ethnography— the field method of anthropology— I thought: this is like journalism, but deeper; this is a way to get beyond superficiality.
And not only that, but it’s an invitation to get out of your chair and away from the phone and go have an adventure. To actually live with somebody else in some interesting place or doing some interesting thing. It would be an education but it was not about formal education. It seemed enlivening and a way to educate myself in a more authentic fashion, to put myself out there and see if I could learn the things I needed in order to live in another world.
You wrote your senior anthropology thesis about riding the rails. Why zero in on trains and hobos?
It probably has to do with growing up out West, in Denver, where all these freight lines criss-cross, and with the fact that Neal Cassady blasts through Denver two or three times in On the Road. When I was growing up there, people older than me, beats and hippies, were celebrating this whole idea of finding America on the road. Just going out there and sticking out your thumb and meeting strangers. To me it came to seem actually not just a counterculture thing, but a Will Rogers thing, a Walt Whitman thing, a piece of American democracy that you didn’t find so much in other countries. This idea that we should all be able to talk to each other—and might want to. My take on it was that if higher education made that more difficult—put distance between me and a truck driver— then that education was not doing the right thing. So, I liked the idea of education through travel and through transcending my circumstances as a middle class son of a lawyer in Denver and seeing if I had the ability to make it in a different, and in some ways more difficult, kind of world.
Did you take a year off from school to ride the rails?
It was more like five months that I took off. I had to do it that way because, reasonably enough, they wouldn’t give me credit for riding the rails.
What did your parents think about you doing that?
Well, it wasn’t the first travel project I had proposed. Right after high school a friend and I rode our bikes from the West coast to the East coast by ourselves. And actually, when I was fifteen, another friend and I had done a thousand mile trip through New England because I liked riding my bike and I liked the self-determination of that kind of journey. I had also spent a summer abroad in Pamplona, Spain, when I was still in high school. So my parents were used to me coming up with ideas for getting away. But this was taking it to another level, riding freights. I know they were worried, but at the same time, to their considerable credit, they were able to keep their worry in check enough to let me learn by myself.
I think some part of me was looking for rites of passage. For ways to establish my independence and my wherewithal and my ability to do things on my own. Conveniently, it also looked to be good material for an ethnography.
How did you go about actually doing it?
Awkwardly, I did it awkwardly. I made mistakes. I hopped on a freight in St. Louis that I had found by looking at a map. I didn’t appreciate that sometimes the tracks on the edge of a yard are not the main lines, and I got on a train that went two miles and then was left on a siding at dusk. The next car I climbed into was left on a siding in Jefferson City in the middle of a rainstorm, in the middle of the night. I made several mistakes like that. And then I made several mistakes introducing myself to people. For example, I thought I should disclose my intentions for honesty’s sake, that I should admit I was a student. It was a couple of weeks before I realized that sometimes that could be like saying, “take my money.”
There are ways of presenting oneself that are appropriate for every situation and it took me time to learn them. Like, you don’t offer your hand when you’re meeting people [on the rails]. And usually you don’t say your name at first, because that implies some sort of goodwill or bonhomie that you shouldn’t assume is there. Most of the people I was with were significantly older than me and I think a lot of them were afraid that I was predatory and wanted their stuff. Which I solved once I realized it by carrying more stuff than they did. I’d have an extra bag, my own cigarettes, my own wine, my own bedroll.
But it takes time to learn that. And while you’re learning, you just have to hope you’re not going to meet somebody bad who’s going to take advantage of you. So, I’m careful, but I also haven’t had terrible luck. I’ve met good people, repeatedly, who’ve helped me over the bumpy first parts.
I asked William Finnegan about how he inserts himself into dangerous situations, and he said something to the effect that he’s not brave, he’s just not afraid. It was an interesting distinction between bravery and a lack of fear.
I admire Finnegan and I think I know what he’s talking about. Bravery sounds like an assertive, noble quality, something maybe you shouldn’t get credit for if you’re simply able to subtract from your mind a fear that’s entirely natural.
I’ve had to do that a lot and I’ve come up with a slightly different way to talk about it: sometimes I think bravery is about actively repressing your fear. Not being oblivious to fear, in other words, but saying, I’m going to believe that this will work out. Acting confident despite reasons not to. It’s a little bit related to when you’re underage and you walk into a bar. If you’re thinking I’m so out of place, they’re going to catch me, they probably will. But if you’re like, Don’t bother me, I need a drink, your odds of succeeding go way up.
