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Family Stories
The Weight of Wealth
Mark, Diane, Thomas, Alexander, Andrew, and Emily
Mother & father, late 50s, eldest son, 36, twin brothers, 32, youngest daughter, 26
Background
Mark and Diane built a vast business empire together, becoming one of America’s wealthiest families. Coming from modest, hardworking backgrounds, they were unprepared for the extreme privilege that came with their meteoric rise in wealth. Their new world was filled with hyper-competition, fair-weather friends, an ever-present entourage, and access to rarified luxury. It was as if they were air-dropped into a whole new culture—a world that was foreign but aspired to and a world for which they did not have a map or trusted guides.
They became consumed by endless demands, rapacious schedules, exposure to unimaginable luxury and power, and mistrust of others, all while drifting further from themselves and each other. Their four highly educated children had access to the best of everything, but alongside this unparalleled fortune came a complex web of silent struggles.
Emily, the youngest, contacted HOME after a particularly extravagant family vacation where the level of seething anger, drug use, and joylessness was impossible to ignore. During that trip, Emily’s brother Alexander came out to her and confided his deep sadness about not being able to bring his boyfriend.
Assessment
HOME discovered that each family member was orbiting around wealth and their unique relationships to it, rather than one another, while trying to please the wealth-creators, in order to feel important, safe, and connected. This unintentional but powerful dynamic caused severe fragmentation.
Three of the children were over-identified with family money: it completely funded their extravagant lifestyles of private jets and homes all over the world while also fueling their low sense of self-worth. Emily was a celebrated artist, but her work was insulated by limitless resources and had never been tested by struggle. She moved through life buoyed by status and experimented heavily with substances to numb an inner emptiness. Thomas, the eldest, was a successful professor at an Ivy League university but privately struggled with a gambling addiction, infidelity, and escalating debts.
Andrew, one of the twins, worked for the family business and was idolized publicly, but quietly battled severe anxiety while feeling massively insecure and lonely.
Alexander, the other twin, was under-identified with family money. He rejected it entirely, choosing to live as a writer on a farm in rural Italy. Despite his determination to forge his own path, he lived in near-poverty and struggled to come out to his family as gay.
Meanwhile, Mark and Diane’s marriage had become fragile, marked by infidelities, a culture of excess, and a shared but unspoken loneliness. They initially refused to see themselves as contributors to their family’s dysfunction. They were quick to label their kids as “ungrateful”, “entitled”, and “unwell” even as they contemplated their divorce. They were accustomed to listing off each other’s flaws while not being willing to shed light on themselves.
Interventions
- HOME worked closely with Emily to create an entry point for family healing by raising awareness in a thoughtful way around the most immediate crisis: Thomas’s gambling addiction and unraveling marriage.
- Through facilitated family conversations, Thomas agreed to enter an intensive outpatient program for gambling and process addictions. This allowed him to stay at home, and also provided an opportunity for his wife and him to begin a therapeutic couple’s process.
- Alexander, after nearly a year of private processing, came out to his family in a way that was carefully prepared and facilitated. It took great intention, and in many ways, the family was able to lovingly receive the news because of the psychoeducational retreats HOME had provided on the importance of listening, receiving, and accepting.
- The family embarked on multi-day intensives, working through the 11 dyads of relational awakening and confronting their collective relationship to wealth, identity, and self-worth. They also created a Coat of Arms that outlined their values and behaviors that aligned with the values; this became their North Star.
- Andrew began honest conversations with his parents about his mental health and the pressures he felt inside the family business. He joined a young men’s rising generation therapeutic group that helped him to feel a deep sense of worthiness and belonging.
- With gentle persistence and daily therapeutic support, Mark and Diane paused their divorce and reluctantly stepped into a shared exploration.
Breakthroughs & Challenges
As a conductor of care, HOME helped guide the choice of treatment for Thomas, providing a few resources from which he could choose. HOME also collaborated closely with Thomas’s treatment team. Additionally, an entire parallel process with the family was begun to address generational patterns, individually and collectively. Thomas experienced several relapses but continues to engage in repair processes. He and his wife have separated but are focused on rebuilding trust and intimacy.
At the same time, Alexander’s openness about his sexuality challenged the family’s old narratives and invited deeper vulnerability. Diane initially struggled and, while attempting to be supportive, was mostly reacting with rejection and shame. She slowly began to participate in healing with continued engagement, family encouragement, and Alexander’s insistence. Her patterns of disconnecting, shaming, and collapsing were explored, and it was discovered that it had less to do with Alexander’s sexuality and more to do with her unintegrated trauma.
Although very reluctant at first and prone to sabotaging the process, Mark and Diane slowly uncovered their early traumas: childhood neglect and a relentless drive to prove their worthiness through success. They came to understand how their overreliance on performative successes and material provision as a form of love had left the children starved for emotional attunement and inner security.
Andrew negotiated new boundaries within the family business and began envisioning a role more aligned with his mental health and personal values, encouraging his parents to loosen control and rethink legacy. He received tremendous support and validation from his young men’s rising generation group. This allowed him to build an intrinsic sense of worthiness, and he became more focused on his own meaning-making.
The process helped Emily find her voice and become a grounding presence for the family. She began to channel her art more as a form of self-expression rather than a sign of her worthiness, helping her step back from substance use and be more gentle with herself and others. As a result, she became the healthy gatherer of the family, calling her parents and siblings together for regularly scheduled therapeutic retreats, along with experiences that allowed them to be present and have wholesome fun together.
Outcomes and Reflections
Emily got engaged, and her wedding was an authentic celebration of family connection rather than a day of ostentatious display. Alexander proudly attended with his partner.
Mark and Diane have become more active participants in the family’s growth. They now gather at quarterly retreats, cultivating more intentional connection and inspired dialogue, sparked by the books they read together throughout the year.
Alongside HOME and trusted succession advisors, they are redefining their legacy, moving from a focus on financial inheritance to one of relational richness and emotional sustainability. Andrew was asked to be the CEO of the Family Office and was thriving in the role. Alex and his partner moved back to the United States to spearhead philanthropic endeavors. Thomas thrived as a highly-regarded academician; he decided to take a step back from the family and to embark on a year-long sabbatical with his wife, which would allow him to go deeper into some spiritual practices rooted in solitude and inner wisdom.
Today, the family is learning, albeit slowly, to transform wealth from a corrosive force into a generative one, weaving new patterns of truth, compassion, and collective flourishing.