Kevin M. Kearney: On Work In the Time of AI, Being More Than Your Job, and His New Novel ‘Freelance’
If you’ve been lucky enough to interact with Kevin M. Kearney, then you likely know he is a true gem of the indie lit community. I first came to know of Kevin through his story “Persuasive Essay Essay on Why My Uncle Joe Should Not Go to Prison,” published in XRAY Literary Magazine (another indie lit gem!). I loved it so much that I taught it in a handful of my classes. At some point on Twitter (when it was still Twitter), I put out a tweet asking writers to message me any experimental stories that played with form because I was looking to shake-up my curriculum. Kevin sent me a link to his piece and I replied that I was actually already using it in my classes. And thus an online indie lit friendship was born. Over the last few years we’ve taken turns editing each other’s work for the magazines we work with, and this spring I was lucky to meet him in real life after he invited me to read at his Small Press Nite at The Book Catapult in San Diego. It was one of the coolest readings I’ve been to and it seemed to have a devoted group of regulars in attendance. Kevin is the kind of writer I think we should all aspire to be like. Not only is he a very talented writer, but he is a true supporter of other writers and has worked hard to create spaces for writers to exist.
This year he published his second novel, Freelance (Rejection Letters, 2025), and I gobbled it up in a matter of days. Freelance is a wild dystopian romp of a novel that follows a naive rideshare driver as his work app begins asking him to do stranger and more dangerous things. It is as playful as it is smart, reminiscent of Philip K. Dick’s Do Androids Dream of Electric Sheep. Freelance is a novel about existing in the digital age, what it means to be a worker in a mechanized world, and ultimately what happens when we blindly put our faith in technology—a rare book that manages to ask serious questions about our current age without ever sacrificing entertainment.
I met with Kevin earlier this year via Zoom to talk about Freelance, the indie lit scene, and being a worker, all while he was on the road on the way to Alaska.
Shelby Hinte: So you are Zooming in from the side of the road. How’s the Alaska trip going?
Kevin Kearney: It’s great. The only difficult part is finding time to get all of my work done and also drive six hours a day. It’s a delicate balance.
SH: Well, that sounds like a good place to start since I was so interested in the way you depict work in the novel. Freelance felt a little bit like a dystopic take on the gig economy. One of the things I thought you did really well was writing about the precarity of trying to make a living in a society that makes it so obvious that it just does not care about workers. What’s your relationship to work like?
KK: I started writing this book when I first moved to California, and that was in August of 2022, after living in Philly or the surrounding area for pretty much my whole life. At the same time, I had just left teaching. I was a high school teacher for ten years at that point. So I was in this brand-new place, and I was suddenly out of this career that I had really sort of subsumed with my identity. I was left very confused and trying to figure out who I was outside of this ready-made identity that I’d leaned into.
At first I thought I was just writing this story about a rideshare driver because I thought it was a good narrative structure—this character would get to interact with all these different people who jump in his backseat. And then I realized, “Well, no, I need to learn more about what it actually means to be a rideshare driver.” So, I started reading not only driver forums, but also sociological reports on what people involved in the gig economy, and specifically Uber, go through and what their finances are like. The more research I did, the more I realized I was not just writing about a rideshare driver, I was also writing about teaching. The more I dug, the more I started to realize that, “Oh, I think I’m actually writing about what it means to be a worker.” So, I think work for me was something you were called to do, or at least that I felt I was called to do. And I became a little disillusioned with that. I think writing this helped me process that a little bit.
SH: How have you come to navigate that relationship between being a writer and being a worker while also having some sort of value in a capitalistic society?
KK: I’m really trying to get away from any sort of title. I realize that sounds kind of woo-woo, and I'm really self-conscious about that. But for so long I considered myself a teacher and I felt like when someone asked me what I did, and I said I was a teacher—maybe I was projecting this onto them—but I got the sense that they then assumed that I was a decent person, that I cared about the right things, that I had chosen idealism over money. And I think now, even with my artistic practice—like calling myself a “writer,” I think, is descriptive and accurate—I’m trying not to attach myself to that title in the same way. I’m really trying to just think of myself as a person, which is easier said than done most days. And then anything I do for income is sort of a bullet on the résumé.
SH: What does that internal work look like in order to combat finding your identity through a work title?
KK: The first thing that comes to mind is not so much inner as it is outer. Like, now, when I first meet someone, I intentionally try to not ask that most basic question when you’re getting to know someone: “What do you do for work?” I don’t know if it’s an East Coast versus West Coast thing, or if I’m just in a different headspace now, but I’ve found that since moving to California, fewer people ask me what I do. That seems to be less top-of-mind for folks. I don’t know if that’s actually true or if it’s just that I’m less interested in it, and so I’m not getting into that conversation.
As for the inner work, I think just reminding myself that any successes that I have related to work or even related to my art is secondary. The reason why I work is so that I can afford my life. And the reason that I make art is because it makes me feel more like myself rather than, I don’t know, attracting the attention of someone or racking up some sort of accolade. I like those things, obviously. I’m doing this interview. I want attention. But I think with my first book, I was very hung up on whether or not I was going to be noticed. And with the second one, I’m just interested in talking with people about what they took away from it.
