Claire Bullen is Clearing Away the Thorny Brambles

We’re going behind the scenes for today’s episode!

I’m honored to share a conversation with the editor of Boss Barista, Claire Bullen. Claire is a London-based food and beverage writer, editor, and author of the book, The Beer Lover’s Table, a book filled with delicious recipes designed to pair with beer.

I met Claire in 2018 while we were both working for Good Beer Hunting, an industry publication dedicated to the culture surrounding beer. Claire has not only edited my work, but has edited hundreds of pieces of writing and I got to see how Claire took pieces and somehow make the words feel more authentically like the author’s. Watching her work was a privilege I’ll never forget, and Claire is the reason I’m able to take my writing more seriously and write with purpose.

This episode is a little different—and a lot longer—than other episodes. We talk about the nuts and bolts behind the Boss Barista newsletter and then expand out to writing and editing more broadly. We try to answer some common questions and go back and forth on tips and tricks we’ve learned along the freelance writing journey. Getting to know and work with Claire for almost five years has been such joy and I’m thrilled you folks are getting to meet and hear from her as well. Here’s Claire.

Ashley: I am so excited to be recording this episode because I feel like I refer to you constantly in my writing, and we're finally going to meet the person who basically makes Boss Barista sound good.

So, Claire, could you introduce yourself?

Claire: Hello! Yeah, my name is Claire Bullen. I am the editor of Boss Barista, which has been so much fun. Before that—or until recently, I was the editor in chief of a drinks publication called Good Beer Hunting. I'm also the author of a cookbook called “The Beer Lovers Table,” which is all about beer and food pairings.

And beyond that, I do general freelance writing and copywriting and all kinds of things. So all of that somehow cobbles together into a full-time living. But yeah, living that freelance life, very much so.

Ashley: You and I are both in pretty similar boats where we cobbled together a litany of items to make one full-time job. Maybe? Kind of, sort of, but it's all different things that we take from different industries. A little bit of this, a little bit of that. Sometimes I'll name stuff that I'm like, oh yeah, I do that.

And I'm like, wow, that's a whole mess of stuff.

Claire: Exactly. Sometimes I even forget stuff that I do or stuff that I did a year or two ago because it just feels like there's a constant pile of things that are being balanced and somehow all seem to…it's like juggling, juggling plates. Somehow they're all on the air and they haven't crashed to the floor yet.

I don't know how, but that's freelance media life in the Year of our Lord 2023.

Ashley: I imagine this conversation to be a little bit more back and forth, a little more Q&A, maybe with Claire talking about her role as an editor and how she approaches looking at work, trying to find themes, punch things up, make things sound coherent. And then I would talk a little bit about my role as a writer and how I view the writing process, how I view generating ideas and things like that.

But I'm gonna start this conversation where I start every Boss Barista conversation, which I know you're familiar with, but did you grow up with coffee in your life?

Claire: Yes. I'm so excited that to be asked this question!

I guess I did. My parents—I remember them drinking coffee before work and on weekends when I was a little kid. At that time it was Folgers or whatever, it was really basic stuff. I personally did not start getting interested in coffee until I was a high school student because I think my first class started at like 7:20 in the morning, like some ungodly hour.

I am very much a night owl by nature, so having to wake up before 6:00 AM to get ready for school was really hard for my teenage self. So I started bringing thermoses of coffee to school every day with me, probably from when I was about 15 or 16 onwards. And I think back then it was just your very basic again, Folgers-level coffee.

I was also starting to go to Starbucks at that time, getting frappuccinos and things that were mostly not coffee, but very slowly edged me into that space. And then by the time I was like 18, moving on to university, I had a full-blown coffee addiction. And I think once I moved to New York for university, I started actually appreciating better coffee or started ordering better—I guess specialty coffee is what we would call it now.

So being in the city helped me get more familiar with just what was beyond the commodity coffee my parents used to drink. So I'd say it was a slow process and has been an ongoing, very important part of my life for about half my life.

Ashley: Darn. Yeah, you're right. Half your life. That's wild to think.

Did you always think that you were gonna be a writer or you were gonna work in media in some way?

Claire: That's a good question. I think on some level, yes. I'd always been really interested in reading as a kid, and I remember writing my first short stories when I was six or seven. Really small, basic fun stories. And then by the time I was in high school, I was doing honors English, I was on the literary magazine staff.

I think we all had to do final projects in our senior year when we were 18. So mine was starting to try and write a novel, which I did not do as an 18 year old, but it was a fun exercise. I majored in English as a college student and I did a creative writing masters a couple years after that, when I had moved to London, where I live now.

Kind of in parallel with my education, I was starting to freelance a little bit. I had a blog in the early kind of mid-2000s, which was very of that era. Some of my first jobs out of school were—they weren't quite the media jobs or publishing jobs I wanted since I graduated into the Great Recession, basically—but I worked for digital marketing agencies. I worked for a food website. I was an audience development manager or a PR manager, but writing was starting to become more part of my life then.

Later I graduated into writing for a travel guide series here in London, and then picking up more and more freelance work, a lot of it beer and beverage related, which was my interests—still is my interests, one of my major ones. So it all kind of organically bloomed from that. So to answer your question, tl;dr I guess the interests and motivation was always there. I didn't necessarily know the direction my career trajectory would take.

And it has taken some interesting twists and turns, but I think writing has been there for a very, very long time.

Ashley: When did editing become part of that equation? Because I don't necessarily think that writing equates to editing, and when I met you—we used to work at Good Beer Hunting together—I knew you as this incredibly accomplished editor. So when did that process sort of start to come together for you?

Claire: Oh, thank you. Honestly, that was something I kind of stumbled my way into as well.

