S5 E50: Who Gets to Be a Writer with Pilgrim Founder Ashley Halligan

Get the show’s transcript

[INTRODUCTION]

“AH: We do have this misconception that you have to create constantly, all day, every day, you write, or you paint, or whatever your medium is. We get these narratives in our minds that we are not something because we think that we have to achieve X, Y and Z, or we have to produce so much material, or we have to be given a particular accolade. And I just don't think that that's true. And I think those self-limiting beliefs are really – They can be very devastating. You don't have to be published to call yourself a writer. You don't have to have an exhibit to call yourself a photographer. As long as you commit to your art in some capacity, you are that thing, and you can be many things.”

[00:00:39] 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 stories are as 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. 

[INTERVIEW]

[00:01:15] YD: Ashley Halligan is the founder of Pilgrim Magazine, which was an idea born in the Peruvian Amazon. She has been published in places like Backpacker and Alaska Magazine and worked with outdoor brands like Patagonia and The North Face. Ashley's a skillful storyteller, and our conversation is probably one of the most soulful conversations you’ll hear on this podcast. But that's not even why I want you to listen to this episode. I want you to listen to it, because somewhere along the way Ashley does a very, very important thing. She liberates us from the pressure of having to pitch, create and produce constantly and support ourselves only with our creative work. 

I'll say this again, because I think this is so, so important. In our world, the legitimacy of who gets to call themselves a writer, a photographer, a storyteller, a creator comes from doing this fulltime. You're only legitimate if you support yourself with this work 100% of the time. 

In this episode, Ashley and I break that apart and lift that expectation from our weary shoulders. Ashley is not only the founder of Pilgrim, photographer, writer, storyteller, but she's also a content designer on Instagram and a content strategist for brands. She says, “You don't have to be published to call yourself a writer. You don't have to have an exhibit to call yourself a photographer. As long as you commit to your art in some capacity, you are that thing. And you can be many things. You don't have to be just the writer to be a writer.” And I love that so, so much. 

Beyond that, we discuss what working with Pilgrim Magazine looks like and why, if you have even the slightest kernel of an idea, you should absolutely pitch Ashley. We also talk about the Portuguese island of Faial in the Azores, and why it's Ashley's favorite place on Earth. This episode is one of my favorite episodes to date on our podcast, hands down, and I hope you enjoy it. Alright, let's get into it. 

[INTERVIEW]

[00:03:24] YD: Dear Ashley, welcome to the podcast. I am so excited to catch up with you and interview you today for our Genius Women podcast.

[00:03:33] AH: Thank you so much for having me. I'm excited to be here and having this conversation.

[00:03:36] YD: Me too. Me too. And like we were talking just before we started recording, we connected at the beginning of this year, and I can't believe that it's already been almost a year since then. Like just time is always speeding up it seems like. Crazy. Crazy.

[00:03:51] AH: Yeah. I mean, it's the theory of relativity and action. I mean, I feel like the last year has completely melted away. We've been kind of on this cusp of going through the strange spectrum of the pandemic and kind of not being able to move. And then having that brief glimpse of time where it was like things are back to normal. And then suddenly they weren't again. And so I feel like, yeah, this entire year has completely melted away. 

[00:04:14] YD: This and the past, right? Yeah.

[00:04:16] AH: Absolutely. It's like one big blur. 

[00:04:19] YD: It is. It totally is. So I want to jump right in into one of the stories that I read on Pilgrim Magazine that I think actually is the reason why Pilgrim Magazine as it is today exists. So I would love to hear that. But I read your story called Lost and Found in the Peruvian Amazon. And for our listeners, we will link to it. Be sure to go and check it out, because it's so beautifully written. But what was so striking to me was how vivid your storytelling and your writing is. 

There was a phrase that you had in there called – The phrase, “When something like sloths looking on with a stone gaze as we pass them by,” and I literally – Like as I read that, first, I chuckled, of course, but I also like could see those sloths looking at you. And just all the imagery that you put into that story of your experience in Amazon, in Peru, I mean, my God. It's just so incredible. 

So I think you mentioned somewhere that the idea for Pilgrim started there. So can you tell us more about how that came to be?

[00:05:28] AH: Yeah, of course. So I think a little more background for Pilgrim. Originally, it started as an outlet for just my own stories. I was doing some freelance work. This was back 2013. So a couple of years before the kind of big epiphany that happened in the Amazon. And so it was called Contemporary Pilgrim at the time, which is, of course, my Instagram handle. And so it was contemporarypilgrims.com. And it was a place where I could write my memoirs, my short essays, my travel writing. The stories that I didn't want to sell to other publications, because they were so intimate or personal that I wanted them to be part of my own brand that I was building. 

So fast forward to 2015, I went to the Amazon for – It was about three weeks, and I had really just stretched the edges of my comfort zone. Like at the time, that was by far the most provocative, challenging, difficult, but beautiful journey I've ever been on. And so I had been deep in the Amazon. Four hours by boat from Iquitos, with an Amazon lodge, with an American biologist and his family. And I was there at the beginning of rainy season. So there weren't really other tourists. So it was really me in the jungle and a female naturalist that was assigned to me because she knew I was there as writer. 

And I really got a really incredible introduction to the Amazon and rainy season. Everything's flooded. Everything was green, and dangerous, and lethal. It was just really fascinating. And so I really had this time to sit with myself and just watch the rain come and go every day, which just revealed the most incredible skies and rainbows. And it was just me, and the kitchen, the chef's that would put together these beautiful feasts. And even though I was just one of the few people there, it was as if they were cooking for an entire party. And so I was just really inspired the entire first – I think it was 10 days that I was there when we were tracking the new monkey species that they thought that they had discovered. 

So then fast forward to a couple of weeks later when I went to a retreat outside of Iquitos, and I was there with a shaman and his family. And what I thought had already been stretched in terms of my comfort zone deep in the Amazon four hours by boat, it was pushed even farther in this particular place, because I was sleeping alone at what's called a Tambo in the jungle. And these moths would get inside of my room that literally had the body mass of small birds. And I had a net around me, but like everything would hit you with this just like veracity. 

