James Grippando of Boies Schiller Flexner in Fort Lauderdale

Thirty years ago I decided to write a novel. Six years later, when “The Pardon” finally hit bookstores—you remember bookstores, bricks, mortar, sales people who actually know how to read—there was one question my lawyer friends couldn’t help but ask: “Are you going to keep practicing law?” I told them I saw no reason to quit, to which the typical response was something along the lines of “Gee, I’m really sorry, I hope your next book does better.”

Twenty-six novels later, the question is not why but how do I do both. A dual career has gotten easier to manage over the years, due in no small measure to changes in the legal profession.  “Flex time” and “telecommuting” were unheard of when I wrote my first novel. Changing attitudes and better technology, however, are not the entirety of it. I don’t have all the answers, but this article offers some guidance to any lawyer whose goal is not just to write but to create published works that will appeal to a mainstream market and actually sell to readers outside the immediate family.

Step One:  Take an honest look at yourself

Here’s a list of questions to ask yourself before setting off on a dual career.

  • Do I read for pleasure? That may seem like a funny question to ask, but if you don’t read or “don’t have time to read” for pleasure, you might want to re-evaluate your decision to pursue a writing career.
  • Do I have the discipline to write? Contrary to popular misconceptions, an “idea” for a book is not the hard part. The self-discipline of sitting down day after day to write is what separates writers from dreamers.
  • Do I have talent?  I used to think that everyone who’s ever read a book has at least one novel lurking somewhere within their creative spirit. With the proliferation of self-published works in digital format, I have changed my mind. Determining whether you have talent begins with honest self-evaluation, but honest self-evaluation has nothing to do with fear of rejection or embarrassment.
  • Assuming I do have talent, can I live with public accusations that I don’t? Some readers will love your work. Some will hate it. Goodreads, Amazon, and other online platforms afford readers easy opportunity to express their views, fairly or unfairly. If a one-star review will ruin your day, you’ll need a much thicker skin.
  • How will my clients react? Most clients understand that you cannot take their call if you’re in court or with another client. Don’t expect anywhere near the same level of understanding if your unavailability is due to a promotional event for your book. My personal rule of thumb is that a call from a client takes precedence over a call from my editor, my agent, or anyone else in the publishing and entertainment industry—with the possible exception of Steven Spielberg, Leonardo DiCaprio, and 98 other people on the Hollywood Reporter 100.
  • How will my partners react?  All of them—especially the ones whose draw is at least ten times your advance—will expect a free book. Your response: “I’m a writer, not a publisher.”

Step Two:  Can someone actually show me how it’s done?

Legend has it that, following the publication of his classic work, “The Jungle,”Upton Sinclair was invited to speak at a Harvard University graduation ceremony. His topic was “the key to writing a great novel.” After being introduced by the university president, he walked to the lectern as the crowd gave him a warm reception. Finally the applause silenced. He looked out into the audience and said, “Why aren’t you at home, writing?”  Then he returned to his seat. That’s honest advice—but not the only advice—for aspiring writers.

If you’re thinking about a career in writing, you’ve probably been told—perhaps all your life—that you’re a good writer. But thousands of lawyers are good writers. Our profession demands it. So how does a lawyer develop the skills to transition from legal writing to entertainment?

On one end of the spectrum is my late friend Barbara Parker, who quit her job as a Miami prosecutor to go back to school and get a degree in creative writing. She developed her novel as part of her coursework, and upon publication it was nominated for an Edgar Award, the mystery writers’ equivalent of the Oscar. On the other end of the spectrum is my friend Phillip Margolin, a Portland trial lawyer who was invited to write a book at a time when agents and publishers were actively looking for “the next John Grisham.”  Phil has never seen a rejection letter in his literary life.

Between these extremes lies a world of options.  If you work well with other people and can learn in a group setting, perhaps a creative writing course or seminar is for you. A good course with a talented instructor will do more than sharpen your technical skills. It will teach you to recognize good material and use it effectively, and to find material in your imagination and develop it. Courses are a safe place to experiment and make mistakes. You’ll learn not to be shattered by criticism nor blinded by praise, and you’ll become more discerning about which advice to accept and which to reject.

Another option is the editorial consultant. A consultant works with you to improve your manuscript and, in addition to a fee, usually takes a percentage of your advance on publication.  I would recommend this route only after you have taken your script as far as you can on your own. It goes without saying that you have to be wary of scammers. Always insist on references.

Step Three:  Write what you know—sort of

“Anatomy of a Murder” (1958) by John Voelker, writing as Robert Traver, was reportedly based on a case Voelker handled as a young trial lawyer. Don’t go that route. The odds are virtually nil that a case you handled will also launch your writing career.

So, why do lawyers make good writers? If I had to point to one thing, it would be this: motive.  Convincing fictional characters have strong and believable motives, and successful lawyers understand what people want, why they want it, and what they’re willing to risk to get it.  Published lawyer/authors make good use of that understanding.

A Final Tip: Be realistic

This may come as a complete shock to your friends, but not every book sells as many copies as, say, The Bible. If you’re lucky enough to have your book published in bound format, a typical novel sells somewhere between 2,000 and 3,000 print copies. If you publish strictly in e-book, the current per-page compensation rate from Amazon under the Kindle Unlimited program works out to about $1.50 for a 300-page novel.

Writing probably won’t make you rich. Or famous. But if you write your favorite restaurant into the story, you might get a free bottle of wine with your next dinner. Trust me. That much I know.

James Grippando is counsel at the law firm of Boies Schiller Flexner and a New York Times bestselling author of suspense. “Gone Again” (HarperCollins Publishers) was the 2017 winner of the Harper Lee Prize for legal fiction. “A Death in Live Oak” (HarperCollins 2018) is his twenty-sixth novel. He is also an adjunct professor of law and literature at the University of Miami School of Law.