The Life Choices of Wealthy Men

Part One

Introduction and Summary

When I returned to Boston in 1985, I was 46. By then, I had spent 20 years in Washington DC. I took consulting assignments in more than 40 countries, working mostly for the peaceful wing of the US Cold War effort, the US Agency for International Development (USAID).

But by 1985, I was lost. I had gone to Washington to “serve” in the spirit of Kennedy’s “ask not what your country can do for you — ask what you can do for your country”. It might seem strange today, but many of my generation were inspired by JFK. He filled us with hope for the future of the world and we wanted to serve. But in 1985 with Reagan in power and three of the world’s most inspirational leaders shot to death (two Kennedys and Martin Luther King), I returned “home”.

I took a job teaching at Boston University, but my heart was not in it. And five years later, I decided to find out how men of my age with similar backgrounds had chosen to spend their lives. I ended up interviewing 17 men who like me knew at an early age they had some independent wealth. That independent wealth meant they had some freedom to choose what they did with their lives.

The interviews were fascinating. Each one lasted more than 3 hours. None of the men had ever been asked in a systematic fashion the reasons for the important life choices that they made. The results? In my judgment, 9 of them lived conventional lives. 4 of them could not effectively deal with life and in one way or another went “off the tracks”. The remaining 4 lived quite special and interesting lives: they took advantage of their wealth, status and connections to do interesting things.

But these summary judgments are only the “tip of the iceberg”. In this and the following two articles, I will provide in more detail on what I set out to do and what I learned.

Where This All Started – Reunion Books

When I was in my early teens, I happened upon my father’s 50th reunion book from Harvard. I was intrigued by the write-ups, just as later when I read the write-ups for my 50th reunions from Milton Academy and Williams College. To be sure, most writers painted rosy, superficial pictures: they reminded me of those holiday cards with pictures of the entire family, including children, grandchildren and assorted dogs with comments on what a great year it has been for all. But most contributors to the reunion books did at least some reflection on their prior 50 years. And that intrigued me.

More specifically, I was interested by the forks in the road taken by each. I was most interested in the reasons for taking specific forks. Sadly, many did not divulge the reasons. They just described what happened.

In his poem “The Road Not Taken”, Robert Frost reflected on life’s choices:

Two roads diverged in a yellow wood,

And sorry I could not travel both

And be one traveler, long I stood

And looked down one as far as I could

To where it bent in the undergrowth;

Then took the other, as just as fair,

And having perhaps the better claim,

Because it was grassy and wanted wear;

Though as for that the passing there

Had worn them really about the same,

And both that morning equally lay

In leaves no step had trodden black.

Oh, I kept the first for another day!

Yet knowing how way leads on to way,

I doubted if I should ever come back.

I shall be telling this with a sigh

Somewhere ages and ages hence:

Two roads diverged in a wood, and I—

I took the one less traveled by,

And that has made all the difference.

Life’s Choices

What do I mean by Life’s Choices? I am talking about defining moments in our lives – when we made decisions (or decisions that were made for us) that defined how we spent our lives. Most people follow the line of least resistance – stick within your social group, join a church or some other institution of social engagement, and use your connections to get jobs. Globally, most men marry, have children and work to support their families as long as they can. Think of the American dream: after school, get married, have kids, buy a house…for most parents, these decisions (or non-decisions) mean they will spend the rest of their lives working to care for their families.

But don’t such choices “lock them in”? That sounds bad. But is it? I suggest that most humans and other living beings want and need a framework to live in. In my view, Dostoyevsky’s Grand Inquisitor was right to tell Jesus to leave when he said he had returned to “give man his freedom”[1]. Most men do not want freedom; they want structure.

For the men interviewed for this series of articles, some freedom was possible even if they married and had children because of family wealth and connections. I now briefly describe my background and consequently the type of men I wanted to interview.

My Background

My family was well-established in the Boston community. And we were well off. I grew up in a house with two grand pianos and I think I was twelve before I learned that “butter balls” came from sticks of butter.

Butter Balls

We were not fabulously wealthy like the Rockefellers or Carnegies. But well enough off so I knew I had some independence in choosing how I spent my life.