And yeah, so I was just alone with everything that made me uncomfortable. And one morning, it was one of my last mornings there. So it must have been close to that three-week mark. I was laying in bed, listening to the howler monkeys, and just all of the symphony of the jungle. And all of a sudden it dawned on me. Pilgrim Magazine just came like so clearly. It was like a message from the beyond really. And all of a sudden just everything made sense, because I know so many incredible storytellers. I know so many incredible people who've had these fantastic journeys that don't consider themselves storytellers. 

And so all of a sudden, like the idea just transformed and evolved. I didn't want to be my own outlet. It wasn't ever really intended to be a place just for my own voice. It was more I was trying to create an ecosystem where people could share really raw narrative stories, but also where I could elevate the voices of people that maybe didn't realize that they were storytellers yet. 

And so when you go to a place like the Amazon, the people that you meet are quite fascinating. When you're in a very remote place that takes a lot of effort to get to, you kind of have – You've got very interesting people in pockets of the world like this. And so I think at that point, I had met so many colorful people in my travels. But I already had a roster of people to pull from. So in my mind, I'm like, “This person that I met in Spain, or here in Peru, these would be incredible stories.” And they're not writers. Completely different professions. And so just that morning in the jungle, everything made sense. And so I think I had two more days. And I came back to the US and really just started committing so much energy to this project to bringing it to life.

[00:09:20] YD: Wow, that's such a beautiful story. And what you said about elevating voices of people who don't necessarily consider themselves storytellers, that resonates with me quite a bit.

[00:09:31] AH: Yeah. I mean, I think some of my favorite stories that we've published with Pilgrim and even some that are in queue that haven't been brought fully to life yet are people that I have found, a lot of them through Instagram, actually. And I read a beautiful caption that's maybe a paragraph, and I'm like, “Okay, let's create an entire story with this.” And I message them, and they're like, “We've never written anything ever. We're not writers. We’re this or that.” And I'm like, “You don't have to be a writer.” And I think that that's the most fundamental part of storytelling for me, it's about humanity connection, and it's enlivening. It's enlivening people to tell their stories. And it enhances that connection among people.

[00:10:09] YD: Yes, it resonates with me so much. That's totally what I believe in as well. I think, for me, what I always talk about is that telling stories are so natural for us as humans. It's such an innate quality. And we do it in different ways, perhaps, right? Somebody is better suited to do that with words, written words, spoken words, photography perhaps. But to tell stories, this is so natural to us. 

And so what I always say is that if you feel some of that, if you're unsure, if you have what it takes to tell the story that you want to tell, well, just know that you do have what it takes. It's innate to us as humans. So that helps me when I sometimes have those moments of doubt, I think about that. It's a human nature. I look humans most days. 

[00:10:58] AH: And it's necessary for humanity. And I think, particularly in the last couple of decades where we've become so much more digitized, and with that comes the abbreviation of communication. We don't speak in prose so much anymore. Everything is edited. It’s, I don't want to say, superficial, but we lose sometimes that depth of explanation, and communication, and connectivity because I think we've we exist in this ecosystem that is purely digital in many ways, and fast-paced. We're all in a hurry, and everyone is busy. 

And I think when we can divert our attention back to storytelling and having true human connection, like making eye contact, and having a real conversation, that's what I want to reinvigorate again, because I think so much writing on the internet, too, it doesn't have the narrative quality. And of course, I understand that there's a time and place for lists and for just get to the point kind of writing. But I think it's that human-based memoir-focused. Just the rawness of telling a story. It doesn't have to be perfect grammar. It doesn't have to have zero mistakes. 

I've been reading a lot the last couple of months. And what I've really been paying attention to are the nuances of different author voices and how much I appreciate the imperfections, or what I consider to be an imperfection as a writer where I'm scanning something and I'm like, “Oh, like, I would have done this differently. Or is there a comma missing?” It's not about perfection, though. It's about rawness. 

And I think with the digital world, we get so focused on editing and making things perfect and polished. And we kind of take that human quality out. And by virtue of doing so, that I think I really like to leave the raw, rigid edges of things intact, because that's what gives a voice its individuality. And that's what we want to preserve.

[00:12:43] YD: Yeah. That's so beautiful. And I think it shows up in a lot of the stories that you tell in the magazine, for sure. So how do you go about doing that, right? So you said you had a roster of people that you knew, storytellers, or people who you thought would have great stories that didn't necessarily consider themselves storytellers. How do you go about creating something out of nothing?

[00:13:03] AH: Well, I would say nothing truly begins with nothing. Like, the substance, even if it's not material, is often so pronounced that I'm so fixated – on that. That's my focal point. Like, if I see the substance, there's already so much to work with just from that. 

For example, one of our biggest stories with Pilgrim and one that we publish at our launch was the Felicity Buckwinder Series. And the author of that series, Jessie, she is an incredible photographer. So she is a storyteller in that sense, in a visual way. At the time, she had explored some kinds of writing, but she had never really published like a long form story. And really, that story was centered on a mother's voice. So we were taking the journal entries of her mother who had passed away when Jesse was a teenager. 

And so we had just this wealth of imagery of journal entries. And then we had Jesse's voice. And then we had Haley's voice, who was the editor of that piece. And how do we merge these three things together to create like a cohesive, beautiful story arc? And it took a lot of work and finagling for that one in particular, because there was so much material. But, originally, when I was courting Jesse and I was trying to encourage her, like, we really want to publish this. The story is there. I think it was maybe a little overwhelming, because how do you tell such a big story, and when you don't necessarily consider yourself a writer in a given period of time? But it was all there. And we knew it was there. It was just a matter of shaping it, and finessing it, and kind of organizing, and a lot of back and forth. 

I don't know, I think for me, it's really natural to focus on that substance. And then the writing for me is natural as well. So I can help someone formulate a piece from even just one line. There was a writer whose story we have not published yet. In fact, actually, she's not a professional writer, but she's a mushroom forager. She's obsessed with mushrooms. And she's a traveler. And she does kind of the freelance patchwork lifestyle. She does a lot of different things, but not necessarily writing. But she published a caption that was about reading a book in a bookstore in a foreign country, like just skimming it. 