SH: Well another thing about you, and something that I just really admire about you, is all of the community building you do. I’m curious to hear a little more about the writing communities that you’re a part of and why community is so important to you.
KK: I think that for me, art is primarily for two purposes. The first is, like I mentioned, because it makes me feel more like myself. And then the second is that it’s an incredible way to engage with other people. There’s some art that I’ll never share with other people because it’s either not good enough or it’s just for the sake of my own practice. But I think most people make art because they want to bounce it off of other people. I think that it’s really important to not just make the art, but also make the places and the spaces where that art can be received by other people.
I was a part of several music communities growing up and I think they formed the way that I think about art-making and also being part of a community. When I started taking writing more seriously, I was astounded that there wasn’t an immediate parallel. So when I got the opportunity to start something after moving to California, which was sort of just happenstance, I was very intentional about trying to make something that felt more like those music scenes that I had been a part of, which was that pretense was sort of left at the door. It felt more like a house party or a basement show than a stuffy lecture. And [I think that made it feel] like something that was fun, rather than something you did because that’s what writers were supposed to do.
SH: What advice do you have for writers who are looking to either join a community or maybe build their own?
KK: You need to sort of surrender to the naturally embarrassing part of reaching out to total strangers, which did not come easily for me. But I moved to California, and I didn’t really know anyone aside from people who had gone to high school with my wife. So I was doing things like cold emailing writers that I knew lived in San Diego and just saying like, “hey, I like your writing. Could we meet up sometime and get a coffee or a beer?” And I was tweeting things like, “I don’t know anyone in the San Diego literary community, can you reach out?” It almost felt like dating in a way, where I was just like, “maybe we’ll be friends.” I’m really glad I did that because it led to a lot of genuine friendships, even outside of any creative conversation.
SH: God, I think that is so brave. I literally started sweating when you described cold emailing.
KK: I know, I know. And I’m friends with some of those people now, and I look back on the initial reach out and I’m like, “Jesus Christ.” I can’t believe they were like, “yeah, sure.”
SH: I want to go back to your book, and maybe we can start with the protagonist, Simon. I found him to be such an endearing character. He’s so gullible and he seems to take everything that he sees online at face value. He doesn’t do a lot of questioning of the information he’s fed from the internet, and it ends up making him very easy to manipulate. With all the talk about misinformation and AI these days, what are your feelings about safely or ethically navigating the internet?
KK: I’m glad that you found him endearing. You’re right that he is entirely gullible. And I think that much of that was shaped by my years in the classroom. Because high school kids are always gullible, right? I mean, they’re still developing intellectually. They’re still developing emotionally. And I think in my time in those ten years between 2012 and 2022, I saw how the internet exploited that gullibility. The more time went on, the more I saw how problematic that was.
There were two kids [I taught] that were eventually radicalized by neo-Nazis. It came out in varied ways, but one of them was very public. One of them was very private. It led to a real period of disillusionment for me because I taught about conspiracy theories and media literacy and how antisemitism has existed for centuries and yet that did not apparently reach these kids at all… At the end of the day, the internet was more compelling. What the internet said, despite what they were being told in a classroom, was far more convincing. And that really changed the way that I looked at the internet and at young people who were engaging with it. For so long as an educator, I, and I think many other people, assumed that what happened in the classroom was so sacred and so important that we were going to be able to teach through all of this misinformation. I started to really doubt that through those experiences. And I think that through COVID I started to see that what previously had been difficult conversations taking place in the classroom began happening online without any teacher present. I don’t know what the answer is to combating misinformation or even disinformation, but I was sort of left at a loss.
SH: What are your feelings about the relationship between writing and the use of artificial intelligence?
KK: I mean, it scares me beyond belief. I think that a lot of people are interested in speed and simplicity, and I think that the people who make the internet are happy to provide those things for them and aren’t necessarily concerned with the larger-scale impact of what exactly that means. It’s about a very, very quick and very, very direct answer, even if you’re asking a question that has no quick or direct answer. I’ve seen some people say that writers will be more important than ever. That would be great. I don’t know that I necessarily buy that, but I think that there will be a place, and I think that people are already making it, for people who aren’t interested in an internet infested with ads, SEO or AI slop. It’s just a question of whether the people who actually have their hands on the larger machinery of the internet are going to listen to that or not.
SH: A character who feels in direct opposition to Simon is Dylan. I feel like all of us have one of those guys in our life who has a lot of philosophical ideas and opinions about labor they’ve never done before. This book definitely touches on the class disparity between the people who make the rules and theorize about jobs, and the workers who are actually working the jobs. What inspired the Dylan character specifically?
KK: Like you said, we all have a Dylan character in our lives, and I don't know that he’s unique to our time, but he’s definitely very present in our time, especially in spaces that you and I move through, right? There’s no shortage of Dylans in the writing world and especially in the indie writing world.
