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Episode 5 ● Part 1

Saul Elbein

The art of the pitch: advice from a freelance journalist

Saul Elbein’s reluctant to speculate about the future of news. There are too many uncertainties, too many factors. Too much has changed in so short a time already to be able to predict, with much chance of success, where this vital industry is now going.

There is one thing he’s reasonably certain of, however, and that is that he’s going to be a part of it. As a freelance journalist, Elbein has learned the fine art of being many things—salesman, debt collector, researcher—without losing his ability to specialize or being caught in the web of attempting to be and do all things at the expense of his time and bottom line. He has learned to be practical without losing his passion.

And Elbein shares some of the wisdom he’s picked up along the way in the form of practical advice for current and future journalists. Specifically, Elbein discusses the fine art of making a pitch—convincing an editor not only that you have a story, but that you are the best person to tell this story.

About Saul
Freelance journalist

As a journalism student at the University of Texas in the mid 2000s, Saul Elbein was haunted by the idea that he was being groomed for a role that no longer existed. Inside the classroom, he was being prepared for a stable job in a big-city newsroom; outside, the newspaper and magazine industries were in free-fall. So he dropped out of journalism school to pursue his passion for exploration and storytelling as a freelancer. In nearly a decade spent writing for publications such The New York Times, Al Jazeera, The Texas Observer, The New Republic, and This American Life, Elbein has gained some hard-won insights about making it in a still-uncertain industry.

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The Interview

How do you find your stories?

There’s not really a rule to it. As I’m walking through the world things will just sort of ping. Since I’ve got started I’ve noticed that there are stories that grab me and grab the people around me. My sort of rule of thumb test for that is, I call it the “bar stool test”. Which is if you’re sitting at a bar and you tell someone this story will they do a spit take—will they be like, “What? That’s crazy!”

The first American Life story I did was about this doctor in West Texas, he was a Filipino—let’s just say this doctor in West Texas who with his crew of police and his tattered administration took over the town and was doing these weird, almost medical experiments. So, like, West Texas mad scientist doc, ding—tell me more, I want to know more. Some of those stories start out weird and then the weirdness fizzles out fast, but a lot of them don’t. Like in that case there had been a couple of nurses who had tried to report him to the Texas medical board, and then he had gone to his buddy the sheriff and gotten them arrested. It was a weird story. I think a lot of people when they are getting started they’re like I want to do a story about X issue, I think X issue is really interesting. Great. I want to do a story about—I feel like there’s something here, fine, but I think when you find the thing it is obvious, like you are obviously interested, like you can’t fake interest in yourself or anybody else and I think if you’re interested that’ll transfer.

So what comes first, the specific story or the area that you’re searching? With legacy publishers, writers have beats, right?

What I’ve noticed is you can make more money more easily if you are working a beat because you’ve got to do less of the sort of familiarizing yourself with the basics. Like, it would be hard for me to go report on an education story right now. I could do it if I found one that really grabbed me, a story that really grabbed me, I could learn what I have to learn, but it would be hard, I would have to learn all this policy.

There’s a certain amount of stuff you have to learn to live in the world that you’re going to tell a story in, and if you can’t do that, until you integrate that you’re likely to tell a really weedy story. So, I was just down in southern Peru doing a story on illegal gold mining and probably like three weeks of time I was running around just trying to get a sense of the legal framework in which this is happening. That’s not interesting to the story I just have to know it, but now I do know it. The next environmental law story I do, the next story about resource extraction, I’m a little bit further along. But, at the same time I wouldn’t want to be on the environment beat, I wouldn’t want to be on the energy beat. I just find that to be sort of limiting. But I noticed that it’s very easy, in the same way that a river channels over time, it sort of carves itself deeper and deeper over time and a faster course, I think that it’s very easy to do that in the sort of work that we do.

I’ve had a lot of younger freelancers ask me, if you send somebody a pitch what’s to stop someone from just taking your idea? And I think at the very beginning of your career that’s possible, but as it gets deeper and deeper, yeah they could hire someone else but does that person know what you know? Do they know who you know? Could they write like you do? And these things come into a beat, but in the sense of a freelancer you would probably talk more about experience or area of expertise.

Take me from your journey in school? You went to UT right?

I did, I was in the journalism program for about 2 years and then I dropped, and I graduated basically from an honors liberal arts program—just a general humanities program.

So I tried out for the Daily Texan, the student newspaper my freshman year, didn’t get it, and then my friend who was living in Israel told me that the Jerusalem Post, which is the main—one of the main English language dailies in Israel—there’s the Haaretz and the Jerusalem Post—that the Jerusalem Post was looking for interns.

Basically, there are an enormous amount of resources for young Jews to spend time in Israel. The Jewish agency will just throw money at you, and they happened to have an internship program where they would hook you up with free room and board and a very small stipend and a place to work. And I sort of managed to hustle that. I found a cheap trip for Jewish students to Israel, I got into the Jewish Agency program and then I was like well, they’re not offering an internship at the Jerusalem Post, but I can get it myself, will that work for you? Basically it was a hustle, which it turns out that’s just what it is. I was figuring out how to ride different trains to get where you want to go—and I did a summer at the Jerusalem Post, then I came back and that was the first time I was ever doing real journalism, real kind of daily newspaper journalism—and I wrote some news features and I got some stuff published in a major international paper or semi-major international paper.