Of course, working for a year at Sing Sing is taking it to another level. Having an air of confidence, whether felt or not, is terribly important there. It keeps you from turning into prey. On the other hand, you shut out all fear at your peril—you might think you’re fine when actually you’re not. So it requires some middle ground of realism, where you are cognizant of risk but not paralyzed by fear.
There is a romantic idea of the railroad, which does not exist in Sing Sing. There is the fantasy of the kind, nearly literary figure of the hobo.
Exactly! It is not a segregated world of criminals.
And even if there can be some sort of romanticizing of prison life, as a guard you are always the bad guy.
That’s right. I’m the one if you could get him alone … watch out. But outside of a prison setting, I think the most realistic fear for many of us is the possibility of random violence. The night that I was most scared on the rails I had a transistor radio and heard that John Lennon had been killed. The first report seemed to indicate that it was just somebody out of the blue. And that to me was the most frightening thing, that you wouldn’t be killed because you got into an argument with somebody; you’d be killed because, randomly, you ended up in the wrong place at the wrong time. Not that I would handle a situation wrong, that I wouldn’t even have a chance to handle it.
Your first book, Riding Nowhere, is about when you rode the rails. How did the actual book come to be?
Because the student paper at Amherst was pretty conventional, I got involved in a non-hierarchical, alternative magazine called In Other Words. When I returned from riding the rails, I wrote a story about a hobo for In Other Words. They ran it deep inside. And then, two weeks later, the college alumni magazine saw the story and asked if they could run it—on the cover. This in turn led to an interview with a wire service reporter in Springfield, Mass. His story went out first on a regional wire in New England, which resulted in a local TV appearance, and then it went out on a national wire, and everything really exploded. Everything happened at once. All Things Considered, The Today Show, and Good Morning America all called in the same day. I was trying to finish my thesis in the middle of all this.
I hate to tell this story to young writers because it’s unlikely this would ever happen again to me or to most people. But I also don’t like it because it makes me wonder if I would have had the guts to push ahead as a writer if I hadn’t gotten that concrete feedback. Most writers labor for a long time with no publicity or recognition until finally they get a break. My break came very early. It made me forgo a summer job I had lined up with a newspaper in Indianapolis. Instead, I decided to write a book proposal.
Did someone call you up and propose you write a book?
Nobody sought me out. I did, however, realize that this might be my chance, that I had some concrete evidence that people were interested in my story. I had only been to New York City twice in my life before then, but a friend of a friend had the name of an agent and I went to see him. He wanted to see what writing I had done. I had the article from the student magazine and some other pieces, and he said he thought he could sell it if I would write a first chapter and all that.
I went and saw him right after I appeared on The Today Show. I love The Today Show. There was something dreamlike about it all, and I worried that meant that there was also something flukey about it— like, the stars have aligned and now the rest of life can never be as great.
On the other hand, when I was riding the rails I had also met all these Mexicans who, it seemed to me, were the true new American hobos. So, I knew the next book I wanted to write. And I knew that they would talk to me. That is the other piece of it, which might have discouraged someone else. I had walked under a highway overpass and seen Mexicans up there waiting for a train, and said “Cómo están ustedes?” and they said, “Bien, que estás haciendo?” And I’m like, goddamn, they’ll talk to me.
So, I like to think that I made my own luck in this way; that I had put myself out there and had seen things that my classmates hadn’t seen so I knew things that not everybody would know, about what’s possible to do and who would talk to you even if you are a college kid.
Where did you write your first book proposal?
First I went to Cincinnati where my girlfriend lived. Then I moved to Denver, and eventually she followed. But I wrote most of my book proposal in Cincinnati and moved to Denver to await word. Once I had the contract, I tried to figure out how to make enough money to support myself, because the book money was not enough for the time it would take to write it.
So what kinds of jobs did you have?
I became an apartment manager. I got free rent in exchange for looking after this building for half a day. I did SAT prep for Stanley Kaplan, and I tutored kids in Spanish. I taught aerobics.
Yeah. Me and Richard Simmons…
The little shorts?
Well, they weren’t like his … and I never said, “Make it burn!” But I got in great shape, better than I’ve ever been.
