S5 E54: Pitching Insights with Travel Editor Ashlea Halpern

Get the show’s transcript

“AH: I would also say to clearly put – this seems really basic – but clearly put the word ‘pitch’ in the subject line. We’re getting 50, 100, 200 emails a day, half of them come from publicists, so you’re scanning very quickly. Often, you don’t even click in. You just delete it based on the subject line. Make it clear there’s something exciting inside; ‘pitch’, colon, very quick description of what that thing is.”

[INTRODUCTION]

[0:00:28.3] YD: Welcome to the Travel Media Lab Podcast. I’m your host, Yulia Denisyuk, an award-winning travel photographer and writer, entrepreneur, community builder, and a firm believer that every one of us can go after the stories we’ve always wanted to tell with the right support, encouragement, and structure. 

I’m on a mission to help women storytellers everywhere break into and thrive in the travel media space. If you’re ready to ditch your fears to the side, grow your knowledge and confidence, and publish your travel stories, you’re in the right place. Let’s go!

On the podcast today, I want to share with you a part of a very special conversation we had in our membership, The Circle. Inside our membership, we run a weekly check-in, monthly brainstorm meetings and workshops, and more, all with the goal of helping our members publish their travel stories. And occasionally, we invite wonderful people from inside this travel media industry to share their knowledge with us. This is what I’d like to share with you today.

We held a workshop with Ashlea Halpern, a veteran travel editor who has worked at publications like AFAR, Conde Nast Traveler, Bon Appetit, and more. In this hour-long workshop, Ashlea covered her tips for working with editors, what to include in your pitch and which ideas would get the editors excited. Our members also had a chance to ask Ashlea just about any question on working with travel editors.

I really love the space and the community we have created inside The Circle and I hope that in today’s episode you’ll get to feel a bit of that support and community too. If you're interested in joining us inside The Circle, I want you to know that we have three different levels at which you can join us and start working toward getting your own travel stories published.

By the way, all of our workshops get recorded, so when you join, you get access to the full conversation with Ashlea. Get more information about The Circle and join us at travelmedialab.com/circle. All right, let’s get into this episode.

[INTERVIEW]

[0:02:43.7] YD: All right, welcome everyone to our workshop. I’m really excited that we were able to do this with Ashlea today and we’re going to give people some more minutes to join us but while we are, I’ll introduce the wonderful Ashley Halpern who is just such a joy to work with and a wonderful person who I’ve met, I had a pleasure of meeting in person during the conference at IMM, International Media Marketplace, a couple of years ago now, right? I think – was it 2019?

[0:03:18.3] AH: It was right before the COVID shut down, the first COVID shutdown.

[0:03:22.7] YD: The original shutdown. Yes, we were – I was very lucky to do work with Ashlea and then we became good friends. Ashlea’s an incredible storyteller, editor, writer, traveler, very savvy traveler who seeks out just really wonderful stories around the world and of course, Ashlea was on our podcast as well so if you guys haven’t had a chance to listen yet to our episode, please do because she shares lots of insights there too. 

I thought it would be really nice for her to come in and talk to you guys face-to-face and really just give her perspective and lift the veil, although, I don’t really like that expression so much but lift a bit of that mystery that we have about working with editors and what is that all about, you know? 

In The Circle, we often talk about how much trepidation we have pitching editors and we often have a lot of different fears associated with that so I thought it would be so great to meet the real person behind the editor’s job and see how wonderful she is and how much she can share with us today.

Without further ado, I introduce to you guys the wonderful Ashlea Halpern and yeah, very happy to have you here tonight, with us Ashlea, so welcome.

[0:04:44.1] AH: Thank you. I can’t possibly live up to everything she just said so prepare to be disappointed right form the start. 

[0:04:50.5] YD: No way. Well, so, I think the way I was thinking that we can take this is that perhaps for the first 30 minutes, Ashlea can share some thoughts on this topic of working with editors, working with freelancers, some best practices, some insights, some things that she has seen over the years and then, I’m sure you guys will have some questions so then we can have a bit of open conversation later on which I thought will be just really wonderful as well. How does that work for you, Ashlea?

[0:05:20.0] AH: That’s perfect. I should say too you know, I’ve been an editor in-house at a lot of magazines, I’ve worked with the contributing editor and large various publications but I also write a lot. I know both sides of the fence, I have dealt with the same fear and trepidation and especially cold pitching people, people you don’t know, feeling like you had the best idea in the world and then it’s similarly rejected by every outlet you’ve ever encountered, it sucks, I get it. So, I think I can speak to both sides of the equation and I’m happy to answer any questions you might have to the best of my ability.

