I like to interview people around here, something I’m sure you’re aware of by now—but I’ve never really been interviewed, at least not in-depth about my writing process and whatnot. Until this week.
Take it away, Jeff:
Hope you had an enjoyable weekend — especially if you watch Breaking Bad. Below are questions I have about how you went about the writing/reporting process for your story. Browsing your website, I see you’ve done similar types of Q&A’s (it’s great how many of these guys — and you’re included — are so willing to help), so I look forward to seeing how you do on the other side of the process. Thanks in advance for taking the time.
Yeah man, I had a great weekend. I actually forced myself to chill out some, because I’m not very good at that. Spent most of my Sunday afternoon just watching Breaking Bad and playing Halo and sleeping. It was awesome.
And yeah, Breaking Bad was as awesome as ever. “Tread lightly.” (For some reason I just imagined the Dos Equis guy saying that. “Tread lightly, my friends.”)
I’m glad you’re digging those Q&As. They’ve helped me out a ton, but I’m always glad to hear they helped other people too. And this reminds me I told someone I was going to send him some questions, and I totally haven’t. I need to get on that.
And as far as how I’ll do on this side of the questions—probably terrible, but I just drank a Red Bull, so it’ll (hopefully) be entertaining, at least.
1. I guess to start out, as someone who’s currently in the middle of an internship that’s nearing its end, I’ve become increasingly interested in the trajectory that some of my favorite writers have taken. No matter how talented, no one starts straight at the top (unless you’re Tim Rohan). I’m assuming you worked on your school newspaper, but how did you get from college to where you are today?
Tim Rohan is ridiculous, in a really good way. The dude just works his tail off. (Have you read how he got that Boston bombing victim story? Go read how he got that Boston bombing victim story.)
Yeah, I worked for my school paper, and I was lucky enough to go to a really small college with a small newspaper, and I sort of had free reign to write and do practically whatever I asked for, and that let me make a lot of mistakes, which means I got to learn a lot really quickly. I’d never done any kind of journalism and never really cared about it, to be honest. I just loved reading and writing, but even that was secondary to baseball at the time. I thought I’d be a pro baseball player someday. (And I failed pretty badly at that, but that’s another long story that still gives me nightmares.)
My college adviser was an excellent human being, and he really did an amazing job teaching me how to be a journalist. I’m just glad that I fell in love with journalism along the way—and luckily, my adviser gave me even more opportunity to get better at it. My junior year, he hired me as a staff reporter and the sports editor for the weekly newspapers that he owned. It counted as my internship, too. It was awesome. And I got to do a lot of random stories about wild characters, because these papers were based in a tiny Southern town. I’ll never forget my first assignment: Write a feature about a local schoolbus “roadeo.” It was incredible.
My senior year of college, I decided it’d be a good idea to have a book to my name as a young, aspiring writer, so I started writing one. I graduated (in May 2009), got married and moved to Wilmington, NC, where I freelanced for the local paper and everywhere else in town that would hire me, mostly writing features and profiles. When I wrote those freelance pieces for those small papers and magazines in Wilmington, in my mind, I didn’t write just for them—I also wrote for big magazine editors, hoping to produce something good enough to send them that could maybe, just maybe make them think twice about me.
When I finished that book, I thought it would get published by one company but then didn’t—another complicated story—so then, rather than shop it around some more and spend another two or three years waiting for it to come out because I wanted to be all impressive to magazine editors and junk, my wife and I created our own company, hired our own editors and a printing company, and then published and marketed it ourselves. (Man, that was a long sentence.) My wife did an incredible job designing the book and its website and all the promotional materials, and it was just a blast, really. We made a decent bit of money off of it, which was nice, and it ultimately became the perfect new business card.
I also emailed a ton of journalists and authors asking for advice, and only heard back from three—Jeff Pearlman, Ryan McGee, Chris Jones. (And Will Leitch, who later graciously gave me a nice blurb for my book.) The advice they gave me, about many different things, has been invaluable. McGee told me one of the most helpful things I could’ve heard when I was first starting out. It was the summer after I graduated, and somehow I got ahold of his phone number—I think my dad knew a guy who knew him who put us in touch—and this was before my book was done. He said it was good I was at least working on something big, and staying busy, and all that, because a lot of guys who want to write for places like ESPN The Mag and whatnot just sort of want it but don’t do anything to work toward it.
