AT THE HEART OF all good writing is learning how to craft a story. Note that word “learning,” in the previous phrase. Writers learn every day — or we should — and despite the recent craze for the word “mastery,” writers are always better off accepting a more receptive position about learning from all we read than we are trying to conquer the craft. One of the people from whom I learn about how to craft a story is my friend Jack Hitt, one of America’s finest storytellers. You’ve probably heard him on This American Life, or The Moth, or perhaps on the Peabody-Award-winning podcast, Uncivil. You might have read him in The New York Times Magazine or Harper’s, or in one of his books. Listen in as we talk about how to craft a story and see what you can learn.
Read along as you listen to this episode of QWERTY. You can subscribe to all future editions on iTunes, Spotify or Stitcher. (The following transcript has been edited from the original recording).
Marion: I’ve been reading Jack Hiit’s work for 35 years, I think, in places as varied as Harper’s and GQ. He writes for The New York Times Magazine, Outside and Mother Jones, Rolling Stone and Wired, and the marvelously named Garden & Gun. He’s the author of two books, Off the Road: A Modern-Day Walk Down the Pilgrim’s Route into Spain and Bunch of Amateurs: Inside America’s Hidden World of Inventors, Tinkerers, and Job Creators. He’s frequently heard on public radio’s This American Life, has appeared on The Moth, and co-founded the Peabody-winning podcast, Uncivil. To this listener and reader, Jack is one of the finest living storytellers on any platform. So, welcome Jack. It’s great to have you here.
Jack: Hey Marion. Gosh, you can introduce me anytime. Thank you.
Marion: And you bake a mean cherry pie, I happen to know. I know you roast a whole pig. We’ve been down that road.
Jack: Yes, I also roast whole pigs and whole lambs. So, yeah.
Marion: Good. So we can bring you into anything. As I said, we’ve been friends for 35 years and meeting all the usual things like weddings and birthday parties and the like. But for the purposes of this discussion, it means I’ve also been one of the many test audiences for your product. Qwerty’s audience is predominantly writers so let’s talk about the value of testing your stories at home and to friends and how that helps craft a tale. How important is it to get them to listen early and often into your writing and thinking life?
Jack: Well, I think all of us have someone we turn to to read something before you even show it to an editor. Most of us, it’s our spouse. So Lisa Sanders is my spouse. She’s also a columnist for The New York Times Magazine, writes the Diagnosis column. And yeah, she’s the first person to ever read anything I write and vice versa, often. But I will say that both of us, after 30 years of marriage and many, many articles and columns, still report that first impression, still give the news in what we call a sort of love sandwich.
Every critique sort of goes like this, “Marion, this is fantastic what you’ve written. I love it. There’s just so much great writing in here, and I really love the way your ideas flow. There’s a couple of things that I just want you to think about.” And then you go on and decimate everything in the entire piece and then say, “But you know, overall, I mean, I really… God it’s just, it’s fantastic. I love it.”
So, yeah. So, the good news sandwich is really no one ever escapes their own ego, and you have to hear that news in a way that allows you to hear it. And I think just vain flattery is the way to hear any piece of bad news. Is wrap it in some Pulitzer Prize winning bullshit. And then the writer can sort of hear like, “Ah, I haven’t signposted enough,” or, “I’ve gotten lost here,” or, “This extended tangent just goes on and on forever and bores the reader to death.” You need to hear that stuff, but you have to hear it in a way that you can hear it and come encased in a handful of love is really… That’s our recommendation. I can speak for both of us.
Marion: It’s good advice, but I wonder about the input. I remember being in my twenties when I first heard your tale, that would become Fiasco, one of your segments on This American Life. The one that’s about a hilariously disastrous school production of Peter Pan. When did you decide to start telling it? I mean, how do you get that place to that place? Because you got to get to that place as a storyteller where you say, “I think I have a story and I’m going to start telling my friends this tale.” Do you remember the moment where you said, “I’m going to start telling this tale.”
