The Freelancers’ Roundtable

A conversation between freelancers Eva Holland, Josh Dean, Jason Fagone, and May Jeong about pitching stories, negotiating contracts, and breaking into a tough industry.

Eva Holland | Longreads |February 2016 | 25 minutes (6,339 words)

 

There’s been more talk than usual lately about the state of freelance writing. There are increasing numbers of tools for freelancers: among them, the various incarnations of “Yelp for Journalists.” There’s advice floating around; there are Facebook support groups.

With the exception of one 10-month staff interlude, I’ve been freelancing full time now for seven and a half years. I’ve learned a few things along the way, but I also still have a ton of questions, and often feel as if I’ve outgrown some of the advice I see going by in the social media stream.

So I gathered a handful of well-established freelance writers and asked them to participate in a group email conversation about their experiences and advice. Josh Dean is a Brooklyn-based writer for the likes of Outside, GQ, Rolling Stone, and Popular Science. Jason Fagone lives in the Philadelphia area and has recently published stories in the New York Times Magazine, Mother Jones, Matter, and Grantland. May Jeong is based in Kabul, and has written for publications including the New York Times Magazine, the Guardian, and Al-Jazeera America. (She managed to fit in her contributions to this roundtable while reporting from a remote corner of Afghanistan, so thank you, May.) As for me, I live in Canada’s northern Yukon Territory, and my work has appeared in AFAR, Pacific Standard, Smithsonian, and other places on both sides of the border.

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Developing Stories

Eva Holland: I like to gripe on Twitter about overdue invoices as much as the next freelancer, but for all the talk about finances, I think my biggest challenge is still in story idea generation: I have plenty of half-baked ideas, but which ones really matter? Which ones will sell? Which ones will result in stories that people care about and remember? The experience of idea generation as a freelancer is so different from being on staff, where you have a roomful of colleagues to kick things around with, and you can really tell when the group is getting excited—that’s when you know you’re onto something.

So I guess I’m wondering: What’s the hardest part of the job, for you guys? Coming up with ideas? Working alone? The writing process itself? The relentless, but necessary, grind of self-promotion? Getting paid? (All of the above? Ha.)

Jason Fagone: So right out of the gate you asked the big question! For me, the hardest part of the job is finding and developing ideas. When I read interviews with other journalists, sometimes I skip through the interview to see if they talk about how they find ideas, because that’s what I really want to know. Unfortunately it must be difficult to talk about this subject or else I would not still be staring at this sentence thinking about what to type next.

I’m not sure if there’s a way to do it aside from trying to read a lot and being honest about what sticks with you and makes you want to know more. I used to use a trick to bring myself into contact with stories from lots of different sources—I had a string of Google alerts for various words and phrases—but I found myself automatically deleting the alert emails instead of scouring them for story ideas, so I eventually just shut off the alerts. If I’m being honest, I get most of my news from Twitter, so that’s where some of my longer stories begin, with a link in a tweet to a story or a site. I get curious about something and look to see what has already been written, and if there’s nothing in-depth, or nothing very good, and I think I can sell the piece to an editor, I start to report and get a pitch together.

The tricky thing is knowing how much time to commit at that point. As a freelancer I have zero sense of what other people are working on and no way of finding out. And I’ve always hated direct competition. The worst times for me professionally are when I’m in a press conference or a locker room or some situation where there are other reporters around, trying to write about the same thing. I just think, this is dumb, what’s the point of me being here? You don’t need 40 unique perspectives on a football game. It’s insane to me that networks send hundreds of reporters to cover a political debate. Like, you are aware that we can see this too, on our TVs at home? That is so baffling and it just seems like hell, for everyone.

I want to write about whatever other people aren’t writing about. But of course I have no way of knowing what other people are working on, and I don’t want to commit months to a project only to get scooped. So I think I look for stories that require things that other journalists couldn’t easily get, like a cache of documents or interviews with people who haven’t spoken before. And sometimes—I guess ideally this is what happens—I get to the point where it’s like, “This is a good story, and I’m not sure it would ever get done if I don’t do it.”