I came back and I was in the journalism program at UT, and I woke up. I was taking a class from this guy Bob Mann who used to be Ted Kennedy’s chief of staff and sort of like from the traditional newspaper age, like the kind of guy you would imagine to have a fifth of whiskey in his desk drawer while he was beat reporting, like that scene. And for whatever reason he took a liking to me. There was one morning where I woke up, I think kind of hungover. It was a Saturday morning at 9 o’clock—it was unacceptably early—and my phone was ringing and it was Bob Mann, and he’s like “Saul, The Texas Observer is looking for interns. I put your name in, you’re going to go apply.” Click, the end. And I was like, “Fuck, I guess I’m going to go apply to the Texas Observer.” I had applied before by the way and I hadn’t gotten it. And I went and I got an internship there.

The thing about journalism internship programs generally—and I had been applying to journalism internship programs like crazy with almost no luck—the thing about internship programs is that, first off, they’re essential if you want to learn the business, and you want to establish your cred, and you want to have real clips. But I always felt that there was a sort of like, we apply for internship programs because we are journalists. It was sort of curiously unconnected from the actual business of making a living. We were always encouraged to apply, and there was this idea that if you did enough programs you graduated and got a job, but there was no direct 1 to 1 correlation: do this work and get money. Which is important because I got to the Texas Observer and it was cool to be there and I really liked the staff there, I really liked what they were having me doing, I really like the work, but I was also sort of like, I’m in school I got stuff to do.

There was this sort of watershed moment where I’d published a few small pieces for them and the big goal of an intern there, as at a lot of magazines, is that by the end you will publish a long feature, a piece of 3,000 words or so that will go in the magazine. And I just thought that that was the reward, the reward is that you get to publish something; the end, thanks for your time, because the internship was unpaid. And I’m sitting at my desk one day, and the office manager hands me a check, and I’m like, ‘What is this for?’ And she’s like, ‘Well, I mean, you’ve been doing stuff for us,’ and I said, ‘But I thought this was an unpaid internship?’ And she said, ‘Oh, yeah, you’re not paid for your time, but anything you publish we pay you freelancer rates.’ And I was just sort of like, and I had had this idea for a feature that I had been half-assedly working on, but suddenly I was like, that 3,000-word story they are going to pay me 50 cents a word, this is actually money, this is actually a business, like my skills are actually valuable.

It was around that time that I dropped out of the UT journalism program, and I was like if I’m going to do this then I’m just going to do it, I don’t really want anyone to teach me about it. I freelanced for The Observer for the rest of school and then afterward and then I was freelancing for them and freelancing for some other people. Pretty much from that point on I was a freelance journalist. Instead of getting a job at a coffee shop or a bar I was working as a journalist.

The Jerusalem Post was great too. I feel like if there’s anything to be drawn from those experiences it’s that the less organized, the more sort of like smaller seat-of-the-pants type operations, they just tend to need more hands on deck. At the Jerusalem Post their policy was like, look we’re not paying you, but you can work as hard as you want and if you want to get a story on the front page you can, and if you want to sit around and fuck around on Facebook all day you can do that too, we don’t care, but we could use you because you’re free labor and you make our lives easier. Whereas at the New York Times, maybe, I don’t know, but I imagine at a place that is sort of more institutionally together there might be fewer of those opportunities.

Let’s see if we can wrap up your epiphany into a sentence or two as advice to an aspiring journalist.

I think what I would say to my 18-year-old self would be, if you are going to be good at this then you have to accept that it’s a job, and it’s a skill that people should and will pay you for, and your goal is to figure out how you’re going to be able to convince them that you can do the job.

That’s all clips are, that’s all your first bylines are. It’s just a way, when your name comes up, attached to a story that you want to do, or you want to sell, that somebody believes you can do it. There’s a lot of ways to do that, there’s a lot of ways to get there, but a clip—which is what you’re working at in the beginning part of your career for—is one of the best ways. It says that you are able to create the product that is what the business is about.

I would say, 2, early in your career it’s okay to not make that much money because you are just trying to create that product, but that is not the end goal, the end goal is to be able to make a living at it, because you won’t be able to do it otherwise.

You have to be your own brand, and that comes from the work you’ve done. And I think this is a really important point. We all as artists have this difficult relationship with money and the idea of making money and this sort of like, is it selling out, we should be doing it for the love of the thing not for money, but we are professionals creating a product that makes other people money.

When I was in journalism it was like, you’re going to get a job with these large faceless operations and you’re going to make your editors happy, and you’re going to serve the common good, but the question of how you’re going to make a living was never treaded on when I was in journalism school. But on the flip side there are a lot of people who are starting out who are writing for Vice or Salon, or all these sort of like entry level that don’t pay very much, but are still reasonably reputable, and who bitch about the idea of being paid for exposure, and I think at some points early in your career and also later on in your career, I think exposure is actually worth a lot of money. It’s just not money that you can pay your rent with yet. I know a lot of younger journalist’s bitch about shitting writing gigs as if the publishing industry has ever not been horribly exploitative.

