How to Pitch Stories and Build Relationships With Editors

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Speaker 1: This Ad Free podcast is part of your Slate Plus membership.

Karen Hahn: More. Hello and welcome to another episode of Working Overtime, working as bi weekly advice focused Side Hustle. I’m your host, Karen Hahn.

Isaac Butler: And I am your other host, Isaac Butler.

Karen Hahn: Isaac, how are you?

Isaac Butler: You know, I’m doing okay. I guess it’s been kind of a stressful week. A lot of things, not a lot of time to myself that I don’t know. The Supreme Court said anyone can carry a gun. Dogs can concealed carry. New York now? I don’t know. It’s been a weird time. How are.

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Karen Hahn: You? Yeah, I would say about the same. Honestly, I don’t have too much to add to that conversation.

Isaac Butler: Don’t you think? It’s also like I know you’re in that weird time where you have essentially finished a big project, which is the book, although there’s a lot left to do once it comes out and everything like that.

Karen Hahn: Yeah, that’s true. I have my first, like publicity meeting with the publisher in five days or so.

Isaac Butler: Yeah. And it’s just such a big year change from like, I have to sit at this desk and get this book done if it kills me, and then all of a sudden it’s like, Oh, now what do I do?

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Karen Hahn: Yeah, absolutely. And also it’s like, well, I guess it sort of isn’t my skill set in that I have like I’ve moderated Q&A as before and I’ve talked to like theater managers and stuff about that kind of thing. But like setting up this kind of event is not, I would say, something that I consider a job that I want to do. You know.

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Isaac Butler: Now the hunter has become the hunted. Yes, you are. Has become the heir.

Karen Hahn: Yeah.

Isaac Butler: So what are we talking about today, Karen?

Karen Hahn: All right. So I really, really love taking listener questions, but I thought that I might pivot a little this week. And since we’re both familiar with the freelancing lifestyle address, a question that I think a lot of us had when we were starting out and I think is still a question that a lot of people have, even if you are in the thick of it, which is how do you pitch a story together?

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Isaac Butler: And don’t, don’t.

Karen Hahn: And to give a little more context to the advice that we’re going to be giving. I wanted to ask you, how did you get started pitching and what was your experience beginning as a freelancer?

Isaac Butler: I kind of backed into it in a weird way, like I was a blogger in the aughts, you know. And through that I met a bunch of people who went on to become editors and things, the two most important ones being Rob Weiner, Kent, who became an editor and then the editor in chief of American Theater. And Dan Coats back when he was at New York magazine, actually. And they reached out to me for pieces, I think was actually how it started at that.

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Karen Hahn: Point is blessed. Like you were very, very lucky.

Isaac Butler: I was lucky in that I backed into it and a little spoiled by that. You know, the way this is contextually matters is I still get a little weirded out by pitching. You know, it’s still a little bit like, oh, god, this is a person I don’t know. And I’m so used to doing this with my friends or, you know, whatever.

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Karen Hahn: Yeah, I will say that I started out writing when I still had a day job. I would go home and then write posts for a personal blog that I set up and I would start using those posts to send to editors of smaller sites to sort of show that like, I can write something that’s pretty coherent. And once I started getting on to the smaller sites, I would use those as my clips, as we call them, for bigger size and bigger editors to land kind of bigger gigs. Obviously, there’s a little more to the story, but that’s pretty much what we’re going to get into in the meat of this episode.

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Karen Hahn: And I wanted to know, did you look for advice on pitching when you started out and did you ask friends how they did it? Because it feels like your relationship to pitching might be slightly different given that your start was a little different as well.

Isaac Butler: Yeah, I absolutely though ask for advice. Early on, I even asked people to show me pitches that had gotten accepted places so that I could see what the format was. And actually I should shout out my friend Jason Zimmerman, who has pitched a bajillion pieces of bajillion places. And when I was first starting out, he was like, Look, this is what your pitch needs to do. It needs to do X, Y and Z. And he was extremely helpful in explaining that world. I do think that pitching can be really, really mysterious and the mysteriousness of it can be really anxiety provoking to people. At least it was to me when I’m first starting out. So I’m glad we’re demystifying it today.

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Karen Hahn: I’m sure we’re going to talk about this later, but I think a lot of that anxiety comes, especially when you’re just starting out. It feels really personal. It’s hard not to get emotionally invested in something, even though ultimately the reasons that an editor will say no probably just have to do the fact that either they already have something similar in the work or they don’t cover the kind of thing that you’re trying to pitch. Or it’s usually not like we don’t like you.

