A Conversation with Quintessential Chicago Man of Letters Randy Richardson
Novelist, Chicago Writers' Association President, & Hemingway Aficionado
Where exactly did this past year go? The cosmic vacuum is hair-raisingly efficient. đł A year ago today, June 15, my third story collection Direct Sunlight was published. âWedding Party,â a story in D.S., also appeared in Electric Literatureâs Recommended Reading and can be accessed here. And âMaâam?â appeared online in Another Chicago Magazine last June.
On Sunday, June 23, 2 PM PT/5 PM ET, for monthly and annual subscribers, Iâm hosting a Bookish Office Hour/AMA-L (Ask Me Anything-Literary) Zoom meet-up. Please RSVP by replying to this email. Subscriptions are 20% off this month.
Indelibly characterized by poet and journalist Carl Sandburg as the City of Big Shoulders, Chicago is also knownâin no particular orderâfor its legendary skyline, Oprah, the Bulls, deep dish pizzas, the Democratic National Convention of 1968 (and soon, 2024), the White Sox, the Art Institute, the Bears, and the beloved northside baseball team the Cubs.
The Cubbies, the Cubs, the lovable losers won the World Series on November 2, 2016 and forever endeared themselves to their tenacious, adoring fans. Among their most devoted champions is Randy Richardson, the subject of todayâs interview.
Author, attorney, friend and supporter of so many writers, Randy has had an important role in my own career. In 2009, shortly after I learned my first book, Portraits of a Few of the People Iâve Made Cry, would be published the following year, he helped me create an author website and quietly insisted that I establish a platform to promote my work. I was inclined to let the Fates have their way, but Randyâs encouragement helped me get off my duff and start sending up a few flares about my forthcoming book.
Without more introductory jabber from me, here is our recent interview:
Christine/Bookish: You're an attorney as well as a writer. How do you balance your day job with your writing?
Randy Richardson: Itâs never an easy balancing act, but it boils down to commitment and setting priorities. Itâs not just the job and the writing. I also have a volunteer job as president of a 900-member writing community (Chicago Writers Association), and I have a family. All these roles demand a lot of my time. But theyâre all important to me so I make the time to do them.
The reality is that my family must come first, my job second, and my writing third. That doesnât leave a lot of time for writing. Fortunately, for me, I donât have to make a living as a writer. Thatâs what my day job is for. I write for the love of writing. Iâm not sure I could make a career as a writer, at least not at this point in my life. Maybe that will come when I retire from the day job.
Despite writing not being my primary source of income, I approach it with a professional mindset. Each aspect of my writing life, whether it's drafting a manuscript, promoting a book, or participating in writing community activities, is treated as a separate segment. For example, when I'm actively promoting a book, I dedicate a specific period, typically six months, solely to marketing activities. Once this period concludes, I transition back to writing, giving my undivided attention to crafting new stories or refining existing ones.
The simple answer to the question is that I canât give adequate attention to all needed areas, so I compartmentalize as best I can and focus on one at a time and do each as best as I possibly can.
CS: You've written three novels and co-edited a collection of interviews about the Cubs. You also write essays. Perhaps you like writing fiction and nonfiction equally, but I'm guessing you have a preferenceâwould you talk about what sparks you to write essays, and similarly, what spurs you to begin a novel?
RR: Deciding between fiction and nonfiction writing is akin to selecting a favorite child â I find it impossible to favor one over the other. Fiction serves as an escape, a realm where I can weave narratives inspired by real-life events I've encountered. It allows me to explore imaginative landscapes and characters, offering a form of creative release.
On the other hand, my nonfiction writing, particularly essays, serves a different purpose. It provides a platform for me to confront my personal experiences head-on, delving into my inner thoughts, frustrations, and observations about the world. Essays allow me to engage deeply with real-life situations, offering insights and reflections that resonate with readers on a more personal level.
In essence, both fiction and nonfiction writing are integral parts of my creative process, each fulfilling distinct needs and motivations. While fiction offers escapism and imaginative exploration, essays provide a means of introspection and commentary on the complexities of life.
CS: You've been the president of the Chicago Writers Association for a number of years, and you've also been a board member of the Chicago Literary Hall of Fame. How did you get involved in these organizations - and why, specifically?
RR: My journey into the realm of literary organizations began in 2005, fresh off completing my debut novel, Lost in the Ivy. Like the protagonist of my story, I found myself navigating a landscape of uncertainty and sought solace in writing communities. It was during this quest that I stumbled upon the Chicago Writers Association (CWA), initially just a Yahoo! group. As I immersed myself in the discussions and camaraderie of the email group, I realized the need for a tangible community of writers.
When CWA transitioned into a nonprofit organization in 2006, I stepped into the role of president â a position I continue to hold today. Over the years, we've witnessed remarkable growth, evolving from a modest steering committee to a thriving network of over 900 dues-paying members. I'm proud of the role CWA has played in fostering a supportive and vibrant community for writers, filling a void that was palpable during my early years as a writer.
The inception of the Chicago Literary Hall of Fame stemmed from within the CWA fold. When [fellow writer] Don Evans joined CWAâs board, I encouraged him to embark on a personal project. He proposed the Chicago Literary Hall of Fame, which was obviously very ambitious, but we managed to do it and launched it through CWA and supported it for the first couple of years until it outgrew our organization, and we made the shift to make the Chicago Literary Hall of Fame its own nonprofit organization.
While I was never a board member of the Chicago Literary Hall of Fame, I was actively involved in developing it and supporting it as it transitioned into an independent nonprofit entity.
In essence, my involvement in these literary organizations is driven by a belief in the power of writers coming together to uplift and empower one another.