How do you develop a story into a product?

I was talking a second ago about how you have to convince somebody you can do the story, but also you have to ask them, and the formal request in our business and a lot of businesses you call a pitch. This is one of those things that is endless fascination to people, which I don’t fully understand but, they’ll ask, do you write the story first do you write the story and submit it, and the answer is almost never. And the reason why comes down to, first off, money. My time in researching for a story is time that I’m not spending working on something else, there’s a real opportunity cost, and it’s better for me if I can manage not to do any work that I’m not being paid for or work I’m pretty sure I’m not going to be paid for.

There’s a certain amount of work that you need to do to convince an editor that you are able to do a story and if there is a story, and I try not to do any more than that. I try to do enough work to get a pitch out. So the pitch is a document that is supposed to hook the editor but also that there’s a story and that you’re the one to tell it. It is, I think, even more than the finished article, or online with the finished article, it is the foundational document or form of being a freelance journalist. And by form I mean it’s a form like the sonnet or the Haiku, or the 4,000-word feature profile. It’s that important because you’re writing to an audience of a couple of people, and you’re trying to let them see the outlines of a story that does not exist yet, and to believe that you can see something that they cannot. And that’s a huge thing that’s a huge ask.
It takes a fair amount of work to produce that product. There’s an interview with Susan Orlean that says that she does 10 interviews per pitch which is somewhere between 5 and 10 hours of work I’d assume. And that she gets 1 out of 10 pitches picked up. Now she’s got a stable job, she can afford to have a 10% hit rate—I can’t. But I think roughly though, the idea that most editors pass on pitch and that it takes some time to produce a pitch, I think that’s really important.

Let’s talk about the structure of the pitch.

Okay here’s how I do it. I don’t actually remember where I learned this, who taught me, but this is how it is more or less done. So again, the two goals are: hook an editor, and convince them that you can do it. Or actually there are three goals: hook an editor so they read the pitch, convince them that there’s a story, and that you are the one that can do it.

I do it in a 3 or 4 paragraph, depending on the story and what feels right, but we can break it into three parts. The first part is a hook. My friend Eric Benson who I’ve learned a lot of freelancing from, he will imagine if he were to get the story and if he were to write the best lead possible for the story, what he’d do as his first paragraph, the hookiest part. My friend Erin Miller who is one of the best freelancers I know up in Canada, says she never gets closer to fiction writing than when she’s writing a pitch, because you kind of have to project a little bit, you kind of have to play a little bit with.

There’s some dangers there where you can overpitch something—but generally you want to have a really kind of grabby first paragraph or first couple of paragraphs that really lay out the central themes of the piece. Then in the body of it you lay out the structure of the story the statistics that the story will hang on, the sort of main developments that you’re going to be writing about. At the end you make the case of why it’s you. The traditional way of doing that is saying what your area of expertise is and who you’ve written for before and including links to some relevant clips. If you don’t have those relevant clips then you ask yourself, what would make an editor think I can do this, and you’ve got to sort of answer that for yourself. And I’m hesitant to give too many answers because every story is different and every case is different and every editor is different. That’s more or less how you do it. Step 1 is grab them, step 2 is layout what the story is, step 3, why me.

And then also accept that most pitches get passed on by most editors, and that doesn’t necessarily mean that the story wasn’t good, it means that it didn’t fit with what they were running, they couldn’t see what you see, they already have somebody that covers that, editors are generally conservative, they are terrified of getting into the position where they’ve commissioned a story and then it collapses and there left with nothing. So you can write a great pitch and not get the story. But one thing that I’ve learned is that a pitch does two things: first is that it might get you work, it’s the necessary thing to sell a story, but it’s also, and this took me years to learn, it’s also something that sells you. Let me say that a little bit more clearly. A pitch can help sell a story, but it can also help sell you. If an editor gets a pitch from a writer that is a story that isn’t right for them, but they are impressed by the story, that’s great, that’s a win.

My first 3 pitches to the New York Times they didn’t take. I got nice responses every time, so that’s a win, but they didn’t take the stories. I feel like sometimes there’s a three-date rule for working with a new editor. It takes some time to figure out if you’re going to be able to work together. And one of the key things there is that you have to kind of like get to know each other, and how each other think. And If I get a story before an editor and they say this is a great idea but we are going to pass. That’s great because in 2 or 3 stories they may not pass, and I think it’s easy to get discouraged by a no, and not to understand that no is a lot more common than yes and that no is not no forever.

Is there any kind of trick to knowing who to send the pitch to if you’ve never sent a pitch to the Times before?