Jack: Well, I was at a former military boarding school in Tennessee. I’d been sent there as a very badly behaved teenager. And at this place I found myself just being bullied and beaten pretty much every day by some very bad people. And so one way to stop the blows from coming was to entertain the idiots. My first stage was a very desperate one. But I remember we all went to this play and we all came back just overwhelmed by how stupid and how incompetent this play was. But I started going over my own version of what the story was and then hearing how other people told the story and eventually put together… This is one of my life saving anecdotes in high school because people would say like, “Hey Jack, tell that story again about the play.”
And normally most storytellers hate it when someone says, “Hey, tell me that funny story you tell.” But in this case it was either that or get the hell beat out of me by Mack Piniella or Mackey Crosby. So fortunately I got pretty good at that story. I’ll tell you one thing about that story that when I first told that story to a bunch of people sitting around the table, you might even been there, but Ira was there. And he got up and left in the middle of the story, ran away.
Marion: Ira Glass from This American Life.
Jack: And he just ran off from the table, and I thought maybe, “Oh maybe I’m boring him or something.” And then later he came up to me, he said, “I didn’t want to hear the rest of the story because I want to hear it in a studio.” And so that’s when we recorded it the next day. But he just wanted to be able to laugh fresh when had happened. Nice.
And I think the other thing about that story that that’s a little instructive for me really is that after we aired that the first couple of times, people would write in and say like, “There’s no way that can be true. He must have made all that up.” “There’s no way that many accidents and terrible things could have happened in one play.” And that kind of hurt my feelings. I remember reacting badly to these people. And then in the midst of that, I got a letter from the MC of a show in Las Vegas, a guy named Troy Tinker who turned out to have been in the play. And he wrote this note to Ira and me, the show on the website back then. And he said like, “Oh, Jack didn’t tell enough of the story.” And then he went on to tell several more moments in the play that I had forgotten about. There were even more outrageous.
Marion: That’s great.
Jack: So (A) the story is true, but really one of the questions that come out of that is like when you’re telling a story, some people do what I call collect string. Like I was just always like anybody who told that story around me when it happened, I would just listen. I just instinctively was just listening for like the best possible turns in the plot, right?
Marion: Yeah.
Jack: I think that’s really stuck with me the whole time that I’ve either written or done radio or podcast or anything, it’s just pulling together all the different threads of a story and trying to put them in an order that keeps the bullies from punching me in the face.
Marion: Well, that makes perfect sense to me. So, along with the bullies, let’s talk about some other influencers in our lives. We both have fathers who are sports writers, and I know the influence in my life of that grace in witnessing another human being’s delight at the games that others play. But what connection do you make to your father’s work in your own outlook as a storyteller?
Jack: Well, I’m actually the product of two storytellers. My mother always gets short shrift in this, but my father Red Hitt was his name was a sports’ writer and had a column in The Charleston News and Courier called Hitt’s, Runs, and Errors.
Marion: Of course.
Jack: Yeah, that’s right. And my mother wrote a society column called Gather Ye Rosebuds, and those two met in the newsroom. And they married and I am the result.
Marion: And that’s almost the same story as my parents. My mother was a society columnist and they met at the race track. So yeah, I think that upbringing is very important. And so you always heard stories at the table and the permission to tell them then is just there. And then you sort of get to the point where you’re elbowing out your siblings to be the one that everybody laughs at, right?
Jack: Absolutely. So there are five kids and two parents in my family. When I was little, all of us are storytellers. And most people from big families always tell some story about how like the youngest one learned how to eat fast or something because you had to get the food. That was really never the issue in our house. Food. There was always enough for everybody. It was really commanding the dinner table. That was the competition.
And I do remember when I was very young kid coming home from school being so eager to like join in in the merriment of the night. And I told some story where I think I made fun of some kid’s speech impediment in school, and it’s the first time I ever felt like the air go out of a room. I had lost my audience. It was crickets out there, and it was just clear my parents and my siblings were just letting me know that like, “Nah, that kind of story, that didn’t wash.” I remember my oldest sister put her hand on my arm and said, “Brother, you’re going to have to do a lot better than that if you’re going to come to this table.” And I don’t think I told another story for a year, but I got over it.