And the way that she wrote just these three sentences about that experience, I immediately messaged her, and I'm like, “Let's turn this into a bigger story.” And it's become like a work in progress where we're back and forth. So I think it's just a matter of like identifying that thread, that thread that can be woven into like a much more beautiful, bigger tapestry. And when you see that in someone, it inspires them and it encourages them. And it also causes a lot of reflection, self-reflection, where they're like, “Wow! I didn't necessarily realize that this was a story in itself. And actually, a story that we'll be publishing in the next couple of weeks.” 

Similar thing, we found a husband and wife, or a partner, a couple. They're traveling photographers. They live on the road. And they had this amazing story about this old man that they found painting a landscape on the side of the road, like an old, tattered, rusty camper, or camper, van, whatever it was, and they wrote one paragraph. And so we worked with them to turn that one paragraph into an entire story that is so touching and so compelling. And it's just a micro moment of the human experience where you're on the road, and you share this. It seems like a light conversation. The old man clearly inspired them, because they wrote a short caption about him. But I don't think that they saw the breadth of that piece and how it could grow to become something bigger. And so I think that's what me and Rachel, our current editor with Pilgrim, do with people, as we see that fragment are that micro moment that could just be carved into something larger. And we work with people to bring that to life.

[00:16:37] YD: God. I love that. And so many questions I already have for you. But first of all, I think this will be really interesting for our listeners to hear, is how do you know if the story is there or not? Because as our listeners and people in our community, in our circle membership, and the class, we often talk about putting pitches together, approaching magazines. And is there a story in here? And sometimes, it's really difficult to say if there is a story in here or not. Because it sounds like you have a really great eye, or nose, or whatever for it. I mean – 

[00:17:10] AH: Yeah. Honestly, I wish that I had some kind of compelling wisdom to share on that. I think so much of it, for me, I feel like is intuition. And it might also be kind of my narrative imagination. I'm really good at creating entire narratives in my head, which can be a blessing and a curse. But it's like I see something that's so beautiful. And just one line, for example, or you watch a moment unfold. And I don't know. I could create a novel out of nothing. And so I think that that's just kind of like an intuition-based thing for me. 

I will say, I did a few years ago a writing workshop in Zanzibar with a couple of journalists that I think are incredible women. And the focus of this writing workshop was duality of the human experience. So how we can be two opposite things at a single time? Or feel completely two different emotions on the spectrum of feeling at a given time? 

One of the writing exercises that we did was we did a free writing exercise. They would give us a prompt. And we didn't have much time. So it was like a very loose, maybe we would end up with 200 words or something. Well, then what we would do – And so of course, that's a framework, right? That's kind of a blueprint. So what we would do later is we would go back and we would add within that beginning to end that we already wrote, we would expand, expand, expand, expand, expand. And so we would go through what we had already written, which seems like a very lean, maybe even meaningless piece of prose that we had put together. And then we would create like this beautiful, full complete story out of it. 

And by complete, there's not a defined word count that makes something complete. I think a story is complete when it's well told and it completes itself. I don't think that there is a word count that can achieve that. But it was a really interesting exercise for me. And it's something that I've continued to practice since that writing workshop, where, as a writer, I think sometimes you're driving down the road and all of a sudden it's like something comes to your head and you have to like get it out. And so I'll pull over and I'll put something into a note, just keywords. A lot of times my writing is a list. The number of lists that I have from my travels that are just completely random keywords that I know will prompt a larger memory when I go back to revisit that. I kind of use that as the same kind of framework where I go in and it's like, “Okay, I can expand on all of these keywords,” and then you have a complete piece of work. 

And so I think maybe the beauty of observation is what makes something complete, because if you have that micro moment that you can fixate on, if you can draw recollections of all the things that surrounded that, from a sensory perspective, from an awareness perspective, I think presence is what makes a story complete. Because if you're completely disconnected from a moment, you're not going to have all the elements that make it complete. So I think maybe that's what it is. Maybe it's the art of being present and having the ability to recollect details because you were so present in a period of time to recognize that there's so much more complexity to a moment. Everything is three dimensional, four dimensional, five dimensional. If we pay attention to the complexity of – Yeah, the complexity and the layers of our experiences, I think the stories are endless.

[00:20:02] YD: Oh, that's such a beautiful advice, I think. And definitely a piece of wisdom for our listeners. I love how you said that if we're able to put ourselves back in that moment, or recollect that moment through all of the different senses, emotions, experiences, that's what really makes my story compelling. And I do that, too. I don't do lists. But I have like these sort of run-on sentences, almost like little short phrases of things that I was thinking about in that moment, or things I was noticing. And then yeah, when you come back to it, you are able to weave that narrative from that skeleton, or that structure that you're talking about.

[00:20:42] AH: That's what it is. I've been entertaining the idea of writing a book of short, kind of creative nonfiction, but short stories, because, really, I don't know that I have an individual arc to tie them all together. So for me, I think it would be a collection. And so I've been going through – I have just envelopes and folders full of napkins from a restaurant in France, or from a hike in Nepal, where I would just get these ideas and I'm just pouring out those key words, or those fragments, or the run-on sentences, like you're saying. And it's fascinating what we might not think about again if we didn't have that orientation, that piece of material, that artifact to take us back to a moment. And then suddenly, it's like I can't stop writing, because I've been able to revisit this moment. And I think it's absolutely incredible what humans can retain. And if you can activate that, and you've got a way to kind of revisit a moment, I think that you're just sitting on treasure that's just waiting to be told.

[00:21:36] YD: Yeah. Oh, I love that. I love that. So when somebody sends you – It sounds like – Oh, actually, sorry. Before we go there, I wanted to comment on one more thing that you said, which I think is also very important. And that's a theme and a thread that's been sort of showing up again and again through all the different interviews that I'm doing with people, which by the way, for me now, as a podcast host, it's so interesting that I can start seeing this parallels, because so many women that I'm interviewing, they're from all over very different backgrounds, very different stories, but the threads are all the same, which is sort of cool to see. 

But what I was going to say is that the fact that you are reaching out to people who post something on Instagram, post a caption, a little moment, a tiny something, recollection, it just reminds me that we never know who looks at or listens to what we have to say in any given moment. We just have no idea. And so I think it's so important to be able to share what's on your mind, to share your thoughts, share your inspirations, share your projects. If you want to work on something, share it with the world, share it on Instagram, share it on TikTok in a funny dancing video. But we just never know. We just never know who sees something that we do and it can spark a really beautiful chain of events that wouldn’t never otherwise happen if we didn't share it. So I think that's just something that really strike me from your story of reaching out to people and doing that.