That’s one thing I’ve always had going for me—I have a tendency to obsessively work toward a goal. It’s how I was with baseball in college, and it’s how I was—and still am—with writing. It’s a little dangerous because if I’m not careful, it can consume me.
I also learned a lot from this thread at SportsJournalists.com.
Meanwhile, just before my book came out, I got lucky and landed a freelance assignment for ESPN.com. I then asked that editor for the name and email address of an editor at ESPN The Magazine, whom I then emailed a quick note along with some of my better clips. I’d done this to several magazines, and I heard back from none of them.
My book came out, it did well enough to give me a little credibility and earn my wife and I a decent bit of money … and then, in December, came my bit of fantastic and not-at-all-deserved luck. I got an email from a different ESPN Mag editor than the one I’d sent my clips to, just completely out of the blue. He said part of his job was to recruit new young talent to their stable, and he liked my stuff and wanted me to pitch him ideas. I freaked out, both because I was happy and because I had no idea what to do with that. I didn’t actually expect to hear back from any of those big mag editors—I just sort of figured hey, it’ll be fun to try. And then, that.
I was 23 years old, and yeah, I had a little talent, but if I’m being honest now, I have to admit that it took me a minute to understand how to put together a piece of longform narrative journalism. Okay, a few minutes. The more feature-y stuff is simpler, but telling a really compelling story is so much trickier than I thought.
And it didn’t help that I basically just overthought the crap out of everything because I felt like I had to prove myself to them for awhile, which really hurt my writing. (Which, ironically, takes us back to what hurt my baseball career … but we’re avoiding that topic.)
For a little while there, I always just sort of felt like I was flailing. I had some pretty gnarly bombs. But nowadays, I’ve chilled way out, and I’ve learned what it takes to make a story good. Those in-depth, intimate, character-driven stories are my absolute favorite to write, by a long shot. I finally feel 100 percent comfortable taking on any story of any subject matter and of any length.
This Bill Dillon story is the longest, most convoluted story I’ve ever written, and I think it’s also my best work yet. It took the least amount of editing after I turned in my first draft. I’ve learned so, so much over the past couple of years, and really, over the past year in talking with a lot of really amazing editors and writers.
Now, I don’t really get anxious about new assignments—I just get giddy, like it’s Christmas. I just love having a story to find and then tell.
I’ve also been incredibly lucky to have gotten a lot of help from a bunch of smarter people—writers and editors alike—from a bunch of different places. And I learned a lot while in grad school getting my master’s in English. And I have a phenomenal wife who’s been as supportive as an overly ambitious young writer can dream of.
And man, I’m rambling. I blame the Red Bull.
2. How did the story come about? Billy does a lot of talks, we learn later in the story, so in some ways he probably made for one of the better subjects to center a story around. He reminds me of R.A. Dickey in Gary Smith’s recent story for Sports Illustrated.
I found Dillon’s story a couple of years ago, and without getting into the whole thing, I’ll just say that a magazine that was going to do something on it never did. Then, a few months ago, I began working with Glenn at SB Nation Longform, where they are doing some truly remarkable work. After my last story—the one about Montaous Walton—I was looking for something new. I have this folder full of ideas on my computer, and I came back across Bill Dillon’s, and did a bit of Googling and made a few phone calls, you know, to get an update on his life, and then I called Glenn and talked to him about it. He told me to write up a couple of paragraphs for him to circulate with the SB Nation crew, they liked it, and so they assigned it to me.
3. What was the reporting process like? How much time did you spend with him in his town? Who did you interview? How many times?
Everyone you’d expect. As far as in person, I spent a couple of days with Billy and his girlfriend, but they were super busy getting ready for a big cross-country trip they were taking in their RV—and then I had some emergency family stuff come up, which cut my trip to Chapel Hill short, so I didn’t get all the access I might’ve liked, but when it comes to family you kind of quit worrying about work and just sort of figure it out later. Turned out, I got enough. I did have some followup stuff I wanted to ask them about, but they never got back to me until after the story ran. That was frustrating, but so it goes sometimes. Fortunately, I was able to dig up tons of old articles and records and everything else—I realized that an astonishing amount of information was available online once I twisted the right knobs on the Google machine.
4. A lot of this story seems reliant on recreating scenes through interviews. What types of questions are you asking so that you can paint as vivid a portrait as possible? And was there any trepidation with relying on solely his memory? Those types of things can be difficult to confirm/fact check. And when you’re providing details, how do you know which to include and which aren’t as necessary?
