It’s mid afternoon and the Breslin Bar is dark as a cave. Patrick deWitt, 40, folds himself into a corner table and orders the Flatiron Fling, a complicated potion topped with a thick, tea-colored head of egg foam. This is precisely the kind of cocktail he would have refused to make at the Hollywood dive where he worked in his 20s, while pouring years of work into a first novel, Ablutions: Notes for a Novel (HMH, 2009). Back then, deWitt, a well-read high school dropout, was reluctant to undertake a book set in a bar, and wrote it with “a certain trepidation,” he says. “I didn’t want to add to that canon. I wanted to write some grandiose novel of ideas, but I didn’t have the life experience or point of view to see a project like that through.” He sips his pretty beverage. “I have a paranoia that Ablutions is the best thing I’ll ever do,” he says. “Writing it, I felt like I was channeling something very pure and deep in me, and I haven’t been able to tap that well again.”

Ablutions traces the whiskey-soaked decline of a young bartender’s health, life, and morality, leaving him, in the end, wrung out but at least free of barflies and junkies. When the manuscript sold, deWitt put the bitters behind him, moving to Portland, Ore., to become a full-time writer. When the novel came out—and got noticed—deWitt was often asked about the extent of its autobiography. “That dialogue became tiresome very quickly,” he says. “I knew I didn’t want to write another book about myself. I needed to make a clean break and write more from my imagination.”

Enter two unusually thoughtful brothers hired to assassinate a thieving prospector at the height of the California gold rush and the dawn of dental hygiene. The Sisters Brothers (Ecco, 2012), deWitt’s second novel, began as an exercise that got away from him. Watching a spaghetti western with his father one day, deWitt found himself wondering, “Where does Lee Van Cleef go shopping? He just crossed the desert and he looks like a supermodel. I approached it from a smartass’s point of view,” he says. “What are these people thinking? Why are their feelings so hidden away? I realized you’re rarely granted access to the inner workings of the minds of the killers in westerns.” So deWitt entered two words into the little book he carries always: sensitive cowboys. That idea spawned a long dialogue between two fellows on horseback, “bickering about something totally inconsequential,” deWitt says. “It had an energy to it.”

DeWitt didn’t always know to follow that energy, and admits that he has wasted much time ignoring it. “I was young and impressionable and thought you were supposed to be serious and dour, to share grand truths,” he says. “I was intentionally curbing the impulse to be funny, and hiding the ability. I wrote any number of very serious attempts at poems, short stories, novels; horrible. At a certain point I recognized that it was fun to write dialogue that had a degree of lightness and humor. It was years before I could fully engage in it. Some deeper part of me wants to write comical dialogue; I’d be foolish to not follow that impulse. Now I recognize that if there’s energy to a section of work, you go where the energy is. It’s a living thing and you just follow it.”

That energy flowed more strongly than ever during a two-week period when deWitt wrote the first pages of what became Undermajordomo Minor (Ecco, Sept.), his third novel. Writing had never come so easy to deWitt, so he decided to sell the book based on this slim partial manuscript. The same publishers who did The Sisters Brothers bought Undermajordomo Minor: House of Anansi in Canada, Granta in the U.K., and Ecco in the U.S. “They gave me a year to finish the book,” deWitt says. “More than enough time. I thought I’d be done in six months.” A second Flatiron Fling in front of him, he raises it carefully to his mouth. He has long, delicate fingers and long, delicate arms covered with a few faint tattoos. “Something happened,” he says. “After those first 40 pages, man, it was just fighting tooth and nail. It took me a full extra year. The publishers were all very gracious about it, but this book was a motherfucker.”

Inspired by macabre European folktales, Undermajordomo Minor begins when young, self-important Lucien “Lucy” Minor leaves his indifferent mother to assist the majordomo of the nearby Castle Von Aux, whose baron, it turns out, is struggling with his sanity. With section headings like “The Inveigling of Klara by the Strange Eastern Stranger, Godless Corrupter,” dark, surprising twists, and characters constantly pitched into humorous, off-kilter discussions, the novel further establishes deWitt as a writer in possession of distinct vision and talent. Before embarking on the book, deWitt found himself reading old folktales to his son. “I was enjoying them unabashedly,” he says. “So strange and really very dark and twisted and sick. Some of the moral lessons are so perverse. I felt that envy you feel when you read something truly fine. Not that you wish you wrote it, but you wish you could feel that way, when you’re firing on all pistons. I recognized that envy. I was having dinner one night, and I recognized that I was going to junk the book I’d been writing and write this one.”

Junking one book to pursue another is, it turns out, an action with which deWitt is all too familiar. In fact, for every book the author has published, he has discarded another. “It’s a horrifying realization,” he says. “If it happens every single time, I’m fucked.” Between Ablutions and The Sisters Brothers he wrote and junked two books, partially salvaging one by adapting a section of it into Terri, the 2011 film starring John C. Reilly (who holds the film rights to The Sisters Brothers). Between writing The Sisters Brothers and Undermajordomo Minor, deWitt was halfway through a novel about a charlatan and happy with the way it was going. “Then one day I recognized that I was bored stiff. A contemporary story about a man who amasses a lot of money illegally?” he says, shaking his head. “I was dreading sitting down to work every day. It wasn’t just a phase. I’m either enjoying myself or I’m not. And if I’m not enjoying myself, something’s gone terribly wrong.” He takes another frothy sip. “What you want a book to be and what it becomes are never the same thing. If you’re fighting it, you’re going to fuck it up.”

DeWitt doesn’t lament the arduous path he’s taken to get to where he is today, but he doesn’t recommend it either—“to anyone.” He never bothered to get a GED, calls his younger self “an unemployable and extremely unambitious pain in the ass,” and doesn’t think he would have fared well in an M.F.A. program. “I wonder if they would have even encouraged me, because the writing was so poor for so long,” he says. “What kept me going was the idiocy of youth. If someone had told me I wasn’t great, I might have believed them.”

Drinks finished, deWitt heads into the sun to smoke. “Some artists have the luxury of intellect. They can approach something coldly, they know it’s going to work because the odds are in their favor or something,” deWitt says, sitting on the lip of the window of the Opening Ceremony store and lighting up. Behind him hangs a $130 T-shirt, emblazoned from chin to crotch with the words, I Just Want to Enjoy Myself. “It’s not that simple for me. It’s more like a human relationship. Sometimes it goes the distance and sometimes it doesn’t. There’s a symbiosis and energy or it’s just not there.”

“One of the most appealing aspects of art making to me is you don’t know what’s going to happen every day when you sit down. Oftentimes these are unhappy surprises, like recognizing a book is garbage,” he says. “The disappointments can be crushing. But it also adds to it in some way. The stakes seem very high at times. It can fall apart at any moment. That’s part of the appeal. I never wanted a steady job. If I knew what I was doing every day, I’d become bored very quickly.”

Mike Harvkey is the author of the novel In the Course of Human Events.