This summer, I had the great pleasure to interview Finnegan Shepard, author of the Issue 41 story “The Gallery”. We started off with an in-depth discussion of the story itself, then transitioned to discussing the busy life of a writer and entrepreneur.

The following interview took place via Zoom and has been edited for clarity. 


Finnegan Shepard is a published trans writer, classicist and entrepreneur with 1/3 of a PhD in philosophy and 3/4s of an MFA in fiction. Finnegan is the founder and CEO of Both&, a storytelling and apparel startup designing for transmasculine bodies, the co-founder of Limns, a bi-monthly newsletter that explores concepts through etymology and photography, and the author of Tilt. More about Finnegan and his various projects can be found at finneganshepard.com.


Berkeley Fiction Review: I’m here talking with Finnegan Shepard, the author of our Issue 41 story “The Gallery”. “The Gallery” is so deeply personal and detailed—I think the first impression a reader gets is that of being dropped right into the middle of another person’s life. How did you work to develop the character of Tilo and his backstory?

Finnegan Shepard: It’s one of those stories that just flowed out of me in one sitting. Obviously I came back and worked on it, but what interested me from the start was dealing with the idea that relationships don’t end when they end in the objective ‘real’ world. We continue constructing them in our mind and building out fantasies around them. I saw a sort of analogy there with transitioning gender as this deeply imaginative space in which the self really is constructed in the mind, and then how it interfaces into the real world doesn’t always map on in the ways that we think it will. And so, to me, that sense of dropping right in—I wanted it to have that incongruity between the imaginative fantastical world and what is really playing out in real time. 

Another aspect is that I think a lot about how the stories that we have about transitioning tend to have a very specific narrative arc. You begin in the past and you build up a person through the reveal and the recognition. “The Gallery” is very much just rooted in the present. You don’t focus on the past, you just sort of arrive into the moment as experience, rather than creating all this justification for why people are what they are in the present because of the past. Certainly backstory gets woven in and it’s important for the way that the story functions, but I really wanted it to genuinely be just the backdrop—just something that’s operating in the background while what we’re really focused on is this intersection between the imagined or fantastical and the reality in the present day.

BFR: Yeah, I think you definitely achieve that really well. Did you find it difficult to work in all of the details of Tilo’s life that happened long before this story takes place?

Finnegan Shepard: No, those details just felt absolutely natural to what the story needed to be and never like the real emphasis. I felt they were the details that needed to occur for the plot in the present to exist—they followed naturally, and were what I needed to have the present day story function.

BFR: That’s really interesting. As our staff first began to discuss this story, the most contentious character was definitely Madeline—she’s perhaps the closest thing the story has to a villain and yet she is also so vulnerable and relatable at many points that it seems silly to even compare her to that label. What aspects of Madeline’s character did you try to accentuate to place her in such a gray area?

Finnegan Shepard: I really don’t think of Madeline as a villain. I can understand why readers would, but I feel as though that’s more a product of reading in our time, rather than the actual story. I think it’s more of a knee-jerk reaction to the way that we’ve come to speak about trans experience and how one ought to be in relationship to that. If you zoom out and look at who Madeline is, what she says in any given moment, on the scale of virtue between honesty and kindness she definitely errs towards honesty–she’s not about the little white lies that can make a person’s life easier. But I don’t think that makes her a villain, I just think it’s a different value system. I think why readers could be so sensitive to it is that we sense how devastating that kind of honesty could be for a character like Tilo. But if you look at it in a more objective way, she’s not being intentionally cruel. She’s not saying anything that is out to hurt him, she’s being honest and asking questions that are true to her own experience. 

I think just because the reader is centered in Tilo’s experience–which is a sort of hypersensitive experience, and you so want him to hear what he needs to hear–you want to make her a villain. But the reality is that the story, and Madeline in particular, is just pushing on that deeply sensitive space that I relate to as a trans person, of wanting to feel like you’re not crazy, that what is going on in your head is what is also read by the outside world. It really pushes the question: “Well, if it’s not read in the same way, is it better for a person to lie to you about that?” 

I mean, I think the truth of the matter is, they’re clearly not compatible. They’re deeply incompatible in a relationship, as well as erotically, and that is clear to everyone, including Tilo, by the end of the story. But it’s not a question of good guy bad guy so much as a question of whether these people give each other what they need. The answer, in the end, is no.