I wanted to be a journalist. I had a Wall Street Journal scholarship to work in the summer of my freshman year at Williams at the Quincy Patriot Ledger. I loved it. I knew that being a journalist did not pay well, but I did not care. In my senior year at Williams, I got a job offer from The New York Times: they would pay me to be an intern and teach me Spanish to work for Juan de Onis, their chief Latin American reporter. Sadly, my Williams’ economics professors talked me out of it. They said I could always get a newspaper job and “much higher up” if I first got a Ph.D. in economics. So they got me a Woodrow Wilson Scholarship. And I dutifully proceeded down the career path: an economics doctorate from the Johns Hopkins University and a job at the University of Michigan.

When I was at Williams, I was continually told that I was special and had a responsibility to be a leader. I was never told that accomplishing anything meaningful takes a long time and a lot of hard work. I was told that when you are not learning anything new in your job, you are wasting your time. As a consequence, I have never had a full-time salaried position for more than 2.5 years. I left Michigan after 2.5 years.

Finding Men with Similar Backgrounds

To find men to interview, I simply called people I knew in Boston, New York, and Washington DC. The educational backgrounds of the men interviewed are given in Table 1.

Table 1. – Education of Men Interviewed

Their backgrounds are strikingly similar. Keep in mind that at the time these men went to school, getting into the “good” schools had at least as much to do with family status as intelligence. And these men were from well-established and wealthy families. And back then as now, connections made in these institutions are important for business advancement.

Interview Methodology

Each interview started with questions about the importance of family influences. Questions then addressed the reasons for school choices, and the reasons for choices they made after leaving school. At the end of the sessions, the men were asked to reflect on their choices: knowing what they know now, would they have done things differently. The interviewees were told their names would not be mentioned in whatever I wrote.

When I started this study, I thought it would be interesting and useful to develop summary statistics on how these men’s life choices worked for them. I originally had three categories, and rankings within them:

  • Those who made a mess of their lives – fumbled around, no real direction, and maybe too much drinking/drugs.
  • Those who lived conventional lives – pursued American dream via marriage and children, stayed in their family’s economic and social circles, and
  • Those who did something quite special – took chances, really believed in what they were doing.

However, every time I read over the interviews, I realize how superficial these categories really are. But in what follows, I do want descriptors for each man. So these men are identified in the first column of Table 1 with an “S” if special, a “C” if conventional, and with an “M” if in my limited view, they made a mess of their lives.

Précis of the lives of three “special” men follow.

S1 was born into a family that gave considerable sums to support the arts, classical music in particular. He wanted to be a musician but his father said “don’t embarrass us” and “If you become a leading musician that is fine. Anything else would be self-indulgence.” The most important event in his life was his sister’s death when he was 17 years old and she was 22 years old. She did not like music. S1 has “a strong association of music with her death”. Too much! So he gave up his music career.

He went to medical school because his Harvard roommate was going. Medical school fit his image of “doing good and it was not risky”…. I can’t believe that the Harvard Medical School let me in [but] once you are in, all you have to do is show up”. S1 has had a successful practice as a child and adolescent psychiatrist and has served on many important boards. But that is not what makes him special. He is special because to satisfy his artistic interests, he went back to writing on weekends and in odd hours. And two of his novels have been published.

S2: Shortly after a military tour of duty in Japan, S2 was trying to choose between schools for a graduate degree. He was then offered a job at a major US magazine. S2: “…and then in just one night I said screw it, I would really rather get working than spend three more years in school and another three years as a draftsman.” S2 later became one of the first international radio correspondents. After another decade, he was in line to become the editor of a major East Coast city newspaper. But he was troubled that global news and journalistic coverage was dominated by Americans. He decided to turn down the editor’s job to launch his own magazine that provided perspectives on world events by non-American journalists. It failed after more than a decade, but credit goes to S2 for taking a chance to do something he believed was important.