How did you get into teaching aerobics?
I was looking for a gym, and my mom said, “You should come look at mine, there are all kinds of nice young people working there.” I had taught skiing, so I had some experience of telling people how to move their bodies—at least, that’s what I told the aerobics director at the gym. She said she would give me a try. It was fun. It was great, actually. I still have my tapes. I had two tapes— you don’t want to do the same music over and over!
Did you get a lot of followers who came to your classes?
I did. They were men and women. This place also had a bar, so you could have a beer after.
How does that even make sense?! That is nothing like the gym culture of 2010…
[Laughs] No, back then there were no algae drinks. But I had regulars, some of whom I am actually still in touch with. See, that appealed to me too. I have always resisted being shoehorned, and I am fascinated by different identities. And you risk ridicule when you take on an identity like that, but you learn fascinating things too.
Being a writer is not exactly a stable profession. Did you ever feel pressure to be more stable/practical, either from within or from without?
Oh, both! All of the above. My parents spent a lot of money on my college education and I felt the least I could do was get a reputable job of some kind. I had a book contract, so it was OK for a while.
So the book contract was very important. Do you feel it gave you license to take an unconventional path?
Yes. It still does. I am still riding that high.
Were your parents supportive of your choice to take this unconventional path?
I’m a big saver of old letters, and I have all these letters from my mom. It’s so funny, last week I was reading one of them. I wrote it from England where I was in graduate school because I had gotten a Marshall Scholarship to study English literature and Latin American studies at Cambridge— I applied for it as I was writing Rolling Nowhere. I didn’t really know what I would do after that. I was agonizing over summer plans and about the same girlfriend I had gone to Cincinnati with, and my mom wrote, “It might really help your decision-making if you decided what you are going to do with your life.” [Laughs] It was my mother feeling like I was adrift and saying that I should get a grip. She had never concluded that because I had written a book, I was going to be a writer. She had not arrived at that. It’s a nice item on a resume, I guess is how she was thinking about it. But in my last term at Cambridge, I wrote a proposal for a book about travel with Mexican migrants because that is really what I wanted to do more than anything.
I now see a pattern that I’ve had in my life in which I alternate between engaging with and cherishing higher education and then needing to get away from it, as far away as I can get. Then I come back, and then I go again. That has been a cycle repeated several times in my life.
I don’t know at what point my mother realized that it [writing] was going to be a serial thing. I do remember that as the hobo book was coming out, my dad half-jokingly referred to the freight hopping that preceded it as a boondoggle, like something not really serious. I don’t remember them disparaging people who pursued art or who got up after ten or eleven in the morning, but I certainly internalized a certain middle-class skepticism toward artists and it was hard to get past it and think: “Maybe I can put together a life of doing this.” It was hard. There was some inbred resistance to that.
Has that unease totally gone away?
No. It never totally left me. I still feel guilty about sleeping late! A woodcutter I met in the Peruvian Amazon told me, “La cama mata al pobre.” Bed kills the poor man. I thought, “We have the same parents.”
Where did you do your writing back then?
In Denver, I found unused rooms in friends’ garages that I turned into my office. And on another occasion I rented an unused corner of a lawyer’s office. I found it really helped me to have a place to go to work outside of my little apartment. I would just try to do some writing everyday. But my so-called career is different from a lot of other writers’. I didn’t come to New York until I was writing my third book. And I had only written one or two magazine articles at that time. So it’s all been kind of backwards for me.
What was the living like in Denver during that time?
There weren’t many other writers to hang out with, so my friends tended to be from high school or later, and they tended to be self-employed. I was part of a group, we called ourselves the Entrepreneurs’ Club. We’d meet Friday afternoons at a dive called Don’s Mixed Drinks. It’s still there on 6th Avenue in Denver. One of my friends was a city-planning consultant, another was a graphic artist, another was a music therapist for kids with disabilities.
If I had been in New York I would have been with a very different cohort on a Friday evening. I think there was possibly a cost to that, in terms of worldliness or artistic sophistication. But in another way there was a benefit that came from being outside the mainstream. Being away from the center of things and being able to think a bit differently from friends of mine who’d gone straight to New York.
How do you look back on that time?
