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Lawyer/ Writer…Writer/Lawyer

By Robert Rotenberg

In early 2011, after my first novel, “Old City Hall,” was published, I was fortunate to move my criminal law office into Eddie Greenspan’s building. Eddie was a terrific writer who worked hard at his craft. Late one afternoon in my first weeks there, he asked me: “Tell me, how hard it is to write a novel?”

“It’s easy,” I said, “just set your alarm for 5:00 a.m. and write for two hours every day. For twenty years.”

His blue eyes lit up. “Okay,” he said, laughing. “I can cross that off my list.”

It’s the question I am asked by fellow lawyers, judges, and readers all the time: how do you practice law full time and write novels? The easy answer, I suppose, is that I just do it. But the real answer is: I always knew I was going to be a writer, it just took me a while to get here.

In high school I took every English and writing class I could find. At U. of T. I studied English and creative writing and screenwriting. Then I took a year off to drive a cab, travel around Europe and write a novel. Well, two out of three does not a novel make.

Hair down to my shoulders, I went to law school. My first-year criminal professor at Osgoode, Graham Parker, was obsessed with how badly lawyers wrote. I was reading and re-reading Raymond Chandler to keep myself sane at the time and on my first Christmas exam I wrote my answer as if I were Sam Spade…The fog was rolling in over Frisco Bay, I was sitting in my office smoking down my last cigarette when this dame, Lady A burst in the door… I figured it was 50-50 that I’d get kicked out. I didn’t. But I spent the rest of my time at law school telling anyone who would listen I would never, ever practice law.

I certainly tried not to. Ten days after my call to the Bar, I was working as an editor for an English-speaking magazine in Paris. A year later I came home and started my own city magazine in Toronto, which ran for six years. I spent a year at a film company, a year at CBC Radio, then, with our first child on the way, and dead broke, I stuck my tail between my legs, put $3,000.00 on my credit card, and opened my law practice.

My first day as a lawyer, April Fools Day 27 years ago, I trucked out to a dreary strip mall, home of the less-than-stately Scarborough Provincial Court. Back home that night I started my first novel. For ten years I was up at five and wrote for two hours until the kids came down for breakfast.

I had my tricks. As a former editor, I edited, edited, edited (Scott Fitzgerald famously said: there are no writers, just re-writers.) I never left home without at least three chapters printed out for me to work on during the interminable hours lawyers spend waiting in courthouses. Back then the battery on my second-hand IBM notebook lasted about an hour, so I got to know every restaurant near every court in Southern Ontario where I could sit down and plug in. 

After ten years of hardscrabble scribbling, I typed: The End. As determined as I had been not to be a lawyer, I was equally determined not to write a book about lawyers. And yet, when the novel was submitted to publishers, the chapter they liked best was the only one with a lawyer in it. The day my agent told me she couldn’t sell the book, I wrote “Much to the shock of his family, Mr. Singh, rather enjoyed delivering newspapers,” the first line of “Old City Hall.”

It’s the old adage: Write what you know. It seems so obvious now. But no one said this was easy. I spent five years writing that manuscript, got half way through, and realized I was stuck. I’d heard of the famous summer writing course at Humber College. I dug into my line of credit and spent seven of the most intense and exhilarating days of my whole educational life, immersed in writing. My teacher David Bezmozgis, gave us the greatest piece of three-word advice I’ve ever had about writing: “Don’t be boring.”

Next I took Humber’s six-month correspondence course. At one point, my teacher, Michelle Berry, wrote back: “This is pretty good, it might get published one day.”

I worked on the manuscript for a few more years. I’d graduated to a new laptop with a better battery; I stole time out of the office to write; I avoided lunch with colleagues. I wrote when I took my kids to swim lessons, drama lessons, ballet classes, hockey games. In year ten I completed the novel and the miracle happened. I was offered a two-book North American deal and sold the manuscript in nine foreign languages.

But now I had a different problem. I had to write a second book in one year, not ten. I changed my law practice. I gave my associates Alvin Shidlowski and Jacob Jesin the big drug, fraud and murder trials and focussed on simpler cases.

Now as I start work on my sixth book, I look back and see how the writing made me a better lawyer, and being a lawyer has made me a better writer.

If you are reading this and think, as Eddie Greenspan did, All well and good, but I don’t have twenty years, then cheer up. My favourite novelist these days is an Italian writer named Andrea Camilleri. He writes compelling little mysteries set in Sicily that are best sellers around the world and the TV spin-off is one of the top-rated shows in Europe.

He’s my hero, in no small part because he was born in 1925. He’s 91-years- old and still cooking with gas. And he’s never boring.

Robert Rotenberg’s new novel, Heart of the City, will be published August 1st by Simon and Schuster Canada.

Robert Rotenberg Headshot

Heart of the City Book Cover