[00:23:10] AH: Yeah. And I think, too, it's that domino effect of humanity as well. And it's like if you read something that someone posts that resonates with you in some way, just the inspiration, the domino effect that can come from being inspired or touched. Or maybe somebody shares a really difficult life moment, or they're kind of publicly processing or sharing one of the hard parts of the human experience. I think there's really a deep beauty and that willingness to be vulnerable and where that can lead to. So you can share the funny. You can share the hilarious, the travel mishaps, the profound moments that you had with a stranger, or the heartbreaking. The moment that was just – Where you're on the ground crying in tears. Like, I think it's important, if you're comfortable, of course. Not if you're not comfortable. But like if you are comfortable, just the impact potential of that is limitless.

[00:23:10] YD: Yeah, definitely. So I wanted to ask you, as an editor, and as a founder of Pilgrim Magazine, what do you look for in stories? So when people send you emails with ideas, with pitches, how do you know if it's a Pilgrim story or not?

[00:24:20] AH: So there's a few things. And we don't have a formal style guide right now. It's something that we're working on. But I also recognize that we're continually evolving, and especially over the last two years with the state of the world. But I think does it make you feel something? Does it teach you something? Is there like an important human lesson in the material? 

Yeah, if it connects us to humanity, if it transports us to place in a beautiful, respectful way, we're actually – I don't want to call it a formal rebrand. But we are really focusing on stories that encourage mindful travel, being respectful of local cultures, of connecting with a place in a way that honors where it is without Americanizing everything or having American expectations of everything, Western expectations. 

And so those are some things that we're really looking for. So anything that's raw and human. Even silly. Like, if there's a silly moment that's just hysterical, or random, or just sometimes the universe is mischievous, and you end up in these scenarios that are just too comical for words sometimes. 

One of our stories, it was a piece about a woman in Ireland who found herself at a pub at the end of a very long, rainy travel day. And these local Irishmen were dissecting a bird within the pub, because they were doing an autopsy of – I think the bird had died. And I kind of forget the entire narrative. But it was just such a comical, hilarious thing. There was no animal cruelty or anything like that for the record. But it was like this moment where this woman just happens upon this place and observes this incredibly ridiculous thing. And it's like those moments of just comedy, where it's just like, “What in the world is happening?” Things that you can't make up. So those are some of the things that we look for.

[00:26:13] YD: Yes. That's really interesting. And I think just to have a little proud moment here for a second, that one of our photographers and writers in our community, in the Genius Women community, Vanessa Dewson, recently published a story with you guys, with Pilgrim, about the Amazigh culture in Morocco. 

I told Vanessa – We had a conversation about it in the circle, that's this was the story that I wanted to say, to tell, for such a long time. Because when I went to Morocco, I learned – I sort of went on the same evolution that Vanessa went, where you hear about berber, berber, berber. That's a very common term. And then when you go there and you actually meet the people, and you spend some time with them, they will tell you, “Well, no. Don't call us berber,” right? Which was the title of your story. We are a Amazigh. And they're very proud. And the culture is so beautiful. And I pitched that story to National Geographic and it never went anywhere. 

[00:27:10] AH: That's a bummer. 

[00:27:11] YD: Well, it's funny, because it was my first pitch, I think, ever. And it was not a good pitch.

[00:27:18] AH: It takes time. 

[00:27:19] YD: It definitely does. Yes. But that's also why I was so excited. I'm like, “Vanessa, you're telling that story that I feel so strongly about.” So yeah, just a little shout out to Vanessa. And – 

[00:27:30] AH: Yeah, that story really resonates, especially with kind of that, not new direction, but really a focal point that we've got at the moment. And that is like bringing more awareness to global things and maybe terminology and beliefs that are kind of outdated and explaining why. 

Even as a writer, I didn't know that the term berber was frowned upon term. I had no idea. In my mind, berber was always – I would think Berber rugs, Berber textile, Berber artisan works. And I had no idea. So I'm constantly learning as an editor, especially now having writers from all over the world, new things that are really powerful and important. And Vanessa's piece was gorgeous. And it was also one of our first pieces for a new section that we launched with our – Relaunched this summer, called Portraits of Humanity, which is where we're really trying to do the deep dives on humaneness. 

And some of the stories are lighthearted. Some of them are deeper and have historical and cultural significance, like Vanessa's piece does. And some of them are more lighthearted and just they might be more image-centered and less about the longform narrative. Another piece that we're working on that's in the same vein that I think is really important as well is a writer from Austin, who has a Romani background. And she's doing a piece about the phrase gypsy and how that is truly a very racist term. But it's been romanticized, especially in the Western world, as a bohemian, traveling, magical kind of woman or people. 

And she's working with Romani portrait artist, portrait photographer, as well to kind of bring the story to life. So it might be some time before it's ready, because there's a lot of creative components to this. But it's really important. And I was guilty of using the word gypsy in that same way that misused years ago. In fact, recently, I did an audit of my own Instagram and went back and changed every caption from – I’ve been on Instagram for almost 10 years now, where I was using that word, misusing it, and without knowing. It's ignorance. 

And I think it's important to also be very, like, humble and honest about that, that we're all constantly learning. And I think we're now in this time in the world where it's important to be honest about the lessons that we're learning and share them outwardly. And I recognize that we all have so much to learn. The world is full. Millions of cultures. And we can't possibly know everything about all of them. And we don't always know the origin or the history of things. 

So I think if we can continue to share these stories that teach people to be more responsible travelers and humans and more self-aware and culturally sensitive, I think that that's one of the most impactful and important things that we can do. So more stories like Vanessa's, please. And you could always pitch us. I know that you've traveled extensively and spent so much time in Lebanon and places like that, which I really hope to join one of these journeys soon. I know that you've got a lot of expert insight into some of the struggles that these communities have and some of the myths portrayals they have within the news, and just stigmas and things like that. And we want to reverse that. And we want to learn as much as we want to teach. And so that's like a really important part of our ethos.