But it’s not a question of good guy bad guy so much as a question of whether these people give each other what they need.

BFR: Yeah, I really like how you achieve that gray area and it’s a really fascinating narrative device.

So, as “The Gallery” begins, readers find that Tilo has already imagined how the opening scene would happen several times, a scenario which he calls ‘the fantasy’. Of course, in real life, circumstances occur slightly differently than he expects. Why did you juxtapose Tilo’s fantasy scenario against reality here? What inspired this unique aspect of the story?

Finnegan Shepard: There’s a way in which, at least from my own experience, being trans is extremely fertile ground to prompt a sort of hyper imagination, which you could see as a good thing or a bad thing. For me, it’s required me to live in my imagination more, but then the plus side of that is, well, having a really well-developed imagination. Through this experience, you begin to understand that these are not perfectly separate things—what you imagine does impact the world that you live in, and vice versa, but they’re not neatly related, they’re relationality is messy.  

The fantasy concept was a very compressed lens to explore how the ways in which our imaginative landscape plays an important part in how we experience a real, lived encounter with another human being. To route that encounter through one person’s mind and draw parallelisms throughout forces you as a reader to have somewhat of a split allegiance, to be in some ways disoriented–or maybe enriched–by the juxtaposition of these different narratives and how they’re playing out against each other. When I read the story, I see so early on how the fantasy and the real world are slightly off: they’re supposed to meet in a gallery, but actually it’s the MET. It’s like that concept of a rocket ship taking off one degree off course: it might not seem like much, but after thousands of miles you’ll be in an entirely different part of space. So, maybe these small details don’t seem like that much of a big deal, but they are also meant to instil a certain foreboding in the reader, the sense that those tracks are going to keep separating as the characters hold tighter and tighter to a thing that’s moving further and further apart, and that they’re not going to get what they came here for. Which is, of course, what Tilo discovers by the end.

BFR: That’s a really cool way of thinking about it, as sort of a foreshadowing device. Yeah, I didn’t think about that. So, why did you choose New York for the setting of this story, like what was your thought process in creating this very artistic and cultured image of New York?

Finnegan Shepard: On a personal level, it’s been about a decade since I lived in New York, so it’s a place that’s familiar to me but already has that crustiness of nostalgia, which I feel is deeply ingrained in the story itself. So, the choice was partially just leveraging my own personal relationship to New York as a space that I wanted to feel familiar but also filled with longing or distance. 

Then on a craft level, there’s a way in which New York is the perfect place to play with this idea of what is real and what is an image of itself. The city is always signifying itself, and in fact Madeline sort of says this—they’re in the taxi and they’re watching the ad of the couples in New York, and she has this line about how New York is so self-referential it’s as though it’s on repeat without realizing it. And I think that that’s very true and I think for a story (especially with the title of “The Gallery”) that is about what it means to look at something and construct a meaning for it beyond the thing itself, and for there to be a triangulation of this, of the looking and the constructing and the being, of all the cities I know, New York is the most potent place for that. New York is a kind of set. You live there and you’re also on the set of what New York is.

BFR: Yeah, that’s a very detailed way of thinking about it. I’m glad that so much thought went into it. So, this story is titled “The Gallery” and throughout, Tilo closely observes both others and himself. How does seeing and being seen in this story relate to art and trans identity? 

Finnegan Shepard: It’s less to do with art specifically and more to do with what happens in art, which is essentially that we try and capture something and in that capturing we actually translate it into something more than itself, and that we assign meaning to that act. I don’t really think art plays a role in the story beyond that, other than some thematic touchstones on Madeline as a character. I know there’s a line in the restaurant where it talks about her as a person who’s most naturally at home in places with clear hierarchies, where being a critic is something that is not just accepted but embraced.

I do believe that we live in a time where there’s a tension between a more relativist, horizontal view of everything (which is probably more on the side of, “let’s be kind to Tilo, let’s tell him whatever he needs to hear even if it’s not truth with a capital T”) versus a stricter, critical hierarchy, which is what we tend to associate with art. (And arguably what art depends on.) It comes back to this tension of value systems, and which of those structures of seeing the world is right or relevant in any given moment in the story.