I was lucky, my dad was a part of the Jewish Youth Groups in San Antonio with a guy who ended up on the science beat at The Times. He got me an email address of the relevant person. Could I have done that without that? Yeah, probably. If you think of the journalism world or really any freelance world you may enter as a labyrinth with an infinite number of doors you’ve just gotta find one door that leads to other doors. My door was this guy at the Times, but there are other doors. I got into the Observer because a journalism professor opened the door. I got into the Jerusalem Post because a friend let me know they were looking for people and any of those could have led somewhere else. At some point that guy at The Times is sitting at his desk and he’s wondering how he is going to fill the number of columns that he’s assigned, and anybody that can do that for him is helping him. So the fact that I come recommended or the fact that I know somebody else at The Times will get my email read but at the end of the day it’s my work that’s going to I think that’s going to stand for whether I get work from him.

It’s like anything else you need people to make the connections.

I would go further than that and you only need people, almost. Obviously your work is really important, but if you’re going to ask about the future of news, I don’t know if it was always this way, but I feel like now the way that it is, is that you’ll have to have people that you’ll work for because people move around so much. Institutional loyalties may be less valuable. For me one of the key things in my career was that there was a story I pitched to the New York Times Magazine that the editors kept leaving; it was accepted it was assigned to an editor, then the editor got a new job and it was assigned to a new editor, and then that editor got a new job, and it was assigned to a new editor, and the story never got written, it’s still—I might actually do it in the next few months. It was about forensic anthropologists in Guatemala.

But the point was, the editor that left the first time, that liked my work enough to take it was now at The New Republic, I did a story for him from Guatemala. A story had come across his desk and he didn’t know anyone who could do it, but remembered me. The second editor that it had been assigned to went to the Sunday Business Section, and I did a story for her so it was like, there’s sort of this theme of exodus as people jump around from media job to media job, and I think in that sort of environment personal loyalties is more important than a longstanding institutional relationship. Although I think that other people have had different experiences.

When you graduated in 2010 it must have been like the sky was falling for most folks?

There had been this narrative that journalism was collapsing since pretty much when I got into journalism school. I look back at it now and I feel like I had a sense that I had been preparing for a role that no longer existed. Like there wasn’t going to be a newsroom job for me most likely. Maybe there would have been. Obviously there are still newsroom jobs and magazine jobs and it could be that if I had stayed in journalism school I would have one of those. I would have a nice cushy job at The Times Magazine or some place. Kind of doubt it though. Yeah, there was a narrative that the sky was falling. But I was more or less able to make rent by just writing. So I just kept my head down and kept doing it.

I read an interview with James Baldwin recently—do you know James Baldwin? He’s an essayist he’s worth reading—he was sort of one of the foundational philosophers of the civil rights movement. He just writes beautiful, beautiful stuff, but there was an interview with him in the Paris Review where someone asks him what advice he would give to young writers, and he says something like—I’m just going to paraphrase—“Keep writing, and if you can’t do it, nothing I say will help you, and if you have to do it, nothing I say will stop you.” And it was just like this is what I was doing. I never ran up against a hard enough wall to stop me. It was tough, but it was never a question of whether I was going to be able to do it.

But here’s the thing, Andrew, I don’t feel like I was all that tenacious, I feel like I followed almost the path of least resistance and ended up here. It was obviously very very difficult a lot of times, but it doesn’t ever feel like there was another choice.

One of the advantages of working for an institution is that you’re credentialized. You get access easier, people return your calls, etc. What does that look like for a freelancer?

If you’re working on a story for an institution it works the same way. I’ve been on stories where I was working for the New York Times, where I almost felt like my presence suddenly as a New York Times reporter warped the room around me. It almost had this quantum effect on the people that I was around. Because suddenly the eyes of the newspaper record were there in that room—for all of us. So that doesn’t make much difference. Those people don’t really understand that I was a freelancer. Most people aren’t super cued in to the vagaries of the media business, like you’re with the New York Times, you’re with the New York Times. It’s powerful enough that there’s always the temptation to lie about who you’re working with for a story. Maybe fudge a little bit about, this is who I hope to be working for.

Generally, when I’m reaching out to people to interview I’ll try to say who I’m doing it for. And at this point usually that’s true. At this point if I’ve sat down with an Al Jazeera editor and I’ve run a story by her and she likes it, even if she hasn’t commissioned the story yet, if I’m reaching out to sources I’ll say I’m with Al Jazeera, because I am. Not every story works out for all publications, even if I were on staff at Al Jazeera, I could reach out to people for Al Jazeera and not have a story get made. I was talking about how you have to convince an editor that you’re serious, you also have to convince a source that you’re serious, and it’s much easier to do when you have a name that you can attach to it.

There’s this three-way balancing act to do the work that I do, which is largely foreign, travel intensive, longform journalism. You have to convince an editor at the same time you are convincing sources, so there’s almost a triangle reciprocal relationship. There’s editors, sources, and funders. The funders aren’t essential, but the truth is they are essential if you are going to be going across the world. And nobody wants to make a move until somebody else has. So an editor doesn’t really want to commission a story until they know there’s a story, which means you have to be talking to sources. The editor doesn’t want to send you to Latin America or Africa unless they know it’s going to get paid for. The funder doesn’t want to give you money until they know the story has been commissioned. The source doesn’t want to talk to you unless they know you’re for real which generally means that you’re attached to somebody. And there’s not like a solution, it’s just a dance, you have to balance these things. So it’s like doing a multivariable equation.