Isaac Butler: Yeah, totally.

Karen Hahn: That said, on my end, I don’t know how much advice I asked for, but I definitely went looking for it. Like I would just kind of Google like are there pitch guides? And what’s also useful is that you if you find editors on Twitter, more often than not, occasionally they will post calls for pitches where they explain what they’re looking for and in some cases will even post like, Here’s a guide on how to pitch our publication, specifically how to structure your email and what kind of thing they’re. We’re looking for it, which will make your job as a pitcher a lot easier.

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Isaac Butler: Absolutely. I should also say one of the really good examples of that is actually Slate’s How to Pitch Slate Go. It’s very specific. It’s very detailed. It has a list of exactly who you should send things to and an example of a successful pitch that they took.

Karen Hahn: Yeah. So looking at the guys is going to be really, really helpful for you to like to be specific as possible. For instance, like, I know I have a lot of friends who are editors now and they will often get pitches. They’re like for this publication that you aren’t actually a part of, Can I write this? So it’s like you really have to be as specific as you can in the email, even if you are sending it to multiple people. Like make sure the details are right. Make sure it works for that site.

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Isaac Butler: Absolutely. And we’ll have lots more tips about pitching after this.

Karen Hahn: Hey, listeners, is there a crucial part of pitching that we’ve missed that you want us to address? Do you have a pitching secret? Let us know by emailing us at working at Slate.com. Or even better. You can call us and leave a message at 3049339675. That’s 304933w0rk. So speaking of how I found these guides and so on, this brings me to another question, which is how do you figure out who to pitch? And I’ll throw that first to you.

Isaac Butler: Is it? Well, one thing that I would say is that publications have gotten a hell of a lot more transparent about this stuff than they were when I was starting out, which I think due to our relative age difference, was actually a few years before you were starting out. And even in the gap between, those have become a lot more transparent. Absolutely. When I was starting out, you know, Twitter wasn’t that old. And I don’t know that most editors, buyers would be like pitch me at in there. They weren’t necessarily thinking about it even as a professional thing. And now most places you can Google how to pitch X and find it. And so in my day, that was really in my day.

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Karen Hahn: So what was it like getting paid in just like turkey legs and bones.

Isaac Butler: Paid in Turkey? Yes. And you know, I would go and post my articles on Friendster.

Karen Hahn: You nailed them to the front of the, like, church door.

Isaac Butler: Yeah, exactly. Nailed to the front of the church door by my Shakespeare analysis. No, you know, slate. I would just send the email to Dan, and Dan was like, I’m the wrong person to send this to you. He’d forward it to someone. You know, we we developed a relationship very quickly as writer and editor within like two or three pieces, we were corresponding pretty regularly. And outside of that, you know, I would just have to find someone who had been published by the place that I knew and been like, who do I pitch at this place? Who do I pitch at that place? And they would sort of let me know. But, you know, okay, I have do have a funny story about this that is also about how I got my start. If you can bear with me for a second.

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Isaac Butler: Okay. One day on Twitter, I had just gotten off a flight and I was feeling very punchy and I just started tweeting about how Hamlet is fat and what is fat. We don’t want to talk about this. It’s a national scandal, but there are no fat hamlets. And a friend of mine wrote me and said, who shall remain nameless, but a friend of mine wrote me is like, this is a hilarious idea. Here’s my editor’s email address. Write him, impeach him. You know, CC me, we should definitely do this. I wrote that editor. I didn’t hear anything back for a couple of days and I was like, Well, clearly they don’t want it. I’ll write down and see if Dan won. They wrote Dan and Dan wrote back immediately. That’s hilarious.

Isaac Butler: Yes. Let’s do it right. And I did it. And that piece was called Is Hamlet Fat? A Slate investigation was a big hit. I mean, people still joke about that piece with me today or talk about it today for whatever reason. And after it was a big hit, the editor at the original magazine writes me back and says, Hey, I’m really sorry that I missed this. Obviously, we should have published it. It came out really well. You know, I hope we’ll be able to work together in the future. I wrote back and said, Hey, no hard feelings. It’s great. I totally understand you’re busy. I actually have another idea for a piece. Here it is. And then he never wrote me back. I mean.

Karen Hahn: Come on.