BFR: This story is part of a collection you’re working on called Tilt. What are the overarching themes of this collection and how does “The Gallery” fit in?

Finnegan Shepard: Earlier I talked about how I’m interested in exploring universal themes around identity construction and sexuality and gender, but–to use the title—through a kind of tilted angle. I think that we can have a very narrow definition or interpretation of what queer literature is. So when I started writing this collection, I realized that they’re all ‘queer’ stories, but sort of in an old-school form of the word–they’re strange stories. Some deal directly with gender or sexuality but a lot of them don’t. There are plenty of cis and heterosexual characters as well.

Within the collection there’s a consistent play with fantasy, with a slightly tilted or borderline surreal aspect. It definitely transgresses on the line of what’s real or imagined and questioning what is unreal about the imagined. So, “The Gallery” definitely fits within it. It’s the first story in the collection, and I think it kind of sets the tone of the collection. 

What I’m most interested in is trying to open up that definition of queer literature and also making space for voices that I haven’t really seen in fiction thus far.

What I’m most interested in is trying to open up that definition of queer literature and also making space for voices that I haven’t really seen in fiction thus far. For instance, going back to the question about Madeline as a villain. I don’t think we really have much space in literature to talk about that perspective and the legitimacy of a character who identifies as a cisgender bisexual person and used to date somebody who was a lesbian at the time, and who now has a hard time seeing that person as male. Ultimately, it’s a reconstruction of their own identity as well, to see that.  

In fact, the novella that finishes the collection is all through the perspective of a previously cisgender, heterosexual woman who’s dating a trans man and who is going through that process of thinking about what that means for their own identity and navigating how you make another person feel seen in that identity. I think literature offers an opportunity very different from narratives in social media or even TV. It’s a space where you can—where you have to—read between the lines. That allows for a lot of room to explore different voices and expand into a broader definition of ‘queer.’

BFR: That’s a really great mission. Exciting! Yeah. So what has it been like working on a whole collection? I know you also write flash pieces and individual pieces. Is it different? Is it more or less challenging?

Finnegan Shepard: This collection is by far the easiest thing I’ve ever written. I’ve been writing in a pretty dedicated way since I was like eight years old, but mostly really obscure literary fiction that nobody cares about. Historically, I’ll finish a manuscript, turn back to the beginning, read a page or two, and go: “It’s awful, I need to burn the whole thing and start over again.” 

That was the pattern. Then, when I started medically transitioning about two years ago, the stories just started flowing out of me. I was actually about five drafts into a literary novel set in Cornwall in the 1990s with a Lego container spill and a grieving expat German woman and these two repressed British innkeepers, and I just couldn’t focus on that. I just wanted to be writing these short stories. I didn’t really know where they were coming from, and I didn’t know what the goal was, either. They just kind of flew out of me.

The first draft took around eight months, and then I probably spent another year revising and tweaking them and getting different readers to workshop them and looking for magazines. And now I’m doing some final edits on the collection with an agent and hoping to find it a home.

BFR: That’s so exciting! I hope it goes well, your search for publication. So, now we’re just gonna move on to talking about writing in general. So you publish both fiction and nonfiction memoir-like pieces, how do you juggle those two genres?

Finnegan Shepard: I’ve gotten pretty good at developing a sort of a gut instinct for what I feel like spending my creative horsepower (which is always about two hours in the early morning) on. I’ve just sort of built that muscle over the years. There was a long time when I felt guilty about being a writer who only likes to write for a limited time every morning. But the fact of the matter is, those few hours in the morning are almost always an enjoyable time period—I very rarely have writer’s block. I sit down, I think, I write, stuff comes out, and I generally like what I write. And then I’m ready to go do different things with the day. 

As of the last year or so, that’s worked because I’m now doing all this entrepreneurial stuff in my life, but for a long time I felt guilty that I couldn’t just sit at my desk and write all day. I thought that if you’re a writer, that’s what you should be able to do and you should be able to enjoy it or at least withstand the suffering. Eventually I just kind of came to accept it that delineating my writing hours makes it a really enriching, joyful thing that energizes me for the day. On the mornings I don’t write, I’m always in a worse mood. So I do a good job of making room for it, though it can really vary both on the micro scale of day-to-day and on the macro scale of year-to-year. There are some years where I’m more focused on poetry or more focused on nonfiction. Right now another thing I do is a monthly newsletter that explores a single word. I studied the classics, and I love entomology, so I send out this visual and etymological exploration of a word every month. Sometimes when I sit down in the morning, that’s what I’m inspired to do.

