November 28, 2018 Articles

From Appellate Practitioner to Author: So You Want to Write a Legal Novel

An interview with appellate lawyer and prize-winning fiction writer Cindy Tobisman.

By Mary-Christine Sungaila

Cynthia Tobisman, an appellate partner at Greines, Martin, Stein & Richland, won the 2018 Harper Lee Prize for her novel Proof. The award, which was authorized by the late Harper Lee (author of To Kill a Mockingbird) and is coproduced by the University of Alabama and the ABA Journal, is given to a book-length work of fiction that illuminates the role of lawyers in society and their power to effect change. Tobisman received the award at a ceremony held at the Library of Congress in association with the National Book Festival.

The Appellate Practice Journal caught up with Tobisman to ask her about her dual legal and fiction-writing careers and how the prize has impacted her. Mary-Christine Sungaila conducted the interview.

How long have you been writing fiction and comic books in addition to appellate briefs?

I’ve been writing fiction since grade school, but I got serious about it about 10 years ago. My midlife crisis was realizing that no one ever taps you on the shoulder and tells you it’s time to chase a dream. My life was always going to feel too busy. If I wanted to write, I needed to make it happen. So, I’ve been writing books for about a decade and graphic novels for about eight years. 

Tell us about your novels and comic books—what inspires them, why do you write them, and who is your favorite character?

A good book is magic. We read words off a page and hallucinate wildly. We walk in other people’s shoes. We experience other worlds. From the time I could read, I wanted to write. 

For inspiration, I look to my own experiences (no big surprise), including what it’s like to be a female lawyer handling a big case where the rest of the folks working on the case are male. I also write from the stuff I wrestle with in the middle of the night. The frustrations and dark desires. The unsolvable conundrums in my family. 

Caroline Auden (my protagonist for Doubt and Proof) is a hacker-turned-lawyer. She’s grown up with a parent that suffers from drug addiction and mental illness. That type of background makes a person think they can always fix others. They end up with a superhero complex. So, Caroline’s tendency is to get too enmeshed with her clients and to follow an investigation places that prudence suggests she shouldn’t—and her hacking skills let her pry into secrets she isn’t supposed to see.

What do you find most satisfying about being a fiction writer? About being an appellate lawyer?

Writing is often its own reward. Generating fiction from life and imagination is a sort of yoga—it keeps me engaged in the world and helps me move through difficult experiences. But I’d be lying if I said I didn’t want my writing to find an audience. Ultimately, writing is a dialogue with a reader. They bring their own life experiences to the reading process, and it’s very gratifying to get email telling me how this or that part of the story resonated. 

Being an appellate attorney is creative. There isn’t some monolithic “law” out there waiting to be found. There are often only disparate opinions on tangentially relevant fact patterns. We must find and synthesize what’s out there and turn it into a persuasive argument for why a case ought to come out a certain way. The process of researching the law and creating an argument is gratifying. We bring order from chaos. We bring clarity. Plus, there’s the challenge of making complex concepts easy to understand. 

How has your nonlegal writing impacted your appellate brief writing? Has your legal writing morphed or changed at all? Is there an interplay between your nonlegal writing and legal writing?

Storytelling is at the core of everything I do for both my vocation and avocation. When I’m writing fiction, I’m bound by the rules of plausibility and story logic. When I’m writing an appeal, I’m bound by the trial record and the standard of review. But the principles are the same—you have to tell what happened in a way that conveys the essence in a compelling fashion. 

Cases can be won or lost on the strength (or weakness) of a statement of facts. Judges are human beings. They form opinions about advocates they like (and don’t like) based on the story. This is one of the reasons issue selection is such an essential aspect of appellate practice—because it lets the appellate attorney create the most compelling narrative possible given the available standards of review. 

How do you balance your fiction-writing career with the practice of law? What advice do you have for attorneys who might aspire to become novelists?

It’s difficult to find balance if you’re waiting for the perfect circumstances to write fiction. There’s always an easy excuse not to write. Balance is attainable if I treat my life as Swiss cheese—I write fiction in the holes. I dictate scenes while driving to meetings. I edit them after work when my kids are doing homework. The stories grow bit by bit, page by page. 

My advice to attorneys who want to write is to keep at it. You become a writer by writing, day after day. Lawyers have the advantage of understanding that writing is work. Sure, inspiration is great, and the feeling of flow can be a joy. But it can also be a slog. 

As lawyers, we also understand that our best work is often collaborative. Treat your fiction like a motion or brief—it’s a thing outside of you that you’re trying to make as good as you possibly can. Critical input from editors, friends, and writing groups can be instrumental in achieving that goal. Plus, there’s a whole world of freelance editors that will critique your manuscript (for a fee). Invest in your writing and be willing to hear criticism.

You won the 2018 Harper Lee Prize, besting longtime novelists and fellow finalists Scott Turow and Lisa Scottoline, for a novel-length work of fiction that best illuminates the role of lawyers in society and their power to effect change. What was that like? How did it impact your fiction-writing career? 

It was a complete shock to win the Harper Lee Prize. I am a working lawyer who writes books from the back seat of my minivan in the parking garage at work. I’m not a professional, full-time writer like Turow or Scottoline. I don’t have their fan base or publicity muscle. When I got an email from my publisher to tell me that Proof had been short-listed, I was stunned and gratified. But I was quite sure the selection committee would choose a brand-name winner (i.e., not me!).

Winning the prize is one of the most exciting things that’s ever happened to me. The prize itself is remarkable. Authorized by Harper Lee before she passed away, it is sponsored by the University of Alabama Law School (Lee was a student for a short time) and the ABA Journal to celebrate Atticus Finch’s conception of how a lawyer can make the world a better place. The folks who choose the winner are a fascinating and diverse group of academics, writers, and other thinkers. I’m thrilled they saw something of Atticus’s spirit in Proof. The signed copy of To Kill a Mockingbird is also cool! 

As for how it’s affected my fiction-writing career, the answer is that I’m working on a new series now, based on conversations between my agent and an editor at a major publishing house. The Harper Lee Prize should open doors, and I fully intend to do my best to walk through them.

Mary-Christine Sungaila is a partner at Haynes and Boone LLP in Los Angeles, California, and is a cochair of the ABA Section of Litigation Appellate Practice Committee.

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