The hidden struggle: understanding addiction in privileged families
Part 4 of 5: Beyond the Golden Ghetto
Happy New Year! The following post was not easy to write because some of it triggered troubling memories and filled me with fear. Yet these are stories that need to be told—stories about addiction, privilege, and the price of keeping up appearances.
During this past holiday season, I discovered Wim Wenders' film "Perfect Days." It’s the story of Hirayama, a Tokyo toilet cleaner who escaped his family’s life of privilege, abuse, and addiction by embracing simplicity, routine, and mindfulness. His journey mirrors a troubling reality: according to a 2017 Arizona State University study, young adults from affluent backgrounds are two to three times more likely to develop drug or alcohol addiction compared to national averages. This piece explores the unique pressures, enabling factors, and hidden struggles that fuel addiction in privileged families—and offers paths toward healing.
Part 4 of 5: Beyond the Golden Ghetto
Happy New Year! The following post was not easy to write because some of it triggered troubling memories and filled me with fear. Yet these are stories that need to be told—stories about addiction, privilege, and the price of keeping up appearances.
During this past holiday season, I discovered Wim Wenders' film "Perfect Days." It’s the story of Hirayama, a Tokyo toilet cleaner who escaped his family’s life of privilege, abuse, and addiction by embracing simplicity, routine, and mindfulness. His journey mirrors a troubling reality: according to a 2017 Arizona State University study, young adults from affluent backgrounds are two to three times more likely to develop drug or alcohol addiction compared to national averages. This piece explores the unique pressures, enabling factors, and hidden struggles that fuel addiction in privileged families—and offers paths toward healing.
The perfect storm
The weight of legacy
Like Hirayama, whose wealthy sister is startled by his modest lifestyle, many from privileged families grapple with the burden of expectations and identity. Having descended from a great-great-grandfather's railroad fortune and an ancestor who wrote Harvard's mathematics curriculum, I've felt this weight firsthand. I also had a client who was William V, carrying the weight of being the fifth in his family line to bear the name. It was expected for him to take over the family business, but the combination of genetics, stress, sarcastic shaming and belittling at the dinner table, and feeling invisible as a child led to a life of treatment centers and regrets. The pressure to match or surpass previous generations' achievements can be crushing. While Hirayama finds peace in simplicity, many turn to substances or workaholism as coping mechanisms.
Performance at any cost
The pursuit of perfection in affluent communities often exacts a devastating toll. Students turn to stimulants to maintain impossible academic standards—I took caffeine pills in high school to power through late-night papers. Recently, one client's son, who abused ADHD medication to study, began using marijuana to manage his mounting anxiety. He ultimately required treatment for both addiction and mental health issues. Another client's husband, a tech entrepreneur, would rage at his wife and children if the house was less than perfect when he came home from work, as if a less than pristine environment would reveal his inner turmoil. He later left his wife for an employee, and his company went into bankruptcy—a stark reminder that the facade of perfection often masks deeper instabilities.
The isolation of privilege
Social isolation can be devastating when wealth creates barriers to authentic connection. One client described losing a friendship after her friend saw the inside of her elegant home: "It was as if my house told her everything she needed to know about me."
I understand this alienation—at age eleven, I moved to an estate on Newport's mansion row, Bellevue Avenue. As a European transplant entering this world in my pre-teens, I felt like a perpetual outsider. With frequent moves, private schools, and boarding schools, my children and I have experienced a profound sense of rootlessness and disconnection. Our social circles span various locations, leaving us searching for a true sense of belonging—what many refer to as Adult Third Culture Kid (ATCK) syndrome.
Books and piano became my refuge until adolescence, when I discovered that tobacco and alcohol could buy social acceptance at parties and boarding school. They became the one common denominator. For many, substances—whether alcohol, marijuana, or prescription stimulants—offer a similar escape. As one friend shared, “alcohol gave me wings; but eventually it took away the sky.”
The glamour trap
In many affluent circles, indulgence and excess are mistaken for sophistication, reinforcing harmful behaviors that lead to addiction. One client's father marked her return from rehab with champagne, triggering a life-threatening relapse. Was this mere ignorance, deliberate sabotage, or maintaining appearances?
Hollywood amplifies the glorification of substances and hyper-sexualization. Consider Marilyn Monroe's telling line in "Gentlemen Prefer Blondes": "Don't you know that a man being rich is like a girl being pretty?" Such cultural pressures often fuel addictive behaviors, creating a cycle of escapism and emotional emptiness. The connection runs deep—more than 40% of people with a relationship or sex addiction also struggle with substance abuse.