Isaac Butler: Right. But again, it’s not personal. It’s all your it’s not personal. It’s just, you know, he had a million other things to do, and it just slipped his mind.

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Karen Hahn: Yeah.

Karen Hahn: I feel like I see this a lot in our kind of more advice oriented episodes, but it really, in every aspect of your life, it is really important to just exercise some common sense because as you’re saying, like one of the really important things to you is like developing this relationship with Dan and it is really crucial to develop a good working relationship with your editors. And that’s only going to happen if you use your common sense in how you interact with them, like respect their time, respect the time they’re spending on you to look over your work and stuff. I mean, not to rag on people, but talking to my editor friends about some of the worst experiences that they’ve had, they’re always like, This person doesn’t take any of my notes. They just reject everything. They pretend that they basically haven’t heard me. That’s not a good way to work with somebody. Like if you get a note that you don’t like, don’t pretend it’s not there. Like try to work it out with the editor. It just like be nice, be a nice person.

Isaac Butler: I do think, you know, the editor writer relationship is a professional one and it’s a creative one. But you are also two human beings, you know, and you have to remember that, particularly if it’s an online publication that editor is dealing with, like dozens of moving parts at once.

Karen Hahn: And it’s not hundreds.

Isaac Butler: If not hundreds. Yeah. And one of the things that you can do that will make you more employable with them in the future is to not make their life more difficult.

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Karen Hahn: Yeah, exactly.

Isaac Butler: That’s not to say hide a disagreement if you have one.

Karen Hahn: Yeah.

Isaac Butler: You shouldn’t avoid conflict or anything like that, but it’s just like file, clean copy, you know, try not to make mistakes, be considerate of their time. Try not to create fires that they have to put out and, you know, take their point of view seriously and write and deal with them in a polite fashion.

Karen Hahn: All right. So now let’s get to the really big question, which is how does Isaac Butler structure a pitch? Walk me through what your typical pitch email looks like.

Isaac Butler: Sure. So I do it by hand delivery.

Karen Hahn: That’s right. You know, to the.

Isaac Butler: Letter glitter inside, you know. So they open it and glitter. Wrap it up and put it on.

Karen Hahn: The leg of a pigeon.

Isaac Butler: Yeah, exactly. No. So this might sound obvious, but to get back to how beleaguered our poor ed friends are, the finger pitch needs to do is to convey to a very busy person what the piece is actually going to be like in a way that is exciting to read. Like the pitch needs to be exciting and fun to convey some of the sense of excitement and fun, both of the piece itself and of what you will be like to work with.

Isaac Butler: Editors work extremely hard. As we’ve all said, they have to feel the bajillion things an hour. So I start with a greeting. I do a grabby sentence or two. You know, think of it as like the cold open, you know, the freeze frame with like, yep, that’s me. You probably wonder how I got myself. No, but you do a you do a grabby sentence or two about the main thrust of the piece. Then explain in greater depth why someone is going to want to read it. What you have to say about it. You know, what is the burning question you have here and what your provisional answer is? Don’t just ask questions because then they’ll be like, Well, do you have an answer for that? What’s going on, buddy? And if I don’t know them and haven’t worked with them before, I’ll do a couple sentences, maybe a paragraph about myself with links to representative clips and pieces.

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Isaac Butler: So again, with that Hamlet piece, you know, I started with I want to write is Hamlet that a Slate investigation? Because I knew what Slate investigations were. I knew that this was like the perfect fit for that. And if I gave it that title, Dan would know exactly what I was told. And then I sort of went into that being like, I want to use this as a way to introduce readers to how Shakespeare scholarship really works and how you know what Shakespeare meant when he said anything, you know, and then what are the issues in there, etc., etc. and so forth. And then because Dan and I already knew each other, I had written one piece for him already. I did not do the whole. As for me, yeah, I mean, blah, blah, blah, you know. What about you?

Karen Hahn: I mean, I think you basically have it down like that is what a good pitch should look like. So my answer is going to sound a little bit repetitive. So for me, pitches roughly follow this structure. Do you say hello? Obviously. And then you have to light paragraphs about what you’re pitching. The first one is where you really put in. This is my thesis. This is the main topic of what I’m going to talk about. And the second one, usually we’ll explain it a little further, kind of getting it more granular details.

