By Colleen Jurkiewicz Reporter Published Aug 03, 2013 at 9:02 AM

Take a maximum-security prison in northern Wisconsin. Throw in a seriously bitter paraplegic social worker, a Special Education teacher with a tragic past and the incestuous (but entertaining) workings of a small Midwestern town, and you’ve got Wisconsin author Jess Riley’s latest novel, "Mandatory Release," a humorous but poignant account of how we move on from the crises that threaten to cripple us – literally or figuratively.

Graham Finch is a wheelchair-bound social worker whose paralysis has given his already-cynical personality a dark, twisted edge. He works in a prison in the fictional tourist town of Laurentide Bay, Wis., and has a nasty habit of deliberately sabotaging most of his romantic relationships. He reconnects with Drew Daniels, a friend from high school (though he wanted to be more than friends, even then) who comes to work at the prison as a Special Education teacher.

Drew, for her part, is injured in another way – deep in the throes of a quarter-life crisis brought on by a humiliating scandal, she is vulnerable and lost, trying to find her way back from a difficult betrayal. She is, ironically, escaping to prison.

Together, Drew and Graham navigate the choppy waters of 30-somethinghood as they struggle to come to grips with the reality that sooner or later, you’ve just got to let go.

"Mandatory Release" is Jess Riley’s funny, reflective answer to the age-old "when life gives you lemons" scenario. As in, when life gives you lemons, fashion a prison shank, make lemonade and spike it with some really strong liquor. I have to start by asking about your own experience working in a prison. The whole time, you must have been thinking, "I need to write a novel about this!" What were some of the more surprising aspects of the job?

Jess Riley: I think that there was so much hope and optimism in what most people would assume to be a scary, dark place. The staff had terrific senses of humor – you have to, when you work in a prison – and many of the inmates did, too. I saw the full range of humanity on display: the heartbreak and brutality, unexpected kindness and ridiculous humor, cynicism as well as

OMC: Graham is such a great and funny character, and you write on your blog that you don't believe in "tidying up the male point of view." What's it like to write a bitter, paralyzed guy, who also has a wicked sense of humor?

JR: Graham was so much fun to write! I love writing characters that experience the usual frustrations and challenges of life, but with an added complication – kidney disease in my first novel, a spinal cord injury in this one. You get an extra layer of depth, as well as more opportunity for wry humor due to how others act around them. There’s a running gag in "Mandatory Release" about strangers approaching Graham to suggest he play quad rugby, "Like those guys in Murderball!"

People want to help and end up bungling the moment. I also love building that raw feeling of being an outsider looking in, of wanting a different kind of life, which most of us have felt at some point in our lives.

OMC: You say in the end that this novel is loosely based on another piece you wrote about 14 years ago. What was the evolution of that like, and how did it become "Mandatory Release?"

JR: Oh boy. That first novel was my "practice book." It integrated some facets of my experience working in a prison, but I doubt even a full sentence from that original draft made it into the final cut. It was the novel that taught me how to write a novel, so the experience was invaluable. Having so much time between "visits" to the manuscript gave me the brutally objectivity I needed to rip the book down to the studs for a complete rebuild.

OMC:Your book has been described as a mashup of "Girls" and "Oz" and that's actually a very accurate assessment. This novel was laugh-out-loud funny, but also deeply profound. How, as a writer, did you combine the levity and humor with the backdrop of a prison, along with storylines that included paralysis, pedophilia and even murder? Did you find that challenging?

JR:I love juxtaposing heartbreak with hilarity, because that’s how real life can be, as long as you’re being honest about how people really think and act. Sometimes you get an inappropriate urge to laugh at a funeral, just as you might feel an unexpected, crushing sense of loneliness when everyone around you is laughing and celebrating at a wedding. The characters in my books talk the way people you know talk, and they make the familiar mistakes we all try to avoid and sometimes make anyway.

Some of the prison storylines were tough to write, as well as a few of Graham’s more honest, dark feelings about his physical situation. I tried to handle these issues with sensitivity, authenticity, and compassion, and all I can do is hope readers feel I addressed the darker themes fairly, from my characters’ honest perspectives.

OMC: Can you tell us about creating the town of Laurentide Bay?

JR: Laurentide Bay is pretty much a fictional version of Sheboygan – or Two Rivers or Manitowoc or Sturgeon Bay. Again, like juxtaposing humor and heartbreak, I loved setting the prison against a scenic, tourist destination, complete with upscale restaurants along the piers, yachts moored in the harbor, a lighthouse at the end of the breakwater and sand dunes, maybe even with two empty Adirondack chairs facing the water. All so scenic that "Hardly anyone cares that at least one inmate manages to escape every ten years or so."

OMC: The novel contains some great little "Wisconsinisms." Can you talk about creating the town of Laurentide Bay and its inhabitants?

JR: I get email all the time from people who tell me they love reading the little "Wisconsinisms" I tuck in my books. And as in many tourist towns in Wisconsin, there’s a fun mix of blue-collar locals and wealthier out-of-towners. Supper clubs and bistros, drive-ins and taverns, ice cream parlors and, of course, the prison tucked in the woods behind the dunes. The character of Joe was fun to write because he’s a fairly typical Wisconsin guy in his early twenties, with the attendant hobbies, attitude, and vocabulary.

OMC: It's not every book that ends with a customized playlist. Did you really listen to that music while you were editing?

JR: I absolutely did!! When I wrote the flashback for Graham’s accident, I listened to the same song playing on the radio at the moment of impact – "Girl Can’t Help It" by Journey – and I did the same thing while writing or editing other scenes, to help set the tone.

OMC: What's next for Jess Riley? Are you working on anything new?

JR: I’m actually mixing things up and working on a novel I suppose you could call dystopian or sci fi. The vibe I’m going for is "Margaret Atwood meets Hugh Howey with a sprinkle of Ernest Cline’s Ready Player One," for kicks.

Read more about Jess Riley at her blog, Jess Riley Writes.

Colleen Jurkiewicz Reporter

Colleen Jurkiewicz is a Milwaukee native with a degree in English from the University of Wisconsin-Milwaukee, and she loves having a job where she learns something new about the Cream City every day. Her previous incarnations have included stints as a waitress, a barista, a writing tutor, a medical transcriptionist, a freelance journalist, and now this lovely gig at the best online magazine in Milwaukee.