As Bernie Taupin captured in "Goodbye Yellow Brick Road," seeing through wealth's illusions can be sobering, but for those who remain in the penthouse: "It'll take you a couple of vodka and tonics, to set you on your feet again."
The enable and shield pattern
Affluent families often enable addiction by shielding children from consequences. Parents hire attorneys to make legal troubles disappear and pay DUI fines without hesitation. Crashed cars are simply replaced with new ones. The absence of financial pressure means no urgency to get up and go to work. Some expensive rehabs might seem beneficial, but many fail to address the underlying causes of addiction. Meanwhile, money allows individuals to maintain a veneer of functionality despite serious substance abuse.
This enabling extends to what Dr. Paul Hokemeyer calls "hyper-agency"—the ability to literally fly away from problems. When things get painful, wealthy individuals can simply jump on a jet and leave, never dealing with the underlying issues. In recovery circles, we call these escape attempts "geographicals," but money makes them particularly effortless and frequent.
Access becomes effortless. In my own home, my mother's wine cellar was constantly replenished for frequent entertaining. Even more telling was my friend's grandmother—a Newport blue blood—who kept the liquor store delivery number at the top of her house's emergency contact list.
The pattern starts early. In the luxury ski resort of Gstaad, boarding school students spending their winters at the school's winter campus are equipped with their fathers' black American Express cards, checking out of dorms to party all weekend in hotel suites. One nine-year-old we knew had never been on a "public" airplane and went helicopter skiing each weekend. Such early exposure to extreme privilege can distort children's sense of reality and boundaries.
The mental health-trauma connection
Content warning: This section discusses sexual abuse and trauma
Addiction in affluent communities often intertwines with mental health challenges, as Jessie O'Neill explores in "The Golden Ghetto." These challenges frequently stem from what Joyce LeBeau termed the "silver-spoon syndrome"—a prioritization of public image over private well-being. The consequences are severe: chronic depression, emotional emptiness, lack of empathy, and an obsessive pursuit of pleasure, all fueled by the belief that money can fix anything.
Within this culture of image maintenance lies a darker reality: the prevalence of sexual abuse. One experienced therapist observed a higher incidence of sexual abuse in aristocratic families, noting how children become conditioned to associate love with secrecy and shame. This pattern often begins with having to hide affection for non-biological caregivers, creating a foundation where blurred boundaries become normalized.
Gloria Steinem, as cited in O'Neill's work, provides a chilling insight: "As a man's financial worth increases, so does his perceived power and his sense of ownership of women—a noblesse oblige among men, if you will... there is more reluctance within the legal system to punish those at fault when they are surrounded by the increased protection of wealth."
This toxic combination of shame, secrecy, and entitlement creates perfect conditions for abuse to flourish. One client's story illustrates this pattern: After losing her father, she endured sexual abuse from her aristocratic stepfather while her mother busied herself with entertaining and her new family. When she finally expressed her pain about being cast aside, her mother responded with mockery, choosing to protect her image rather than acknowledge her daughter's trauma. Even after achieving long-term sobriety, she continues to struggle with feelings of despair.
Asking for help
Stigma surrounding addiction runs particularly deep in image-conscious families. In one devastating case, a husband preferred letting people believe his wife's overdose was an accident—or even that he was responsible—rather than acknowledging the truth of addiction. Such denial and stigma prevent families from taking action until it's too late.
Watch for these warning signs:
Preoccupation with substances or behaviors
Persistent cravings
Withdrawal symptoms during attempts to stop
Deteriorating relationships
Mounting negative consequences (health, legal, financial)
If you're concerned about your own or a loved one's substance use or mental health, reach out to the Arise Network, find a therapist who specializes in addiction, or connect with support groups like Alcoholics Anonymous or Al-Anon. Prioritize your own well-being through exercise, mindfulness, breathwork, hobbies, and maintaining connections. You don't have to navigate this journey alone.
Finding our own ‘Perfect Days’
Recovery in affluent communities extends beyond mere abstinence—it's about discovering, as Hirayama did, that a meaningful life emerges from embracing simplicity, routine, and presence. You might find contentment in observing sunlight filtering through leaves, engaging in acts of service, or enjoying quiet moments between events.
Like Hirayama's journey in "Perfect Days," try this Two Weeks of Presence exercise:
Document your daily routines (morning, lunch, evening, night)
Select two habits you typically rush through
Practice full engagement, free from distractions
Observe your physical sensations, emotions, and thoughts
Keep a brief daily journal of your experiences
True transformation comes not from wealth or status, but from finding meaning in connection, authenticity, and life's simple joys. Recovery is not just survival—it is rediscovering the beauty of living.