Mostly fondly, though not entirely. I tried writing in the mountains, an idea that sounded good: alone in a cabin, with a dog, that whole thing. But I was very unproductive in the cabin and realized that if you are spending every day in your own head, you need people afterward. Denver suited me better. I welcomed the distractions of the city after a day of work.
Part of becoming a writer is learning what makes you write, what schedule and what social world. Early on, somebody said to me: “If you are really going to be serious about this, then some of your friends are going to make you want to write and others have the opposite effect. You have to get rid of all the second category of friends.”
Did you have a great Conoverian purge?
It was a gradual thing, but I did make some changes. There is still something about the idea that makes me uncomfortable.
Can you recall any great challenges you faced in your early career as a writer?
I don’t talk about this too much— maybe it is superstition— but if I go far back enough it feels safe. I can tell you that there were times when I was writing my first book when I was totally blocked. I had no confidence that I was doing it the right way at all. I was fortunate enough to have a good editor, Rich Barber, at the Viking Press. I actually made a special trip to New York and I said [to Barber]: “I’m having this trouble.” And he said, “Is it possible your trouble stems from the fact that you haven’t written a book, so you don’t know whom you’re writing for?” I said, “Yes.” He said, “Is it possible that you’ve always written for a teacher or for an editor?” And I said, “Yes.” So he said, “Instead try this: try writing to either a real or an imaginary best friend. You haven’t seen him for three years and finally you guys have dinner, and you have wine, and there is a fire, and your friend says, ‘so tell me about the last three years.’ And he’s such a good friend that (a.) he’ll listen and he finds it all interesting, and (b.) you are going to cut to the most meaningful things, because he’ll appreciate them the way only a friend can.”
It was really good advice because it helps keep away any formal tone. And it helps you cut to what is real. That advice had a visceral power for me because it is basically saying: cut the bullshit and talk about what really matters. And do it with the confidence that they’re going to keep listening.
It also helps you visualize a reader with a friendly face as opposed to a blanket crowd that you have to impress.
Yes! Or a panel of literary critics…
Has the way you work changed now that you have a family? Do you take less risks in your immersive research?
For The Routes of Man, I decided I would not be gone more than a month at a time. So I had to take three trips to Peru, two trips to Kashmir… Would I have preferred to do it differently? Sure, in some ways. This way cost more, for example. On the other hand, it kept me from too great a distance with my family.
As for the danger, let’s be honest: the worst thing that has happened to me health-wise in the last twenty years happened in front of my house last month [he fell on his stoop and dislocated his shoulder], so I think a bigger risk for me than going to the West Bank, frankly, is not going to the West Bank. I am a healthier person when I engage with the world in these ways, and I am probably a better dad and a better husband. So I think— and I don’t think this is just a selfish spin on it, I think my wife would agree— that as long as I am careful and sober, I don’t expect to find myself in mortal danger on my trips. I don’t mind taking chances but I do mind getting hurt and I very much want to be around for the next project. My mom tells people, “He has a strong survival instinct.” That’s her shorthand, and I guess it works for me.
Julia Alvarez told me that she thinks writers should do things in life that feed their writing. She quoted Charlie Parker, who said, “If you don’t live it, it won’t come out of your horn.” You seem to be quite a proponent of that idea.
I like that, that is a great quote. And I think particularly if you are a nonfiction writer, unless you’re a serial memoirist, you are going to need subject matter outside of your immediate life. I have been able to find that, time and again.
I was also able, up to The Routes of Man, to find work that helped me both pay for the writing and gave me something to write about. For example, to meet migrant workers in Arizona, I volunteered with a farm workers’ group that was teaching English classes to undocumented people after their days in the orchard. That was perfect, because I could be useful to them and get to know them at the same time. In Aspen, I drove a taxi and I worked for the Aspen Times—both of them ways to pay bills and do immersive research at the same time. I like that approach when it is possible.
Do you have any advice for young writers?
One is just to be wary of proven paths to success, because your own path may be a variant that does not look promising. Often I think the well-trodden path is not the most conducive to originality. And particularly in writing, originality is extremely important. There is just a huge value in being able to articulate your own take on the world and to risk a bit of transgression for the sake of interest. I think there is some truth to the idea that some of the best art is made in resistance to something. And so maybe my advice to young writers is to be attentive to that which makes you want to resist and consider what form your resistance might take.
Interview by Astri von Arbin Ahlander
Photo by Angela Jane Evancie