How do you find yourself working in Latin America?

We talked about passion, I mean I fell in love with Latin America, it’s the truth. I feel in love with Spanish first, and then the Latin American culture that made it here, a lot of the pop culture really, like Latin music, and movies. I think the first time I went there it was just a new world, there was just a vibrance to life that I hadn’t experienced here. And I’m not sure if that was because life was necessarily more vibrant, but because being in a new place you are forced to reflect on not only that place, but I think it’s a lot more colorful palette than most places. Latin America is just more colorful than the palette in Austin. But also it reflects life back home in a way that you wouldn’t have seen back home.

There’s something else, too. Which is that I feel like one of the institutional realities of the journalism business is that the money and the stories are controlled by people who largely spend their lives in relatively small offices in midtown Manhattan office buildings. And they wake up in the morning and they take the train into the city, and they work all day, and at the end of the day they take the train back home. And that’s their lives. It’s not a bad life. Most of the editors in New York love that life, but nonetheless they are circumscribed by a very limited reality, and they are aware of that. They want people out in the world that can tell them what’s going on.

I think we often forget, because of how much news we see, how little we know about what’s going on in the world, and I think your ability to make money in this business is greater if you’re able to be someplace new and are able to tell stories that are new. I was lucky in that—Latin America is not the most newsworthy place. Americans don’t care really all that much about Latin America, but nonetheless it’s a different place, and it’s a place that not a lot of news is coming out of, and it’s a place with lots of interesting stories, and I found that if I could be on the ground there it was much easier to sell to editors that were in New York the stories that I was finding. And I think that was true in Texas too. I think Texas is not a lot less exotic to people in the north east, still to this day, than Guatemala or Peru.

You’re multilingual, not bilingual right? How big of an asset is that as a freelancer?

Being able to speak more than one language if you are going to work overseas is invaluable. It’s invaluable for the obvious reason and also for a less obvious reason. The obvious reason is that you can communicate. If you can’t communicate you can report in places where you can’t speak the language but it’s very expensive because you have to hire a translator and a good translator is expensive, their day rate, 120 would be cheap—$120a day to $250 a day—that adds up pretty quickly. Whereas for me—and to be honest I’m just not that organized, it’s very hard for me to get everything together in 3 or 4 days—since I speak Spanish, since I’m working in Latin America, I can set up in a city, and I can bounce around, and I can let a story develop slowly.

When I was in Cambodia reporting in Kahmer—I don’t speak Kahmer better, and this point not at all—about well enough to catch the bus and order some noodles, which are great, it’s better to be able to do that than not to be able to do that, but I wasn’t interviewing in it. That meant that effectively my day-to-day costs were upped by $150 a day, which meant that I couldn’t report for as long, which meant that I couldn’t go as deep. So being in a place where you can communicate you don’t have to do that.

The other thing that really helps in learning new languages is that you’re forced to be the person that you are, a competent adult, where you communicating at the level of a reasonably educated child. Because that’s the way it is at first, and it’s still that way sometimes for me when I’m tired or hungover or something. It forces you to really ask yourself, what am I saying, and sort of break down meaning into—you stop trying to translate because you can’t translate. You have to breakdown what you are trying to say in its most essential parts, and there is no better skill I think for writing effectively. You have to ask yourself what am I really saying. I think often people want to translate English literally. And colloquial English doesn’t really translate, and this is one of the beautiful things about English, it really is a singular language in that way. So you have to break down, what am I really saying, but why am I saying it? Is this even a thing that needs to be said?

I also found that not speaking a language very well, and even Spanish, I’m fluent in Spanish one on one but in a party situation or when I’m with a group of people, it’s kind of like riding a motorcycle at 100 miles per hour, I’m just holding on and I’m hoping—it forces you to be aware of things that you wouldn’t be aware of otherwise. It forced me to realized how little information is actually conveyed through speech. How little of what is said is of the larger picture.

Whether or not institutions fail, it seems like more and more people are consuming more media. Is that true? Do you think people are reading more? That there’s more of a need for material?

I think that people are carrying around these little readers with them all the time. That’s potentially a huge asset to people who want to create. That they can read on those things. I don’t have any statistics about this but my sense is that in terms of the conversations that I’m having with people, and granted my friends are skewed toward people who read, but I feel like there’s still a lot of demand for interesting stories told in interesting ways and I think in a lot of ways my sense having coming up during the “great dying” of the news media—the great crash—was that, it seemed like there was a lot of self-serving bullshit about how, oh the internet killed it, oh people don’t want to read good stories, and it’s like, either you can do it or you can’t—either we can do it or we can’t, and there aren’t really any excuses.

One of the best things I learned in journalism school, which was a class taught by basically an adjunct it was not anybody, it was a guy not much older than I was, but he asked us who is the main competitor for the New York Times? Oh, well,, The Washington Post, The Boston Globe, you know, these would have been the answers 20 years ago I think, and he kind of let us brainstorm, and then he said, well how about anything else that’s interesting? And I think that’s what it’s got to be. Is it really anything else that’s interesting? That might be too broad, but I think there is the challenge of hooking people, which applies to our profession as much as anything else.