Marion: So let’s talk about the heritage that you grew up in South Carolina and that heritage thrums in some of your work, particularly I think of course in your podcast, Uncivil, which you co-founded, in which you have been the narrative that we were all taught in school and bring us the stories that were left out of the American telling of the Civil War. It’s just a wonderful, wonderful piece of work. But listening to it and reading some of your pieces, especially reading this stuff in Garden & Gun, I was started to think we, I think, we get pretty good at storytelling only after we get pretty good at knowing ourselves.
So talk to me a little bit about the place we need to make in our storytelling selves for what we really believe. Like how and when do we get good enough, and where is that self knowledge piece? Because a lot of people listening to this are writers and they just don’t know when they’ve got that kind of authority.
Jack: Gosh, wow. There’s a question. You fail a lot. I mean, I just telling this story… And let me just say storytellers are not born. It’s like listening to standup comics. You have to fail for years in the third level circuits before you can feel comfortable enough to get to The Comedy Cellar. And it’s the same with storytelling. You know when you’re losing an audience. And like I said, my audience was otherwise going to beat me up. And that story is true, and it was absolutely influential in how I became the class clown or whatever. It was really an act of desperation. But it came through a complete failure. You have to know how to work a room. And the only way to do that, I’m not… The self knowledge comes from knowing how you operate with your audience. That interaction is just, that’s everything. And there’s no other way to learn that relationship except to try it out, and no one ever does it right the first time.
Marion: Let’s talk about the trying out things. So some of your stories that I’ve heard on This American Life I know were also pieces that you had written. One of my favorites of those was Dawn about your life and growing up near Dawn Langley Simmons, an early recipient of sex reassignment surgery. And that was also a magazine piece I believe. So let’s talk about that kind of testing and adaptation. I mean, do you test some of these pieces as magazine pieces first and then make it a live version? Well then that piece in particular, and I’ll run all the links to all the references we make here, which came first in that, and how did you move across that adaptation?
Jack: That story first was on This American Life and when Ira was first starting the show, we had coffee somewhere and he was telling me that he was going to start this new show that was going to have stories that weren’t necessarily pegged to news events. This would be at the time a very novel invention for public radio. And he said, “I want stories that just have great hooks and get you caught up and carried away.” I started just telling the story that dated all the way back to when I was like 10 years old because Dawn was in my life for about three or four years before she was run out of town. And I told the story and I said, “Well, something like that? Like a British novelists who moves to Charleston has one of the first sex change operations in America. Marries an illiterate black shrimper, overturns the miscegenation laws in South Carolina. He gets married, becomes an international news event and then a year later has a child by some mysterious biology and then is basically chased out of town by racists. That kind of story?” Yeah.
But see that’s the kind of story. I used to tell that story. I wish I had a recording of me telling that story in high school because that was also one of the stories I told. Because when you’re in your early teens, everyone’s like, “Oh, I know all about sex.” It’s like yeah, you might know about sex but here’s what I know. I knew about something that was so new. Dawn was I believe the first American to have an actual sex change operation at Johns Hopkins. She might’ve been second or third. But anyway, I had told that story. But what really made it was Ira telling me, he’s like, “Go find her.”
So she had disappeared for some 20 years, and I did find her in Hudson, New York and then interviewed her. I was talking to him earlier about just collecting string. I had this sort of like narrative, this well-polished sort of memoir-y story about what happened to me many, many years ago. And then what made it was to catch up with the protagonist in the story and find out her version of all of that, her version of what happened to her, and have all of my well-polished anecdotes kind of roughed back up again by this alternate version. That’s what really made it good.