Eva, you mentioned that one possible hurdle for freelancers is getting paid. I wanted to say that anyone who freelances full time should consider having a lawyer on retainer, a couple hours at a time, to help negotiate rights and contracts. I only did this in 2015 and I’m so glad about it. I thought it would be prohibitively expensive but I was wrong, wish I’d done it years ago. I’ve never had a lawyer send a letter to a publication about payment issues, but I have to think it would work better than sending tweets.

Josh Dean: I think we’re probably all going to agree that finding ideas is the single hardest thing about this job. It’s surely the single hardest thing about any kind of writing, at least once you get some experience and have built enough of a reputation to get past the gatekeepers. I can imagine that if there were a very young and new writer in this group, he or she would say that getting attention, getting ideas looked at, is the hard part. And probably also getting paid, if you’re working primarily in the realm of newer magazines/websites/content providers, where what gets paid out probably depends heavily on what gets paid into the coffers. Those are frustrating things we’ve probably all experienced, and there are occasions where I still have to fight to get paid promptly, but fortunately that’s pretty rare these days. So I’m definitely in agreement with Jason that finding ideas is what keeps me up at night.

It’s funny that you set up a bunch of Google alerts and then found yourself deleting them, Jason, because I’ve had the same experience. I’m still having it, actually, because I can’t bring myself to delete those alerts, in the faint hope that one day one of them is going to yield a gem. But how would I know, when I’m mostly just deleting them. I wrote a book about dogs, and really the dog alert is long since obsolete for me, so I probably should delete that one, and I have pruned them back so that most of the ones I still get are very specific and pertain to people or places or events I’d still like to write about someday. In those cases, I might get an alert once a month, if that.

Also like Jason, I find more and more ideas through social media, especially Twitter. I think Twitter has done two things, which are basically in direct opposition. One is to make sure that even the most marginal and overlooked ideas, if they’re interesting enough, eventually come to the surface. Someone finds them and shares them, often not a person who wants to write about that thing, but just someone who’s interested in that realm. That’s where Twitter is great. You follow the people who love the things that interest you. The other thing that happens, of course, is that those ideas get seen by many of the same people doing the same thing as us. So there are days when I think, “Thank god for Twitter” because I never would have heard about that thing, and there are days when I think, “Fuck Twitter, because I would have found that anyway and now 500 other writers are probably chasing the same story.”

What’s true for me, and I suspect true for you guys, is that I have come to know and understand certain magazines and editors to the extent that I can pretty quickly tell when an idea is going to get serious consideration. I’m not always right, and sometimes they reject good ideas for reasons beyond our control—who among us doesn’t hate the, “Well, we’ve already done an Africa story this year” response—and there are weird outliers, still. There’s actually an idea I love that I’ve pitched probably five times to places and people I was sure would take it over the past year, and failed every time. At this point, I should just accept that I’m wrong about it, but I can’t quite get there. Maybe it’s just a blind spot for me, or maybe I care too much, or maybe I’m annoyed that I can’t convince people I felt I could convince. That’s more the exception than the rule, though. When I see something I think I can sell, and I’ve done enough ass-covering research to know that it’s not something that’s been done recently, or done well, I then feel like I can devote some time to reporting enough to pitch it. That’s helpful, because as Jason notes, this is an investment of your time—time that is not paid—in the hopes of developing an idea to a point where it can be pitched.