[00:30:37] YD: Yeah, that's so beautiful. And that really resonates with me a lot. And I believe you guys have your pitch guidelines out as well, submission guidelines. So we'll link to that in the show notes. So if you guys have people who are listening, if you have stories that fit any of the things that Ashley just discussed, just covered, please don't hesitate to reach out to Pilgrim Magazine. 

But I want to sort of jump a little bit. You mentioned Instagram. And I know that you've recently also started working as a designer on Instagram. And congratulations, by the way. That's pretty awesome. What I want to talk about a little bit next is this idea that how do you manage all these different things that – You mentioned earlier, being a freelancer and patchwork of projects. There is a sense out there that I sometimes come across, that if you're not working solely as a writer, then you're not really a writer. Or if you have some other things that you're working on, then you're not as legit or whatever as you could be. 

And on this podcast, I actually talk about this often, because I believe that that's just BS. And your path is your path. And however, your path makes sense is what makes sense. And there is nobody that needs to sort of validate it and say, “No. Well, you have these other things that you're working on or supporting yourself with. And that means you're not a writer.” And I do see this in the industry. And so I just want to talk about that a little bit and sort of find out how you think about that.

[00:32:11] AH: Yeah. I mean, it's funny, because I think so many authors that I love their material, but they weren't successful till they were dead. And I think that that's a really important thing to remember that we do have this misconception that you have to create constantly. All day, every day, you write, or you paint, or whatever your medium is. And you need to be successful at it to be able to call yourself something. And I think imposter syndrome is also a big part of our culture. And I've struggled with it at different times. 

And it's funny, I don't consider myself a photographer. But I do often shoot my own photos. I love photography. I have a great camera. But I would never call myself a photographer. And sometimes people will introduce me, “Ashley is a writer and a photographer,” and I correct them. And I've had other people that I've looked up to in the industry who will say to me, “But you've sold photos, and you've been hired to like cover events, or to do street photography of a place.” And I'm like, “Well, yeah, but I wouldn't feel comfortable shooting a wedding.” And that's kind of always what I say. That's how I caveat it. I wouldn't want to be the person that's responsible for having perfect wedding photos. And I've been corrected. “Well, so you're not a wedding photographer? Like you're kind of a humanity photographer.” 

And it's funny how we get these narratives in our minds that we are not something because we think that we have to achieve X, Y and Z, or we have to produce so much material, or we have to be given a particular accolade. And I just don't think that that's true. And I think those self-limiting beliefs are really – They can be very devastating. 

I think you don't have to be published to call yourself a writer. You don't have to have an exhibit to call yourself a photographer. I mean, the beauty of being an artist of any kind is that we're constantly evolving our art. And I look back at some of my early work that I was paid for and it makes me cringe sometimes. And I'm just like, “I can't believe I wrote that that way. Or why am I so ellipses happy?” I used to use a lot of ellipses. 

And it's funny. We are our own harshest critics. And anyone that tells you otherwise who's within the field, I think that that is motivated by ego. And I think ego, it can be the biggest blocker that we have for anything. So I think, as long as you commit to your art and some capacity, you are that thing. And you can be many things. You don't have to be just a writer to be a writer. I consider myself lots of different things. And there's dreams I have that are not connected to what I'm doing right now and today that I'm going to eventually be that thing. I want to be a children's book author. I really want to shoot album covers. Completely random dream I have. And I'm not those things yet, but I will. I'll become those things, because I want those things. 

And so if you have to have a job in tech, or not even have to. If you enjoy a job in tech or in any other field and that helps sustain your craft, do that. I could never do my art all day, every day. I go through these ebbs and flows, these creative waves where sometimes I can't produce anything. And I get really hard on myself. And it's like I have endless material within me that I've not produced on paper yet. So many stories that are unwritten. And sometimes like I catalog those and I inventory them. And I think, “Oh, you're just wasting time. Like all of this time is passing.” But it’s like, me personally, people work differently. I can't just sit and write long form constantly. When the wave comes, the creative wave, I commit to it, and I write it, and I hibernate, and I turn away social invitations. And it's like I just have to like hunker down and like get the art out because it's calling me and I feel compelled to get it out. 

And so that's when I produce my best work, when I'm bullying myself or trying to give myself kind of a ridiculous deadline that's for no good reason, I don't produce my best work. So it's like you need to foster some sense of grace for yourself. And you are whatever you want to be.

[00:35:58] YD: You said that you can only produce some of the some of the best work that you do when that creative wave comes over. And so you can't really create all the time. And I think that's really important, because that's something that I talk about on the podcast a lot too, is that we have this insane pressure to produce in our culture. We do, right? With Instagram, with TikTok, with all these apps. It’s like it trained us to think that if we're not constantly posting, we're becoming irrelevant. 

And I think it seeps into our creative work and life as well, because we feel like we need to do it. But I am so 100% with you on that, that our wells need to be restored for some of that work to be produced. And you can't always just create it. You need to restore. And that takes time sometimes.

[00:36:46] AH: Yeah. I used to doodle the words nourish, replenish, create on things that I wrote all the time. And it was something – When I was editing a magazine, and often more than a decade ago, that was my that was my MO, like, as a reminder, nourish, replenish, create. And I think two thoughts came to mind when you were talking a second ago. And one is that, as humans, we have a certain amount of energy at the beginning of every given day. And we can spend it in numerous different ways. Maybe it's through hiking, maybe it's through writing, maybe it's through emotionally exhausting dynamics in our interpersonal relationships, or maybe a taxing profession that drains you. 

And so maybe you're only actively doing something a few hours a day, but you find yourself exhausted at the end of the day, and then you're pressuring yourself to create on top of that. And that just creates a really unsustainable cycle. And something that I struggled with, and I've been trying to become a lot more mindful about, is that when things become kind of centerpieces of my to do list, I tend to almost get like this wall of anxiety around them. And even if it's something creative that I want to produce, that I’m excited to write, excited to put together, if it lives as too much of a centerpiece within my to do list or my Google Calendar, I almost build a resistance toward doing that thing. So I've tried to kind of take the pressure off of myself to do a certain thing on a certain day, which is a self-imposed deadline, and allow it to kind of come to fruition via more organic ways. And it's those creative waves that I'm really trying to tap into an exercise when they come, and then give myself the other time, the downtime, to replenish, to restore, to do other things that are just good for my soul. And everyone has their own things that are good for them. And I just really tried to honor and give myself that space. And it's okay to not produce something for a period of time. 