S3: “I went to Yale simply because my father had been there”. He left to join the military after one year. After military service, he went to the University of Chicago to get a college degree. And then: “…friends of mine from Chicago were going into government – particularly the Central Intelligence Agency, and they convinced me to join them and that is what I did.” After 15 years in the CIA, S3 then started a successful major city magazine: “It took 10 years to turn it around”. His final job challenge involved revitalizing a major art museum. S3 showed an amazing diversity of talents and took the time in each assignment to master it.

Cross-Cutting Issues

In what follows, a number of the cross-cutting issues that came out of the interviews are presented and discussed. In Part 1, parental influences and money are discussed. Parts Two and Three will cover: important influences from schools, military service, alternate strategies/outcomes, the chance element of choices, reflections, and significance for today’s parents and children.

Parental Influences

Many men sensed a strong but vague pressure to do well from their parents (S1, S2, S3, C3, C4, C8, M2, M3, M4).

S2: “Dad’s approach was you did well at what you do. He wouldn’t tell you to do well; you sort of knew you should. I do remember shortly after I got my license (16 years old) I asked to borrow a car. Dad had a very coveted 1953 Corvette, which he still has, and I sure as hell didn’t ask to borrow that and that’s what he gave me. It was almost as if this burden of responsibility was controlling my youthful desires more than anything else. The very fact that he gave it to me without a word of caution was dad’s attitude. “

M4: “With dad there was much more of a feeling of things that I was expected to do which were not really defined. It is not that he said to me this is what you should be doing with your life; this is what I expect out of you. Instead, I perceived that I was failing to meet expectations. But I didn’t really didn’t know what they were.”

M4 “A sense of appropriateness which overpowers anything else…..Yankees are not successful because they kill their own, especially the talented ones. God forbid you are creative.”

Some fathers exerted specific pressure: C3: “get into production company”, M2: be a doctor, C8: go to business school, C1: join my law firm, S3: maintain my museum. C7’s father wanted him to take over his vacuum cleaner business: “”I had a strong sense of duty and obligation to my parents and one doesn’t disappoint one’s parents. Why should I be involved in the cockamamie business of vacuum cleaners? I was shackled to a family business that interested me very little. It was dull, the people uninteresting, the job pedestrian. I never had a friend who was a vacuum cleaner salesman”

Elliott: My father had been crippled at an early age by polio. He recovered and made the Harvard tennis team in his last year. He never said it but I know he wanted me to be a great athlete: the pressure became so great that I told him not to come to sporting events when I was playing.

Several fathers indicated they did not want their sons to enter certain industries: S1’s father told his son to steer clear of finance – “a dirty business”. Elliott: My father (a banker) said “don’t go into banking or stocks – these professions just make rich people richer.”


It was interesting how money issues were addressed and how they influenced the interviewees’ life choices.

M2: “Money was not something that one discussed. It was there. I remember my mother telling me repeatedly you don’t have to worry, you will never have to work if you don’t want to. You are all set, so don’t worry about it.”

S3: “My family was isolated, art oriented, and not worldly. I was never exposed to businessmen or standard career people. The family never talked about money. There were odd awkward moments when a trust officer came in and he had to have us sign something. I had to fight to come to grips with money in the real world.”

C6: “Because my step-grandfather held the purse strings so tightly, I got no sense of the value of money. Instead, I learned how to manipulate them for money”. He also said: “I never applied for a grant because I didn’t feel right about depriving someone else who needed the money. I have heard it said that if I had not had money, I could have been a first-rate scholar.”

C4: “I feel a little embarrassed about my wealth. I like cashing a pay check. I can’t take any credit for inheritance, while a retirement check will really be mine; I earned that.”

S3: “If I were growing up now I wouldn’t feel as impelled to work so hard. I was always embarrassed by living well, in a big house. In the army I concealed my background, it was liberating, helpful. I was independent.”

There were also speculations on what income earning paths should be taken. C8: “A friend of mine in California told me to stay there in real estate and in 10 years you will have as much money as you need to do anything you want. It was probably good advice”. C8 did not stay in California. C8: “Money buys you choice and power to bring about change. I didn’t have the wisdom in the ‘60s to say one would be more effective to build a base than to chase causes.”

Parts Two and Three coming shortly.

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