I think the fact that I’ve never specialized in a subject helps me. I write about nearly every topic possible, the only commonality being that they’re stories that interest me, for whatever reason. In that sense, the world of possible ideas is vast. There are times when I’m doubtful of this, and jealous of specialists, because if you’re really into the environment, for instance, you know exactly who to follow and what to read and where to look and what’s a great idea versus what’s an idea that’s been done well already. But specialists can be too myopic, too. I’ve written science stories where scientists and even science writers are like, “Why would do you do that story that’s already been done a million times,” only to write it and hear from regular folks, general interest readers, that it’s the first story they’ve actually read on the subject. This happens quite frequently about my current big project, a book about this huge CIA covert op from the ’70s. If you’re from that era, or have a deep interest in intelligence, this is not a new story. There have been a few books. But they were relatively small books, and covered things from a specific perspective. The larger, more sweeping narrative still has yet to be done. I think that happens all the time with magazine stories, too. The chances of uncovering something that’s never been done, by anyone, are so slim now. You can’t let that be your bar or you’ll never get anywhere. You just need to be confident that either you’re doing the story in a new or fresh way, or doing it bigger and better than anyone else.

Now I need to hear more about this lawyer, Jason. How and when do you use him/her? I’ve never once considered this, but maybe I should. Other than buying property, I’ve never paid a lawyer for anything, but suddenly everyone’s recommending them. Jason Leopold, the FOIA expert who Jason profiled for Matter, recently told me to consider using a lawyer to fight and contest FOIA denials, and I’m seriously considering that now too. Which is kind of upsetting, because I hate most lawyers!

Jason: Josh, about the lawyer, I hire her two hours at a time—a two-hour retainer. She charges an hourly rate like every other lawyer and I find that it’s manageable. She works at a firm that specializes in media law, so she knows a lot about journalism and copyright issues. Aside from her help with contract language etc., a lot of what I get from working with her is peace of mind, knowing I have someone to call if I have a legal question.

May Jeong: The most difficult part of the job is whatever stage I happen to be going through at the time!

If I am working on a pitch, it feels like an interminable process; if I am in the writing stage, my dilemmas feel intractable; when I am going through revisions, it feels like I won’t get out of this alive and so on.

But the part that I never tire of is the part where you’re building the story. I am my best self when I’ve let myself go where the story goes.

Josh: Haha. We could probably start an entire thread about revision nightmares. When you have a good thing with an editor who you trust, revision is an important, helpful, and often even rewarding thing—good edits make stories better. But what’s surprising about this until very recently desirable and competitive industry is how many bad editors have been elevated to positions where they can make decisions and influence stories. There are few more painful experiences for me than abiding by edits that I know are bad and wrong and making the story worse. That sounds like the complaint of a grumpy writer who hates people misunderstanding his art, but it’s not that at all. I’m happy to play along when the editing is smart, and I know very well that I sometimes submit drafts that are FAR from ready, but there are plenty of cases of bad editing in my past where I’ve had no choice but to bite my tongue. We have no recourse in that situation. What do you do? Go over the editor’s head? Bad idea. Walk away? Bad idea. Both burn your bridge, almost certainly.

May: I dream daily about an editor who I can grow old with. I was talking about this with someone at a party the other night—how we both want people in our lives who will be our literary lodestars.

Jason: May, I think about this all the time. How do we find such people? I know and work with many great editors but they move around so often. Maybe the nature of the business in 2015 makes this dream difficult or impossible to achieve.

Negotiating

Eva: That’s so interesting about the lawyer, Jason. I’ve never thought of doing that. This year, for the first time, I’m taking the very big step of paying an accountant to handle my increasingly complex taxes, instead of trying to muddle through them myself. (Canadian taxes are simpler than American ones, from what I understand, so it was pretty straightforward to do them myself until recently, when my increased freelancing tangled things up.)

On a related note: I signed with a literary agent this past spring, and we set things up so that while she would primarily handle my (entirely theoretical, at this stage) book projects, I also have the option to bring her in on story contracts on a case-by-case basis. I’ve heard of some writers using their agents as a proxy in negotiations with magazines, and on a big enough contract they’re coming out ahead even with the commission factored in. Do any of you have any experience with that? I can see how it would be nice to have an intermediary, kind of a pinch hitter I guess. I hate negotiating, mainly because I’m very, very bad at it.

Agents and lawyers aside, do you have any tips or tricks for the negotiating process? Step one seems to be: “Actually do it.” I think a lot of newer writers find the idea of asking for more money absolutely terrifying. Assuming you’re beyond that stage, how did you get past it?