As an artist, I think that there's times that we produce a lot, and then there's times that we consume. And that's something I've been thinking about a lot too. It's like I don't always read and write at the same time. Sometimes I go through periods where I’m just thirsty for books and thirsty for poetry. And then there's times that I don't – I've got piles of books, which kind of is their own to do list in a way, which can become daunting. So I've been trying to like move away from that too. But then there's times where all I want to do is just absorb the stories that are on those pages, and I don't produce anything, and then vice versa.

[00:39:01] YD: I love that. I love that we're having this conversation. This is something that we recently discussed in the circle. We call it the create restore cycle, right? And again, that idea that you need both, but it's a cycle. And it needs to be in balance in order for us to be long-term sustainable committed to this path. 

And what you talked about earlier, I was inside, I had butterflies, and I was just like so happy to hear you say that, because I think this is probably one of the most important messages that people will hear on our podcast ever. It's so liberating to know that your path and how you choose to support yourself financially, whatever, what you choose to work on is absolutely valid. And really, no one, besides yourself, gets to determine and define who you are, who you want to be, who you will be in the future. And I loved everything that you said earlier. I will listen to it many times, I'm sure. Because even myself, I go through these struggles myself too. 

I also do many different things. And I think you're right to say that it's a combination of ego/imposter syndrome/very rigid definitions in society that say, “Okay, you're not really legit if you're not doing this one thing fulltime, or if you're not successful with it 100% all the time.” And so when you were saying all those things, I was just like screaming inside, “Yes! So liberating. I love this. I love this.”

[00:40:34] AH: That's awesome. Yeah. And I think, just to add to that, too, is I think that there's a stigma around failing or not doing something well. And I mean, fail, fail hard, fail often, fail with passion, and then learn from that failure. 

I've failed a lot in different ways. And I think that, especially, again, I go back to the perfectionism that comes with the digital world where it's easy to kind of present the idea of perfectionism. And so we try to live up to that. And it's just not human. And I think that let's talk about our failures. Let's talk about our slip ups, our moments of imperfection, or works of imperfection. And what did we learn from those? How can we elevate that? And take a lesson to improve our work going forward, or improve ourselves going forward? And it's okay? There's not an artist in the history of the world that hasn't failed. 

Again, some of them failed, or they thought they were failing until long after they passed away, and then their work became some of the greatest work of all mankind. And so I think it's important to recognize that our work matters. We don't have to be award-winning. We don't have to have every major byline. We don't have to have editors respond to every pitch. Are we proud of our work? Does it honor our soul? Does it reflect like who we are? And does it have a positive impact on the world? And I think that's what motivates me more than anything, is it doesn't have to be a Pulitzer Prize. Like it can change one person's course, or their life, or inspire them. And to me, that's worth all of the creative investment.

[00:42:05] YD: Ashley, I needed to hear this today. So thank you. 

[00:42:08] AH: Of course. Thank you for having me.

[00:42:10] YD: That is so beautiful. That's really – Thank you. Tell us a little bit about the island of Faial. It has a special place in your life and in your heart, doesn't it?

[00:42:24] AH: Yeah, it really does. So I was invited a few years ago to join an expedition, a cetacean migration study as a writer. And I almost declined the invitation because I already had plans to travel [inaudible 00:42:35] in Switzerland that winter. And then I was familiar with the Azores, but I'd never been there. But I was already in love with Portugal. And I'd already had this wild dream that someday I wanted to own property on the mainland of Portugal. And I don't know why. I've just always felt called to the land. 

Even before traveling there, I remember saying that I would never skydive again, unless it was in the Algarve. And I'd never even seen the Algarve. And this was like a very young Ashley statement when I was in my – I don't know. I think I was still in college when I would say that. And I don't know why. I always felt drawn to the country. 

So I started researching the Azores right before I was leaving for my Switzerland trip, and just like a dreamscape. And so I decided to alter the course of my plans and go. And so, in the winter, it takes a long time to get to the Azores from a place like Switzerland, because there's just few flight paths. And it took me about two and a half or three days to get there from Zurich. And I landed, and I had a driver pick me up at the little airport there in Faial to take me to the guest house that I was going to be staying at. And I took a time lapse, which isn't something I normally do. Occasionally I take a time lapse. But for some reason, I took a time lapse from the moment we started driving until we arrived at the guest house. 

And I remember just thinking, as soon as I saw Pico emerge from – Which is the volcano on Pico Island, the tallest Portuguese mountain. As soon as I saw it emerge, it was like I was just captivated. And I thought this is a place I could live. So I was only supposed to be there for three or four days. And I ended up changing my entire travel path. I didn't go back to Switzerland, except for to catch my return flight home a couple of weeks later. And I booked the guest house that I was staying out for every night that it was free. So basically, that's what determines how long I was staying, was how many nights I could stay there in this guest house because it overlooks Pico, and the marina, and I had a little writing desk right in the window with the mountain sitting there. And so I would watch the sunrise. And it was just such a special place. 

And one of the things that really drew me there as a storyteller is the history. Because until the 80s, whaling was legal there. And that's not that long ago. So whaling was the foundation of the economy in Faial for a very long time. It's also a very important marina in the world, because anyone doing a transatlantic crossing generally stops in Faial because it's got an international marina for provisions, fuel. And it's often the first place that sailors will touch lands in between continents.

[00:44:54] YD: Even the US military stops there to refuel and recharge on the way to the Middle East, which is how I know, and how I've been to the Azores as well.

[00:45:04] AH: Yeah, exactly. So it's fascinating, like, convergence, history things and culture things. But the whaling was outlawed. And then now the culture has been replaced by marine research. And it's one of the most important marine research hubs in the world. And English is the shared language of science. And so I was able to communicate with international scientists from all over and just hearing the things that they were studying, the effects of climate change on whale migration patterns, the plastic crisis, deep sea things. And so I just got this fancy idea that I'm going to move here. And so that was in April of 2019 that I was there, March, April. And so I came back to the United States with this vision and this dream. And I left with my dog in October of 2019, and spent a little over a year there. 