Yeah, there’s always a little trepidation, and there was especially in this case, because some of the things Billy and Ellen told me went directly against some of the police reports, but that gets us into very complicated things that I don’t think you care to have me ramble on about here. Ultimately, I just tried to write as honestly and fairly about everything as I could.
I have a theory about journalism, at least this narrative journalism I love so much, and it’s probably really cheesy, but whatever, I’m a deep-fried cheeseball at heart: I think that sometimes you might not be able to nail down exactly which facts are correct, but I also think that you can always nail down the heart of the story. That’s my goal, anyway. It goes without saying that I want to get all the facts right—but beyond that, I want to really understand the heart of who I’m writing about: What is the most accurate, truthful version of who this person is today, and how have they become that?
I worry that sounded just noxiously pretentious, but that’s just what’s in my brain.
I got a lot of details about the Dillon story’s scenes from a lot of different places. There were several videos that were really helpful because a lot of local stations covered Dillon’s story, and the Innocence Project of Florida did some documentary-style coverage of Dillon’s case, and that was invaluable.
As far as which details to include and which to leave out—I can’t really tell you how I choose. It kind of goes back to being as simple as I can. I try to be as simple and as clear and as engaging and as not-boring as possible.
5. Something I often struggle with is figuring out how to best tell a singular story while including all of the interesting things I gather through the reporting process. There’s so much stuff I want to use, but it doesn’t necessarily work within the framework of the story I’m trying to tell. Is this something that you too find challenging, and what advice do you have, not just in regard to this one story, but in general?
This is something I’ve really struggled with in the past, too—it’s part of that flailing I talked about up there. In the past, I would obsessively try to fit in every detail I found. But that’s as vain as trying to write a really fancy sentence. It’s saying, “Hey, look how awesome I am at reporting stuff!” At least, that’s how I came to look at it.
But more importantly, it’s bad storytelling. Details make a story, sure, but details can drown a story, too. Like everything else in life, too much of a good thing is a bad thing.
I finally had to say to myself, look dude, you’re writing a story, not a research paper.
Along with that—and this is something I’ve talked a lot about with my editors and writer friends—is it really helps to nail down exactly what your story is about.
Stick with me on this next paragraph, because it gets super nerdy and a bit heady and possibly even more pretentious …
I forget who said this, too, but they were a really smart writer, and they said that if the only thing your story is about is what your story is about, you’re not going to tell a very good story. And that’s part of what I’ve really learned how to feel out in the past six months: In the past, I would just write about whatever my story was about.
For instance, Billy Dillon’s story is about a man who should’ve made it in baseball but instead got wrongfully imprisoned for 27 years. In the past, I would’ve gone detail-heavy and believed that’s what made the story good. But when I was writing it, I was thinking about how this entire story is about a man trying to find his quiet place in life—he’s a man who is, like most of us, trying to find peace. And that made the story so much more focused.
Does that make sense?
When I do my best writing, it’s when I’m focusing on a theme like that, something that threads through whatever the narrative is that I’m writing.
6. What’s your writing process like? I often can’t start unless I transcribe every last piece of audio, which is something I’m trying to deviate from just because it’s so time consuming? How would you describe the amount of time you spent reporting, conceptualizing and then actually writing? Outlines? Multiple drafts/discussions with editors?
I used to do the same thing. I’d report, report, report, then organize and transcribe and organize and transcribe until my eyeballs dried out. With Bill Dillon’s story, though, I tried an entirely different approach—and it worked so much better than my process in the past. I barely transcribed anything. I just wrote the story—and then, when I had it pretty well in place, I went back through the audio and listened to all of my interviews, and I went back through all of my notes, and I read through the story as I did, fact-checking myself along the way. And yeah, I had to make some corrections—but I also got to make some really solid revisions, too.
I don’t know if this is right for everyone, but it worked really well for me. When I wrote, I felt a lot more free—and my storytelling was more focused than ever. I think that’s because I wasn’t drowning in all the details I’d gathered. I was able to write the story I felt was best, and then go back and sprinkle in details as needed. And the funny thing is, this is my longest published story yet, at over 8,000 words.
As far as the actual writing process: When I’m done reporting, I write what I call a Zero Draft—I just sit down and write and write and write until everything I can think of about the story has been poured out of my head and into the computer. This is usually obscenely long and detailed and unprintable.