I came on as a staff writer at Good Beer Hunting, I think in 2017, at the end of 2017. And by late 2018, I'd come on as an assistant editor. I had a good relationship with the editor at the time, his name was Austin L. Ray. He is a wonderful writer as well. You can find him on social media in various places. But he was a really great mentor for me.

I was already writing all the time, so editing then didn't feel like a massive stretch. It felt like a lot of the same skills, although as an assistant editor, you're learning more about the functioning of a publication, the day-to-day production schedule, what it's actually like to work with writers and deliver feedback to writers—those kinds of things I didn't have much experience with or understanding previously. So it was a really good learning opportunity.

Then the next spring, I think this was spring of 2019, Austin had decided to step down as editor-in-chief. It was quite a small publication, there wasn't a really deep leadership hierarchy, so I was kind of the person waiting in the wings behind him. And him stepping down is what vaulted me into this editor-in-chief position, which, at the time I think I felt very green and was quite nervous about it. But I was in the role for four years.

I just stepped down in month or two ago. And over that time, I think I really got into the groove and honed more skills and worked with more and more people and got more and more comfortable in that capacity. So it was sort of unplanned or I didn't see it going that way years in advance, but it was fortuitous to find myself in that position.

And it was definitely an ongoing learning position.

Ashley: No, that totally makes sense. I feel like what's fun about this conversation is that I feel like I've gotten a really good behind the scenes look at this process and seeing you—like I remember when you got promoted and I remember seeing you almost start to shape things in a way that I was like, “I can tell Claire edited this.”

I even think I remember giving you that comment once. There was an article that you published by Helena Fitzgerald (side note: Helena also publishes an amazing newsletter called Griefbacon) and I think that that was the first one where I was like, “I see Claire in this.” So seeing you develop your editorial voice was really, really fun. It was a privileged process to watch.

And I think another thing too that I really got to see—so the way that Claire and I worked together at Good Beer Hunting was that she was commissioning articles, she was working with writers, and then I was the person who would make the articles actually appear on the website. I would load all the photos, I'd make sure like we had all of our assets.

I would sometimes poke Claire and be like, “When's this article coming out?” And we managed this whole calendar together. So I would see an article when it first came in, and I would see this process that you would take the authors through. I maybe wouldn't see the back and forth between authors specifically, but I got to see an article when it first got to you and what it looked like at the end.

And to see that process happen was so illuminating because I feel like it's easy to see editing as like, you're going in there and changing things. I think when I first started as a writer, that's how it felt to me. I was like, “Oh, this editor's changing all this stuff and I'm bad and I'm doing a bad job.”

But what I saw you do was really make people's words more—I don't wanna say profound, that's not the right word, but more impactful. I still see this person's voice in here, but I see a total transformation of this work and it's gone from wherever a piece started for an author—and they can all start in different places—to something that felt like this really beautiful expression of an author's work.

It's almost like a designer, I think when they say, the best designers—you don't see their work. You can't tell where they did their work. I would see that in you.

Claire: That's wonderful to hear. Thank you for that feedback. I do remember you saying like, “Oh, I can see your touch on this one,” or, “I can see your editorial voice in this one.” And that was always really cool. But you're right, I hadn't actually clocked that you had seen the before and after for all those pieces, so you could really trace their development. That's cool.

But I think that's exactly right. My goal as an editor is not to impose some kind of exterior message on a piece of writing that the writer disagrees with. And it's not to impose my own worldview or my own voice necessarily.

If I can distill it down into one clear objective, it is about clearing away the thorny brambles that might be getting in the way of clarity. So whether that's maybe the structure of the piece is a little bit confusing, so the main ideas don't come through as strongly as they could, or maybe a writer uses a lot of hedging words or hedging phrases like, “this maybe happened some time ago, we're not sure. I don't really wanna make this argument.”

Clearing away anything like that that gets in the way of impact and clarity. Really, there's lots of different techniques and tactics that you can take to make a piece of writing really sing, but my goal is always to make a writer sound as clearly themselves as possible.

My goal is also to make the writer's objective for a piece come true and come across clearly. So ideally, this is a really collaborative relationship. It's a really intimate relationship. It's often quite a vulnerable relationship. You don't wanna be a kind of dictatorial figure who has an iron will that you're wielding over a piece and a person and they're unwilling to take that on board—you wanna be a teammate for your writer to help them tell the story as clearly as they can and to make sure their ideas are as impactful and present as possible.

I think I had worked with some editors in the past who maybe didn't take that much care or were kind of the harsh disciplinarian figures, which can be really tough if you're a writer who's just coming up or you don't have as much experience, or maybe you haven't worked in these kind of publications or workflows before. It can be kind of gatekeeping and intimidating in a lot of ways. So for me, successful editing is all about making you feel as collaborative and proving to the writer that you're there to be their collaborator.

You're not there to be the punisher or the leader in that way.

Ashley: It's funny that you were talking about pushing away the brambles. I'm looking at a tree in front of me—and obviously that's not a one-to-one comparison, but the metaphor that kind of came into my head was that a really good editor is like pruning away the things that you don't need to see the full structure even more clearly.

You didn't craft that structure—that was made by the author. So it's really about making the tree look prettier or getting rid of the branches that are no longer necessary or are no longer serving that tree. I don't know.

I also have a lot of plants. I could have used that as a better metaphor because I'm always pruning plants to make them grow healthier. If there are branches that are dying or have brown leaves on them and stuff like that…

I think sometimes it can feel like the editor relationship is really adversarial because this person is, maybe figuratively, maybe literally, taking a red pen to these precious words that I wrote and is saying that these are no good. But really—and I learned this from watching you—I think the editing process is really about making somebody's work really shine.

Claire: Yeah, absolutely. The pruning metaphor is really spot on. Or there's also, what was it? Michelangelo, he saw the sculpture in the block of marble or something? A piece comes to me as a block of marble that's been mostly chiseled, but actually maybe the face isn't very defined or like, “Oh, that finger looks like it's going in the wrong direction. Can we correct that or can we articulate this process better?”

