Edited by Judy Carmack Bross
Congratulations to Scott Holleran who this month marks his year’s anniversary as our Short Stories Editor and who has just published Long Run, a collection of his short stories, many of which were published in Classic Chicago Magazine. Always in awe of this genre since my father first read me O. Henry’s Gift of the Magi, I wanted Scott to tell me more.
SH: Long Run was published October 29th. It’s an e-book on sale in Apple Books, available direct from the publisher, me, and available on Amazon for those who have a Kindle. You can read it on an iPad, an iPhone, or a computer or any device.
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JB: Great. And how long has it taken you to write the book and how would you describe its content?
SH: It’s a collection of 16 short stories which have been previously published in various publications, such as Classic Chicago, for the past 16 or 17 consecutive months. So, that’s about how long it’s taken to collect the stories in this volume.
JB: Do the stories have any sort of unifying theme?
SH: I think so. Ultimately, the reader can judge, decide and discern various themes. I think recurrent themes are resilience and resolve. Particularly through dark or even dire times of despair or dystopia. And yet most of the stories blend optimism, lightness, even some humor here and there, and a sense of hope.
JB: What led you to share that sense of hope? Would you describe yourself as a hopeful person?
SH: I don’t think I’m especially hopeful. I know I’m an optimist. I’m also a realist, so I’ve tried to create characters that are interesting—that the reader can relate to on some level or at least take an interest in—even with the most villainous or dark or brooding character, I want there to be something about him or her. I want the reader to be looking for a way out or a way up, something to root for in each main character. It’s not always possible, but I think most of the time it is. So, I’m an optimist, and I look for that because these are challenging times for everyone. I don’t know anyone who’s not facing some sort of challenge, particularly in the last five years since the pandemic and lockdown. Everyone I know — of all ages, in every socioeconomic status — faces some kind of personal reflection and is challenging herself or himself in some way. I wanted to create characters to reflect that in some sense.
JB: What is the nature of a short story? What can you accomplish with a short story that maybe you can’t accomplish with a book?
SH: It’s like a three-minute pop song versus an aria or a long-form piece of music. I think that’s a decent analogy. The short story is a great art form that really took off to my knowledge in the late 19th century with O. Henry, whose stories I’ve found engaging, breathtaking and humorous for many years. O. Henry’s stories inspire me. The short story is a concise way to express a theme or an idea. This can make the reader think, smile or laugh or be moved or find meaning. I can think of a number of examples by Ray Bradbury, John O’Hara, O. Henry, Shirley Jackson. It’s a challenge to the author to create something meaningful and powerful in a relatively short art form. And then, for the reader, or the audience, it can be an elevating experience without taking much time. The short story can draw you in. Shirley Jackson’s The Lottery comes to mind. It’s a powerful story. I remember reading it in middle school and thinking about it for weeks, months, years afterwards, any time I would encounter the herd or mob mentality or any time a collective, whether a team or the in crowd or popular people were clamoring to ostracize someone for being different, I’d think of The Lottery and how people might respond to that herd mentality in a constructive way and what one can do. The short story is a great art form.
Of course, it has a history in Chicago with Ernest Hemingway and other writers such as Nelson Algren, who have written short stories. I’ve enjoyed writing short stories since I was a kid.
JB: How old were you?
SH: I was eight years old at Central Elementary School in Wilmette, though that’s not where I learned to write. I was always writing short stories as a boy at home at my desk or at the dining room table. I remember writing my first story. I thought it was a book because I couldn’t differentiate between a story and a novel. In my mind, it was a novel, but of course it was a short story, really, and I put it together in an orange binder. I still have it somewhere in a closet or the garage. I titled it The Devil and Other Stories. Afterwards, I was so proud of it that I took the book in hand, such as it was — all 16 pages of it or whatever — in longhand, of course, to the local newspaper in Wilmette which was then owned by the Pioneer Press. I asked the receptionist to see the editor and publisher. She thought that was amusing and asked why. I told her I would like him to publish my book — my manuscript — and of course I had no idea that’s not how book publishing worked. She checked with him and escorted me through the newsroom all the way to a corner office where newspaper Editor and Publisher Kay Schultz was seated, smoking a pipe just like in an old-fashioned newsroom. He greeted me and sat with me, asking questions about The Devil and Other Stories. Then he quietly explained why he wouldn’t be able to publish the book, that that’s not how a newspaper printing press works — that they don’t publish whole manuscripts.