Karen Hahn: This is also where people tend to say that you need to explain why you think you should be the person to write this piece, which I think is crucial to understand, can be kind of on two different levels, whether it’s because you have a really personal connection to the material or because you’re an expert on the subject, have something unique to say, which is maybe the most important thing because you don’t want to pitch a piece that somebody has already published to them. And then after that, you have a couple lines with a little more background about yourself and links to other works that you’ve published that will show off what you’re capable of. And like other people who have trusted you basically to write something for their site and write a nice thank you and a sign off.

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Karen Hahn: All right. So now that we’ve talked about how to get the plane off of the ground, what do you do after that? How long do you wait to hear back before you follow up with the editor?

Isaac Butler: Okay, let’s be honest. What I do after that is I reload the inbox every 5 minutes. Yep. And I go, Is my career over? Do they hate me? Is this the worst pitch they’ve ever seen? Oh, my God. Am I going to be drummed out of the industry? What have I done? What have I done? What have I done? And then I’m like, Just put your phone down and do something else. Butler And then I go do that.

Isaac Butler: But in terms of how long you wait? A week, tops, I would say before following up, I usually do less than that, actually, if I’m worried about the story going cold, you know, it’s a movie coming out and you might, you know, you need to get in touch with the PR person and book an interview before a thousand other outlets do or, you know, whatever it is, I might follow up faster than that, but either way, the follow up should just be short and sweet, you know? Hey, Karen, just checking to see if you’re interested in move this to the top of your inbox. You know, hope you have a good one, Isaac. It should not be anything like more needy than that. And then pretty quickly after that, if they don’t get back to you, you should probably start pitching it somewhere else.

Karen Hahn: Yeah, I say I usually give it a week or a week and a half. I should also mention that I really tried not to send any emails, whether it is the initial pitch or a follow up on Fridays, because I think that’s kind of the worst day to send anything because that’s when you don’t want to have anything new in your inbox. Mondays is kind of similarly dicey because they’re getting a lot of emails over the weekend, but at the same time, it’s still a better bet than Friday, in my opinion, at least when it comes to my email reading habits.

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Karen Hahn: That said, as you were saying, if it’s time sensitive, sometimes you will want to follow up more quickly and that can get a little bit tough because it does feel like you’re being annoying. How do you handle that?

Isaac Butler: How do I handle the being annoying? Oh, God. I mean, I am someone who has difficulty asking for things in general. That’s my favorite thing to do. You know, I’m someone who, like, wants to do everything myself. And I don’t know, it’s hard. And so you just. I just kind of have to get over that. And I just try to be as polite and friendly as possible and, again, keep it short so that I’m, like, out of their hair. And I just let you know if it is a quick turn around thing I do say in the initial pitch as early as possible in because they might not read all the way. You know, a publicist just wrote me and the press day for this is in three days. So, you know. Can you is there any way you could let me know within the next day or two? I’d really appreciate it. You know, I do something like that. Editors know that writers have difficult schedules and tricky things. And the PR people, especially when it comes to movies and TV, you know, junket days and everything like that, it’s very complicated and they understand that. And so you just have to know, like they’ve been through it before. Just. Just be kind about it and expect the same from them.

Karen Hahn: Yeah. Basically, like be as patient with the editor as you hope that they would be with you is a good rule of thumb. I feel like that said, I get really anxious having multiple irons in the fire in the event that more than one person get gets back to you at the same time about a pitch you’ve sent out. But in cases like this where you are trying to pitch something really time sensitive, I’ll usually send one pitch to the place that I really, really want to place this piece at, and then I’ll give it a couple of days before one. Following up with the initial editor and then to sending the pitch to a different place as well. Because again, editors like they know what the writer’s life is like and they’re generally pretty understanding if it ends up having been sold somewhere else before they get back to you.

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Karen Hahn: And I guess there’s one last thing about pitching that we should talk about, which is getting paid for it or negotiating your rate. Because the truth is that a lot of publications, not because the editors, malicious or anything, will try to lowball you just because they don’t have as much money as they’d want to pay freelancers. And it is really tough to write back and be like, Can I get more money? Because it feels like being ungrateful to someone who’s already said that they want to publish your work. So how do you handle negotiating rates?

Isaac Butler: It’s really tough. My friend Jamie GREENE, who’s a wonderful author and editor. Her piece of advice about this is just always ask for more money and always ask to keep ownership of the writing. Mm hmm. And her point is, just do it every time. Every time, reflexively. And then it will get easier to do if it’s just your policy that no matter what, I’m going to ask you for more money and I’m going to ask for ownership of the work, then it will stop feeling as bad.