Both of them feel like they get to that idea where the writer is doing the vast majority of the work, they're the ones shaping this thing in the first place. So my job is really just to come in later on and prune or help them make sure it's as clear and healthy and everything that they had envisioned for the piece as possible.

Ashley: So I feel like the eternal question that I think about still, as a person who writes a lot, and maybe you even think about this too because I'm not sure how often you're doing this, but what makes a good pitch when you get a story pitch? What are you looking for?

Claire: Ooh. Yeah, that is a really good question. And I think obviously, some of these specifics will vary publication to publication or editor to editor, but for me, I think the first starting point is just making sure that the person has done their research. That they understand your publication enough to know the kinds of stories you're likely to take.

They've researched to make sure they're not pitching an identical idea that has appeared on the website previously. That's a big one. Obviously, the small stuff is appreciated, like spelling a person's name, right? I will not ever turned down a pitch because someone has misspelled my name, but I think taking care with the details is always a positive sign that someone is doing the work and is on top of it. So that's just a really basic start.

I think one key thing is that people often pitch topics rather than stories, and that could be a hard thing to feel out the difference between.

But if it were a drink publication, let's say someone pitched a story about, “I wanna write a piece about margaritas.” And you're like, “Okay, well that's not really a story, that's a topic.”

But if they pitch, “Hey, there's this bartender in the city and they're doing this new technique with margaritas, and actually someone else is doing something kind of weird in another city as well, so I wanna write a trend piece about the evolution of the margarita.” You already see how that's a very different piece that's gonna come out of that.

I think doing the research, having real clarity and specificity in your idea is always really important. Your pitch doesn't need to be super long to make an impact.

It can really be just three or four paragraphs. But the idea should just be expressed as clearly as possible. Show that you've been paying attention. Show that you know the outlet you're you're pitching to. It'd be great to include a little bit of background about yourself too—not that you need to have written for all these other publications to qualify, but why are you interested in this story? Why do you wanna talk about this? What's your connection to the topic? So a little bit of brief background, your interests, maybe other clips if you have them, just to give an indication of your writing style.

And speaking of that, actually keep in mind that a pitch is the first example of your writing that an editor will see. So the writing in the pitch itself should also be free of typos and free of grammatical issues, all that kind of thing. But also think about it as a piece of writing that should be written in your voice.

It should be a living example of your perspective and the way you put words together on the page. So I always love to see a little bit of voice or character or personality in the writing itself. These are all quite general pointers, but I think if you follow them, that already takes you a lot of the way there.

Ashley: The thing that I really have been trying to pay attention to lately is specificity. And I think for me, the evolution of Boss Barista has been to get more and more and more specific and to not be afraid of that. Because I think what you're saying about topics versus specificity is actually a really big point.

Something that I see writers in my role as an editor is take on really big topics. I think the idea is that the bigger the topic, the more important it is. But I think actually the more specific topic is, the more important it is—and it lets you write within the confines of writing too, you know what I mean?

One of the struggles that I've tackled with Boss Barista and I think I've gotten a lot better at—and maybe you can tell me if I'm wrong or no— is that I feel like the topics have gotten narrower, so it's actually been a lot easier for me to write on them.

Claire: Yeah, actually I was just thinking about that piece that you wrote, I guess it might have been a year or two ago where you were reflecting very actively on this ide a that at first you thought you needed to be as general as possible because the most readers possible would connect with a broad topic and that by speaking generally, you would hopefully have the widest readership or interest, the greatest number of people.

But you discovered in the course of your writing and research and career and progression, that actually, paradoxically, if you wrote really specifically about a situation that was unique to you, but you wrote it with a lot of clarity and voice and really told a story in a way that was powerful, that resonated with people more than a broad overview—maybe tell me if I'm summing that up incorrectly, but that was my takeaway from the piece. And actually even in my own work, I've thought about that takeaway since editing that Boss Barista piece you did.

Just a really good reminder that—talk about the realities of your own life. Talk about your specific experience because that is captivating to read. It is more captivating than a general primer on a very basic, broad topic.

And when AI just seems like it's gonna accelerate that sort of content even more, the thing that distinguishes content from writing and the thing that distinguishes your writing specifically is that individual experience that you have, your voice, your writing style, your observations, the sensory details that surround you and that mediate your existence.

All of that is human and immediate and engaging and as a reader—at least as for me me as a reader, I find instantly engaging. I think it's good advice no matter what kind of writing that you're doing. It's cool to see you putting that into practice on Boss Barista in a way that, to me, has felt really impactful.

Ashley: What do you look for in a story? I know that that's a big question, so maybe we can break this up into tangible and intangible things, and maybe we can even look specifically at something that I've written maybe recently—we can almost give people like a living document.

Maybe this is something we should do later—maybe publish something before edits and after edits. That might be a wild thing to do, but when you first get a piece, what are you looking for?

Claire: Ooh. I think there's some kind of more basic technical things that you look for. First you wanna make sure that the piece met the brief, so it should ideally be within the right word count range. If you have certain specs that you needed to follow, for instance at Good Beer Hunting, we had long, generous word counts—we're all about the long form. But we have specific formatting things like most long form pieces need to have a minimum of three quoted sources, for instance. That's our thing. So there's gonna be a whole list of the technical specs that I want a piece to adhere to when it first comes in.

Other than that, I'm looking for narrative flow—that’s a big one. Not just in terms of the argument you're advancing throughout the piece. If it feels coherent, if it's moving forward, if it's not doubling back or too recursive, unless it's doing that as a stylistic thing. But the flow is clear and progresses forward as it should.

