I grew up with a certain amount of upper-middle-class wealth, but never fit into the world my parents inhabited.

In 1961 we began to make summer trips to Nantucket, MA. This was long before the island really took off as a vacation spot for the wealthy, and in the early 1960s, Nantucket was still a sleepy place, relatively unknown.

That is not to say that the island did not have wealth. I remember the golden tanned athletic boys who sailed out of the private Yacht Club and would race their boats in Nantucket harbor. Their world was not a world I could enter on many different levels. I would sail our Sailfish from a very young age in Nantucket Harbor, and I was quite a good sailor, but their world was impenetrable to me. 

At that point in history, the 1960s and 1970s, the Yacht Club did not permit Jews to become members. I do not know if the club ever opened up to Jews. But as a young boy who would be gay, it was not just the Jewishness that stopped me. I felt like I did not fit in the world of young, athletic, self-assured, handsome, and tanned boys. There was a type of young man, with a breezy self-assured athletic prowess, which I did not have, who always made me feel unsure and bad about myself.

In my preteen years, I was overweight, un-athletic, and lacking in self-confidence. I hated organized sports and hated that the private schools I went to required us to play after school sports every season. I did not fit in the world of boys that surrounded me. As a young man, I was a very good sailor and an expert snow skier, but I did not see these things as having the same value as football or baseball, both sports which I did not understand and could not play.

I loathed the tanned, handsome young men that inhabited the Yacht Club world I could not be part of. They were the same young men who treated me like an outsider in the small Episcopal private boys school that I attended from third to sixth grade, and later the same kind of boy that did not even acknowledge my existence at the small Quaker private school I went to from seventh grade through twelfth grade. I felt bad about myself and was sure there were things wrong with me that were better off hidden.

Nantucket was never a place that I felt comfortable. I was always the outsider in the worlds I inhabited as a young man. At the time I did not understand my differences. I didn’t know that the young man who felt so out of place would be the same young man who at 14 years old would discover that he was gay. In my teenage mind, being gay was just another way that I was an outsider. I did not see, as a young gay man, that my story of separateness and outsiderness was a common theme among many men who would later be gay.

As soon as I was able to I fled the world of money that I grew up in. I held jobs through college and graduate school, and as soon as I could support myself, stopped taking money from my father. I wanted desperately to be independent as soon as I could and knew that part of my self-worth was tied to my being able to make a living in the world without my father’s help.

In work, I found for the first time people who thought I was smart, clever, self-driven, and always delivered what was asked. In work, I found the positive acknowledgment of my worth that I could not find growing up. Work became my salvation and my independence. Work had me feel good about myself in the world for the first time, in a consistent way, day after day, year after year. I have always worked hard at the jobs I have held and have enjoyed continued success.

But that early outsider feeling around people with money has continued to this day. I do not have friends who are wealthy. I am not a member of any private club and do not enjoy going to the resorts of the wealthy. I find most people with money boorish and self-centered. Their goals of having a certain lifestyle and owning certain objects are not my goals.

In 1971 my parents bought a house in Nantucket, fully furnished, sight unseen. It has been the family vacation home ever since. At least once a summer I have visited the island when my family members would gather. The old feelings from my childhood have never changed. Today as I walk down the carefully maintained red-bricked sidewalks, look in windows of the expensive stores, and cross the cobblestones of Main Street, while beautiful, I feel like I did as a child, an outsider in Nantucket’s world of wealth and privilege. I am a stranger in a strange moneyed land that I do not understand or fit into.

The process of coming out, first to my family and friends, and then last year coming out at work, changed the feeling of separateness I had for so many years. For the first time in my adult life, I am integrating the gay man that I am with my work and personal life, and it is freeing and empowering. I no longer feel the deep separateness I once felt and I am more clear about money and the effects of money on a person.

Even so, towns like Nantucket still feel foreign to me, but I am beginning to feel at home in the wider world. Coming out has the power to heal in a way I could never have imagined. I have felt happier and more at ease in the world these past two years than ever before in my life.

Have I solved all the money questions? No. I think the study of money and what it does to people is a life long study. I have watched my father’s continuous financial support of my sister cripple her life. Conversely, my burning desire, beginning as a teenager, to be financially independent of my father, has been a very positive thing for my life.

My aunt said to me a few years ago, that among my siblings, I was a ‘self-made man’ and the only one of my siblings who did not rely on my father’s money for my success. This is true, but it was my father’s money that also allowed me to go to college and graduate school, and graduate without any debt. So I am grateful for the advantages that my father gave me in education. But I am so glad that I walked away from his money as a young man and navigated my own success in the world. My relationship to money, I think, is sane.

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