On all of this—lawyers, agents, accountants, negotiating your pay—I think there’s probably a good argument for treating your freelancing like a real business from the outset, and not waiting to reach some imagined level of “success” before you start doing things like hiring an accountant or getting legal help. Easier said than done, obviously, in terms of the money. But if you were going to open a bar or some other business, you wouldn’t expect to operate it without any overhead or start-up costs, right?

Jason: Eva, I do have a literary agent but there’s no overlap. The lawyer is for smaller-bore magazine stuff that a book agent wouldn’t handle, and for peace of mind/backup in case of a lawsuit.

Ok, negotiation. I used to be a terrible negotiator. This spring in Michigan I took a class on negotiation, an intensive several-day experience that involved role-playing simulations, and in my first simulation I got a score of zero—I was supposed to buy a shipment of tropical nuts for use in a beauty product of some sort, and I was negotiating against a guy who was trying to buy the same nuts, and after 15 minutes of arguing I just told him, “Look, that’s a good argument, you can have all the nuts.” And I gave away all the nuts. By the end of the class I had gotten better, though. I now take negotiation seriously and try to do it competently.

I don’t know why I used to feel strange about asking for more money, because negotiation is such a standard part of every other profession. Maybe there’s a sense that the pie in journalism is smaller, and publications have less leeway? But I don’t think that’s true. The latitude is definitely there. Magazines and sites find the money for the writers they want. I think Taffy Akner (the great writer / reporter / freelancer) has the right view of this. She was tweeting encouragement to freelancers a while ago, basically saying, don’t worry about all the downbeat freelance chatter you see on social media, you can do it, and a friend of mine chimed in and said something about how you can do it if you’re okay with being broke, and Taffy Akner just said no, there’s no rule that you have to be broke, and maybe part of what’s keeping you broke is that you think being broke is inevitable.

Josh: I also use my agent only for books. He’s great, and I suppose there are situations where I *might* involve him, say, if something like a huge contract from the New Yorker or Vanity Fair came along. But I’m hardly holding my breath for that. I think it’s smart that Jason’s got the lawyer on retainer now, for individual cases where there are contract issues that might arise. Conde Nast, for instance, now tries to grab all film/TV rights, which is a natural reaction to a constricting industry, but it’s also bullshit because those have long belonged to us, the writers. I refused to sign that, as have others, and if you’ve had things optioned in the past, they are willing to give up that fight. They’re also willing to do it if the EIC goes to bat for you. But that’s probably a case where having a lawyer to call in would help bolster your case. I know some of the newer longform publishers—Buzzfeed, for instance—are in the process of sorting out how they’ll handle rights, since they make their own movies, and want to do it more. So it’s going to continue to be a thing where contracts change and evolve and I’m certainly not trained to know how to read them, or amend them to help keep my best interests in mind.

I can’t say I’ve had to negotiate much, but Jason’s right that no one should feel weird about it. Every other job/contract situation involves negotiation and the worst that can happen is the editor/magazine says no. If they want you and your story, they’re not going to fire you just because you asked for more money, and if the editor really has your back, he/she can lobby to the higher-ups to find a little more money.

Regional Ties

Eva: May, I’m wondering about your experience freelancing from Kabul—I’d imagine that editors’ ears perk up when they hear about your location and access? But then there must be downsides, too, to being so removed from the big publishing hubs?

May: I feel so far removed from everything! Until this autumn, I had stayed away from the U.S. for two years and by the end of it North America was beginning to feel like a mythical place. I am not sure if being in Kabul helps or doesn’t help my career, but I don’t think that should be a consideration. You should live in a place that intellectually challenges you, where you feel like you have purpose.

Eva: Do you think about chasing stories outside of Afghanistan much, too? I don’t know much about how easy it is to get in and out of Kabul, or how convenient it is to connect to other centers. Do you view the broader region as your playground, or do you tend to focus pretty locally?