P.S. I write all my blog posts myself. But I use AI to help correct grammar and spelling mistakes once I've finished. Since you've taken time to read this, I think it's important for you to know.
You can use the chat below to share your process, or I invite you to learn more about my coaching practice. Currently, I’m all booked up, but I’ll be opening a few spots for new clients soon. If you’d like to join the waitlist and be the first to know when spots become available, click here to sign up.
Living authentically: trusting yourself in a world that judges
Part 3 of 5: Beyond the Golden Ghetto
In college, I loved reading Thomas Mann's "Clothes Make the Man." This short story follows a character who, by wearing elegant clothes, is mistaken for a nobleman. But his charade unravels, and he’s humiliated when his true identity is revealed.
Ironically, I lived the inverse while living in the Swiss Alps: I wore trekking clothes and tried to hide any signs of wealth to avoid judgment.
The fear of appearing arrogant was one factor. Learning about my father’s world was another. My father had been a mountain guide who had painted houses, coached hockey, and worked as a lumberjack and stunt man in a James Bond movie (a Pitz Gloria guard). While some might have distanced themselves from their humble roots, I took pride in mine.
But pride didn’t shield me from reality.
Part 3 of 5: Beyond the Golden Ghetto
In college, I loved reading Thomas Mann's "Clothes Make the Man." This short story follows a character who, by wearing elegant clothes, is mistaken for a nobleman. But his charade unravels, and he’s humiliated when his true identity is revealed.
Ironically, I lived the inverse while living in the Swiss Alps: I wore trekking clothes and tried to hide any signs of wealth to avoid judgment.
The fear of appearing arrogant was one factor. Learning about my father’s world was another. My father had been a mountain guide who had painted houses, coached hockey, and worked as a lumberjack and stunt man in a James Bond movie (a Pitz Gloria guard). While some might have distanced themselves from their humble roots, I took pride in mine.
But pride didn’t shield me from reality.
Early warnings
People tried to warn me. My Swiss lawyer advised: "Don't reveal anything personal to your neighbors." A child psychologist added, 'You’ll never fully integrate into the community.'
Initially, I dismissed these warnings as elitist and small-minded, and lacking generosity of spirit. I didn’t yet understand that privacy wasn't about superiority—it was a defense against the gossip and judgment that thrive in a small, tight-knit community. I also didn’t understand that my lifestyle would be seen as a threat to those who struggled to make ends meet.
At the time, I brushed it off, determined to make it work.
Disappearing to fit in
I convinced myself that appearing modest was the right choice. Having just received a settlement from my family trust, I felt an even stronger urge to downplay my circumstances. But no matter how much I tried to blend in, I couldn't shield my family from the repercussions of our lifestyle choices. When I bought my children new bikes or bought flights to the US to visit family—or even traded my old Outback for a new one—they came home in tears, bullied by their peers, kids who had to muck out cow stalls before school. My “playing small” wasn’t protecting anyone.
Each choice to blend in slowly eroded my sense of self. My children’s tears and our collective isolation made it painfully clear—I wasn’t just blending in; I was disappearing.
Reclaiming myself
Friends from my past life came to visit and reminded me of the person I had once been. Yes, I was sober, working on my black belt in karate, and physically healthier than before, but I wasn’t living authentically. This realization prompted change. I began making different choices: upgrading my wardrobe, caring about my appearance, getting a stylish haircut, joining a writing group, taking piano lessons, and enrolling my children in private school.
These decisions came with their own set of challenges. A neighbor asked:
“Now that your kids are in private school, will you deem to spend time with us?"
I responded, “Of course, don’t be silly,” but I felt a growing chasm in our relationship. At the same time, an intimate relationship ended—I had gone to another world, he said.
To navigate these shifts, I hired executive life coach Grant Calder—a high school friend living in Stockholm. Together, we worked to clarify my values, create a vision board, identify where I was stuck, and to develop a plan to move forward.
Understanding toxic dynamics
I bought a summer home in Newport to spend time with family while maintaining boundaries. But this brought a new kind of discomfort. People who had ignored me during my years as a struggling journalist and newspaper manager suddenly sought my friendship. My wealth had become my calling card, and the attention felt hollow.
My experiences in Newport reminded me of a client who had faced a similar dynamic. After generously supporting a friend—covering rent, food, and expenses—he discovered that what he thought was a friendship had turned into resentment. The friend became a self-appointed "spy," relaying negative comments others had made about my client. This dynamic exemplifies what Brené Brown calls "common enemy intimacy"—a false bond built on shared negativity. True connections elevate; toxic ones corrode trust and self-worth.