There's no confusion. There's not too much repetition. It's engaging all the way throughout. That's one of the things I look for. I pay attention a lot to prose quality, so I am always looking for a deft turn of phrase. I really appreciate writing that is beautiful, not necessarily writing that is purple or over the top or over described because there's a very real risk of that too. It doesn't need to be a big adjective pile on to fit, but you can tell when writing's got verve or rhythm to it. And that is something that I personally really enjoy.

I think making sure there's a good balance between the narrative voice and any quotes that are in the piece is an important one to pay attention to. I know there's some writers who will get a lot of great quotes from a lot of sources and get excited about it. At some point it feels almost like the speakers or the sources have taken over the narrative and that we've lost as the reader.

We've lost the writer's narrative voice and that's guiding us through the story. So you have to make sure that the balance is always still towards the writer's own voice. Scene setting—I really appreciate multisensory details. I often like starting a piece with a really immersive kind of in media res set piece. Almost like, can you not just describe a scene but situate us in a moment. What does this place sound like, smell like?

What's going on? Who's over there? Have you talked to not just the expected person in the room, like the business owner, but have you talked to the customer or the person cleaning the toilets? I think having that expansive vision and veering beyond what just seems to you to be the expected narrative or the most basic received narrative, I think brings a piece to life both in a way that's aesthetic and I don't know, can be beautiful.

Immersive, but also in a way that gets beyond just the most basic boring story and shows a wider truth or multiple perspectives. So that's a long-winded answer and I'm sure that's not everything I look for, but off the top of my head, those are a lot of the qualities that resonate with me.

Ashley: One of the things that your answer reminded me of is one of the very first articles I wrote for Good Beer Hunting. It was about a brewery that I worked at in Oakland called Temescal Brewing. And the first note you gave me was to set the scene—describe what Temescal not looked like, it was more about like where is it, give me some details that maybe feel unexpected.

That note recalled to me that the owner, Sam Gilbert, had once told me that the brewery used to be a movie theater and that the floors were slanted, which you can imagine if you go to a movie theater, the seats in the highest rows are the highest up, and then you go down and down and down and down.

And he told me that the seats at one point were slanted, so they had to even out the seats. It's one of those things that I would've never thought to include in the story if you hadn't prompted me to include details.

Claire: Cool. Yes. That's a perfect example.

Ashley: Right. Exactly. That's why I was like, “Wait a minute, Claire has done this to me before.”

I guess we forget how rich details can be in terms of scene setting and bringing your audience into the story with you. So what details can you include to set that up? And I agree. I really like when the beginning of the story kind of feels like it starts in an unexpected place and kind of brings you right in immediately. That's really fun.

I think something that you said too that I thought was interesting was this feeling of like narrative flow and things are moving. I think something that I've noticed recently, both in my own writing and in others writing, is that there are moments where you can take part of your story or part of your argument or even part of some of the quotes and almost weave them together like it's a story, like things are happening sequentially or things are moving in order.

And not to say that like you're crafting a whole new story out of nowhere, but like bringing details together where it feels like something's happening, then something else happening, then something else happening—is also really compelling to me. It's something that I've been thinking a lot about.

Claire: That's cool. In terms of using quotes to feed that momentum or create a kind of dialogue or exchange or crescendo in that way—that's a really good thing to keep in mind too. I love that. And I think all this gets back to your thinking about the example of the sloping floors.

To bring that back to what we were talking about before, again, I think that's actually specificity in action too. So it's not just the specificity of your topic, but it's not so interesting or engaging for a reader if you say like, “I walked into Temescal Brewery, they have a bar and there are fermentation tanks in the background. It's a popular brewery space.”

That just sounds like quite a generic beer business. To me, there's nothing really about that description that feels standout. But if you say, “It's situated this neighborhood in Oakland that used to be a movie theater. The floors are slanting,” all these small details, all of a sudden you're really getting at the heart of what it's like to visit that place and the reader can almost see and imagine it.

And that is the goal, I think.

Ashley: What's your writing process like? I know that's like a ridiculous question, but I've actually thought a lot about processes because I think that the more—I don't wanna say disciplined because I'm not disciplined—if you're looking for the procrastinators club, you found the two biggest procrastinating writers alive, I think.

But I think that I have gotten a little more rigorous about how I approach writing if only to meter my time a little bit better. And I wonder if you have a way that you approach writing that has helped you maybe be more structured or get things done faster?

Claire: Oh man, that's a good question also because, just to reflect where I'm at now, editing has taken up a lot of the last four years of my career and working life, and has been by far my primary focus. So the kind of writing I've done over the last four years has not been so much these big chunky, long form pieces. I do content writing or branded content or copywriting just as a financial safety net for myself and have done since I've gone freelance.

That's been a consistent part of my career. I write some shorter pieces including two food and beer and food and wine recipe pairing columns for a London based bottle shop here. Most of the writing that I've done for the last four years has been smaller and more piecemeal and not these kind of big, ambitious stories.

So you're actually catching me at an interesting moment where I'm just starting to redefine what my process looks like and get back into the flow with longer pieces of writing again. So I don't know if I have a great answer for you yet, because I think I'm still figuring it out. I do know that I want to work differently than before.

I'm a night owl by nature, so I often would be writing until two o'clock in the morning and I'm looking for a bit more balance and sustainability and health in my creative process. And I think for me, that's gonna look like carving out regular windows of time, if not every day, then most days of the week.

I recently came across a book called “The Artist's Way” by Julia Cameron, which I think has been around since the nineties. A lot of creative people in all different disciplines have recommended it to me recently. I haven't started it yet, but what I know of the process is that it stipulates quite a regular creative practice.

For instance, you wake up every morning and you do your morning pages, which is three long form handwritten notebook pages, right when you wake up, kind of free flow. They don't have to be, they shouldn't even really be, a piece or a project that you're working really consciously on, that's just to kind of get in the groove and unblock you and get into the flow. So I love the idea.