And also just she was still married to John Paul, this shrimper. Her daughter Natasha was 27 years old when I… That baby was now 27 years old when I caught up with her. She was on the vestry of her local Episcopal church and was the den mother for the local Girl Scouts and so on. No one in town knew her history. Or well, probably some people did, but most people just knew her as this kindly old lady. So there was a whole other narrative to catch up on. And so asking like there was my interview with Dawn and then after I put that piece together for Ira, I realized there was more to tell, a lot more to tell. So that’s when I wrote the story for GQ, and then I did it as a one man show. That story became very much the centerpiece of a one man show I did called Making Up The Truth, which was about some of these extraordinary tales.
Marion: So I was going to ask you about that because speaking of that, because we’re talking about adaptation and how you do that. So we go from, in that case, we go from radio show to radio episode to magazine piece and then you adapt it into being part of Making Up The Truth, this one man show that you about your childhood and the outlandish characters you’ve met in your life. So it begs the question and I think young writers want to know this, and it’s very important to know what your boundaries are. Begs the question for you. Is there nothing you won’t talk about or write about? And it’s a more complex question. So is there anything you won’t write about or talk about, and how do we create those boundaries?
Jack: I guess there’s some things that I don’t write about, but not because I’ve considered them taboo for me or anything like that. But just because I’m not interested. Like sex or porn or anything like that. I get these requests sometimes. At one time I got a call from Details Magazine where the editor said that they were sitting around, they’d come up with a package of stories they wanted to do. And they wanted to do a two set stories about men with very large penises and men with very small penises. I said, “Oh really? And which of those stories you calling me about?” He says, “Well, we have a standup comic who makes a big joke out of his very small penis.” I thought, “Oh really?” “And we thought maybe you could go out and find men with very large penises and write a very funny story about that.”
Marion: They did, huh?
Jack: And all I remember was asking like, “In which of my stories that I’ve written made you think that I would be good at that one? Was it the 10,000 word Harper’s piece about the super fund site in California? Well, was it my three month investigation into piracy in the South China Sea for The New York Times? Was it those stories? Because I’m kind of confused here.” Yeah. Okay. I didn’t take that story. Those seem to me too easy. It’s like, I don’t know. So there’s certain stories I just stay away from it. And most of them are… There certain chestnuts in journalism that just keep getting told over and over and over again. And I sense those out there and I stay away from them.
Marion: Well I think it’s good advice to be able to sense those. And some of the stories you’ve told involves some fairly scary people like the superintendent of yours who turned out to be the head of a death squad in Brazil. It’s a hilarious story. And what I’m was fascinated by was you tell it on The Moth Radio Hour and you told it on This American Life. But on The Moth, you have to do it without notes. So that’s its own thrill working without a net like that. But I doubt that’s why you did that. So let’s talk a little bit about the ultimate paycheck. Like what is the satisfaction of telling the story?
Jack: Well, for me personally, I tried other occupations. I was a banker for a while in San Francisco. I did labor. I was a truck driver. I hated all of these jobs. And I realized the only thing I could do is tell a story. And it took me a while to figure even that out. I worked on a newspaper and I was a reporter, but it turns out I’m a really terrible reporter. They used to, at this little paper in Oregon where I worked, they had a Saturday column where you went out and interviewed. It was a soft feature they called it. So back in the ’70s nobody wanted to have anything to do with that because we were all Woodward and Bernstein back then. But I went out on the story and I had to write an a profile of the oldest lady in town. She was like 104. And I got there and we sat down for lunch, and she was so boring. Hours and hours passed and I was like, “Oh my God, I can’t. What am I going to write about this woman? She is so tedious.”
And then after a long time she said, “You don’t really have to write any of this down because I’ve already written it down.” I said, “Really?” She goes, “Yeah, well I started writing my novel when I was 16. And I’m still working on it.” I thought, “What?” “Yes, I have written a novel about my life, and would you like to see it?” “Yeah, sure.” So she took me into this other room and pulled out the boxes and boxes of paper. Thousands of typed pages. It was essentially one extended diary entry. She had been writing… The first page was yellowed and curled because she had started in 1910 or something. And I said, “Wow, let me sit down with this.” And I just flipped through this collection of mass writing and put together a story about this crazy lady with the unending novel. And that was a feature story that appeared in the Saturday paper.
