by Brittany Eve Kass
While attending the NonfictioNOW conference in the summer of 2025, I had the pleasure of meeting author and longtime Slag Glass City contributing editor Timothy J. Hillegonds. While we were chatting, he mentioned that his second memoir, And You Will Call it Fate, was about to be published. I asked him what the book was about and he told me the main themes were addiction, fatherhood, and masculinity. I have watched my cousin, and some friends, struggle with addiction, making this topic immediately striking to me. I also couldn’t help but be curious about his work because I am used to women talking about motherhood, but I hadn’t been exposed to men talking about fatherhood, and my interest was particularly piqued by his theme of masculinity.
Tim came to DePaul University in Spring 2026 to do a book reading and Q&A about his second memoir. He read the first chapter of And You Will Call it Fate and I was instantly excited to read more.
About a week or so later, we connected on a Zoom call, for an in-depth conversation about Chicago, writing, and most importantly And You Will Call it Fate.
BK: And You Will Call it Fate is your second memoir. Was the writing process different this time around in comparison to your first memoir?
TH: It felt like the pressure was off. I was content with letting it take whatever time it was going to take, and I will say it was better that way. With the first one, I was in what felt like a race to get the manuscript into shape and then publish it—and all of it felt hard. This time was different in the sense that I was able to let it be what it was. I sort of gave myself over to the process. The writing still took forever—figuring out what I was trying to write, and then realizing that what I thought was a story about recovery actually wasn’t. I was sort of surprised to figure out that the whole thing was about my relationship with Demsey. But I was much more comfortable this time with just letting it be what it was going to be.
BK: Would you say the second time around was more relaxed?
TH: There was definitely less intensity around it, though I’m not sure I would call it relaxed. The first time around I was trying to prove to myself that I could do it, that I could actually write a book. I had this story that I wanted to tell, and I didn’t know how not to tell it. But that first book covered a lot of really difficult material and it was hard to write, hard to go back to that place, hard to interrogate that person that I was. With this one, the material was much easier for me to write about because I was okay with who I was during that period of time in a way that I wasn’t with first book. And You Will Call It Fate was about unpacking what that relationship with Dempsey meant and what Dempsey ultimately did for me—and then coming to terms with whether or not I accrued a debt I could pay or even owed. Those questions were rattling around in my brain for a long time, and I knew that I would publish a book about it at some point.
BK: Since this is your second memoir, how did you find the balance between telling your new audience aspects of your previous work so they wouldn’t get lost and not being repetitive to your longtime readers?
TH: You have to walk this line between boring people with repetitive details and not assuming that everyone’s read your work. You have to address the needs of a reader who’s coming in cold. Then you have to be cognizant of readers who may have the backstory. Inevitably, you have to repeat some things, but it’s about making sure you’re not rehashing the same story over and over again in the same way.
BK: How long did this second memoir take you to write?
TH: It probably took five-ish years from writing to publishing. For better or for worse, I seem to be on this six-year cadence. Everything in publishing takes forever. The funny thing is that I finished writing this memoir probably three years ago at this point. It’s fun to be on the back end of it now, though.
BK: I’m going on my ten year anniversary of moving to Chicago, and I recognize the love for Chicago in your memoir. While reading your memoir, it felt like Chicago was more of a character rather than a place. I’m curious if that was intentional.
TH: It actually wasn’t—it’s how I’ve always felt about this city. Someone pointed out to me that Chicago was always the place I was trying to get back to, and that’s been a theme my whole life. When I was eighteen, I moved out to Colorado, and it was a complete disaster. Everything fell apart, and the whole time I was trying to get back to Chicago. Then I got back, and my whole life changed: I got sober. And then I had to leave again, and I spent that whole stretch trying to get back here too. It’s a place that’s been with me ever since I was a little kid, and I’m endlessly fascinated by it. It’s the best city in the world. I love to travel, but I always love coming home. I never tire of running the lakefront path, or getting on a bike and bombing through the city, or riding my motorcycle through the streets. When I worked for Dempsey in my early twenties, I started out downtown, and every time I went out for lunch it felt like recess. I’d venture out of the building and everybody was happy. There’d be lunchtime concerts, bike messengers whizzing past, people rushing to every restaurant you could imagine. It was wonderful—the chaos of it all.
BK: How do you feel writing about Chicago is different than other cities?