I think from maybe next month I'll finally start to have cleared some time and settled into this rhythm of waking up, doing some long form writing, setting aside maybe the first two hours of my day for writing or research or reading or any manner of creative practice before getting into the sort of grind of the workday.

I've kind of arranged my freelance schedule to make that possible. I realize this isn't something that can necessarily be replicated across the board, but I'm hoping that will be something that works well for me.

I think another big thing will be letting go of perfectionism—as a writer, before I really edited, I used to think I needed to turn in a piece that was perfect, perfect, perfect, perfect. Like almost airless. Perfect. So perfect. And no one would need to touch or do anything to it ever again.

So that would mean spending ungodly hours working on something, reading it dozens and dozens of times in a row. Every comma, every word, choice, querying every single thing. And it would produce pieces that were quite polished, but it was, I think, a very punishing workflow. Very punitive.

It also sometimes produce pieces that in hindsight feel like they're a little airless or lack some oxygen or breathing room. And it's a reminder to myself that if you're working with an editor as a writer, you're not meant to deliver them something that they don't need to do anything to.

This is meant to be a living collaboration, and it's okay that it's not perfect. In fact, if you're stuck or if you're not sure if something's working, that's what the editor is there for. They're there to help with that. They're there to bounce things off of. They're there to be your collaborator and see something through with you.

It's funny now to feel like I’ve put my writing on the back burner for a few years and to come back to it with all this new kind of context and understanding about what that side of the article production process or creative work production process looks like. And just feeling more open to editing in future—that I don't need to control every single variable and deliver something completely tight and polished at the end, and it's okay for there to be mess and uncertainty and change and collaboration. So I'm excited about putting that into practice for myself as a writer going forward, that's gonna be a step.

Ashley: Something that I had to develop by doing Boss Barista was giving things to you and knowing that there were points that I wasn't sure about. And sometimes I'll tell you where they are and sometimes I won't. With the idea that like, “If Claire doesn't catch it, then it's in my mind. It's something that I'm too close to.”

That's something I also wanna touch on because I think there's this idea that, like you were saying, like you need to turn in things that are super polished, that don't need to be touched upon or don't need to be worked on at all.

And I think that there's—I don't know, everyone needs an editor. I fundamentally believe that everyone benefits from having a second set of eyes on their work if only because it's impossible to take yourself away from the words that you wrote unless you really give yourself time and distance, which like sometimes you don't really have the luxury or the time to do, but things that make sense in your brain, especially when you've just written them down, won't necessarily make sense to another reader.

And that's okay. That's the whole point of having an editor. And it's not to say that you need to turn in something perfect. It would be cool if most of the grammar stuff is kind of taken care of, but like you were saying, things don't need to be perfect for an editor to come in and just give their two cents, just to jump in and say, “Actually I think this is a little unclear. What do you mean by this?” Or, “I think this is what you're saying. Is this what you're saying? Maybe let's rephrase it like this.”

Claire: Speaking to both of your points there: that doesn't mean there should be, you know, carte blanche and you should turn in just a super rough outline where things are all over the place. I think you owe it to your editor to, as you say, take care of the basic grammar stuff. Make sure the names of the people that you are quoting are spelled correctly. Just do that basic level of fact checking and polish. Don't make the editor your garbage person, your cleanup person. You should be able to do the basics.

But in terms of the deeper, richer, structural questions—the flow, word choice, all those other more subjective things—there's so much room for everyone to benefit from the editorial process.

And that was something before I was an editor that I used to fight or I used to think, “Maybe that's true for everyone but not me. I can be good enough that I don't need to be edited.” And you'd feel really protective of the work and your word choices and you wouldn't want any changes.

I don't feel that way anymore and as much as I empathize with that position—because I think there are editors out there who will make all kinds of big slashy changes to someone's writing, and the writer doesn't always feel like they are invited into that process and sometimes it does feel necessary to be protective or defensive of your work if it's being misinterpreted—the power dynamic there can be unequal and it is fair to call that out.

But assuming that the editor is engaged and has a similar goal as you and is a good communicator, you can definitely afford to trust them with your writing and they will just notice things that you, as you said, that you might not notice yourself.

They are the eyes, they are your first reader. They represent your readership. They're the first eyes outside of yourself to look at it and they will notice things that you're too close to see. It's a gift when you're edited well, I think. It's an invaluable process and it makes your work so much better.

So I think we should all be, hopefully, more open to the editing process. I'm happy that I've gotten to the place where I think I've told my perfectionism to sit down or I have better understanding of the process so I can more fully engage in it as a writer as well.

Ashley: Before we did this interview, I wrote down questions that I was gonna ask you, and I've asked about half of them, and I haven't even gotten to our write-in questions. So let's maybe shift.

We didn't get a ton of questions from the audience, quote unquote, but we did get a few, so I thought that we would maybe talk about some of those questions that we got.

So one of the questions that we got is: I'm always curious about how other writers schedule their writing/interview time. How do you know when you have enough material? Also, what do you think makes a successful first pitch from a writer you don't know? So I think that those are probably two different questions.

So maybe we can talk about that first one there.

Claire: Perfect. So that was, “how do you know that you've got enough material?”

Ashley: How do people schedule their writing and interview time?

Claire: Yeah, that latter question is probably quite individual, and it will depend on what your working life looks like. Being freelance, I'm lucky that I can, and as I was alluding to previously, I can carve out dedicated blocks in my day for creative work or my time when I'm free to talk to people versus maybe later in the day, that's what I'm head down doing my copywriting work, so that's not available.

I think you can kind of block that as you see fit and as makes sense. The question about how do you know you've talked to enough people is actually a really tough one. I think that is subjective. A rule of thumb for Good Beer Hunting was talking to at least three sources for a long form piece.