But, really, my very long and rambling answer is: you just make space for it, and you show up for it every day, and I think you have to follow the joy in it, because there’s plenty of frustration and rejection in writing and you don’t want to inflict any more of that on yourself. You want to just, you know, sink your teeth into whatever pleasure you can get out of it while you can. 

BFR: Yes, yeah, I don’t think any of us should be trying to write all day, as much as that’s like the stereotypical dream. [Laughter.] No, and I don’t think it happens for most writers. But let’s see, we’ve already talked a little bit about your day-to-day writing process, but do you have any like rituals or tricks that help you find inspiration? I think as fellow writers, we’re always very interested in these sorts of things.

Finnegan Shepard: I mean the classic one is coffee. I like to be at my desk before it’s light out, I like to get there in the dark. If anyone says hello to me in the mornings, I’m furious. I think that the state of being in a dream world is very close to the state of being in the creative or generative world and I like to sort of seamlessly slip between those worlds. And so even so much as like a hello if I bump into somebody else on their way to make coffee just throws me off. 

Other than that, I really do think it’s just like training a muscle. I don’t think when I write. It’s a deeply meditative state for me. And I have a pretty hyperactive brain in the rest of my life so whenever I tell people that I’m never thinking while I’m writing they always find that really shocking. But that’s just the case for me. It’s really just about showing up with my coffee, being undisturbed, and then having enough confidence and self-love and love of the process to let myself go wherever my ideas are gonna take me. It’s not always good, but that’s okay, it’s not really the whole point of what I’m there for.

BFR: That’s great. That’s really nice. So, you have quite a few other published short fiction pieces, including some flash fiction. Do you prefer to work on shorter stories or longer ones? Does your process change when you’re writing flash?

Finnegan Shepard: Every story needs to be the length that it needs to be. Sometimes that’s 1000 words and sometimes, like in this sort of semi-novella that I mentioned at the end of the collection, it’s 29,000 words, and both feel relatively similar to me and I think unfold in a relatively similar way.

BFR: As a follow-up, here at BFR we run a flash fiction contest every year so we’re always asking people this. Do you have any tips for people writing flash fiction? What does that look like for you?

Finnegan Shepard: I think my approach to flash or my comfort with it is probably informed by spending a lot of time doing and studying poetry. I think that trains an adjacent muscle—it’s not the same muscle but it’s definitely an adjacent activity. I would also say, and maybe I’m taking this from poetry too, but I would encourage people to frame the concept of limitation as actually a practice in freedom.

I think sitting down and allowing something to be whatever length it’s going to be can easily present a certain tyranny of freedom. I remember the first time I was assigned to do a poem in a particular rhyme scheme. I remember being furious at first, and then actually I thought: “This is such a relief!” Because, if you end on a certain word, you’re already so boxed in to a certain degree but then you realize,  “Okay but within that boxed-in-ness, what are the most interesting things I can do in that space?”

I highly recommend embracing limitation—it’s something that we’re not very good at these days. Across the board, I would just recommend people to embrace limitations. It’s good for us. 

And then I guess the final thing I would say is that an early mentor of mine once talked about how you can finish a piece of writing, you can close a piece of writing, or you can drop away with a piece of writing. That’s important for all stories and poems, but I think it’s especially important for flash, and something that I think I’ve seen when I’ve worked on other people’s pieces. What they struggle with is this almost more intense push for epiphany in flash (which is sort of an over-obsession in all short stories, I think, and unfortunately so, because epiphanies are actually very rare in our life). So, the need for all stories to be about an epiphany is a tall order. Yes, I would say don’t superimpose that necessity on flash.

BFR: Yeah, that was a really useful thing about endings there, I was just like thinking over all of the many many stories I’ve slush-read and, yeah, that’s pretty much how it goes. 

