​Q&A WITH TIMOTHY O’LEARY

Q: Many of the characters in your stories are men struggling with guilt, shame, confusion, lust, and existential angst. What draws you to these characters?  

You’re talking about the essential building blocks to a healthy existence! Seriously, most of us spend our entire lives wallowing in that emotional stew. 

The night before my father died – at age 90 – he was still feeling angst over his father’s mistreatment eighty years earlier. Eighty years! My Dad was born during a worldwide plague, lived through the Depression, fought in World War II, almost died several times, helped raise five children, managed to construct a terrific life with a great wife and family, and live twenty years longer than he ever could have imagined. But the biggest thing on his mind as he slipped away was his abusive father.  

That incident, along with a personal experience that happened a few years later and which at the time seemed traumatic, was the catalyst that led to my search for emotional peace. I was feeling guilt, discontent, and anger that, especially considering my advantaged and relatively trouble-free life, didn’t make sense to me.    

Writing became my therapy, and in particular, writing about angst-ridden characters became a way to exorcise my own emotional demons. The challenge is to lose the baggage that doesn’t matter, while maintaining a proper dose of self-analysis to keep you from becoming a complete asshole.  

Q: Several of your stories are about the struggle to adapt to a new reality, both from the standpoint of getting older and also because what was once familiar is quickly vanishing as technology advances. A few of your characters see the benefits of technology, but some also experience the downside, like your character in “Hecklers” that becomes an overnight YouTube star. What are your attitudes about technology and how does the tension between getting older and keeping pace with our rapidly changing world inform your writing? 

I am deeply conflicted on the entire issue of technology. It makes me sad to see a couple or an entire family ignoring each other at dinner, their gazes tilted into their crotches, preferring online interaction over the people in front of them. That being said, technology has been very good to me personally, and it seems an essential tool for the challenging future humans face. I am also somewhat of an early adopter, and can’t imagine life without many of my silly devices. Could life exist without Sonos? Of course not.  Plus, not a day goes by that I don’t see some interesting storyline in our love of technology. 

My biggest concern—and the latest literary theme that seems to be driving me—is that we are in uncharted human territory, and we don’t know how this will all develop. Communication has become so trivial, our societal heroes so plastic, that it all feels very out of control. Online communication is uniquely anonymous, so honesty, civility, and compassion are no longer valued. In many ways it has become a digital highway for hate. That was certainly a big part of my motivation for writing “One Star.” 
For the first time, human beings seem to be switching ecosystems. Since our origin we have been part of the interconnected system of living organisms that make up this planet. I spend a lot of my free time working on environmental issues, and one of the things you quickly learn in how connected all living things are, and what seems to be a relatively minor disruption can have major consequences. Our blatant disregard for the earth, and our relentless drive to instead plug into the worldwide web portends a big change. It feels like we might be abandoning this living ecosystem, to jack into a manufactured world that has completely different rules, and outcomes, we might not understand.  

  
 Q: What do you think women would think of the men in your stories?  Do you think most men view women the way your characters do?  

Ah, that seems to be a bit of a loaded question. I am the first to admit that some of the men I write about are truly awful human beings, but hopefully the reader understands that I am usually being satirical, or in my darker stories, exploring those horrifying, yet compelling personalities that make us shudder. And I totally reject the idea that writing should be hampered by political correctness, as life isn’t politically correct. 

You might not like all my characters, but they will never bore you. Sometimes I burden a single character with the terrible traits I’ve observed in multiple individuals to better highlight a point, making that personality a little over the top. Throughout the collection I also hope the reader discovers many authentic, likable men. The man in Costco Girl, and The Tower are confused romantics. The fathers in Midnight Elvis and One Star are emblematic of the strong, wonderful, flawed men I knew growing up that were just trying to provide for their families. 


Q: You’re a 30-year veteran of the advertising world. How does that inform your writing? 

Advertising can be a terrific training ground for a writer. Most importantly, it teaches you creative discipline. You’re not allowed to have writer’s block. Colleagues and clients are waiting, and your job is on the line. You have to create every single day, and meet every deadline. You grow accustomed, and in fact, appreciate constructive criticism and editing. By its very nature advertising forces brevity, and a multi-layered approach to communication, which can be a great asset. 

It also forces you to stay culturally aware, and depending on the kind of advertising you are involved with, it can provide you with a lifetime of interesting characters: crazy inventors, bombastic CEOs (one was accused of murder), sociopath advertising directors, sex fiends, religious fanatics, a narcoleptic woman that would fall asleep in meetings while eating Dairy Queen Dip Cones, Mafia members, movie and television stars both on the way up and on the way out…. A cavalcade of awful, wonderful, slightly insane characters that inspired me with a lifetime of stories. 


Q: You grew up in Montana, but now divide your time between California, Oregon, and Washington. Most of your stories are set in those places. What significance does “place” play in your life and your writing?   

I’m acutely interested in the connection between place and persona, and to understand the connection I think you need to spend time there, so all of my stories are rooted in locations that I know well. I will often research a hundred years’ of a town’s history before I use it in a story. It helps me, and I think it helps the reader. I want them to literally be able to smell the place, and know how the location has shaped the character. 