And again, as a writer, and as I formed relationships, and met people, and made friends, and learned more about the research happening, and also spending the offseason there where there weren't travelers, then entering into the pandemic, it was very much – It was just the local community. And I was able to learn so much about the science happening there, critical science, critical research. I mean, really compelling, amazing things are happening there. 

And the old fisherman, the old whalers, a lot of them are still alive. It wasn't outlawed that long ago. So to see how we can move from something that was economically important, but environmentally devastating, into this new phase, there's so many metaphors and symbolism within that transition, and evolution of a place. And the coexisting is fine. Like, it doesn't really feel like there's animosity or anything. Like they support each other. And so now it's a place that's very protected. The waters are protected. There's a lot of marine regulations and laws that protect the marine life there. And it became just a fascinating place. The landscapes are gorgeous. The Portuguese culture there with this kind of international community is gorgeous. And there's just nothing like seeing Pico every day. Like, the sky can change a million times in a single day there, from rainbows, to 60-mile per hour winds, to clear skies, to crazy colored skies. And there would be whale sharks in the channel, or there would be a lot of the man ‘o wars that would wash up into [inaudible 00:47:17], which is the beach that I lived on. And every day was just captivating there.

[00:47:22] YD: I remember watching your stories on Instagram about that, and just being fascinated by how beautiful that island was. Do you think you'll come back there?

[00:47:32] AH: I hope so. I think in this period of time, it's really hard to plan forward with anything. And working at Instagram, it's Portugal's not a country I'm allowed to work in. But I do think eventually that I would – I still have the same dream. And there's still people there that I love dearly. And it will always be a home. It's a place that I spent a year in a very strange period of the world. And I think that when we go through a collective crises together, there's an even richer and deeper connection in ways because you experience the different realms of human grief, but also – And the gratitude that you're in a place that's so beautiful, and was so protected. They closed our port and our airport for a period of time. And so once the first few cases recovered, we were pretty safe. And it's a very, very special place to me. And I miss my daily routine. I miss dinners [inaudible 00:48:21]. The only Portuguese man to circumnavigate the globe by himself by sailboat, and he's done it twice. And so there's like a significant story there. And all the other people, everyone there, whether it's a scientist or a sailor, there's just more stories that I want to capture and put on paper. So it's a place I'll definitely return.

[00:48:41] YD: Yeah, I wish a return to Faial for you, for sure. 

[00:48:45] AH: Thank you. 

[00:48:45] YD: I read somewhere that you said once that we are all mosaic beings. And I love that phrase so much, because even going back to our earlier conversation about having all these different projects that we work on and having the freedom and liberation to be able to do that, I think that phrase that we are comprised of all the different mosaic pieces that make us who we are. I just love that so much. What does that mean for you, that phrase?

[00:49:14] AH: So that line actually emerged very organically when I was writing a long-form story that was kind of a look back at just everything that can happen in a year. And it was a reflection of a particular year in which a lot happens. And there was beauty and triumph. There was deep grief in that year. Some really big life lessons. 

And as I was writing this piece, it was a piece I was having a really hard time finishing. And it was long. It was maybe 4000 words. So this was a quite a long piece. And it was one that I kept missing the deadline on and I kept asking for a little more time, because I just couldn't get the ending there. I don't know. I think because there was so much emotion within the story that it was just hard to close it. It was hard to find the right way to end it. 

And those words just came to me. And from a metaphor perspective, it means so many things. The line that followed was something like we are all fractured by our stories. And I think what I was trying to do was honor that human experience. Again, I keep talking about the human experience. But the human experience is intended to be made up of triumph, of tragedy, of hardships. And I tend to write very honestly about the things that I've gone through. And so in my mind, to be a mosaic being, it gives recognition to all of the different things that are part of that spectrum. It demonstrates that it's still beautiful, and that we can create art from these mosaic pieces. Just because something's broken, doesn't mean it's broken. And we can recreate and reorganize and reshape. 

And in fact, I wrote something recently that kind of extended upon the we're all mosaic beings line. And it was something about looking back, again, at kind of a strange hard year. We've all struggled in different ways. And kind of seeing the difference between being a mosaic and progress, where we're putting shapes, and pieces, and colors in different ways. Determining the pattern. Or maybe there's is no pattern. Maybe it's completely abstract. But recognizing the difference between that and then seeing something as the grout starts being filled in. And we start kind of finalizing the things. And it's like we like the shape that something's taken on. And we like the colors that we've put together. And then we start making it a little more final. And I think that that's like representative of the art of creating ourselves and recreating ourselves. 

And I think there's periods where maybe we're kind of all over the place, and we don't know how to put the pieces together. And then as we take our lessons and our experiences, and we can kind of shape things in a way that just feels more stable and more whole, if that makes sense.

[00:51:42] YD: So beautiful. Ashley, you're such a beautiful storyteller. I just want to keep listening to you. 

[00:51:47] AH: Thank you so much. 

[00:51:49] YD: That's really beautiful. What would you say to someone who feels like they have a story inside or stories inside, but for one reason or another that we already discussed, like imposter syndrome, all those other things, that tell us we're not a writer? We're not a photographer? What would you tell to them? What would you say to that person to try to encourage them to go out and reach out to Pilgrim Magazine, to other magazines? Write your stories on your blog? What would you say to them?

[00:52:21] AH: I would say, and I do say, I think it's important to, one, have an ally. Like I think having an ally is really, really powerful. I think there were so many times that I was stifled by my own self-doubt that I just wasn't sure how to move forward. It wasn't always so much that I didn't believe in my work, or that I didn't have a powerful or a compelling story to tell. But maybe I just didn't know the next steps. Like I wasn't experienced enough to know what to do next. 

And so much of my success has been based on – Or maybe not based on. It's been enlivened by people who believed in me. But in order to have people believe in you, you have to be willing to share part of yourself. You have to be willing to share a little bit of vulnerability, a little glimpse into what you're working on. Not feel burdensome by doing that. And I think that was one thing that stifled me as well, is that I didn't want to burden people with questions, or with meeting support, or asking someone to read my work. And of course, you always want to be respectful of someone's time and have reasonable expectations. 