I think that's probably a good rule of thumb, just as a minimum to make sure you're getting different perspectives and getting a good grounding in a subject. Obviously, you can talk to many more people than that. It's often good to ask the sources you've identified and are speaking to first if they know other people who they think it would make sense for you to talk to.

Often sources are really good at suggesting other sources or recommending people in the industry to engage with a certain topic who can shed more wisdom. The first sources you speak to might be the people who are the most obvious, whether that's a business owner or an authority on a subject, an academic who has written on a subject, so they're all great to start with, but they might point you to the people who are a little more out of view who would be good to engage with.

Apart from that, I think there is also a risk in over-reporting sometimes, or feeling like you need to write the comprehensive story on a piece, and that means you need to look at everything that's ever been written ever on a topic and talk to every single person with even a passing interest in the thing you're writing on. And that's a risk too, just in terms of your own bandwidth and time and what's feasible.

It's subjective. I can't say a specific number of sources is the right number. Some of this will also depend on the length and scope of the piece. It will depend on how much you're being paid for it. The rate, I think, should dictate some of the level of work or time that you're spending on something. If you're being paid a hundred bucks for an article, you can't really afford to spend multiple days just on interviews alone. So that's something to pay attention to too.

That's probably a very vague, all over the place answer. I think the answer probably is at least three is good, maybe even five, six more to feel like you have what you need but protect your own time and bandwidth and energy too.

Ashley: That's a good point. I wanna get back to that idea of time and money, because that's something that I talk a lot about as an editor is look at how much we're paying you and then divide your time accordingly to that.

Generally it's the interviewing section—fact check and gathering, whatever, all that, that first kind of initial part. Then the writing part itself, which I think accounts for about 50% of that time. And then the editing part, and then take those three chunks and then divide it up by the amount you wanna be paid per hour or per whatever.

Practically for me, the thing that has been the most helpful is determining who I actually need to talk to on the phone versus who I can send email questions to.

Claire: Hmm. Yes. That's a really good point as well. Actually, phone interviews are great if it's a really important person that you're talking to, a really important source. There's a lot of complex information. It's someone who maybe there's a slightly tricky dynamic you're reporting and you don't just want the company line that might come from an email.

You wanna really engage with them, hear their voice, potentially ask questions that might catch them off guard, especially if it's more news reporting. You don't just want the press release version of an answer, you want to really get the answer from them. But if you’re looking at a small facet of the topic or someone who you just wanna check something with, or someone that could be more cursory, then email can be a good time saving way to approach that as well.

Ashley: Yeah, there's there's a story that I reported recently for a publication in Madison. It's called Tone, and it was about a union forming at a bakery in town. And that was one where I was like, I need to interview each of these people on the phone, which I did. But 90% of the time I'm emailing people, if I'm being totally honest.

Claire: Yeah. You do have to still protect your time and the amount of money you're being paid. It's obviously no secret that pay rates in media are really bad and that it's a tough time for the industry and that people don't really get paid enough or as much as they should do.

So that's a difficult thing that everyone needs to engage with and work around in their own way or figure out what they're most comfortable with. For the most part, I advise people not to work for free. For the most part I think it's worth trying to negotiate for higher rates, if possible.

Sometimes publications will say no, they have tight budgets, that's fine, but it's always good to ask. There's small things you can do to see if you can get a little bit closer. But yeah, with that reality in mind, you do have to kind of just correspond to what is practically doable for you on some level.

So, I think email can be useful in those cases.

Ashley: I also really like email questions because people's quotes are accurate. That's also a whole process verifying quotes and transcribing, which can be really difficult. So I think that that's a good distinction, really measuring what the stakes of your story are.

Let's look at that second part of that question: What do you think makes a successful first pitch from a writer you don't know? We talked a little bit about what you look for in a pitch, but maybe from someone that you don't know, is there like some signals that you're looking for to maybe ascertain what this person's capacity is?

Claire: Yeah, that's a good question. I think that's where actually a lot of the previous advice probably most applies to those people. If you already have a prior relationship with someone, your pitches often, at least for me—I was very happy to accept kind of more informal pitches or ideas later on, once there was a proven working relationship with someone or even pitch them ideas back and commission pieces from them.

So I think if you are pitching for the first time, that's when all that pitch advice really does apply. Making sure you're doing your homework, that you have the person's name spelled right, that you've looked into the site, you've made sure it's not a duplicate story. Maybe bonus points, if it seems like they really understand the site, like, “Oh, this is a profile piece. I think this will probably be a fit for this column of yours.”

Also a lot of publications have very in-depth style guides, so if those exist—style guides, pitch guides whatever you wanna call them—if those exist, it's a very, very good idea to go over those quite thoroughly.

Double check your pitch before you send it. Make sure it does apply to everything they're asking for. I was pretty patient as an editor, but the times that I would occasionally feel a little bit annoyed or frustrated is when someone is very much not following the brief or if we put out a general story call, “We're asking for 500 word pieces that profile this kind of business,” and someone sends a pitch for a totally different kind of business, or it just clearly doesn't fit the brief, that is frustrating.

I think maybe writers think that even if it's not quite right, they might be getting the foot in the door or making the contact, but actually, to the editor, it just shows that maybe you're not following the assignment or you're already not paying attention to the instructions. So will this be a fortuitous relationship? Maybe not.

So I think making sure you're just really paying attention to all those things. Again, making sure you've included a little bit of background information about yourself that the piece expresses your voice, to some extent. Bonus points if you mention potential sources you'd wanna speak to for a story or what the general flow of the piece looks like, why it feels timely and interesting to you.

Those are not always required, but I think those are always bonus points. So it really shows that someone cares and is putting in the effort and isn't just farming out a single idea to lots of different publications at once. And I did used to get pitched that way—there were a few writers who would kind of send me a battery of pitches, like one every few days, and nothing in the email was tailored to the publication at all. And it was clear that it was just a very scattershot approach at trying to pitch lots of places all at once.