Then he wrote a paragraph about me in his column the next week in the Wilmette Life. This was such a rewarding experience and lesson in journalism, because it taught me that the good journalist welcomes new ideas, contrary to the gruff stereotype. Though I didn’t get my words in print, Kay Schultz plugged my work, which was a source of encouragement to me as a boy. That started me writing fiction. Later, I became a journalist. I began writing short stories again in earnest as an adult, about 10 years ago, slowly cultivating them and sharing the stories with regular readers of my nonfiction. I started submitting them shortly thereafter for publication in literary journals and anthologies without success until about a year and a half ago. My first fiction was published for the first time in the spring of 2024. My stories have been published every consecutive month since.
JB: What advice do you have for a writer who wants to create a short story?
SH: I have three suggestions. The first is practical: purge or jettison distractions. Go to where you find peace, whether a bedroom, like Maya Angelou, who used to write lying down in a bed, kind of propped up in a hotel room because she had a very peculiar way of coming at it. She wrote short stories as well. At a park, in a Starbucks or a busy sidewalk café, choose wherever you’re comfortable and at peace. Put the phone on mute, or, better yet, power it down. Use a blank journal. I think it’s better to write in longhand with ink and paper than digitally, though if you do write digitally, that’s fine, too. Just make sure your mind is active and that you’ve had enough sleep, enough to eat. Good health matters. The stereotype of the smoking and drinking writer is antiquated and unhealthy.
I think it’s a good idea to write in natural daylight if you can or if you are a morning person. Think about your environment and atmosphere.Maybe you’re a night owl. Tailor the experience to yourself and make it relevant to yourself as an individual — then sit and start to write down your ideas.
Here’s the second suggestion: write like you are around a campfire. Think of it like you’re at the dinner table with a favorite uncle or granddaughter, and you’re just telling a relatively short story. You can think of it like you’re telling the story verbally or orally. That can help you keep it to a proper length. It’s best to outline the story, but that Roman numeral approach to outlining we learned induces performance anxiety and it’s easy to get caught up in Roman numerals and numbers and letters, and this can overemphasize process over results. It’s better if you write your story thoughts with ink on paper in a kind of steady progression of what points you want to make. Note the sequence in which things may happen in your story. Create your story with a specific length or limitation in mind.
Third: read short stories. This is probably the most important advice I can give a writer of any age. Read O. Henry’s stories. Read any short stories you know. There are many out there. Keep reading. Go to the library or look in any bookstore and browse then read the first paragraph. If it grabs you, check it out, buy it, read it. Magazines like Classic Chicago publish short stories. Read them and decide what you think. You may love some, hate some, but you will learn. You will be more likely to become a better writer if you become a better reader.
JB: O. Henry’s short stories inspired you, and no one could create better twists than he did, I feel.
SH: He’s definitely known for having a twist. O. Henry’s a fascinating literary figure. I’ve studied his life as well as his writings. I have his complete works both in e-book and print book. Different editions are useful because different frameworks, introductions and prefaces can add value and make you think twice and three times about his work, which is fascinating. O. Henry’s life was fascinating too. He was imprisoned and he had a tragic life in some ways which affected his writing. The twist is one of the things he’s known for, but there’s depth to his short story writing. Of course there’s his sense of humor. His is an early American or mid-American sensibility. He has a history in Ohio and Texas, which is interesting. There’s an O. Henry Museum in Austin, Texas.
JB: How would you describe the different types of writing that you do and how do they bring you pleasure.
SB: I’m a generalist, I think, as a writer. I’ve never thought you have to only write one type of thing. I’ve recently started writing poetry again. Each type of writing genre or art form can scratch a different itch for you and satisfy a different demand or need you have as an artist, speaking for myself, so it’s not like I consciously set out to be some sort of Renaissance man. A story can take different forms. It might be a nonfiction story like the story of Walt Disney in Chicago or Ernest Hemingway in Chicago, or it might be something to fictionalize. A story might conjure a lyrical point you want to make, in which case poetry might be appropriate.
I think Frank Lloyd Wright or Louis Sullivan were right that form follows function. The choice of writing format is less important than the meaning of the story — the format choice can’t be formulaic or too processed. It has to come organically to you as an individual, as a thinker. When you’re creating, when you’re storytelling, it’s helpful to think of a format in which you want to tell the story, but that often doesn’t come first. It’s more important that you think of what you mean in the story you want to tell. Once you have the particulars and the theme figured out, and you know what story you want to tell, the format sort of takes care of itself and you’ll know which is the right format.
One of the short stories in my book Long Run is 9,000 words and the shortest story is less than 500 words, so there can be a range within the short story format. Once you’re over 15,000, you’re getting into a novelette or a shorter novel of some kind.
