My Mentor Wally
Note: I wrote this in 2002 as my college admissions essay.
I have heard it said that we can only truly understand ourselves in relation to the people around us. At home our roles are defined by our interactions with our parents or siblings and even our pets. But in thinking about myself for the purpose of this essay, I am drawn not to my family but to a man quite unlike my own relatively introspective self who in his exuberant, boisterous, outgoing way touched my life and remains much in mind.
I was working as a busboy for part of the summer a couple of years ago, and was excited when I learned about the chance to sail on Wally Romano’s boat. My brother had become good friends with his son, and so we were both invited to come along for the casual weekly Wednesday night big-boat races on Shelter Island Sound. Even before I met Wally, I had often admired his large sleek yacht in the harbor with its bright red hull and at the stern, emblazoned on the transom, the name “Amazing Grace.” It was kind of him to take us kids along for an adult sailboat race, something none of the other competitors did, especially because he insisted that we actually participate in sailing the boat. A big bear of a man with a booming voice and a million friends (and nearly as many enemies), Wally was extremely accomplished as a competitive racer. He had won countless trophies and despite his lust for success (“Overbearing in victory, surly in defeat!” was his war cry), he allowed his wife to drive the boat and the children to manage sail handling, navigation, and tactics. He was so skilled that we could do extremely well in the races, with him merely instructing and guiding. After the races he would generously invite everyone on the boat to have dinner with him.
Shortly after I met him three summers ago, Wally became a close friend. He owned his own small investment company and when I mentioned an interest in learning about the stock market, he encouraged me to stop by the office he had on Shelter Island. I began to go every morning before sailing practice. Wally taught me a great deal about the workings of the stock market, recommended books for me to read, and gave me personal advice on everything from how to pursue my sailing interests to how to pursue girls. My parents let me use a portion of my busboy earnings to invest and, thanks to Wally’s tutelage and the magic of the bull market, I actually made money. It was a seductive experience: easy money compared to my grueling part-time work at the restaurant.
While Wally’s job was exclusively about money, I soon learned that as a person he refused to let that define him. Despite coming from an affluent family, Wally always seemed slightly uncomfortable about his wealth and was full of interesting contradictions. Half the people coming into his office were wealthy business contacts; the other half were gruff old salts and fly-fishing buddies. He drove a pickup truck to work, but sometimes took his red Ferrari to yacht club functions. Sensitive to people’s reactions to his gleaming red sports car, he would acknowledge it was a bombastically overt sign of wealth but would also gripe, “I shouldn’t have to explain to people that I was battling cancer and thought I was going to die when I bought this car.” It was typical of Wally that I only learned of his two serious struggles with cancer after he made this offhand remark.
After two summers of frequenting his office, I had developed a strong interest in a career similar to Wally’s, despite my literary father’s exhortations to resist the siren song of “financial services.” I remember the time Wally took my brother and me on an overnight sailing race on Long Island Sound. I was alone with him on watch from 4 a.m. to 8 a.m. We started talking about my college plans, when he revealed that he had been accepted to Georgetown and very much wanted to go but wound up at Fordham instead. When I asked him why, he said something about his mother being sick and wanting to stay near home. He quietly added that this was one of the greatest regrets of his life. When I pressed further, Wally said that he had even gone to grad school for a few years, hoping to be an economics teacher, before dropping out. I asked him what motivated him to drop out and he replied only that “the Vietnam War was going on; it was a strange time…” He seemed deeply sad over this decision so I didn’t push him further. I am always profoundly moved when adults, often parents of my friends, reveal regrets about their lives and even discontent with their current situation for the sake of helping me make better choices. I was tempted to ask Wally explicitly whether he regretted not becoming a teacher, but I thought that it was too much to ask someone to acknowledge to anyone, no less himself, that he had made a fundamental mistake in choosing the path of his life. He had given me hint enough.
Perhaps because of his ongoing battle with cancer Wally has the appealing tendency to ignore his serious problems and aggrandise his own small tragedies. He’ll rage about poor cell phone service or those “crook bastards” at the cable company who thought they could put him on hold for ten seconds too long. But Wally expressed his true self in his actions, not his words. I remember the time I went into his main office in Manhattan. Many of his ten or so employees took the time to talk to me, and I was struck by the fact that they had almost all met Wally sailing on Long Island Sound. He introduced me to James, a portly, slightly aloof employee. “Hey Greg, nice to meet you! Here I want to show you some websites on satellites. Have you heard what these guys are doing with satellite technology?! It’s amazing!” James said that Wally had hired him when he was laid off and desperate for work. I mentioned James to Wally, asking why he had an employee dedicated to looking up satellite technology all day long. He acknowledged that James served practically no purpose at the office and despite this he had not only hired him, but kept him employed for over a decade.
Certainly if I had to identify the most important lesson Wally taught me, it is a common one: take advantage of all educational possibilities in life. But he has also helped me with a more fundamental issue: What do I want to do with my life? And a subtler one: How should I live the life I choose? Should I follow Wally to do something with the stock market, perhaps enjoy a yacht, a Ferrari, and a wonderful summer house, like Wally? Well, this summer I tried a different direction and, accompanied by a priest, a doctor, and five of my classmates, went to Haiti where I worked in Mother Teresa’s Home for the Dying, a home for abandoned children and a hospital. That trip, and its haunting glimpse of desperate poverty, is just as strong a memory for me as all the time I spent on Wally’s boat. I know I have no desire to become a missionary, but I could perhaps become a teacher and have an impact on the lives of students.
Wally’s comments on that overnight race made me seriously consider teaching as a career. But beyond that, he had also taught me that no line of work precludes altruism and any job offers the possibility to express one’s best self as a human being. There is an inevitable sadness in a man who has not followed his dream; nonetheless, the challenge is to find a way within the confines of any situation to make a difference. My hope is to meet that challenge.