And I don’t think it does any good anymore to wag your finger at the people who don’t eat their vegetables. That’s fine, and that might be true, they should be eating their vegetables, but what are you going to do? Because I think you’re right, I think there is still a lot of opportunity for storytelling for writing for journalism for interesting products, interesting projects. I mean we are all talking about what happened in Paris. How do we even know what happened in Paris? Or I should say, we’ve all been talking about the Paris terror attacks the last couple of weeks, how do we even know about that? Our discourse in this country has been all about things that are important to us by the news media which are highly responsive to things happening all the way around the world. Those are journalism problems and those are journalism opportunities for people who are able to find them.

You mentioned that you had to go through a period of struggle? Tell me about it.

Sure, like last week, come on let’s be real here, I mean it’s tough, and one of the things that doesn’t get enough focus in the question of the larger media landscape is in my experience dealing with the management and finance department of large news organizations is that they are totally fucked in that part. I feel like I’ve spent, I don’t know, over the last 2 months I’ve probably spent 10 or 12 billable hours just trying to get paid or to find out if I’m going to get paid, which I’m sort of paranoid about now because organizations will occasionally forget about checks and they’ll forget about checks until they are prodded into sending them. What that means is not only am I wasting my time—they don’t care about that, and publishing has always been ruthless—but I think more relevantly they’re wasting their time. A highly trained editor with a whole bunch of things on their plate should not be fielding whether or not I’m getting paid. That’s not his or her job, or it shouldn’t be anyway—but it is. And if they want to make sure that their writers are being treated well, which most of them do, they make it their job. Well what are they not doing because of that?

I haven’t fully thought this through but it seems to me in a lot of ways freelancing is full of these structural inefficiencies like that. I think in a lot of ways the institutional media might have been able to avoid it. I think if I had a newsroom job I could have gone upstairs to finance and yelled at them, why aren’t we getting a regular paycheck? And then nobody would have been wasting their time on these sort of like management things. As it is now I’m forced to do some of management’s job. Editing is forced to do some of management’s and finance’s job, finance is getting yelled at all the time by people they are not directly working with. So, I think there’s a lot of that stuff that doesn’t get talked about. To some extent if everyone’s books had been in order and if everyone had been running their organization responsibly ethe crash in the mid-2000’s wouldn’t have been as bad.

So as a freelancer you’re more than just a writer?

Yeah,it’s a weird thing. I think probably similarly to you, I’m a creative entrepreneur I guess you could say? I am payroll, I am management. When I want to sleep late there’s no one stopping me but me. I am acquisitions I am accounts payable, accounts receivable, all of that. And sometimes if I’m running an investigation someplace else, like this project in Cambodia, I’m a manager myself of translators and transcriptionists and fixers. Yeah, it’s strange in that way because there’s traditionally two different spheres of interest, business and arts, but if you are going to freelance you’ve got to be able to do both.

So aside from the writing skill sets there are other attributes that are very important to the freelancer.

Yeah, I think you have to be able to find work. I think if you’re a great storyteller but you can’t get your stuff in front of somebody you’re not going to be very successful. I think all of the traditional business skills—which I wasn’t trained in—but even being able to write a pitch is a skill that has more to do with sales than it has to do with what is thought of has the traditional craft of writing. And you still have to be able to pitch in large organizations. You know, Susan Orlean who is talking about the 10 interviews she has to do for every pitch, she is pitching herself at staff meetings and that’s still I think more or less sales. There is the skillset of pitching a product, but there is also the skillset of packaging the product, and I think you need both.

You asked about it being hard, and I will say this, and this is something I feel like I can’t say enough, is that a lot of the reason I was able to do it just starting out and I wasn’t always able to make rent, is that my parents helped me, and that’s a huge asset that a lot of people don’t have, and I’m aware of that. There were times where the difference between me making rent and not making rent was my mom putting 500 bucks in my account. And would I have gotten here without that? I think so, but I can’t be 100 percent sure about that either.

And I think the reason it’s relevant is not guilt or anything like that, but it’s to be aware that if you’re able to do it, which the people watching this may very well be able to do, if you really want to do it, it isn’t that that hard if you’re good. That if you’re able to do it there’s some responsibility that comes with that, because lots of people can’t, the question is what you’re going to do. Once you have the door open, once you have a seat at the table what are you going to do?

Has it gotten easier?

Oh, yeah, for sure. It’s easier to find work, it’s easier to find stories, it’s easier to tell stories. I’m getting better. Has it gotten easier, like are the stories easier, I mean, I don’t know. I still have terrified sleepless nights about the projects that I’m working on. But, yeah, it’s easier in that there’s not a question anymore of whether I can do it, it’s just a question of how I’m going to do it, and that’s a much easier question to answer.

So getting that confidence is important?