In my story “Impala,” a boy is kidnapped outside of Sunset Bowling Alley in Billings, Montana. Sunset is a real place that I spent a lot of time frequenting as a kid. I loved it, but it always seemed sinister to me. When I was considering the location for a kidnapping, it seemed perfect. 

A lot of my work takes place in Montana—in fact I’m working on a novel right now that’s set in Montana and Oregon, the two states I know best. Generally, I just like people from Montana. The good ones have a libertarian streak that transcends the usual biases. They tend to be self-sufficient, and are generous. They’re tough, but very friendly. And they never feel inclined to demonstrate how smart they are, it just unfolds in normal conversation. Dewey, the Sheriff in The Purification, reminds me a lot of the men I grew up around. He’s economical in emotion and word, with a deep sense of duty, a wide tender streak, and a surprisingly good sense of humor. Montana also gave me my literary roots. I spent my undergraduate years at the University of Montana.   


Q: Are there particular kinds of stories you’re drawn to? Ones you steer clear of? 

It sounds awfully basic, but I like a story with a beginning, middle, and an end. I tend to value concept equally with craft. I want to take my readers on a journey, as opposed to just painting a beautiful scene, and I like my characters big and messy. I want a laugh, or at least a smile, or perhaps to shock you. 


Q: Some of your stories are based on true events like “Dick Cheney Shot Me In the Face” and “The Big Chocolate Whizzle.” What inspires you to fictionalize and flesh out true events? 

There is a basis of truth to all my stories, as I tend to be a collector of unusual events that inspire me to investigate more, and imagine the circumstances that preceded the story.  

A few years ago I was in Jackson Hole, Wyoming at a fly-fishing tournament. One night Dick Cheney showed up, floating through the room like a smiling corpse, and of course the conversation among my friends migrated to his hunting skills. Cheney is so iconic, and I became very curious. I read a couple books on the man, and researched his background. While my narrator in the story is fictional, all the facts about Cheney are true, and I thought it just became an interesting way to bridge fact and fiction. 

Years ago my wife and I were on an overnight flight from LA to Australia, and when we woke up in the morning I discovered that the flight attendants had handcuffed a young man to a bathroom door in the rear of the plane. Sometime during the night he had gotten drunk, jumped up on his seat, and began urinating on his fellow passengers, which I believe placed him high on the terrible traveler scale. I researched the phenomenon, and discovered it was not all that unusual. Who would have thought that was a thing? The main episode that occurs in “The Big Chocolate Whizzle” is based on a real event I discovered during the research; a business executive overly imbibed on a flight, and ended up ruining his life. I wouldn’t have thought to make that one up. 


Q: Many of your stories are darkly humorous and have hints of irreverence. How do you approach comic relief in your stories without being gratuitous?      

Your question makes the kind inference that my work isn’t gratuitous. I do hope it isn’t, but sometimes it’s difficult not to cross a line, as it is often in the eye of the reader.  About a year ago I received the following rejection letter from an editor: “Thanks for your submission. I found the story very insensitive and offensive on many levels, but I must say it was the best thing I read all week. It made me laugh out loud. Unfortunately, we could never publish it.” A week later another publication accepted it absent any trepidation, and it is in the collection. I will let the reader guess which story he was talking about. 

Wit is its own brand of intelligence, and I admire and aspire to witty writing. Those that do it well can navigate potentially gratuitous subjects with grace. Take the fart joke. As told by guys like Adam Sandler it will always be gratuitous; more shocking than funny. But thirty years ago I read David Niven’s wonderfully witty biography, The Moon’s a Balloon, which contains the greatest fart joke ever told. I still clearly remember it; a wonderful story involving Cary Grant and a surprised fan.    

Sometimes I’m unsure if I crossed a line, and I tend to call on five or six different people that I respect to read the work. Each of them has a different comic sensibility that I understand, and I look to their responses to judge if the piece is working. They almost never agree, and I don’t write by committee, but sometimes there is consensus about something that escaped me that I take seriously.   


Q: What books do you remember most from childhood? Any stories or characters that really stuck with you through the years? Is there a particular book that made you want to write, and who influences you now? 

My literary journey began with The Hardy Boys, Jack London, and Alfred Hitchcock Presents. I remember being obsessed with Treasure Island, The Swiss Family Robinson, A Wrinkle in Time, My Side of the Mountain, The Outsiders, and The Catcher in the Rye. From there I discovered Stephen King, and a host of mystery writers often read via flashlight under the covers.  

Hunter S. Thompson’s work was probably my first major literary crush as a near adult. I’ve admired Gay Talese, especially Thy Neighbor’s Wife, though I have to admit I’m a bit baffled by his newest book, The Voyeur’s Motel. 

More recently I’m inspired by Tom Perotta’s ability to move from suburban wit to dark, high concept tales.  I’ve had a life-long love affair with Elmore Leonard’s writing, especially his incredible dialogue. I’m a fan of Richard Russo’s dry humor, and smart, stoic men. The opening paragraph to his newest book, Everybody’s Fool, was a delightfully humbling experience. I will always read anything Cormac McCarthy writes, though sometimes it’s a bit difficult to stomach. Carl Hiaasen is a wonderfully funny satirist, and I love Dave Eggers take on culture.