TH: I’m not sure I can speak to writing about too many other cities, since I haven’t written about many besides Baltimore. But Chicago feels special—it feels like it’s in a league of its own. I’ve lived in a number of different cities, and I had this weird rule that whenever I moved to one, I always wanted to live in the city proper. When I moved to Baltimore, I didn’t want the suburbs. I wanted the actual city, because I think I was trying to recreate what it felt like to live here. But it didn’t work—there was just no way to recreate whatever happens here. I think some of that is just the difference between the two cities, and some of it’s probably me and the way I relate to Chicago. Writing about this city, to me, is like writing about no other. It almost feels like its own coast, because we’re on Lake Michigan. We’ve got that lunch pail, hard hat ethic, and all the big-shoulders nicknames. It’s a big city, but it doesn’t feel like one. It’s also a city that resists being captured. For a writer, I think that’s the allure.
BK: As a contributing editor for Slag Glass City, do you think your editorial work helped what you wanted the audience to experience when it came to detailing Chicago and the other cities in your memoir?
TH: I believe anything you read shows up in your work somehow, at some point—even if you can’t always put your finger on where. The fundamental questions of Slag Glass City are: what is a city, and how do we relate to cities? Those are fascinating questions, and some of the essays we’ve gotten over the years have widened the aperture of how I think about cities. I’m always interested in the details people bring up when they write about their own cities, and how that differs from what I notice about mine. I think we’re all in one big, long conversation about what these cities are and what they mean.
BK: In a class that I had with Michele Morano, she mentioned how sometimes authors don’t get to choose their own title, and I’m curious if that was your experience.
TH: I lucked out and got to choose this one, though it was ultimately their call. Titles are famously hard. The epigraph is that Carl Jung line—”until you make the unconscious conscious, it will direct your life, and you will call it fate”—and I’ve always loved that quote. That’s what I started putting at the top of the manuscript, and then eventually The University of Nebraska Press let me know it would be the final title. I was pretty excited about it.
BK: Did you have that with your first memoir as well? Choosing your own title?
TH: Sort of, but not quite in the same way, although the first book’s title came from an epigraph too. It was that Tennessee Williams line that ends, “time is the longest distance between two places.” I thought about it a lot. I wanted to call the book The Longest Distance Between Two Places, and I really liked that—but ultimately it was too long, and I started to realize it was getting resistance for exactly that reason. So the publishers said, “what about The Distance Between?” And that opened it up for me to think about the distance between who I am and who I used to be. The distance between me and my daughter. The distance between Chicago and Colorado. It just all made sense in the end. And I was pretty happy with it.
BK: Fatherhood is such a huge part of your identity. In an age of arguing if we should put children online or even write about children, how do you balance consent and autonomy when you include them in your writing?
TH: This has definitely changed over time. Writing about my daughter as a baby didn’t really feel like an ethical choice, because she wasn’t doing anything—she was just existing. Of course, as she got older, she started to have opinions. At one point she told me, I’d rather you not write about me anymore, and I had to respect that. But her relationship to me and to my writing keeps changing too. She’s in her late twenties now, and I’m not sure she cares as much these days. Either way, I respect her wishes.
BK: Your writing is so blunt, powerful, raw, and genuinely inspiring. Have you always been blunt and honest in your writing or was that a learned skill?
TH: That’s an interesting word to use—blunt—because I wish I could be more blunt sometimes. I feel like I equivocate a fair amount. The way I write is a reflection of who I am and how I see the world. I’m constantly rolling things around in my head, thinking about the roles we play in our lives, and challenging my own thinking. I know I’ve been fairly self-aware since I was a little kid, but I’ve also tried to become more self-aware as I’ve gotten older. And I’ve learned that when I’m writing, whenever I hold onto something really tightly, that’s almost always a sign I need to change my thinking around it—I have to interrogate why I’m holding on in the first place. I also have this bad habit of just saying shit to see what happens, which has gotten me into a lot of trouble in my life. My former professor Michele Morano once pointed me to this quote about David Sedaris—that he’d sometimes find sentences in other people’s work and write them out just to see how they felt. I always thought that was such a wonderful idea. I do the same thing with ideas I’m trying to work out: I say them out loud to people, to see how they feel, and to see if I actually believe them.
BK: There were some killer lines in this book. One of my personal favorites was on page twenty, “His came out, as abuse against the world, mine as abuse against myself.” When you write a spectacular line like that, do you know it’s spectacular, or are you surprised at what the audience connects with?
TH: Well, thank you—that’s really nice of you to say. But it’s always a surprise. I definitely try to land paragraphs in a certain place, on an image or a piece of dialogue that really gets at an idea—that was something Michele Morano once told me, that you have to end on an image or a line that’s really snappy. So during editing, I’ll oftentimes go back in and noodle with the lines, trying to get them just right. And every once in a while one comes out and I feel like, that’s pretty good. I was proud of that chemotherapy line in the book—I think I wrote that Dempsey was like a chemotherapy for my addiction. That one felt good.