[0:05:53.8] YD: Yes, actually, if I may share this, Ashlea, just a little tiny snippet of my experience of working with you. I remember how incredibly nice and thoughtful and empathetic you are to every time we communicate about things like rejections, right? For example, when I pitch something and it doesn’t get accepted by the magazine, I just get the most thoughtful and nice thoughts from you about those rejections and I think that is because you have both of those perspectives, right? You’ve been on both sides so you know how it is.

[0:06:24.6] AH: Well, it drives me insane when editors don’t reply, having been on both sides, there’s just no – everyone’s busy, writers are busy, editors, everyone in the world is busy. You can take two seconds to write a two line reply, at least get status check for people, let them know where things are at and I think the most important thing and why at least, with writers that have clearly put effort into a pitch, I try to let them know why it doesn’t work. 

Often, it has nothing to do with their pitch, it has to do with internal agendas, it has to do with top down management, there is like 10,000 things, it could just be about one of those places that, “Well, we did a Philly story three years ago so I think we’ve met our quota for the next three decades, hit us back when you’re 45” or whatever the weirdness is. 

So often, it has nothing to do with you and I feel like that’s really important to let writers know that and encourage them to keep coming back with ideas because at the end of the day, they’re feeling the most of your pages. Lots of cool ideas are generated in-house with some of the very best stuff often comes outside that ivory tower.

[0:07:31.4] YD: Yes, oh my God, it’s so amazing to hear that again from – Charlotte says, add note to calendar for 2061, that’s exactly. It’s so amazing to hear that coming form you, Ashlea, right? Because I talk about this in The Circle, you guys have heard me say the same thing again and again but it’s just so wonderful to hear it from you, so that’s awesome. 

[0:07:53.9] AH: There’s often, I mean, there’s so many ideas. Yulia has pitched so many of them that I think are incredible and just for one reason or another like I want to read that and if I want to read it, even if I was not going to get to read it in whatever publication I’m assigning for at that time, I want to read it somewhere, so I don’t want them to give up on that idea because there’s a lot of publications out there. 

At the same time, I don’t want them to sell themselves too short and wind up selling it for pittance. I’d rather they keep trying some place that’s going to offer some return on their investment in the work.

[0:08:24.7] YD: In that vein actually, I wonder if you could sort of give us your thought on how to manage that push and pull, right? Because there’s this like, I want to place this story, I wanted to find a home, I want to find a nice and appropriate home for it but also, I don’t want to keep pitching it for a year and then the energy dies on it or something. How do you think about managing that tension?

[0:08:49.6] AH: I think it depends on the type of piece, certainly depends, are you picturing something more feature-y, something that’s going to evolve a lot where you’re going to have to keep reinterviewing. How time sensitive is it? Obviously, time sensitivity if it’s pegged to an opening or some sort of major news like say, some UNESCO thing is happening and you know there’s this time sensitive pitch, you have to hustle a little more. You might have to lower the bar a little bit but hopefully that type of story can be a quicker turnaround too.

If your heart is hooked into something that you know it’s important to tell in a certain way and it’s not ultra-time-sensitive, hold out and you do have to hold out. It’s such a slow process, it’s even worse with print editors, like the glacial pace that things move. If you’re open to digital which, let’s be honest, a lot more people are probably going to see, depending on the outlet, go digital for sure.

It's also a better way, an easier way to get in with the publication you have it written for, it’s to start with their digital team to be able to show those clips and be able to segue into print. I’m also – I used to be that person that just was die hard print, everything had to be print and now, frankly, between the quick turnaround, I like the reach of online and I like getting paid faster, so much faster generally with online and print stories.

[0:10:08.6] YD: Definitely. If you could recall some of the best experiences of working with freelancers and some of the, perhaps, pet peeves that we should watch out for. I’m sure you have – 

[0:10:20.5] AH: Yeah, I made a whole bulleted list. One of the first things, especially if you’re cold contacting a place is contact one editor at a time. Don’t spam half the staff. I know it’s tempting when you don’t know who to focus your pitch on but you’re still better off one at a time. Spamming too many or even putting two or three editors on, it can feel spammy and then you’re kind of giving them an out not to reply to you because they’re like, “Oh well, I figured so and so would respond to them” no. 

Laser focus on one person if you can and if they’re not the right person, hopefully they’ll be decent and suggest, “Oh actually, so and so edits that section, contact them instead.” That’s one of the first things. I know, it can be painful to wait but don’t – I’ve definitely had someone pitch and then they will follow-up the next day or three days later. Give it at least seven to 10 days and I would say, if you followed up twice, unless you already have a working rapport with them and you know that they’re just like kind of a hot mess and can’t be on top of their email and you have to pester them to get a response, let it go after especially after a third response, don’t keep, like find someone else on that staff or pick another outlet to focus on. 