Then I go sift back through that and write what Anne Lamott calls the Shitty First Draft. And then I can really begin trying to write something that’s actually decent. And from there it’s usually several more drafts, then I’ll print it out and read and mark it up and then rewrite it a few more times. And then I’ll eventually send something to my editors, and then we’ll go back and forth and talk about what we’re trying to accomplish and such. I’m still learning a ton, but—and I’m sure my editors are very grateful for this—the editing process is getting simpler with each story. It’s been really smooth with the last few stories I’ve done, which has been really nice.
Editors simply do not get enough recognition for what they do. However good you think a writer is, no way he’s that good without his editor.
7. Another thing I’m trying to avoid is overwriting, where I get too ambitious with my prose and then it just sounds stupid. I want to “write smart,” but I also don’t want to be searching for more intellectual adjectives just for the sake of having them in the story if they don’t make any sense or feel misplaced. How do you balance the idea of attempting to “write well” but stay within yourself?
I used to do the same thing, and yeah, I wrote some really bad sentences. I mean, I still write bad sentences, only not as often. I hope.
I used to right really superfluously and then try to tone it back. But Glenn told me once that a lot of times the most literary thing you can do is to just let a story unfold. I came to think of it as telling a story instead of writinga story, if that makes any sense.
Now, my goal is to tell my stories as simply as possible. I’ve found they have more power that way. I’m sure this won’t work for everyone, but it’s what I need, because I tend to overcomplicate things. Now I focus less on the words I use and more on how they feel when they’re read.
8. Who do you enjoy reading? Specific writers? Certain publications? Fiction?
Mostly I follow specific writers. Tim O’Brien—I re-read The Things They Carried over and over again—and I read Wright Thompson, Chris Jones, Anne Lamott, Paige Williams, Michael Kruse, Michael Mooney, Tom Lake, Charles Pierce, Jordan Conn, Tim Rohan, Stephen King, William Faulkner, Jenny Lawson (The Bloggess), Mark Twain—I freaking love Mark Twain—Ted Dekker, Hunter S. Thompson, Joe Posnanski, Jon Krakauer, Steven Pressfield, Jeff Pearlman, and on and on and on I could go. I just read all kinds of stuff, really.
Books-wise, right now I’m reading The Corrections by Jonathan Franzen. It’s okay. I like how he writes but the story is kind of boring—although maybe I’m just not far enough into it yet—and I’d rather read a good story with good enough writing than a boring story with really good writing. I’m also reading a few other books right now—I read several books at a time—the first Harry Potter book, because I’m working on a novel geared toward a similar audience, and The Sun Also Rises by Hemingway.
Recently, I really liked the first two Hunger Games books (although I didn’t really like the third one), and … there’s probably a lot more that I just can’t think of right now.
The Red Bull’s wearing off. I need to go make some coffee.
What’s funny is that when it comes to short stories (something less than like 10,000 words or so), I don’t like fiction as much but I really like journalism—but with books, I like fiction way more. I don’t know why, really. I think it might be because I spend so much of my professional life thinking about real people and the real world that when I want to read something really long that’ll demand several hours of my time, I’d rather it be something that lets me escape. I think escaping this world every once in awhile saves your life.
9. The tricky thing about writing is that it’s a skill learned best by doing, and there’s often little revelations or lightbulb moments along the way that are invaluable? Do you have any that you’d like to share?
One of the coolest things I remember an editor saying to me was a few years ago when he began talking about my story subjects as “characters,” which was a term I’d only associated with fiction until then. I’d never thought of the real-life people I was writing about as characters in a story until then—and I liked it.
Another lightbulb “moment” is what I’ve been learning the past year or so, in learning how to write about bigger things than just the story I’m telling.
10. Anything else you’d like to add?
I don’t mean to get all super earnest or whatever, but this is worth saying: If you’re going to do this, trying to make a career out of journalism or writing, make sure you really love it. That’s what a lot of people say, but it’s because it’s really, really hard and it’s often very discouraging. People often don’t understand what we do. I definitely grapple with it a lot of times. So yeah. Just make sure you really love it. If you don’t have a lot of passion for this, you’ll be miserable and then you’ll probably quit. I think what Steve Jobs had to say about passion is dead-on for writers—and for anyone, really: http://www.youtube.com/watch?v=KuNQgln6TL0.
P.S. Jeff’s on Twitter as @jkirsh91. Thanks a lot to Jeff for doing this—I really had a blast. I’ve never sat down and really thought about my own process. Felt weird. But in kind of a good way. Like when Jack licks my feet.
P.P.S. Jack’s my dog.