The Three Worst Pieces Of Advice I Got About Becoming a Writer

Three months out of Harvard Law School, I was making more money than my father. I owned a BMW, a five thousand-dollar stereo system, and had a beautiful girlfriend with long blond hair.

And I was dying inside.

Law was crushing me, and I had fifty more years to go.

I knew this disaster would happen, from the first week I got to law school and saw that the people who did best, who were meant to be lawyers, seemed the most anal retentive – they liked dotting every “i” and crossing every “t,” adored being careful. They were freaks to me. I had passion. I had something to say. But there was nowhere to say it in law school. No one gave a shit if you were a creative type there.

I figured it would get better once I got a job. I joined a law firm and stayed for a few years. It got worse. I had to get out. But I didn’t know what to do next.

To numb the pain, I started writing stories at night, about things I remembered from boyhood. Time passed quickly when I did that. And the stories still seemed good the next morning, even as I read them while dressed in my suit and wingtips. I decided that, whatever it took, I was going to become a writer. I couldn’t waste away hating my life, no matter how much money I was making.

When I announced my decision, many smart people, including accomplished writers, told me I could never become a writer. This verdict surprised me, not just because it seemed unanimous, but because it always came down to the same three reasons. They turned out to be the three worst pieces of advice I got about becoming a writer.

BAD PIECE OF ADVICE #1: YOU CAN’T WRITE WELL UNLESS YOU READ A LOT

I heard this from every person I talked to, including my barber. And that spelled doom for me, since I didn’t read much. Don’t get me wrong – I read books here and there, rarely missed an issue of Esquire or Sports Illustrated (or Mad Magazine, to be perfectly honest). But I was nothing like most writers, who seemed hunchbacked by the dozen novels they seemed to carry at once. I looked for alternative views in articles, but each seemed to start with the same near-Biblical truth – that the only way to get good at writing is by reading.

By itself, this “truth” might have been enough to kill my writing ambitions. But I was lucky – I hated being a lawyer so much that I sublimated this piece of advice, only to be hit with another:

BAD PIECE OF ADVICE #2: YOU CAN’T WRITE WELL UNLESS YOU WRITE OFTEN

“How the hell do you expect to start writing at age 30?” people asked me. “Don’t you know that writers have journals and notebooks full of their writing stacked up in their closets? That they can’t help writing? You don’t write shit!” And it was true. The writers I knew had written thousands of pages, some dating back to grade school. They always had journals with them. And lots of pens. Other than my four or five recent short stories, I’d penned a grand total of nothing in my life.

My dream of becoming a writer seemed to be slipping away by the minute, but it really took a wallop when I got this final bit of wisdom:

BAD PIECE OF ADVICE #3: YOU CAN’T WRITE WELL UNLESS YOU’RE TAUGHT

Smart people made an observation I couldn’t escape: I’d only taken one writing class (required in college), had participated in no writers workshops or seminars, had never shown my work to another writer, or even to another human being. Most writers I knew, or had heard of, had been through several courses, and many had graduated from prestigious writing programs. They all seemed to have degrees in English or literature or fine arts (mine was in philosophy). They critiqued each other’s work. “Start with some workshops and classes,” I was advised, “and go from there.”

By now, I was ready to throw in the towel. And yet, when I sat down and wrote another short story for myself, I noticed something – my voice didn’t sound like the other voices I was reading. And my writing didn’t seem bound by all the same rules, or rhythms, or approaches of many writers, especially those who’d graduated from journalism schools. Still, the stories seemed decent. I began to wonder if my shortcomings might not be my strengths.

I quit my job as a lawyer and took a six-figure pay cut to work as a data entry clerk in the Sports department at the Chicago Sun-Times, hoping I’d get a chance to write. And I did, first for the Sun-Times, then for Chicago and Esquire magazines, and finally for myself, as the author of narrative nonfiction books. Over the years, I’ve come to realize a few things about writing that, at least for me, have held true.

Writing, I think, is about seeing the shades of gray in things, about detecting what’s beneath the surface, about hearing the meaning between someone’s words. It’s about sensing if someone is hurting or scared or excited, even if they might not yet know it themselves. I don’t think a person can do that just by reading books or writing in journals or taking classes. I think a person does that by living, by being out there, by watching.

I got to do a lot of watching. Growing up, I lived with two very sensitive parents. There was little in their environment that escaped them, especially if it involved a person’s emotions. They could point to the kid at a birthday party with hurt feelings, even if that kid was dancing. They saw dignity in a homeless man’s rolled-up pants cuff.

My dad was a traveling salesman for his own motorcycle paints and lubricants company. He spent eight or nine months of every year on the road. He took me on many of these trips; sometimes I would miss three weeks of school at a time. He wasn’t worried. “I want you to see things,” he said. By the time I was eight years old, I’d been to every one of the continental United States, all by car. We told stories for hours in his giant cars. He died 20 years ago.

When my mom was dying last year, we sat on a bench outside her retirement home. She pointed across the parking lot, to a big, muscular young orderly who was taking an elderly woman for a walk. “He’s paid to do that,” she said. “But look how sweet – he never rushes her.”

My mom always thought I could be a writer.