The Importance of Being Mentored: How 8 Hours with Writer Jean Shepherd Changed My Life
Updated: Mar 7
As a child seeking resources on how to publish my short stories, I marched into the Benton Library, a small neighborhood library around the corner from my house in Belmont, Massachusetts. With my notebook in hand I approached the librarian, Mrs. Kennedy was her name, asking if she could help me compile a list of magazine publishers that accepted childrens' stories. My parents, both college professors and authors, had tipped me off that such publications existed and encouraged me to send query letters. Mrs. Kennedy looked at me inquisitively and asked how old I was. "I'm seven and I have an old soul," I replied. "And I am going to be a famous writer." She nodded and said, "Good for you! You've got gusto." I didn't know what gusto was but her enthusiasm signalled it was a worthwhile thing to have. She helped me compile a list of magazines and editors and went a step further offering to help me write to them. For several days we worked on the query letters. Thanks to Mrs. Kennedy's kind nurturing, I dropped the letters in the post, hopeful I would soon be a published author. A few weeks went by before I heard back from any of the magazines. One finally responded with a rejection letter. I never heard from the others. Crushed, I went to tell Mrs. Kennedy what happened but she was no longer working at the library. To this day I don't know where she went or what happened. Deflated and confused, and still seven, I took her disappearance as another rejection. Though I continued to write in journals, it would be years before I returned to writing stories.
When I was 13, a television production chose Belmont as its filming location. The TV movie, The Great American Fourth of July and Other Disasters, was set in the 1950s and Belmont's Cushing Square with its lost-in-time brick storefronts and throwback Five and Dime store had the perfect look for a period film. Having a movie production in town was exciting enough but when it was announced that the star was actor Matt Dillon, eager residents (mostly teenage girls) showed up in 1950s bobby socks and poodle skirts hoping to be cast as extras. At the time, Dillon was a huge teen star fresh off the hit movie, Little Darlings, which every teenage girl had seen.
The Great American Fourth of July and Other Disasters was penned by writer and legendary radio personality, Jean Shepherd (A Christmas Story). Being the silly adolescent that I was, I only had eyes for Matt Dillon. My friend Jenny and I had scored coveted spots along the sidewalk in front of the set-up for a parade scene. We searched the crowd unsuccessfully for Matt Dillon. Suddenly, a man standing next to us spoke, "The parade's this way girls," he pointed. I was slightly startled, giggling in response. He was older with an Irish cap, similar to one my Dad wore and his smile was disarming. The word, "Shep" was written on his shirt pocket. After composing myself, I replied, "I was looking for the other actors," to which he responded, "Ahh, you want to meet Matt". My eyes lit up. He introduced himself as Shep and told Jenny and I that he was the writer of the film. I told him my father was a writer and we talked about Dad's work for a bit. He said that Jenny and I reminded him of the two girls in the movie, The World of Henry Orient, starring Peter Sellers, which got my attention as my father was a huge fan of Sellers and had taken me to see all of his films.
This chance meeting turned out to be one of the defining moments of my life. Shep talked to me in depth about what writing meant to him. He told me everything; how he got started, what his process was, how he got most of his ideas from his childhood growing up in Indiana. He told me that he got his start in radio when he was in the military. He shared the story behind a famous radio hoax he had pulled off about a non-existent book called, I, Libertine. All of these stories were gold. I was receiving a Master Class in writing and media and I didn't even realize it. Enchanted by his musings, I forgot all about Matt Dillon. My confidence grew as he opened the vault to anecdotes far back in time. So I shared some of my story ideas with great excitement. He listened intently saying nothing for several minutes than remarked, "You're a world builder." If only I had understood the significance of that moment and that compliment. I would have bottled it up and kept it on a shelf for whenever I needed a reasurrance.
As the production was wrapping up for the day, Shep asked if Jenny and I wanted to meet Matt. We were escorted to the area where the crew was assembled and were introduced to a woman who was working with teenage extras. Shep told her that we wanted to meet Matt. Shep and the woman escorted us to a trailer that had been set up in an adjacent parking lot. The woman stayed with us outside the trailer as Shep went inside emerging moments later with Matt Dillon who was smoking and drinking a beer. Shep made the introductions. Without making eye contact, he nodded then walked away. Jenny was disappointed. If I still cared, I would have been too. Many years later when I was working for The Golden Globes I met Dillon again. Sadly, time did not improve his disposition.
As the sun began to set on Cushing Square, Shep handed me a piece of paper with his address and phone number telling me to reach out anytime if I had ideas or thoughts to share. Shep's stories inspired me so significantly. I woke up that morning determined to meet a movie star and went to bed with a new life purpose, writing. As melodramatic as that sounds, it really was true. After meeting Shep I set out on a quest to absorb all of his work, reading everything he wrote and listening to all of his radio broadcasts. And it hit me, I got to spend a day with one of the greatest American storytellers.
I never saw Jean Shepherd again after the day we met. For years I thought about contacting him but every time I would pick up the phone I worried he wouldn't remember me. If I could travel back in time just so I could slap myself in the face for not calling him, I would. He was so encouraging when we met and he literally told me to stay in touch. Meeting Shep unleashed my determination to succeed yet I still wrestled with my fear of rejection.
Many years after we met, now an adult, I decided to finally contact him. The number was no longer active but I tracked down a number in Florida. A woman answered the phone. I'll never forget what she said, "Oh dear, I'm sorry but he's passed." Thud, as my heart sunk deep into my chest knocking the air out of my lungs. I sank and slid onto the floor, tried to compose myself long enough to ask when and how. She told me that he had died on October 16, 1999, two years to the date that I was calling.
There were so many things I wanted to tell him; that he made me want to be a writer, and he changed my purpose and perspective on life, that every day I thought about the things he had told me. He literally changed my life.
That one day I spent with Jean Shepherd cemented my understanding of mentorship. Webster defines a mentor as; a person who nurtures your talent, takes you under their wings and helps guide your path to success. Shep did all of those things in under eight hours. He has left a lasting imprint on my soul. That's what mentors do. They impact your life in ways you could never imagine.
The moral of this story is, don't wait to act on an instinct. If there is someone you are thinking of contacting, call them today. I will regret not reaching out to Jean Shepherd for the reat of my life. Remembering our incredible day together invokes both tears and a smile. Thanks to Shep, I learned the importance of being mentored and it has shaped my life both personally and professionally. I started Payson Road, creative resources and mentorship for people with eating disorders, because of Shep. CAKE, Creative Arts for Kids Expression, pairing kids with professional mentors in the arts, spawned from my encounter with Shep. Nurturing talent and inspiring others to achieve greatness yields riches beyond imagination. Thank you for teaching me this Shep.
Original article posted on Payson Road's The Corner under the title "The Importance of Being Mentored"