And following up on that, for all of you: Matt Power‘s first piece of advice to freelancers was to move away from New York and the other big North American cities, to head to India or Cambodia or El Salvador or wherever and then build a base and some local expertise, and send stories home. I guess I followed that model, in some ways, although I went someplace cold and expensive instead of tropical and cheap. And it’s worked pretty well for me! It was a strategic career move in lots of ways but, along the lines of what May said, it became more than that. Alaska and the Canadian northern territories are places that challenge and inspire me, and they’re places that I truly love, too.

But I worry sometimes about pigeonholing myself regionally. I’m a subject-matter generalist (with a wide outdoor adventure/sports/travel streak) but a geographical specialist, if that makes sense, and sometimes I worry about my credibility to editors when I pitch stories outside my region. On the flip side, there are also limitations to writing and living in a small, isolated community. If I were parachuting in for my stories, I wouldn’t have to see the people I write about at the grocery store the week after the story drops.

Josh and Jason, I don’t associate either of you especially strongly with a particular region or place, in terms of what you write about. Do you ever wish you had deeper regional ties and contacts to draw on? Do you have trouble convincing editors (or yourself! that matters too) that you can pull off a story in a new-to-you place? Or are you generally happy casting a wide net?

May: I have a few stories in other countries, yes, but the learning curve is very steep. It’s easy to lose your perspective reporting on Afghanistan sometimes. You learn everything you can know about a particular sub-tribe living along a particular tributary and then realize that no one but you and your five friends cares to that level of specificity.

Jason: All I ever knew was that I didn’t want to live in New York because there were so many other writers there. I started out working at a magazine that covered Cincinnati, so I felt tied to that city when I was there, and since 2003 I’ve lived in Philly or near Philly, writing for Philadelphia Magazine at first and then branching out. I still think of myself as a Philly journalist, although the journalism industry here is too grim to describe and I have to look outward for projects to make a living, which isn’t bad, because I’m close enough to New England, New York, D.C., and points south to report stories from there.

I’ve never really had a beat, but there’s a certain kind of story I love to pursue. I don’t know how to describe it. I feel like I have a radar for a really specific thing. When I look at my clips I get a sense of it. Stories about conflicted perfectionists, maybe—people who build private worlds that end up transforming them, or others. Stories about people who recognize some flaw or void in the system and step into the gap. Stories about hidden or forgotten crimes, or people who develop and defend elaborate aesthetics against the world. Profiles of engineers or scientists or craftspeople on the verge of some new kind of prominence. I like to watch people make things that matter to them. I realize this is all pretty vague.

Josh: I had the completely opposite impulse. I wanted ONLY to move to NYC, because this was where the writers live, so I moved here after college and never left. I’m not sure it was the right thing to do, knowing what I do now—and considering the absurd cost of living in this city—but it worked out in the end. Of course, as one of a zillion writers, many of whom are true stars, that means I really have no place identity, which probably is part of how I became such a generalist. I’m very comfortable out of my element, and adapt to new situations very quickly, so parachuting in to new places, even tough ones, has never bothered me. It’s hard for even me to find a common thread in my stories but they almost always center on people who I find compelling for one reason or another.

I’m of two minds about Matt’s advice. He was a good friend, and I admired and respected his work—especially his comfort with being uncomfortable. I think that plan can work, especially right now when the big news agencies have closed their foreign bureaus, which has created an enormous opportunity for young, bold reporters and also for upstart news companies, like Vice and Buzzfeed. It’s hard for me, now a parent myself, to imagine telling my son to move to Kabul or Kurdistan or the Ukraine, but I am seeing new voices emerge from these places. Matt Aikins is an obvious example of a guy who’s thrived. Max Seddon at Buzzfeed has been really good on Ukraine and Russia.