Isaac Butler: That said, do I do that? No. Sometimes I’m like, oh, $7 and half a pound of slivered almonds. Thank you so much. You know what I mean? It’s hard. It’s hard for me. It triggers all sorts of weird anxieties for me. But you just gotta get in the habit of doing it. I think obviously, you know, if someone is offering you a rate that’s like $0.05 a word or whatever, it comes out to like $0.05 a word and you are going to counter them with something hugely more than that. Like it has to be a dollar a word or, you know, whatever.

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Karen Hahn: A dollar word is like almost unheard of. You’re not going to get that.

Isaac Butler: I’ve gotten it a couple of times, but it was for actual magazine pieces. But anyway, I’m just saying, it’s like you shouldn’t counter with something that’s outrageous. You shouldn’t counter with something that is unbelievably far and above what they have offered you, you know what I mean? But you should try to counter with a little, a little, at least a little bit more, if anything, just to get in the habit of doing it.

Karen Hahn: Yeah, I don’t think I would say every time ask for more just because that’s a lot of work. But it really helps in these scenarios to have a little experience with it. And I mean this in two ways. The first way is being experienced in terms of having other things that you’ve published, just show that you are in demand or are a good writer who deserves to be paid more. And this will also translate to my second point, which is that you’ll have a better idea of what different publications pay. So when you go back to someone who’s trying to offer you $7 and a bag of slivered almonds, you can say, well, actually, when I was paid for a similar work at X other company, I got paid this much and this is my usual rate. Can you try to match it or at least come close? Like that’ll help a lot to have that kind of context to give to editors.

Isaac Butler: Yeah, absolutely. Absolutely.

Karen Hahn: All right. So do you have any last pieces of advice for pitching?

Isaac Butler: I’m just going to put this out there. And please disagree with me. If you feel like pitching doesn’t feel good, it’s like a feel good. Yeah, it’s not going to feel good. And that’s just. It’s just part of life. You just like sometimes you have to do things in your job that don’t feel good. And if you’re going to be a freelance writer, pitching is the thing that doesn’t feel good. And so you just have to work through it. You just have to work past it. But it’s not some sign that you’re especially shy or you’re a bad writer or you shouldn’t be doing it or whatever. It’s just it it feels vulnerable to pitch. It’s like, you know, back when I was an actor auditioning for things. Yeah, it’s that part of the job. It is. It’s going to make you feel vulnerable. It’s going to make you feel anxious. It’s going to feel a little weird. You’re always going to think, maybe I didn’t write that pitch that, Well, you just got to do it more and more and get used to it. There’s nothing you can actually do about the fact that it feels bad.

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Isaac Butler: And also it’s not personal. Everyone’s just really busy and trying to put out the best website they can in a day or, you know, whatever it is. And so don’t take rejections personally, keep working at it. And also, of course, know the place that you’re pitching and know that it’s the right outlet for the piece. Don’t carpet bomb pitch. Editors can tell and they get annoyed by it.

Karen Hahn: Yeah, I guess I have two last pieces of advice. One is something I said earlier, which is just use your common sense in terms of how to treat people, because that leads into my point number two, which is it is really, really beneficial for you to develop a good working relationship with your editor because as Isaac says, it is really vulnerable to pitch someone and you will feel better about doing it the more you’ve done it, and also the more you trust the person that you’re pitching to be careful with your feelings or to be considerate of your idea and your time that you’ve sent to them. All right. That’s all the time that we have for this episode. Thank you so much for listening.

Karen Hahn: And if you like the show, don’t forget to subscribe wherever you get your podcasts. And if you have ideas for things we could do better or questions you’d like us to address such as Oh, but you didn’t address x part of pitching. Can you please talk about this? We would love to hear from you. You can send us an email at working at Slate.com or give us a ring at 304933w0rk.

Isaac Butler: If you’d like to support what we do, please sign up for Slate Plus at Slate.com. Slash working. Plus you’ll get bonus content, including exclusive episodes of slow burn and Big Mood Little Mood, and you will be supporting everything we do right here on working.

Karen Hahn: Big, big things. To Kevin Bendis and to our series. Producer Cameron Drewes will be back on Sunday with a brand new episode of Working and in two weeks we’ll have another working overtime. Until then, get back to work.

Karen Hahn: So.