I actually sympathize and I understand the economics of that. Pitches take time and can be frustrating and cumbersome when you don't hear back and it can feel like a lot of wasted effort. So to mitigate some of those losses, you just wanna cast your net as widely as possible, which makes a lot of sense.

But I actually think, at least for us, you had less of a chance of landing a story if you didn't do anything that felt like it was personalized to the publication or tailored to the publication or actively went against the kind of coverage that we have.

So I think it is actually worth the time it takes to craft a more personalized pitch because I think you will have a much better chance at landing that commission.

Ashley: I like what you said about knowing where on the website a story would land, because something that I really like, and I think I'm trying to find the line with this because I don't know if I've totally found it, but sometimes when a writer is writing, I'll find an article that I think is similar in style, but not topic, but style to what I think their story could look like.

I've had some authors push back on it and be like, “Well, I'm not gonna write like them.” That's not what I'm saying. It's that this article is, in style, kind of hitting some of the points in a way that I think you maybe wanna approach—flow and answers questions in a way that I think that you maybe wanna think about.

I don't wanna remove any originality from one's work, but people wanna be able to digest information in ways that they know, that they understand it's coming to them. And websites often have a style that's—not mimic-able by any means, but there's certain buckets that a lot of their articles fall into.

It's okay to be like, “I actually read this article and I think that my article could look really similar to the way that this is laid out.” That's not copying somebody's style by any means. It's showing that you paid attention, that you've read articles on the website and you understand how our audience takes in information.

Claire: Yeah, absolutely. For me it shows that you're doing the research and you're engaging with the site, so I would definitely not ding that or say that was a negative. I think it's a positive. I think you can even expand that beyond the publication you're pitching.

There's a piece that I think is still being written right now, so I won't talk too much about it. But I was there for some of the early conversations about the structure. And a story that we were referencing when we were talking about it is that landmark Esquire piece, “Frank Sinatra Has a Cold,” it's one of these pillars of 20th century narrative, long form journalism.

And we're like, “Well, what if we could do a profile of this figure kind of in the vibe and tenor and tone of that piece?” So I think it can often give someone a good shorthand for the vibe you're going for or the flow or the structure as you say. Not a bad thing at all.

Ashley: How do you think about compiling sources? You touch upon this a little bit too—maybe not just talking to like the business owner, but talking to somebody who works in a totally different capacity, is maybe tangentially related to the thing, but still has something to say about the thing that builds out the world that you're trying to write about.

Claire: I think it's good to start with the business owner or start with the obvious stakeholders in that way. But expanding the lens is often where you get the most interesting stories or the most impactful reflections. It could be like people who are overlooked because they're not deemed like, oh, the important authorities or whatever.

But actually they probably can speak more to the truth of the day-to-day runnings than anyone in ownership can. So at a brewery that might mean talking to someone who's literally cleaning it up, talking to some of the production brewers, talking to the person working behind the bar, talk to the customers.

Why are they there? What's drawing them there? That really widely, deeply reported approach where you're talking to everybody in the room, or if not everybody, that at least people coming from lots of different perspectives always seems to yield a stronger story. And I think if you're ever profiling a business, I think it's definitely always worth talking to people who aren't in charge.

Leadership and ownership will have its narrative. But the day-to-day people who are working there and building it with their labor will have a narrative too. So I think it's often a dereliction just to let the people in charge tell the story. The story is really complicated and multifaceted, owned by lots of different people.

So yeah, that’s my advice on that one.

Ashley: Going back to this idea from the first question about how do you know when you have enough material? I think it's also okay to ask lots of people one or two questions. If you're at a brewery and you're just asking customers why they come in, that question's enough: you don't have to do an interview for it to be useful to your reporting.

Doesn't have to be a half hour, it can be like five or 10 minutes. And that's something I've also actually tried to get a lot better at is asking people very few questions, just asking them like four or five and then asking if I can follow up with them. So then maybe you'll get to your writing and realize that those questions were enough.

Or maybe you'll get to your writing and realize, actually I have one or two more follow up questions, but to kind of edit myself even almost from the beginning has been really helpful for me.

Claire: That's such a great pointer. Yeah, I think that's exactly right. Not every conversation needs to be an hour long sit down and those are useful. You have to weight it towards the—I don't know how much space you think each source will probably take over the piece. And it's a good point too.

I actually always do that myself when I'm reporting a piece that I'll say, “By the way, I'd love to reach out for clarifications or questions down the line. Is that okay? What's the best way to reach you?” Just kind of set that expectation up top because I think there will be details you think are maybe a little inconsequential in the day or stories you don't follow up on at the time.

But then in hindsight it's like, “Oh, actually that might answer this key question I have.” So keep those channels of communication open if you can. It's a good way to ensure you get everything that you need.

Ashley: I am gonna end with a version of a question that I ask people at the end of these episodes. This might be hard, but let's see if we can distill it down to one.

It doesn't need to be a perfect piece of advice, but what is a piece of advice you have for writers who are just trying to figure things out or feel like maybe they're not getting where they wanna get?

Claire: Hmmm.

Ashley: I have my piece of advice if you want me to go first.

Claire: Yeah. Maybe go first and then mull as you talk—because that is a good question, but it's a hard question.

Ashley: I have probably found the most success in writing when I gave myself structure, which I didn't think was something I needed. I thought that the creative process was meant to be creative in all aspects, but I think, and you've been part of this process too, when we created like a really strict timeline for Boss Barista, that for me unlocked so much more creative potential.

I think it goes back to something that you and I have talked about as we've edited stories back and forth. There's this school of thought called—you're gonna pronounce it right, and I'm gonna pronounce it wrong—but you know what I'm talking about, Oladipo…

Claire: Oulipo.