Back to NYC, my wife and I talk all the time about where we’d go if we leave. She’s a writer/editor herself, and she currently has a full-time job, but she’d like to get back to writing full-time and technically I could live anywhere. Two things keep holding me up. One is the ease of travel from here. It’s so incredibly easy to catch a flight (often direct) to nearly anywhere on earth, which allows me to do even far abroad stories in a shorter window—which is important now that I have small kids. I often go to the West Coast for a day or two. I’ve done that with Europe numerous times. The other thing is the community of publishing. I know and see editors and writers all the time, and am able to make actual face-to-face contact with some regularity. But do I need that at this point? I’m not sure. I also think that because of social media it’s less important than it used to be. People are friends now without ever meeting. Look at those of us who use Twitter a lot. I’ve actually never met Jason, but I consider him a friend. I’ve never met you, Eva, but I feel like I know you pretty well. The world is much flatter now. Even Tom Friedman is right occasionally.

Side Hustles

Eva: Yeah, I think a lot about the power of social media, and the role it’s played in my career. Twitter in particular has been huge in terms of meeting editors and other writers. I broke in without any initial contacts, no J-school, no internships—basically just sending cold pitches (no pun intended) from Canada and hoping for the best. Twitter let me introduce myself to the publishing world in kind of a low-key social setting, get to know people, joke around, make friends. It’s the reason why a lot of editors recognized my name in their inboxes, I think, and that can make a big difference in terms of getting a reply early on. I can’t really imagine doing things the way I have without it.

Okay, I don’t want to take up too much more of your time! But I want to ask about two more things. First, side hustles. Non-editorial writing work. They’re less and less a part of my life, and I feel like really well established freelancers probably lean on them less, but they also seem like this sort of unspoken, secret world that many freelancers rely on. We all want to tout our best clips and most prestigious bylines, but we don’t talk much about the other stuff: the technical writing, the communications work, and so on. So I’m wondering if you guys did much outside of the world of traditional editorial reporting and writing when you were getting started? Is there anything you’re still doing on the side?

I’ll go first. Early on I did all sorts of writing-adjacent work to pay the bills. A pub owner once commissioned me to research and write about the heritage building his pub was housed in; the blurb I wrote went on the back page of the menu. I’ve edited a travel brochure for a city government and fact-checked guidebook listings for a big publisher. For a while I worked a lot with a handful of small literary non-profits: I wrote grant proposals and a marketing plan, handled social media, solicited advertisers, and organized public events. I’ve done a bit of ghost writing and communications work, and I still do some archival research for hire (which happened to be my last day job before I started writing full time). I also fill in occasionally at the local paper, when a reporter is on vacation, and I work very part-time at a commercial radio station, reading the news and sports on the hour.

One way that I’ve measured my success as a freelancer is by watching the percentage of my income that comes from feature writing—what I really want to be doing—grow and my earnings from the rest of this stuff shrink. But there’s also something to be said for diversifying your income streams, I think?

Jason: Eva, holy crap, that is a lot of gigs. I feel like a slacker. I did a side job for a friend once, revising a marketing report, and it was straightforward and paid well and I’d do it again, but I don’t know how to find other work like that and haven’t tried. In high school I edited the newsletter of a local golf course for $600 an issue. Looking back, that’s a pretty decent rate! Of course I spent it all on dumb shit like music. If there are any golf course managers reading this, and you need someone to spiff up your print newsletter, I am proficient in Adobe Pagemaker, as well as Microsoft Word, Excel, Encarta, and Lotus 1-2-3.

Josh: I’m glad you asked this, Eva. It actually popped into my head soon after I wrote my reply about where we live and how that relates to what we do. It struck me that I envy how Jason seems to write only big features, about things that interest him, while I find myself doing both that and a good amount of stuff I don’t really love to do—celebrity profiles, service, and consulting/mercenary work. I was an editor before I decided to write full-time, so there always seems to be project freelance work to do in NYC if you want. I’ve done stints at GQ, Men’s Journal, Hearst, and even created a one-off Trail Running magazine for Rodale. I don’t mind the work, but it’s not work I’d probably do if I made enough money to only write big pieces that I care deeply about. Mind you, I’m not complaining at all, because I choose to be freelance and I’ve chosen to do it in the most expensive city in the country. If I lived somewhere cheaper, I could probably do just features and books, but that’s not possible for me (at least not right now). So when I was thinking about place, I wondered if Jason’s decision to live in a less expensive place is a big factor in his choosiness about what he does.

