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Giving Up a Dream the Hard Way

Giving Up a Dream – the Hard Way

John, an entrepreneur in his late 60s, is married and has two sons. His younger son is a model businessman who, five years ago, started a company in which John invested and that is now financially successful. John’s older son was a problem child. He experienced difficulty in school, had problems with drugs and alcohol, and saw counselors and therapists, but never demonstrated the emotional composure and wherewithal that seemed to have been bestowed upon his younger brother. Nevertheless, when the eldest son approached his father with a business plan two years ago, John agreed to invest in the business, thinking it would be an opportunity to equalize his financial contributions to his sons and believing that, finally, his older son would properly follow a path that was right for him. This business has been struggling and, until recently, John faced a conundrum—he wanted to complete his estate planning, but felt stuck because he was not sure what provisions to make for his older son.

This is a true story—although names and identifying information have been disguised—and one that many financial advisors will find familiar. What are some of the key psychological and emotional dynamics that evolve in situations such as this, and what can be done?
John was born into a struggling first-generation Italian family and grew up tough on the streets of Chicago. Through physical prowess, natural intelligence, exceptionally hard work, and determination, he created a successful business. Helen, his wife of over 40 years, raised the family while John worked 80-hour weeks. He frankly dreamed of starting a dynasty and, with the births of his two boys, believed that he was on his way.
Like many entrepreneurs, John was decisive and had a clear and persistent vision for his sons—they would be in businesses that complemented and augmented each other. He demonstrated a strong narcissistic investment in his sons following in his footsteps. In other words, part of John’s fulfillment in life—his “quest,” if you like—was to see his sons following his dream. Without that fulfillment, and in spite of all his success and accomplishments, John felt like a failure. This made it extremely important for John to encourage and assist his sons in their lives and businesses.
Like many entrepreneurs, John was a poor communicator of his vision—he assumed that other people saw things his way and understood his intentions and methods. He was not a good listener and never quite understood what his sons wanted and how they differed from him.
John Jr.’s nature further complicated the issue. John Jr. and his brother were polar opposites in temperament—while John Jr. was aggressive, inattentive, and carefree, his brother was emotionally mature, calm, and very focused. Sibling rivalry emerged—comparisons between the brothers accentuated the importance to John Jr. of creating and nurturing his own identity. He was the tough guy and proud of it.
John Jr., being older and also his father’s namesake, was invested with more of his father’s narcissism. As a result, his misbehavior was more aggravating and disappointing to John than was the misbehavior of the younger son. They would argue often, violently on occasion, and Helen eventually came to cover up John Jr.’s misconduct in an effort to maintain family harmony. This created a self-perpetuating system in which more arguing led to more cover-ups, which then led to more misbehavior and sibling rivalry, which in turn created more arguments.
When I first met John, he was thoroughly depressed. He was not sleeping, he was angry all the time, and he rarely enjoyed his family, friends, golf, or cards. He thought he should be retired, but he was working as hard as ever trying to salvage John Jr.’s business. He was constantly haranguing John Jr. about his work hours, discipline, and leadership skills. He vacillated between terminating his agreement with John Jr. and investing more capital and time in John Jr.’s business in order to make it viable. At one point, he said to me, “I’m used to making decisions, but I hate to ponder. Do you want to know what’s happening to me as I get older and this problem continues? I am pondering more and more!” He would not complete any of his estate planning until he knew whether John Jr. was going to be a success in his business. His position at that time was “either John Jr. is a success and he gets an equal share of my estate, or the bum gets nothing!”
At one point, John Jr. said to me, “Shame on me because I want less for myself than my father wants for me.” And therein—in my view—lies the essence of the problem: John wanted more for his older son than his son wanted for himself. He wanted John Jr. to share equally in the dynasty of which John had dreamed. But this dream evolved from John’s experience, not his son’s, and it was based in denial about his son’s true nature, which was a key ingredient in the anger that drove their conflict in the past.
Today, John is a different man. He is not depressed or angry and he is able to conduct working business meetings with John Jr. What happened? Over the course of several months, John began to untangle his dreams from his son’s. They stopped arguing about how John Jr. was a disappointment and began talking and listening to each other about how their dreams differed. John has still not completed his estate plans, but he is far less fixed on whether each son gets an equal share and far more attuned to how his sons need different shares.
When financial advisors make recommendations about inheritance decisions, they often advise their clients to make these decisions fairly (balancing the ­different needs of those involved) rather than equally (treating all parties the same). While this certainly makes sense, it is important to remember the psychological challenges that this presents to many wealth creators: seeing inheritors as they truly are, with all their beauty and their blemishes, and wrenching away the dreams that were crafted out of the wealth creator’s experience, not the inheritor’s. In situations such as these, the temptation is to talk with the wealth creator about finances: What is a fair inheritance in dollars? But I believe that this is not the place to start. I believe that the appropriate starting place is with the dreams of inheritors and wealth creators: What are their dreams? How do their dreams differ? What does the wealth creator need to understand and accept about his beneficiaries that has been difficult until now?
My oldest son, Peter, will be starting college by the time this column is published. Saying good-bye to him has been a mixed emotional experience. In our decision-making about college, I recognized some of John’s experience in mine. When Peter’s acceptance letters came in, there were schools and programs that I wanted him to pursue; he disagreed. We argued. Eventually, I realized that I had to relinquish my dreams for his. It caused me to question how successful I had been as a father, whether I could trust his decisions, and how I would be able to let go. We are all narcissistically invested in our children’s success. But when we put aside our own needs, it’s easier to see that the ability to make independent decisions, and feeling free to have dreams that are different from ours, are at the heart of what we really want for our children in the first place.
This article is reprinted with the publisher’s permission from the JOURNAL OF PRACTICAL ESTATE PLANNING, a bimonthly journal published by CCH INCORPORATED. Copying or distributing without the publisher’s permission is prohibited. To subscribe to the JOURNAL OF PRACTICAL ESTATE PLANNING or other CCH journals, please call 800-449-8114 or visit All views expressed in the articles and columns are those of the author and not necessarily those of CCH INCORPORATED or any other person.



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