I would also say to clearly put, this seems really basic but, clearly put the word ‘pitch’ in the subject line. We’re getting 50, a hundred, 200 emails a day. Half of them come from publicist so it’s – you’re scanning very, very quickly. Often, you don’t even click in, you just delete it based on the subject line. Make it clear there’s like something exciting inside. Pitch colon, very quick description of what that thing is.

I also think, keep it short, like most editors have sort of ADHD, just inability to concentrate anymore. It’s got to be three short paragraphs or less and I know that can feel really hard to boil down something but think of it as the equivalent of an elevator pitch. If you are riding the elevator with Mark Cuban and you have 30 seconds to tell him what your business is, that is essentially what you’re doing with this. “Here is who I am, here is my idea, here is why I am the best person to tell it.” 

Don’t send attachments, please for the love of God, don’t send attachments! Don’t attach clips, don’t, we know how to find that stuff. If you have a great looking portfolio online, by all means, link to it. You can mention a few marked places that you write for just to kind of establish credibility right out the gate but don’t send attachments. 

Don’t send unsolicited manuscripts unless they have specifically requested it. I think the New York Times modern love column might do that, might ask for a full manuscript but most places don’t want that and they’re not going to read it and if it looks remotely spammy, it is going to get deleted or automatically routed to a spam folder. 

I would say one pitch per email. I get a lot of new writers who want to throw all the ideas at the wall and I think they think, “Oh they’re going to see how many genius ideas I have” and that may be true but put your best ones forward first. One or two, absolutely no more than three and still stick to that three paragraph kind of, nothing longer than that because it won’t get read. 

You should interrupt me at any time you like because I’m like 9,000 bullets. 

[0:13:22.8] YD: Oh, this is like gold. I am just loving to hear all that from you. I think one thing I want to just point out because actually for me, it is a great refresher too, just the realization of how freaking important subject lines are.

[0:13:36.1] AH: Yeah, for real.

[0:13:37.6] YD: It is probably the most important thing to get to ensure – well, it is the thing to ensure in the pitch is even get opened, right? 

[0:13:45.8] AH: Yeah and you just have to remember, editors are just being inundated with press releases and you know sad to say, I don’t look at the vast majority of them unless the subject line really catches me or it is coming from a PR person that I’ve already have a relationship with, I know they don’t waste my time with stupid stuff. You want to stand out from that but I almost will always open something if it says ‘pitch’ because I’m like, “Oh, what do we have here? What is this?” 

I do think it is important to acknowledge other stories that have been written on a topic specifically by the outlet that you’re – by the outlet but also by the outlet’s competitors. Make it clear like you’ve done your research, you know what’s already been written about this out there and if there is a lot then say how you’re going to evolve that story. What you’re going to add to spark new conversation around it or make people think about it differently. 

That is why I definitely, I feel like a bit of an amateur move I get from a lot of newer writers is to pitch very kind of generic SEO friendly content like best this, best that, all that stuff mostly is being handled in house or it’s going to already be farmed out to a group of sort of trusted stable of freelancers. The first way to get in at any place is just to have an exceptional idea or an exceptional spin on an idea that’s already out there. 

[0:15:04.9] YD: I think that is a really interesting insight for you guys to take note because actually in The Circle, we talk a lot about getting a foot in the door with some, let’s say, simpler pitches and ideas but you are actually saying no, bring your most interesting and intriguing idea that perhaps no one else can bring, but that’s what you mean. 

[0:15:23.8] AH: You know what though? That depends on the outlet. If you’re – I am thinking of it more like the vast majority of travel editorial I have been doing in the last two years has been with Condé Nast Traveler, so I am thinking more in that vein right now, place like AFAR. If you are pitching places like thrill list, things that are more generalist, less specific then yeah, that approach could work but at least most of that outlets I have experienced with the SEO, those that they definitely do those SEO articles all the time. 

That they often go to staffers, they are often cobbled together from pre-existing content, which is why staffers handle it or it is just, A, we know we have to do this holiday stuff around this time. We’re going to farm it out to a freelancer for a quick turnaround. So I think it’s more of advice for cold approaching someone for the first time, at least those types of outlets, ones that are a little less like Culture Trip, Thrillist, just straight SEO kind of content forms. 

[0:16:21.7] YD: No, that makes sense. 

[0:16:22.9] AH: This is a little more relevant I think for print and I say this also as I used to edit the strategist section at New York Magazine and I was a special projects editor at Bon Appetit for a while, if you want to pitch print, I think it’s really important to think about packaging. How does this look in print? How many pages are you envisioning it? Is it a straight right through? Are there side bars? 