I've experienced firsthand the profound impact of collaboration and support within the literary community. It's a philosophy rooted in the idea that by giving back, we ultimately receive far more in return â a principle that has enriched my journey as a writer in countless ways.
CS: Your novels Havana Hangover, Lost in the Ivy, and Cheeseland are all thrillers. Who are some of your primary influences? And why this genre instead of, say, mysteries or literary fiction?
RR: I never set out to confine myself to a particular genre; rather, I let the stories within me dictate their own course, often traversing multiple genres along the way. While my novels â Havana Hangover, Lost in the Ivy, and Cheeseland â can be classified as thrillers, they also incorporate elements of mystery, romance, and humor. I prefer not to be constrained by rigid genre boundaries, as I find that my stories naturally gravitate towards a blend of various literary influences.
In terms of my literary inspirations, Ernest Hemingway stands out as a significant influence, particularly evident in Havana Hangover. Despite acknowledging his flaws, including his tumultuous personal life and outdated notions of masculinity, I admire Hemingway for his elegant prose and his ability to draw inspiration from his own experiences. Like him, I enjoy infusing my narratives with fragments of my own life, reimagining them to explore alternate outcomes and possibilities.
As a self-professed Hemingway aficionado, I've immersed myself in his works, collected his books and memorabilia, and even retraced his footsteps in places he frequented. Therefore, it was only natural that Cuba â a destination synonymous with Hemingway's legacy â found its way onto my bucket list.
When planning my first trip to Cuba, I made it a point to include visits to key Hemingway landmarks, such as his home, Finca Vigia, and his favorite haunts in Havana â La Bodeguita and El Floridita.
These experiences, intricately woven into the fabric of Havana Hangover, reflect my deep appreciation for Hemingway's influence on my writing journey.
CS: You're presently writing a sequel to Havana Hangover - can you tell us a little about it?
RR: When I initially penned Havana Hangover, a sequel wasn't part of the plan. However, as readers expressed their interest in the continuation of Tanner Ford's journey, I began to ponder the possibility. At the start of this year, I embarked on writing the sequel, which picks up Tanner's story where Havana Hangover left off.
In this sequel, I've envisioned a narrative that unfolds through the perspectives of both Tanner and Dannel. The decision to explore their stories from dual points of view stems from the events that transpired in Havana Hangover, offering insights into their respective experiences and motivations. As their narratives progress, I anticipate their paths will inevitably converge, presenting opportunities for unexpected twists and turns.
While I've outlined some initial ideas for how their stories will intersect, as with any writing endeavor, I expect the journey of crafting this sequel to be filled with surprises and creative discoveries along the way.
I should also note that Iâm simultaneously working on my first collection of essays, tentatively titled, Lovable Loser, a nod of course to my Chicago Cubs fandom. These are essays Iâve written over the last 20 years, and they look at my journey from childhood to parenthood.
CS: You read YA novels as well as books for adult audiences. Can you share a few of your favorites from both modalities?
RR: These are the books that have stuck with me over time and have had the greatest influence on me as a writer.
My all-time favorite YA novels:
¡     Looking for Alaska by John Green
¡     To Kill a Mockingbird by Harper Lee
¡     Me and Earl and the Dying Girl by Jesse Andrews
¡     Circle of Friends by Maeve Binchy
¡     the perks of being a wallflower by Stephen Chbosky
¡     The Carnival at Bray by Jessie Ann Foley
My all-time favorite adult fiction books:
¡     The Sun Also Rises by Ernest Hemingway
¡     Lonesome Dove by Larry McMurtry
¡     The Mezzanine by Nicholson Baker
¡     Train Dreams by Denis Johnson
¡     The Name of the World by Denis Johnson
¡     Wonder Boys by Michael Chabon
¡     High Fidelity by Nick Hornby
¡     Bright Lights, Big City by J.D. McInerney
¡     Presumed Innocent by Scott Turow
¡     The Plot by Jean Hanff Korelitz
¡     Such a Fun Age by Kiley Reid
Future tense/upcoming classes:
On July 20, 3:30 PM CT, Iâll be teaching a one-hour online flash fiction class for the Northwestern Summer Writers conference. More details and registration info here.
Beginning Wednesday, September 25, 6-8:30 PM PT, Iâll be teaching a 10-week online short fiction workshop with a focus on story openings for Stanford Continuing Studies. Registration opens August 19. Title and description:
âFour Beginnings, One Endingâ - The best short stories have the emotional heft of a novel and the narrative energy of a page-turner. The short story is the fictional equivalent of the bouillon cube, the novel the big pot of broth. While novelists can take their time easing readers into the narrative, a short storyâs opening must be especially gripping--it has so much work to do within a few paragraphs, introducing readers to the who, what, where, and often the why of the story. In this course, students will write and workshop three to four openings, receiving feedback to help land on the most engaging before writing and workshopping the remainder of the story. Over the ten weeks of the course, along with what makes for compelling beginnings, we will also explore characterization, voice, and point of view, pairing these craft elements with writing exercises. Along with workshop sessions, weâll read and discuss the work of contemporary short story writers including Alice Munro, Edward P. Jones, Lori Ostlund and Bonnie Jo Campbell, with special focus on their stories' beginnings and narrative structure. The goal, by the end of the course, is to have a new short story thatâs so immersive, your readers wonât be able to stop turning the pages.
Randy is one of the essential cogs in the Chicago literary community, and one loveable mensch. It's good to see his thoughts here.
You forgot the Blackhawks, Grant Park and the Magnificent Mile. And the legendary jazz-rock band named for the city.