I was intrigued by someone who is really, I think, kind of despicable in a lot of ways, and yet is also sometimes like the necessary political conscience in the book, like a reminder of how to process a lot of these things that are going on. And yet the delivery method is just totally reprehensible. I find that throughout a lot of the American Left. Incredible ideas and just horrible delivery that makes people resent those incredible ideas.
SH: All of your characters, whether secondary, primary or tertiary, felt as though they had so much depth. And I think that’s really hard to pull off. How do you approach writing character?
KK: I start by writing one person’s story, and then the further I delve into that, I realize that it would be incomplete if I didn’t delve further in some of these other characters’ stories who have unexpectedly risen to the foreground. So, while writing about Simon, I realized I needed his parents’ perspective in there—at least a little bit of it—because I need the reader to see this from more than one angle. And then that became true of Cassie as well. Her story is so important in the context of Simon’s that it just felt like I needed to dig deeper and deeper into where she came from, how she wound up crossing paths with him, and where maybe she’s headed towards the end of the story. And so I think anyone who’s given at least a chapter from their point of view was just someone who, in early drafting, made their importance evident. They just unexpectedly became a central part of Simon’s story.
SH: I love hearing you say that your writing practice was full of these surprises. Can you talk a little bit about what writing this book looked like? Did you outline it?
KK: Whenever I’m writing something that ends up working, it usually starts as a very rough idea, a very basic premise. In this case, it was a rideshare driver in Philly whose app starts doing something strange. And then I’m just sketching very, very jagged fragments and not worrying about where they fit into a larger story, not worrying about if I have a narrative arc or a character arc, just seeing what I can get down on the page and seeing what arises from that. And I’m doing that by hand, too, to take the pressure off, because when I’m writing by hand, my handwriting is terrible, it’s all incredibly sloppy. And so I know then that it’s not supposed to be good or polished, and it allows me to just continue working. And then, eventually, when I feel like I’ve hit a wall or when I’ve gathered enough material, I start transcribing it into a doc, and I start organizing things a little bit and getting something that looks like a chapter or two or three. For a long time it’s just bits and pieces.
Then, as I’m reading it over and doing very small revisions, I’m starting to see where there’s connective tissue or opportunities for throughlines. I’m starting to maybe see where a story could work. Then I do what I call “reverse outlining.” I’ve found it to be incredibly beneficial. After I have a draft, I start making a very basic plot outline of something that happens in every chapter and seeing which characters are active and who has fallen to the wayside. And from there, I’m able to see who needs more attention, see if the narrative is rising in the way that I want it to, see if multiple plotlines are intersecting in the way that I want them to. And I’ve found that allows me to make a story that feels very tight and propulsive.
SH: Can you talk a little bit about your publication process and how Freelance ended up getting published by Rejection Letters?
KK: I knew that it would be a great fit for Rejection Letters for a number of reasons. The first is that I trust D. T. [Robbins] both in his editorial vision and in his stewardship. When he asked if I wanted to put Freelance out with [Rejection Letters], I was just thinking about the other books that he’s put out, and I was thinking, “these are now my contemporaries.” I’m excited to be what I consider label-mates with people like Lexi [Kent-Monning] or Emily [Costa] or Graham [Irvin]. I mean, that’s like the best roster you can imagine. I don’t know any other press where I literally have all of their books on my bookshelf. But I held off on sending it to D. T. for a while because I didn’t want him to feel like our friendship was resting on whether or not he published it. So I sent it to a number of agents and there was interest, and yet I kept getting inconsistent feedback about why it didn’t work for them. And the inconsistent feedback was what led me to believe that maybe this should be on an indie, because I think these people are thinking about it in a way that I am not. So when I was hanging out with D. T. and he said he was looking for a novel, it sort of felt serendipitous. I sent it to him, and then several months went by and he said, “Yeah, this is great. I absolutely would love to put this out.” I was thrilled because I think all along I felt like it was such a perfect match— tonally and interpersonally.
SH: Okay, last question. I think you have a very interesting relationship to work. And then you wrote this book about work. And then you talked about creative work. So, I’m just curious, if you could give a piece of work advice, either creatively or otherwise, what would it be?
KK: That’s a great question, and I’m trying to make sure I don’t respond with, like, a bromide. That’s my fear. Well, I had a very big realization while I was still teaching, which is that despite doing what I believed—and still believe—was very meaningful work, and even maybe a vocation, a calling, at the end of the day, I was still just simply a worker. At first that really depressed me, especially in the midst of the pandemic. And then eventually I saw that as kind of liberating, that this is a sliver of my life, but this does not define me. I’m something outside of the way that I spend 40 hours a week. So I would just encourage other people to not only realize that, but also reckon with it and embrace it.
*
Kevin M. Kearney is the author of FREELANCE: A NOVEL (Rejection Letters, 2025). He’s had work in Slate, Stereogum, The Metropolitan Review, and elsewhere.