And after that everybody asked me to write the feature piece because they wanted to do real reporting. Go bust the mayor for malfeasance or something. And I covered school boards and cops, and I was like happy to hand that off to any real reporter. And I would just go hang out with sort of marginal characters and old ladies and lunatics. And that sort of developed into my beat.
Marion: And it serves you well because ultimately we get this book, Bunch Of Amateurs, in which you seem to argue that there are these, and not that she was one of these. But I mean this collection, this fascination with characters, it seems to be what drives Bunch Of Amateurs your most recent book in which you seem to argue that there are surges in history of amateurs doing remarkable things. And do you think that all of this idea of not being a great reporter but being fascinated enough to say to someone when they say, “Would you like to see my novel?” And when the 104 year old woman says to you, this is the kind of thing that eventually will feed the book. So the young writers out there listening, they should say yes when the 104 year old woman says, “Do you want to see my novel,” right? Instead of saying, “No, I think I’d rather go cover that school board…”
Jack: Yeah. You never know where a great story is going to be. And it’s almost certainly not where all the heat is at the time, at whatever you’re writing. I mean, the only story I’ve ever walked away from where I was assigned something and I just said, “I can’t do this. It’s just too terrible.” I was the Times asked me to profile Trent Lott, who was in the Senate majority leader. This is 20 years ago. And I talked to him, I talked to his staff, and I just really going over these notes. I just realized how much I hated these people. Not because he was a Republican from Mississippi, but because he was so boring. Every sentence was so manufactured through this like PR lexicon, right? Everything was measured and tempered, and he was being very careful about what he had to say. Same with his staff. And there was not a character in there. And you can’t tell a great story without a great character. That’s always the case.
And politics I think is really hard to write about because these people have essentially erase their souls to get where they are. And I think for a storyteller especially, it’s painful to have to listen to this vacant ghost of a man or a woman try to explain the sort of devilish things that they’re up to. I like politics. I like to read about it, but I would never write about it. It’s just too boring.
Marion: So that’s a really a big talent is knowing when there’s no story there and being able to admit it. And I think it’s something that my dad used to say that he then went on to become the sports editor at The New York Times. And he would say that he respected someone who came to him and said, “There’s no story,” as much as he respected the one who was willing to fight to get on the front page. But what about, let’s flip that around a little bit. So-
Jack: Can I just add one thing? One of my favorite conversations I’ve had with both of my daughters was at different times in their life. I lectured them about something that was the exact opposite of what I’d said all of their lives, which is you have to stick to it. You have to pull through and you have to finish the job. And then when they get older, it’s really just fun to something is good. They are doing something they hate, and it’s just such a great little parental lecture to say, “You know what? Sometimes it’s really important to quit, to walk away and say, ‘I don’t want to have anything more to do with this.’ That’s really hard to do too.”
Marion: Sure. It’s hard to do as a storyteller and it’s hard to recognize.
Jack: And it’s just a great thing to say because it, of course it goes against all the moral lessons that we get from like our Hollywood movies and our TV shows. Always stick with it. Follow through. Can do. But sometimes it’s like, no, can’t do. I hate this. I’m leaving. Goodbye. And that’s also an important kind of level of awareness that you need, especially for a story. And by the way, I teach a class from time to time about how to pitch stories. And I often, I’m very vehemently argue that you should always pitch your stories on paper or written down. And the reason is you really want to convince, not an editor but yourself, that you want to write this story. Because there’s nothing worse than getting an assignment for something like I did with Trent Lott and then finding out the hard way, after you spent a lot of time, that the story just blows. And you just want to get out of there. The best way to-
Marion: Just want to jump out of it.
Jack: That’s right. The best way to find out whether you want to do a story is to do just enough homework to figure out, to write that pitch, and then you can convince yourself. And once you have that enthusiasm to write a great pitch, you’ll probably end up selling the story.