Sure, yeah, and finding people that believe in you and that you can work with. I think if you’re going to talk about what I believe, what a freelancer’s trajectory should be, which I’m not claiming any qualification to talk about beside the fact that you guys have sat me down here and put me on camera. The first step should be finding partners. The most important thing you can do is find people that you can work with. For me it was the people at the Texas Observer and the Jerusalem Post, but more the Texas Observer for longer, who believed in me—more to the point who I knew believed in me, because I know when I pitched ideas that they didn’t take, I didn’t take it as some huge, sweeping, denigration of everything I’d worked towards. Which is easy to do when you’re young.

For my little brother who was also a journalist it was the people at The Bitter Southerner and the Oxford American. And I think as people leave those publications and go to other places he’ll be able to pitch them there. But I think that’s the most important thing, even more important than selling stories early on, it’s meeting people who will be your partners in future endeavors. If you get that and you keep working at it and being out in the world of finding interesting ideas, that’s it, that’s all there really is.

Is the future of news a freelance future? Do freelancers have an advantage?

That’s a tough question. I really am reluctant to speculate on what the future of news is, because I don’t think any of us have any idea. I do think that, from what I’ve seen, being with an let me say it this way: I think freelancers have a future. I think there may be some ways in which freelancers have advantages, but it’s hard for me to speculate given that I’ve never had a newsroom job. I think I’m more diversified than your average institutional journalist, though. I think a freelancer has the ability, if they can do the dance, I think they can do things and have security of a sort that an institutional journalist doesn’t.

What are the best parts about being a freelancer?

I love being able to choose my own projects. I never have to work on anything I don’t want to work on. I really do mean that. I NEVER work on anything I don’t want to work on. The closest I’ll come is sometimes I’ll do relatively easy-money gigs that are in my wheelhouse. And then I’ll sort of bite my tongue. I love the fact that I get to work on what I want to work on, and that I’m constantly pivoting between new projects, and I like the business aspect too. I like the dance. I find it to be really exhilarating.

So you would say the the future of news includes freelancers, at least?

I think that freelancers are having a moment now. I think it might be that a group of very talented freelancers come up through this moment, and when the institutions re-coalesce, they get snatched up. I don’t know.

Are there any new media outlets that you find compelling?

I haven’t read a whole lot of Vox, but I like their Q&A forum. I’ve read a few interviews on there, and it seems like they do a Q&A in a different way, although I’m not sure I could totally articulate what that is. Here’s what I like: … It seems like Vox was conceived with a digital sensibility, in a way that a lot of media hasn’t been. Like, they’ll have a Q&A, but they can draw you out of the story and give you supplementary information in an interesting way. One of the things I really like about Vox is their use of footnotes …

I think there’s a lot of storytelling possibilities in the digital world, or information relaying possibilities that the traditional media has been slower with. I mean even literally: have a footnote up on the side. When you’re not telling a story on a printed page and you have unlimited space and unlimited ability to build it out, but also people have finite interest, like how do you do that? People who came up in a specific way aren’t used to thinking that way, which is why a lot of the early digital journalism was just a page on a screen. It was a direct translation of the book or the newspaper to the screen. The New York Times, up until 15 years ago, if they wanted to distribute their product they had to create the platform. That’s no longer true. NPR, until recently, if they wanted to distribute their product, they had to buy time on a transmitter. That’s no longer true. And that frees you up some as well. And it’s also true for anybody.
I think, in some sense, the New York Times is not free to think that way because it’s a huge institution with a huge institutional memory with a way of doing things that’s suited to a different medium—and they’re trying to adapt that medium. And that’s fine. They’re doing pretty well. Some people weren’t able to do it that well.

Do digital natives have an advantage?

Coming up in this world, you see possibilities, even if you can’t quite realize them, that older people don’t. Yeah I think digital natives have an advantage in digital storytelling. One of the things that we forget about is that the fundamentals of what makes a story “go” haven’t changed that much. In that sense, I think it’s easy to get hung up on all the bells and whistles. I think there’s new storytelling possibilities, there’s probably new forms that can evolve, but in terms of the old forms? Do digital natives have an advantage in writing a 5,000 word magazine profile? I don’t know. I don’t think so.

What of those new possibilities is exciting for you?

I’ve been interested in mapping recently, in maps and infographics as a way to relay information and tell a story. I don’t have the technical know-how, so when Evan Smith talked about “journalists need to be pocket knives,” at this point in my career, the amount of time it would take to develop those skills would be like taking on a new career. And I think it’s more efficient for me to find another meat cleaver—for me to find somebody else who thinks like I do and will work with me on that.

When I was in journalism school everyone was playing with this idea that journalists have to be jacks of all trades, everybody has to be able to do everything. That might be true, but it really hasn’t been my experience. I think to some extent, if I’m working on a big data project, I’m not working on something else. So it seems like just as easily I can bring in someone else who can do the data side, and I just work with them. I think there are some investigative tools that I should have data-wise, and some basic stuff that I should be able to do, but in terms of a big project, it seems like in terms of division of labor, that doesn’t seem like a great way of doing it.

There is something to be said about specializing.

