On the surface, the characters in Greg Jackson’s debut story collection, Prodigals, don’t have it so bad—a breakup here, a druggy weekend there, some rough weather and unusual work trips. But Jackson is a canny observer of the inner emotional storms that such relatively small anxieties trigger. As the title of the collection suggests, the stories’ characters have departed from the norm: a journalist becomes unusually attached to a former tennis star in “Serve-and-Volley, Near Vichy,” a man confronts his awkward feelings toward his therapist in “Dynamics in the Storm,” and in “Epithalamium” a woman embraces the squatter who’s taken up residence in her summer home after a split. In each case, Jackson grasps the ways such changes make people feel wildly out of plumb, even if they won't be permanent.

Back to that surface, though: another thing these characters have in common is that they tend to be relatively young and well-off. Class and privilege have a way of being deadly topics in fiction—if writers choose to embrace them at all—but Jackson, 33, says those characteristics are critical to his writing. “I went to an Ivy League school and was constantly around this [upper-middle-class] milieu, and it just felt like we had to make a choice between our ideals and our desire to retain our class privilege and our class membership,” he says. “That felt like a huge tension to me….I think it would be pretty willfully blind to ignore the class and privilege elements not only of writing but of being relatively young and trying to figure out the new millennium.”

That tension plays out most starkly in the collection’s opening story, “Wagner in the Desert,” which follows a group of friends enjoying (or trying to enjoy) one last drug-fueled bacchanal in Palm Springs before settling down—to, as the story puts it, “unfasten our fingers from their death grips on our careers and wardrobes and topiarian social lives and ne plus ultra vacations in tropical Asia.” The story finds a surprising amount of depth within its trustafarian types. It also makes drugs, as a literary subject, less a symbol of abjection or mysticism than a window of the struggle to live an honest life amid the culture’s encouragement to mediate it.

“I think there’s a lot of explicit discouragement of writing about drugs,” Jackson says. “I think we’re a little bit in denial about how much drugs, or even just drug as metaphor, is a kind of baseline for our lives. That might mean that we caffeinate, that we take antidepressants, that we take benzos for anxiety. That might mean that we have a particular way that we consume alcohol or use nicotine, marijuana. It could be any number of things.

“I don’t think it’s particularly interesting to say that there’s some inherent profundity at all to the experience of being on drugs,” he continues. “But I do think that experience of wanting something, a more saturated version of experience—drugs probably just speak to that desire, and to the difficulty in a society that’s largely not concerned with spiritual matters, that’s more secular, just very busy with more practical concerns.”

Prodigals contains echoes of David Foster Wallace—the willingness to experiment with story structures (like the rhetorical shifting in “Metanarrative Breakdown”), the high-end vocabulary (“epithalamium,” “topiarian”), and an abiding concern with our cultural addictions. While pursuing his MFA at the University of Virginia, Jackson taught a class on Wallace, but the late writer’s influence is more philosophical than stylistic. “He designed a way of being in touch with your own mind and alive to your own mind that was going to rival or be more compelling than the bottom-line things that vie for our attention,” he says. “I think that’s really one of the main goals: to somehow write something that’s very rigorous but also very hard to put down.”

That has meant tossing out a lot of his own work—though many debut story collections begin life as MFA projects, Prodigals was written in the past four years, after he was out of school. “It was a frustrating experience but not, in the end, a bad one,” he says. “I was trying to write novels for a long time, and I think that I needed to be exploring, experimenting, and failing more…. It was not fun to look at everything I wrote and know that it wasn’t good enough. But it didn’t mean I couldn’t trust myself when things started getting better.” One of the strongest signals of that effort paying off was the publication of “Wagner in the Desert” in the New Yorker in 2014. The publication was “incredibly consequential,” he says. But the thrill faded fast. “You would probably do well to go back to the next thing before any tidal wave of success washes over you,” he says. “It’s necessary to be working on your own things, and have that grounding….You wish for the best, but you have to keep grinding.”

At the moment, that involves a novel that’s in its nascent stages, as well as more stories, which still are concerned with the nature of identity in a time that allows us to pick up and drop personas more easily than ever, especially online. “As a writer you hear this a lot—people want to read you into the characters. They say, ‘You wrote all this, of course this is all from you,’ ” he says. “And I reject that so deeply because I don’t think I’m from me.”

Mark Athitakis is a Phoenix-based writer whose work has appeared in the New York Times, Washington Post, and many other publications. He is working on a book about Midwestern literature