Finnegan Shepard: You don’t really want to have to explain it though. It’s kind of like a joke, when you hear that as a writer, you’re like: “It’s so true. Some of them finish, some of them close, and some of them drop away.” But then if some physics major was like, “Okay but like, what does that actually mean?” I wouldn’t have an answer.  Like, if I have to explain it to you, it doesn’t matter. Just walk away, this conversation’s over.

BFR: Yeah, no, let’s not bring any science in here. By day, you run a newsletter and you’re the owner of Both&, a trans and nonbinary clothing line. How do your entrepreneurship and other pursuits interact with your writing—we’ve talked about this a little bit, but like does it inspire you? What’s the balance like?

Finnegan Shepard: Yeah. Being an entrepreneur is a really interesting counterbalance to writing. In some ways I’d recommend it because what it shares with writing is a necessity for creativity. But then, in terms of time scale and how it interfaces with the world, you couldn’t find more opposite spaces. 

Essentially everything about being in a startup is immediate, and really dynamic, and you have to train yourself to never let perfect be the enemy of good enough, as they say. And it’s also really validating, it’s amazing as a person who’s been a writer/academic toiling away on stuff nobody cares about to suddenly be creating something that people value, and will pay money for, and the press wants to interview me, and all that.  I still don’t really know how to talk about success, it’s such a wildly new phenomenon.

So, in some ways it’s a really lovely counterbalance because I think it allows me to have more patience and stability with my writing. I put less pressure on it, it’s something that enriches me and that I will always do and that I hope can be in the world because I hope it can bring value to other people, but those expectations that I had when I was young about being a rich and famous author—I don’t need to be ruled by those anymore. Now I have this other outlet where I can get those much more immediate senses of validation and impact in the world. And so, just psychologically and emotionally that’s been very helpful. 

In terms of how I’ve brought writing into the business itself … we really started out on Instagram with a photojournalism series, (the Instagram is @bothandapparel), but we hadn’t designed a first capsule of clothing yet and everything was just about gathering the research and building community. I knew what it was like to be in my body and try to find clothing that fit (and never succeeding), so I started Both& with the mission of going and interviewing as many trans masculine and non-binary people as I could. And those interviews served as the basis, both for our designs, and also for our photojournalism series. That was really what we got attention for early on. I think people saw the quality of the storytelling, and they really appreciated that, long before there was anything for us to sell.

So I guess the connective tissue is an instinct for the importance of storytelling. I think social media has done amazing things for trans voices and visibility in some ways but in other ways it can be a very regulated space where you’re supposed to be a certain way or speak in a certain way. And it’s really important to me to actually foster tolerance in the root sense of the word, which is to actually allow people to share their experiences rather than sort of regulate what those experiences should be. So, yeah, I would say that’s how all the different pieces of my endeavours fit together.

BFR: That’s really nice to hear, I think as a college student you’re often told: “Oh, your writing will become really useful when you go into other careers.” And it’s always nice to hear: “Yeah, storytelling really is useful.”

I cannot stress enough how shocking it was for me to make the transition from the world of creative writing/academia into more of the entrepreneurship/business world and realize: these skills are in such demand.

Finnegan Shepard: I cannot stress enough how shocking it was for me to make the transition from the world of creative writing/academia into more of the entrepreneurship/business world and realize: these skills are in such demand. It doesn’t have to be mindless copyediting of technical papers—there’s a lot of really creative applications for this skill set. It’s become a bit of an almost ethical mission for me because I’ve seen so many people in my world learn to really undervalue themselves, because of the way the world is structured right now and what you get paid for. But good writing is truly such a gift and such a needed skill.

BFR: Thank you for saying that. Okay, so just finishing up here. We’re always excited to hear about new works being produced even in these challenging times. Are there any new pieces or projects that you’d like to tell us about?

Finnegan Shepard: Just the collection, and Limns, the philosophy/etymology project, which you can subscribe to on Substack. It’s a pretty fun romp through language.

BFR: Yeah, that sounds really cool. Okay. Final question: where can our readers find you online?

Finnegan Shepard: I’m on Instagram @finneganshepard, or on my website www.finneganshepard.com. If you really want to talk to me, you can find my email there. I’m always branching out into new creative collaborations. In fact, right now I’m looking for more visual artists to collaborate with on the newsletter, so if there are some photographers out there who are interested, definitely get in touch.

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