BK: In the middle and toward the end of your book, you discuss the phrase, “just do the next right thing.” What is your current “next right thing?”
TH: That’s a daily challenge. That comes right out of AA where you spend so much time in early recovery or in moments of your life not knowing what to do next or feeling unmoored. The common advice is to just do the next right thing, and at least it gets you thinking about what you think the next right thing is. The thing that I’m most excited about right now is I’m building a startup in the substance use disorder space. In some ways, that felt like the next right thing.
BK: In your book, not only did Dempsey show you kindness when you needed it most, but Andrea showed you an act of kindness by giving you a plane voucher to see your daughter. What have you learned about kindness?
TH: What I’ve learned is that kindness can be such a small thing for the person giving it, and almost always much, much bigger than they know for the person receiving it. The voucher Andrea gave me was a small thing on her end, but it got me to my daughter and ultimately changed both of our lives. Dempsey’s kindness cost him more—rehab was expensive—but in the grand scheme of things, maybe not that much. What it gave me far surpassed what it cost him. That gap is what I keep coming back to, and I think it cuts against the grain of how we live now. The M.O.—which we probably owe to the internet—is to fly off the handle, to get your criticism in first, to land the sick burn or the most hurtful comment. Kindness reads as soft. But the older I get, the more I think it’s the opposite: that it might be the most consequential thing we do, precisely because it’s so cheap to give and so easy to skip. I try to remember that the small thing in front of me might not be small to the other person. And I try to pay it forward where I can.
BK: If you had all the money that Dempsey had, and you saw yourself in someone else, do you think you’d feel inclined to help get someone on the right track as a way of paying it forward?
TH: I think about that all the time. Would I ultimately do what he did? Honestly, I’m not sure I would—it was such an extreme thing. To literally meet a kid in a restaurant and hand him a job. I still don’t know what compelled him, because as an employee acquisition strategy, it leaves something to be desired. Most people are out recruiting at the best colleges in the country. Dempsey’s at Bakers Square. But that’s sort of the whole point, isn’t it? What I take away from it is to stay open to being surprised—because people are surprising, and they show up at different points in your life, from places you’d never expect. I run a business now, I’ve hired people, and I’ve never done anything remotely like what Dempsey did. Maybe that’s the thing I’m still trying to learn from him.
BK: In your epilogue, you mentioned how it’s hard to end a story that isn’t quite finished. Is there anything else you wish you could have added to the story?
TH: In the end, I think I said what I wanted to say. I mulled it over as long as I possibly could, and then at some point I just thought, okay—I’m done with this. There’s that line about how a piece of writing is never really finished, it’s just abandoned, and that feels about right for this book. I’m sure there was more to say. I just didn’t know how to say it, and at a certain point not knowing how to say it is its own kind of answer.
BK: Do you have any plans for a third memoir? What’s your next writing adventure?
TH: Being a memoirist means you write about your life—that’s the job. We write about our lives. And since I’m still living mine, and since I seem to have this addiction, or compulsion, or pull toward memoir, I’m pretty sure that’s what I’ll keep doing. Lately I’ve been circling the idea of a good run. I run a lot, and it’s been a big part of my recovery, so the phrase started as a literal thing—the good run is the elusive one, the one you’re always chasing when you head out the door, where everything clicks and your body and the miles and your head all line up. You almost never get it, but you keep going out looking for it. And then I realized it’s the same phrase we use at the other end of a life. When someone dies, if they lived well, we say, he had a good run. She had a good run. The same three words for the thing you can’t quite catch on a Tuesday morning and the thing we hope to be able to say about a whole life. I keep turning that over—what it means that we reach for the same language for both, and whether the daily one is just the lifelong one in miniature. I want to pull business into it too. There’s this notion that business can’t be literary and the literary can’t be business, and I think that’s hogwash—the two have more to say to each other than people admit. The challenge is finding a form that can hold all of it: the running, the recovery, the question of what a good life even is, the work. I don’t know how to do that yet. But not knowing how to do it yet is usually a pretty good sign I’m onto the right thing.
And You Will Call It Fate is available from the University of Nebraska Press America Lives Series. Preview the book here.
Timothy J. Hillegonds is the author of the memoirs And You Will Call It Fate (University of Nebraska Press, 2026) and The Distance Between (University of Nebraska Press, 2019), a finalist for the Chicago Writers Association Book of the Year and the Eric Hoffer Book Award. His work—exploring masculinity, addiction, and personal reckoning—has appeared in The Guardian, LitHub, The Los Angeles Review of Books, Salon, The Daily Beast, Fourth Genre, River Teeth, Brevity, and elsewhere.
SLAG GLASS CITY · Volume 12 · June 2026
Header image by University of Nebraska Press
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