May: I am lucky in that I don’t need to pay first world rent, and so I don’t have to do as much “non editorial writing work” as you’ve called it. The things I am doing are all related to journalism or writing so I don’t see it as a “side hustle” much. This year I had a few speaking engagements, and next year I’ll be helping a friend edit his book. Do they count as side hustles? I am not sure. They are not strictly reporting and writing, but those experiences still feed into my work.

Words of Advice

Eva: Last question! I purposely geared this thing towards more established freelancers. I feel like there’s a fair amount of information and advice out there for beginners, relatively speaking, but much less in the intermediate-to-advanced range. That said, if there was one piece of advice you could give to someone just starting out as a freelance writer, what would it be? (Jason, I know you sort of addressed this in a recent Medium post.)

For me, I think it would be two things, paired together: First, don’t be intimidated. Don’t talk yourself out of pitching the stories you really want to write to the publications and editors you really want to write for. I spent way too much time (years, literally) telling myself I wasn’t ready, I hadn’t earned the right to pitch the places I wanted to pitch, they would laugh at me, I wasn’t good enough, and so on. But an important follow-up to that is: Do the work. There’s confidently sending off a pitch you’ve done your homework on, and then there’s just throwing shit at the wall to see what sticks. I think when young writers aren’t talking themselves out of things, too often they’re rushing things out half-baked instead. This is still something I fight with myself about, on both sides of the equation.

Jason: One piece of advice to people starting out: Learn how to pitch. OK, two: Learn how to write a book proposal and be open to the possibility of developing a magazine idea as a book proposal instead. Weirdly, the way the business is structured, it’s often easier to sell a book to a major publisher than it is to get a long story in one of the most prestigious magazines. A proposal should take about two months to report and write. If you get to the end of the process and feel good about it, the book is probably a thing that should exist. If there’s no book there, you won’t be able to write the proposal at all. So the mere attempt tells you a lot. Then you put the proposal out to market and see if a publisher will offer you enough to write it. At worst, you’ve wasted two months, which isn’t so bad. I’m happy to chat more about proposals if any freelancers want to contact me directly.

Josh: This one piece of advice thing stumps me a little, though I agree that learning how to pitch, well, is critical. A truly good pitch—thoroughly researched and pitched with certainty that no one’s done this story, at least not in the way you’re pitching it—can get you attention, even from a place you don’t know well. (This assumes the editor is actually reading pitches from unfamiliar writers, and I know that’s not always the case). But half-assed pitches, or pitches that repeat obvious ideas or stories, especially that the magazine you’re pitching has done lately, will do you a lot of harm. Editors will remember that.

I also sound like such an old grump when I say this but I really do think reporting is a skill that’s fading away. This is an inevitable result of industry contraction. Few places can afford to let writers spend weeks on stories (or even days) so what you get is a golden era of memoir and essay and news reaction, but also an era in which very few writers interview more than a source or two (if that) in the course of writing a story. I’m not sure I have the answer for how to fix this, since time is expensive. I guess I find myself hoping that the world realizes that having reporters around improves our lives, and we can have to find a way to pay for them. I also really hope book publishing stabilizes to a point where people like us can write books for decent amounts of money and mix those in with stories and be able to make a career of this. Certainly, the bestseller lists aren’t encouraging—they’re all by famous people or about them (or by terrible political/religious figures).

May: Go before you’re ready!

Eva: I think that’s a pretty good place to leave things.

Jason: Josh, May, Eva, this was fun. Look forward to reading your work in 2016! Eva, thanks for pulling it together.

Eva: Thanks again, all. Honestly, I put this together because it’s the type of thing I wanted to read, so this was a lot of fun.

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Eva Holland is a freelance writer and editor based in Canada’s Yukon Territory. She writes mainly about life in the rapidly changing North.

Editor: Mike Dang, Illustration by Kjell Reigstad

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