Jillian Medoff is sitting in a pub in Midtown Manhattan slowly sipping a Diet Coke and passionately explaining the history of HR departments. When we meet, it’s less than a month since the Harvey Weinstein allegations broke, less than a week since Mark Halperin, a few days since Kevin Spacey. Everyone is suddenly very interested in HR departments; I am suddenly very interested in HR departments. But Jillian Medoff? She has been interested in HR departments for years.

HR is the subject of her latest novel, This Could Hurt, a big, tender book that is very funny and very sad and that contains what are surely literature’s most emotionally affecting org charts. Set in the wake of the 2008 financial meltdown—the novel, which shows off Medoff’s fanatical attention to detail, opens in November 2009—the book follows nearly a year in the lives of the human resources employees at a flailing boutique research firm: Rosa, the corporate matriarch; Kenny, the shiny newlywed with the shiny Wharton MBA (Senior Manager, Compensation); ambitious striver Lucy (VP, Communications/Policy); lovelorn Leo (Employee Benefits); and Rob, an affable Brooklyn family man, who is also casually miserable (Associate Director, Recruiting and Training). If you wanted to tell a tidy story about it, you could say Medoff has been working on it for her entire career, and in a roundabout way, you wouldn’t be wrong.

“I had always wanted to write a book about work,” says Medoff. Work is so common and tedious it’s almost possible to forget that it’s also deeply weird. Your colleagues take up so many of your waking hours, and yet for all that time, you get to know so little about who they actually are. Also, Medoff says, most books about work fail to capture one essential thing, which is the actual work part of working. “I read so many books about work by people who've never worked. And there's such a lack of authenticity to them,” she says. “I feel like it's a literary imagining of what it’s like to be in an office.”

Medoff does not have to imagine. She’s been in corporate offices since her senior year at Barnard and has been in “job-jobs” ever since: marketing, crisis communications, now management consulting. She did a stint selling breast implants. And, for a tumultuous 11 months in 2009, she worked in HR for a difficult boss whose staff was fiercely protective of her—inexplicably, Medoff thought, until she learned the woman had had a stroke a few years before. That grabbed her, the idea of “this older woman who was really at the height of her powers at one point, and she’s diminished.” She wanted to talk about the amorphous boundaries of corporate life, the way “we act out these familial relationships at work,” both consciously and not.

It is possible, of course, Medoff could have written this particular novel even if she hadn’t had the job-jobs. People write novels about wars they weren’t in all the time. But she thrives on the double life. “Having a separate identity as a senior consultant is what saves me. Honestly. It’s the thing that has made my career as a novelist.” It gives her the freedom to write the books she wants to write, she says, to get some distance from the commerce. It’s more than that, though: the double identity means she’s always on the outside looking in.

“I’ll find anything to feel like an outsider so that I can observe and write about it,” she says. It all goes back to childhood, she explains. “My family are middle managers. There was no artistic nonsense.” The daughter of a traveling knife salesman, she moved 17 times by college; now, she’s an impressively credentialed novelist—four books, a MacDowell fellowship, an NYU MFA—who also happens to be an “ostensibly full-time corporate person.” And so wherever she is, she’s not quite there, which, she’s pretty sure, is how she likes it, unless it’s all a mistake, which she acknowledges is also a possibility. “It’s always this toss-up. Did I make all the wrong life decisions?”

“On one hand, you want to feel like, ‘Hey! I’m part of the gang!’ ” Medoff says. “And then on the other hand”—she trails off—“I just can’t get too comfortable. Because I write from a place of rage and anger, and I need that opposition to sort of fuel it.”

At 54, she says, “you can’t compete with first novelists and ingenues and young men wearing black glasses fresh out of Harvard. But that doesn’t mean in the last 30 years I haven’t learned a thing or two.” That’s what keeps her going, “that feeling of, I have got to have my say.”

This Could Hurt is a departure from Medoff’s previous work, which is smaller in scope and more domestic—the kind of witty, female-centered novels that end up marketed as “chick lit.” And from a business point of view, she gets it. But artistically, the category never sat right. “I never intended to write women's fiction—like, I didn't even know that was a thing when I went to graduate school.” And it’s been great, in some ways. “I was really, really grateful that my books were published,” she says; the books themselves, for the most part, have been well-reviewed. Still, it’s frustrating, not because of what “women’s fiction” is but because of how it gets talked about. “It’s almost a cliché at this point to say that domestic issues are not taken as seriously unless a man handles them.” The fact that she’s funny, she says, only exacerbates the issue. “Critics often underestimate how difficult humor is,” she says. “I think I’ve been really hard to categorize.”

That hasn’t totally changed; This Could Hurt maneuvers easily between wry satire and quiet devastation. (She’s worried that people will find it “heartwarming.” “What does that even mean?” she wants to know.) But she’s the first to say it’s a more ambitious book, a bigger book. “And by bigger, I don’t mean it’s better. I just mean it’s a bigger canvas, it’s more characters, I’m taking on themes outside the family.” It took her seven years to finish—the cost of a dual literary-corporate career—although she acknowledges the tortoiselike pace came with advantages. She needed the time to get it right.

“I couldn’t have done this kind of book earlier in my career,” Medoff says. She didn’t have the skill set yet, or at least she didn’t think she had the skill set, which, for practical purposes, is the same thing. “A lot of it is confidence. It’s like saying to myself, ‘You know what? I bet you can’t do that.’ And then it’s like, ‘Oh, I have to do that. Why can’t I do that? Of course I can do that.’

“Writing a novel is like having a conversation with the world,” she explains. It either understands you, or it misses. And when it misses—it always misses, it has to miss—you go back and you re-create that conversation again and then again. “There’s got to be something for me to write against,” Medoff says. “There’s got to be something off-kilter, there’s got to be something wrong. Because I need to right that wrong.

“This book was responding to my fear that if I had not had a full-time job all these years, I would be more successful as a writer. This was my saying, ‘You know what, no. I can do both. Just give me a chance, give me time.’ I’m not there yet, but I’m going to get there.”

Rachel Sugar is a writer living in New York.