Ashley: Oulipo! There we go. But there's this like school of thought called Oulipo where these writers give themselves really strict parameters. And some of them are kind of ridiculous. Some of them are like, “You can only use ten sentences or ten words per sentence,” or something like that. That really inspired me to take parameters to my own writing and allow for creativity to be expressed more within those parameters.

Because without parameters, it was boundless, it could come from anywhere. And it just felt like everything was a mess. I couldn't draw from anything because there was just too much. Choice can be really, really paralyzing.

I have a pretty strict Boss Barista schedule and even then, I deviate from it constantly all the time, but having like, “I'm gonna write a long form piece every other Thursday, I'm gonna write a short form piece on those opposite Thursdays and I'm gonna release episodes every other Tuesday,” gave me so much more freedom than I thought I could ever have.

Going to that idea of turning in things that are not perfect, that really helped me too. Being able to say, “Okay, I worked on this for about four hours—that's enough for right now. I'm gonna turn this into Claire. I wrote it in Grammarly, so hopefully most of the grammar stuff is kind of taken care of.” I write everything in Grammarly, by the way. It's not always correct. Their grammar suggestions are kind of bonkers bananas, but it does catch if I'm using passive voice too much or if I spelled a word wrong, kind of just as I'm writing quickly. So that really helps with a lot of cleanup stuff too. But giving myself those parameters made my writing feel a lot easier.

Claire: That's such a great point. Just to reflect on that, to start with, there's the anxiety of the blank page. There's also so much kind of baggy, unhelpful mythology about what the writing process is supposed to look like, that it's this romantic thing and that the muse strikes and maybe you're writing till dawn and you've got your cigarette, you've got your tumbler of whiskey…

So much of what we think a writing process looks like is frankly complete bs and it's not how people write. Expecting that everything comes to us as this thunder bolt from another dimension and the muse is channeling through us is really not how it gets done. It gets done by having your butt in a chair and just hammering away at something, and sometimes it's working and sometimes it's not.

But the active, regular engagement with it is a really helpful way to ensure that you actually do the writing rather than just waiting around for some kind of mythical perfect moment. And I also don't think you have to write every day to be a writer or anything like that.

There's a lot of kind of rigid, punitive ideas of what writing needs to look like. So in terms of a good writing process, though, I agree with you, Ashley. I think constraint is one of the most helpful things. It's giving a schedule for yourself or it's saying, “I'm writing this many words a day,” or, “I have two weeks to write this story, and that's it.”

Whatever it looks like for you in a way that makes sense, providing that constraint. And it could be in terms of your schedule, it could also be in terms of the content of what you're writing, which is like the Oulipo post style of constraint that you mentioned. Whatever that constraint is, that is often, paradoxically, so much more creatively fruitful than just looking at a blank page and expecting genius to flow through your fingers.

In terms of a practical level, if there's a given industry or topic that you're reporting on, whether it's beer for me, coffee for you, or whatever it is, if you feel stuck or aren't sure what to write about, I think it's always helpful to just be enmeshed in that industry and that community.

That doesn't mean you have to be an insider to write anything good about something, but I just find, for beer—I was at a beer festival this last weekend and I ended up talking to lots of different people, fellow writers, brewers, people in other parts of the industry and just that organic kind of chatter or ability to connect with people who are maybe parallel or some way tangentially interested in a similar topic as you, is a really fruitful place.

And I came out of that with, “Oh, there are a few ideas here,” stories I could pursue after this is over. But regularly engaging with your peers, whether that's following fellow writers or publications or editors you admire, whoever on social media, I think is good. Staying involved in the conversations that are happening in your industry, or at least aware of them, keeping tabs on them.

People are such an asset. And I think rather than that punitive isolation where you have to be locked up in—I think there was just a Twitter discourse about this a day or two ago about someone who, I didn't engage with it too much because it was Twitter discourse, but it was something about a writer saying they turned out every single party when they were in grad school never went out, and that's the only way they were able to sit down and produce their work of genius.

Really, I think it's exactly the opposite. Going out and being in the world and engaging with people, engaging with businesses, engaging with events around you is the way to ensure there's an ongoing cross pollinating of your imagination. I think that's another big tip for me is to be engaged in that way.

Ashley: I just read an article about basketball advertisement that actually fed into the next long form post I'm gonna write. So I think you're right: engaging with not just your peers, but the world around you is so fruitful and you kind of get stuck by inspiration anywhere, which is really fun.

Claire: Yeah, and that's a good point too. That doesn't even need to just be your industry. It's good to keep track of your industry, but you get creative cross pollination from all different walks of life. I also think it's really important to read, read widely, read regularly, read robustly, but that doesn't have to all be the great books or big works of literature.

It could be magazines, articles across the web, genre writing that you don't think you have any reason to engage with, but might actually inform something or for you, sports journalism has become a surprising avenue, and I think there's potential in all of that. So read, read all the time. I think reading is actually one of the most—reading is what has made me the writer I am.

And reading has made me the editor I am. It gives you those instincts and the feel for rhythm and voice and tenor and everything. The best way to learn that is by reading rather than just trying to adhere to those lists of writing doctrine or writing recommendations or tips that every writer should follow.

All that's nonsense. Just read, read widely. Engage with topics in your industry and people in your industry as well as topics and people and publications of writing far outside of it. And I think all of that will ensure you have a creatively fruitful time of it.

Ashley: Claire, thank you so much for stepping in from behind the scenes and getting in on this. This has been really fun and I've recorded like way more, way more material than a normal episode is. So maybe this will be a two-parter, maybe we'll get chunks of this in a paywall. We'll see. But thank you again for taking the time to chat with me and hopefully this won't be the first time we do this.

Claire: Oh, I know. It was such a pleasure. Thank you so much for having me. This was really fun.

This transcript has been lightly edited.