Marion: So what’s the flip side of that? You’ve won two Peabody awards that I know of, one for Uncivil and one for an episode of This American Life. So when do you know you’ve… Well you don’t know you’ve got an award winning story, but what makes an award winning story?
Jack: What makes an award winning story is living long enough to get one of these awards. Everyone gets one in the end. These awards are like white ribbons at children’s hundred yard dashes. Everyone comes away a winner. Awards are atrocious. All of them in the sense that, like I said, if you live long enough, you’re going to get one. Even if it’s only the Irving Thalberg Award for humanitarianism. There’s always somebody out there who wants to give you an award. The real thing I think is to really to just be in love with the story that you’re telling and just feel absolutely compulsive about finishing the story, about figuring it all out. That’s what I love.
I’ll tell you the other thing I love is whenever you start a story and you pitch it, you of course come up with your own theories and hypotheses or whatever about how the story is supposed to work. And one of the most refreshing things about being a writer is that as you push deeper into the story, almost all of your presumptions and prejudices get challenged and often overturned by the reality of what you’re looking at. And there’s a couple of stories I’ve done where I really went in with one perspective, and by the time I finished reporting, I had moved 180 degrees around to the other side.
If you want to see one because I even write about this in the story The Stringfellow Acid Pit story that I did in Harper’s, which is about a super fun site. Sounds really boring. And I went in there doing the usual sort of like, “Oh the evil companies. They’ve polluted this place, and everybody’s got cancer. And there’s a class action suit.” It was the largest class action suit in American history at the time that I was writing about it.
But by the time I got there, I found out that it turns out the companies weren’t quite who we thought they were and the plaintiffs weren’t quite who we thought they were either. Everybody kind of switched places by the time I finished reporting, and I ended up writing a story in favor of the companies. Yes, that’s right. And it’s because stories get shaped when you’re outside the details of the story.
Quite often the way the story ends up getting shaped is through the sort of usual narrative cliches that we all live by. But when you get in deep, you’ll often find that like, oh, those cliches were just like, they were just shorthand for people to sort of tell the story and move on. But once you go in deep, you find this whole other tale.
And I remember calling my editor in despair from Southern California. This was at Harper’s. And just saying like, “Oh my God, nothing is turning out the way I thought it would.” And I was going to give up. And he was like, “The story you’re telling me sounds fantastic.” And I was like, “Oh right. Yeah. Yeah, that’s what I meant to say. It’s even better than I thought.” And by the way, that’s what I always say.
Marion: Really?
Jack: If it’s something totally different than what I’ve found, I always call the editor. Always best foot forward. “The story’s not quite what I thought it was. In fact, it’s much better.” And then you just tell the story that you found.
Marion: And that’s exactly brings us back to sort of where we started in terms of you’ve got some… So if you’ve got someone at home to pitch, who can give you that magic cookie, who says, “Just love that you’re telling this tale, but here’s the problem.” But then you can then work on it. But never, ever, ever get deterred along the way unless you get bored, unless you find that it’s a stinker. Be willing to throw it over. And then ultimately of course, keep that light touch of curiosity so that you always allow the facts to take you the story, the pitch to take you where it needs to go. It’s good advice, Jack, and I could talk to you all day. But we got to wrap it up. So thank you.
Jack: Thank you, Marion.
Marion: Thanks for listening. You’re welcome, Jack. It’s always a joy.
The author is Jack Hitt. His books books, Off The Road and Bunch Of Amateurs are found wherever books are sold, his stories can be heard on This American Life and The Moth and read in Smithsonian, Garden & Gun and elsewhere. I’m Marion Roach Smith and you’ve been listening to Qwerty. Subscribe wherever podcasts are available. Qwerty is produced by Overit Studios in Albany, New York. Reach them at overitstudios dot com. Our producer is Adam Claremont. Our assistant is Lorna Bailey. Want more on the art and work of writing? Visit Marionroach.com and take a class with me. And thanks for listening. Don’t forget to subscribe to Qwerty and listen to it wherever you go.
Author photo credit: Alchetron.com