Yeah, I think so. I think the skill set of interviewing and creating a story out of disparate chunks is a specific skill set. The ability to write those chunks into a straight-through narrative that conveys the information into somebody’s brain is a specific skill set. And I think familiarity with other people’s media, like for example the more that I understand what you do, the more I can work with filmmakers and help them. The more I can understand what a photographer does and what a photographer needs, the more effectively I can work with a photographer. In an infantry squad, a rifleman may know what a heavy-gunner does, but they don’t need to carry the machine gun themselves.

Have you considered making images?

Yeah I take photos, but I take photos because I take photos. Every now and then I’ll find out that I’ve taken all these photos that I can do something with that somebody wants. But that’s not—one of the ideas I was developing a little bit was that it just takes time to do any of these things well on any particular project. And I think if I’m out in the field taking pictures, then I’m not reporting in the same way. So if I were to work at it, I could probably be as good of a data journalist as some of my friends who are data journalists or designers, and could probably be as good of a photojournalist as some, not the best, as some of the photojournalists that I know. But I could just bring them.

Can a freelance journalist get by without a social media presence?

Obviously. Inasmuch as I’m sitting here without a social media presence. I think it might be different if I was trying to raise a lot of money on Kickstarter or do that sort of thing. I think the truth is it’s just never been something that I’ve wanted to do. That might change. Most of the journalists that I know are on Twitter. I know that my girlfriend, who is also a journalist, finds a lot of her sources that way.

When we ask if a journalist can get by without social media, I think what we’re really saying is, “Can you promote yourself?” To a great extent I’m not getting paid by the people who read me, I’m getting paid by the people who hire me. If I had 20,000 followers on Instagram or Twitter, or millions of followers say, I think that would be a pretty compelling reason to hire me, but there are other compelling reasons to hire me as well.

Is the notion that journalists need to have a voice across media and platforms, is that overblown?

It’s hard for me to say it’s overblown categorically, I’ve found it to be kind of bullshit. There’s a lot of people who say that journalists need to have a voice and a presence across all sorts of media, and that may be true for some people. In my life, I’ve found it’s kind of bullshit.

I think that the advantage that a freelance has over an institutional media person, is because they are required to figure out what sells and what’s going on to make money, to make rent, they’re more responsive. That increased vulnerability is also a heightened sensitivity that forces creativity.

Does it force a better understanding of the audience?

I think so. I think maybe. I think at least the motivations are much more intense to figure out what’s going on.

Much has changed in the last 5 years. Do you see anything coming that’s interesting?

I’d like somebody to figure out the magazine payment software system. It seems like there’s a lot of people trying to do something, but I don’t think that anyone has done it very well. So anybody who’s watching this who would like to figure out how to make sure that freelancers and contract people get paid in a way that saves time for everyone involved, I think there’s serious money there. I would like you to do that.

What I’m personally excited about is finally being at a point in my career where I can do the stories that interest me, and where people my age, I’m 27, are finally able to do the stories they’re interested in and we can work together—that’s really exciting. I feel like that’s been what I’ve been working towards. So I can’t talk too much about the future of the industry, but I think personally, and maybe this is the future of the industry too, I feel like though some things are still hard they’re going well, and that might be a reflection of a larger phenomenon.

How so?

Well, in that if there wasn’t anybody hiring, and there wasn’t anybody paying for the work that I would be doing, we wouldn’t be talking right now and I would be doing something else, and you would be doing something else too.

What are the most foundation shaking things you’ve experience over the last 5 years?

The truth is I wasn’t aware, I wasn’t alive and conscious in this world before the sky fell. I only started to meet people in the journalism world in 2007, 2008 when it was already happening. But I think the sky did fall. There’s way fewer serious dailies. And the American news structure is no longer built around the city daily. That’s a big deal. I don’t know how big of a deal it is, or what it means for the future, but that’s a big deal. I think there is more and more focus on news, even serious news, as entertainment, or explanation rather than serious investigation or diving deep into things that are important but not necessarily super interesting, and I think that’s a loss for sure. And it would be great if there could be a way to figure out how to make that marketable again. If it’s a public good, maybe it should be funded as a public good.

But the other thing that happened is that a lot of the more vapid sites, I will name some names, Buzzfeed and Huffington Post, both of them do great long form features now. There is a market for that, even if it’s as a loss-leader to convince somebody that your brand is serious. And I think that’s an encouraging development. It’s encouraging for me, because that’s the line I’m in.
The things that we produce are niche and luxury products, that’s the way it is.

So many people view the Times as an elitist organization.

Well it is! It is an elitist organization. They have a skyscraper in midtown Manhattan. They are an elitist organization. They’re also our national newspaper of record, they’re really important. But yeah, they’re for sure an elitist organization. Look at the way they cover middle America, and by middle America I mean the entire rest of the country. There’s great editors there, but I was talking about people who are circumscribed by their own life experiences—you know, taking the train from New Jersey into Manhattan and going back, there’s a loss of—and this is part of the great tragedy of the loss of the regional newspapers is that the closer you are to the events, the more context you have in how people are living their lives normally. And an editor in New York I think, even if they’re super well-educated and super-sensitive, is going to have a hard time seeing that. And a writer in New York, even more so.

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