But I know that because of how much other people invested in me, and their willingness to help me perfect a piece or introduce me to editors, or introduce me to different people that would be just powerful additions to my story. I'm willing to do that for other people. Like, if I see that promise and someone, I mean, I think that evidenced by the fact I launched a publication in which we've got seasoned writers that have written from New York Times and National Geographic, but we also have people who've never written anything beyond maybe a caption. And, like, that's what we want. 

And so I think feel empowered to reach out to someone and just say, “Hey, I love your work. And I've been inspired because of your work. And I was wondering if you would be willing to read something or point me in the right direction.” Asking for help is, I think, necessary, especially in a world in which sometimes our success is defined by who we know. And that's an unfortunate thing. But there's so many people who are willing to help. 

And I would say also, like, I started Contemporary Pilgrim, because I didn't want to sell some of my most prized stories to other publications. But because I started that, it gave me a platform. And I made no money from it. It was an art thing for me. This was a production of art. It wasn't monetized. I wasn't earning a living, but it was a place where I had a guaranteed home for my voice. And I would encourage other people to do the same. 

My work there wasn't perfect, but it was a place that I could capture and gather all the material from my journeys and from my connections with humans. And from there, it grew and it blossomed. And now it's a community that I don't even have time to write for myself a lot of the times. But I have lots of other writers. So I would encourage people to – If you don't have an outlet, create one. It doesn't have to be perfect. And so much of my old writing, I've repurposed. I've gone back and my voice has matured, my writing style has changed some. And I've gone back, and that work has almost become material to build from. Like it's kind of in the archives, and I can add to it over time, or change it, or pull things from it. And I think as long as you're writing, it's not a wasted exercise. Or creating, whatever you're creating, it's not a waste of exercise.

[00:55:34] YD: Yeah, beautiful advice. And I concurred to every single word that you said. I think it's really important to have allies, to have support. And yeah, putting your work out there and having a home for it that doesn't depend on the on the whims and ebbs and flows of other people and their platform. I think that's a great suggestion as well. 

Ashley, I feel like I could talk to you for another hour. I really, really enjoyed hearing what you have to say. And again, I just want to repeat that you're such a beautiful storyteller, and you have a beautiful way with words. And I think we have to have you back on the podcast to dig into some of the areas that I didn't even get a chance to talk about. I sort of wanted to ask you some more things. But we'll have to have you back, if that works for you, as well. 

But I wanted to close our conversation with this question that I often ask at the end of each episode. And it's sort of a big question, but how would you start thinking about what does it mean to be a woman who is stepping into her brilliance?

[00:56:41] AH: I think that there's a big emphasis now these days on sisterhood. And you're seeing a lot more material, and efforts, and retreats and things that are kind of centered on being a woman and on sisterhood and community. And I think that that is a really magical and beautiful thing. 

I think it's not always easy to be a woman. And we face a lot of unique challenges. And a lot of those challenges end up becoming burdensome to us emotionally, because we get caught in the feelings of not feeling enough or not feeling like we have the same kind of trajectory that maybe a man has in different ways. But I think it's supporting other women. And I think it's being – Yeah, like, I think it's really important to think about the lessons that we are quietly sharing with other women by being willing to be bold, and to do things on our own, and to tackle big dreams, and to have them, and to believe in them. And I just think that there's lessons, residual lessons, that kind of get passed along with a woman who was maybe struggling with their own sense of self, or the ability to just feel empowered in our own sense of self. I think the lessons that we share with those people in that part of their journey are powerful, because it shows them you can do anything, and you can. But sometimes we need reminded and we need to have positive female influence around us to kind of remind us so that we remember. So it kind of brings us back to the home of being a woman. 

And I think leading – So, in a way, it's leading by example. I think but we all have to go through kind of those shared female struggles throughout the course of our lives and careers. And they might be unique in some ways. But I also think that there's a lot of patterns and themes and the challenges that women face. And so I just think once you've established, to some degree, your sense of boldness, and your pride, and like you're actually not pretending anymore, I think it's important to pass that wisdom down and just like empower other women and show up in a sisterhood in a sense.

[00:58:49] YD: And I think doing that enriches your own soul, too, in such a beautiful way. That's what I've experienced with genius women, is that I get so much nourishment from that. It's incredible, you know?

[00:59:03] AH: Yeah, it's symbiotic. I mean, it gives more purpose to ourselves as well to like know that we’re recontributing in different ways to help young women or help older women who haven't found that sense of strength and certainty of self yet. So I just think it's very much a symbiotic relationship, I think.

[00:59:26] YD: Beautiful. Beautiful, Ashley. Beautiful conversation. Thank you so much for sharing your thoughts, and your wisdom, and your experiences with us. For our listeners, definitely check out Pilgrim Magazine. We're going to link to it in the show notes. Ashley's also on Instagram @contemporarypilgrim. And we're going to link to that as well. Check out everything that Ashley has going on. Check out her stories. And don't be afraid to reach out. And don't be afraid to share your own stories, your own ideas. You see how amazingly kind and generous Ashley is. So don't be afraid. And yeah, thank you again so much, Ashley. It was wonderful to have you.

[01:00:05] AH: Yeah, thank you so much. This was an amazing conversation. And I admire your work so much. And I don't know, especially your role in bringing some awareness and education to some of the places that you take travelers to. And I think that's incredible. So it's an honor to be here. And yeah, to any of the listeners who feel called to share something with Pilgrim, like, that door is always open. And we welcome pitches, ideas, even if they're completely disorganized, and not fully formed yet, like, we welcome that. That’s what we're here for, is to kind of help shape the story. 

[01:00:36] YD: Amazing. Awesome. Thank you. 

[OUTRO]

[01:00:38] YD: Thank you so much for listening today. I hope you enjoyed this conversation I had with Ashley. And if so, please consider leaving us a review so that more listeners could find our show. I really 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. So if you've been inspired by something you heard today in our conversation with Ashley, or in any other episodes of our show, please consider leaving us your review. This is one of the best ways you can support us. 

Thanks again. And stay tuned for an episode on NFT's, non-fungible tokens, coming your way next week.

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