Is it a runner plus pull quotes and call outs and a ticker at the bottom with like extra advice? You don’t want to think like a print editor and it just can help with even though it is technically the editor’s job to do that, you are making their job easier. You are already thinking through, “How does this thing look in a print magazine? What makes the package cohesive feeling and how many different elements can you incorporate? 

You can do that a little with digital, sometimes it will add a side bar or something but I don’t think it is as important for digital? 

[0:17:13.5] YD: Two points on that. First, I love that you used that phrase make editor’s job easier because that is exactly what I talk about all the time like put yourself in the editor’s shoes, have some empathy to that job because it is not an easy job by any means and if you have that empathy and that perspective in your pitches, I believe that it will make it easier for you to get your pitches accepted because you have that perspective. 

But for your point about imagining how the print piece would look like, so you recommend that we put it in the initial pitch like as a – maybe a couple of lines at the end like, “This is how I imagine it" kind of thing. 

[0:17:49.4] AH: Yeah, I think it is even one sentence, two sentences, you know? Obviously, I come from more of a packaging background. A lot of my jobs have been heavily packaging when you get some 12-page thing in Bon Appetit and it has 12 different ways to do something in each element and one is an infographic and one is a little essay and one is a – so I think a lot in those terms. 

It could be, you know, I am imagining this as a 600 to 800 word story with two side bars and here would be the ideas for the side bars. It’s just kind of imagine editors as like the laziest people in the world and anything that you can do to make that – to make their job easier when they have to turn around and then pitch it up the ranks or take it to an EIC, you are making them look good. I mean, it’s like, “Oh, they already thought through the packaging in this thing.”

[0:18:35.2] YD: Interesting. 

[0:18:36.0] AH: It is more likely to get green lit that way. 

[0:18:37.5] YD: Interesting and the EIC is the Editor-in-Chief meeting where all the ideas from all the pitches they have been receiving gets discussed usually like once or month or something, right? Although in some places, they continue it. 

[0:18:49.8] AH: Yeah, it depends on the publication. When I was at New York Magazine, it was weekly and everybody dreaded it. It was so much pressure and people would give themselves ulcers dreading those meetings and it was just a really intense atmosphere. Monthly is they might be more once or twice a month and often, they are smaller pitch meetings. You might just be meeting with your team to go over ideas and then everyone sort of agrees on, “Okay, these are our five strong, let’s take those to the IEC or let’s take those to the deputy.” The hierarchies vary from publication to publication. 

[0:19:21.3] YD: That should give you guys insights into one of the reasons why we always talk about why we should not absolutely 100 percent not take our rejections personally because just how Ashlea just not talked about this process, right? You may meet with your team first and discuss all the 30 pitches you got this month and then you’d take the five that are the most best fit to the EIC, maybe one or two of those get accepted. 

You can see how a lot of that is just so much out of your control and it has no relation to how good or how bad your idea is. It is more about does it fit to this publication in this particular time, right? 

[0:20:00.0] AH: Yeah and so, so, so much and I have seen a million fantastic ideas never get green lit and it can be, it can boil down to the bias of one person in a meeting. It can boil down to, like I said, quotas particularly with travel content. You know, magazines will do 7,423 Italy stories or Paris stories but you try to pitch Jordan and it’s like once every ten years and it is super frustrating because me personally, I’d rather go to Jordan. 

I am more interested in less visited places but sometimes that can be a really, really hard particularly for national mass market magazines and that’s I think one of the greatest. 

[0:20:37.5] YD: I’ve definitely experienced – 

[0:20:38.9] AH: Yeah, I mean, you pitched amazing stuff and then it can be incredibly frustrating for your editors too, so again, try to find editors that will explain why something didn’t get green lit, even if it is just one sentence, it can be so helpful for also fine tuning that pitch for other out. 

[END OF INTERVIEW]

[0:20:55.7] YD: Thank you so much for listening today. I hope you enjoyed today’s conversation with Ashlea and if so, please consider leaving us a review so that more listeners could find our show. 

I can’t stress how important it is for us to get reviews of our podcast. It really helps us to get in front of more people who might enjoy our show. If you like something you heard today in our conversation with Ashlea or in any other episodes of our show, please consider leaving us your review. 

That’s one of the best ways you can support our podcast. Don’t forget, you can hear the rest of the insights from Ashlea when you join us inside The Circle. Visit travelmedialab.com/circle to learn more about how our membership can help you with your goals. 

Thanks again and I’ll see you next week when we’ll hear from another wonderful travel industry insider, travel writer JoAnna Haugen. 

[END]