Building trust and reclaiming identity
The path to rebuilding trust and authenticity requires intentional steps:
Invest in relationships slowly: Use Brené Brown's BRAVING framework to evaluate trustworthiness. Watch how people reveal themselves over time before sharing vulnerabilities.
Center yourself in your values: Authenticity isn't about displaying or hiding wealth—it's about alignment with what matters to you.
Cultivate supportive communities: Connect with others who share similar experiences and circumstances.
Choose your confidants carefully: When interactions leave you feeling drained, used, or abused, it's time to reevaluate.
Establish clear boundaries: Do not do for others what they can do for themselves. You don’t always have to be the first to pick up the tab.
Decline relationships or situations that conflict with your values, even when past generosity or loyalty makes it difficult.
Finding your truth
Thomas Mann's character wore elegant clothes to mask his reality. I made myself plain and uninteresting to hide from mine. But in reclaiming my authenticity, I discovered that living truthfully is the greatest form of self-respect.
The question isn't whether judgment and envy will exist—they will. The question is: will you trust yourself enough to rise above them and live authentically?
If this resonates with you, and you’re ready to reclaim your authenticity, I invite you to learn more about my coaching practice. Currently, I’m all booked up, but I’ll be opening a few spots for new clients at the start of the new year. If you’d like to join the waitlist and be the first to know when spots become available, click here to sign up.
Invisible children: the hidden wounds of privileged childhoods
Part 2 of 5: Beyond the Golden Ghetto Series
Hey, what began as a three-part series has evolved into something more expansive. As I've delved deeper into the material and received valuable feedback, I've discovered there's much more to explore. I'm excited to announce that this will now be a five-part series, and you'll have access to all of it in the coming weeks. Now, let's begin.
The aroma of oatmeal wafted in the air filling me with a sense of safety. Cheng’s carefully set breakfast table reflected her approach to everything she did—meticulous care, whether it was folding our clothes or making meals.
While many of my peers saw their nannies come and go, Cheng stayed. She became our rock: a constant, reassuring presence, and a stern taskmaster. I am convinced she's the reason I'm alive today. My story is rare: nannies seldom become family, yet Cheng has been with us for nearly 50 years, transitioning from caregiver to cherished grandmother figure in retirement. Some parents can't tolerate their children's attachment to an outside caregiver. In our case, our mother and Cheng formed a team, united in raising three children.
‘Children are to be seen, not heard’
Growing up, many of us heard the maxim "children should be seen and not heard." For many families, this attitude profoundly shapes how children experience love and connection—or its absence.
A mentor once shared the following with me. His father—a workaholic and alcoholic—couldn't bear the sounds of children in the house. His mother, who struggled with love addiction, initially hired a nanny to care for him but grew jealous of their bond and dismissed her when he was barely three years old. Traumatized, he refused to eat for weeks. When he cried over this loss, his mother berated him, teaching him early that his
Part 2 of 5: Beyond the Golden Ghetto Series
Hey, what began as a three-part series has evolved into something more expansive. As I've delved deeper into the material and received valuable feedback, I've discovered there's much more to explore. I'm excited to announce that this will now be a five-part series, and you'll have access to all of it in the coming weeks. Now, let's begin.
The aroma of oatmeal wafted in the air filling me with a sense of safety. Cheng’s carefully set breakfast table reflected her approach to everything she did—meticulous care, whether it was folding our clothes or making meals.
While many of my peers saw their nannies come and go, Cheng stayed. She became our rock: a constant, reassuring presence, and a stern taskmaster. I am convinced she's the reason I'm alive today. My story is rare: nannies seldom become family, yet Cheng has been with us for nearly 50 years, transitioning from caregiver to cherished grandmother figure in retirement. Some parents can't tolerate their children's attachment to an outside caregiver. In our case, our mother and Cheng formed a team, united in raising three children.
‘Children are to be seen, not heard’
Growing up, many of us heard the maxim "children should be seen and not heard." For many families, this attitude profoundly shapes how children experience love and connection—or its absence.
A mentor once shared the following with me. His father—a workaholic and alcoholic—couldn't bear the sounds of children in the house. His mother, who struggled with love addiction, initially hired a nanny to care for him but grew jealous of their bond and dismissed her when he was barely three years old. Traumatized, he refused to eat for weeks. When he cried over this loss, his mother berated him, teaching him early that his feelings and thoughts didn't matter.
Jessie O’Neill captures this dynamic well in her book The Golden Ghetto:
“With each successive loss of a loving and attentive caretaker, the child becomes less willing and less able to attach and commit to a lasting relationship for fear that it will also be taken away. The trauma is heightened by the fact that one person the child loves (the nanny) is being sent away by an even more important love object (the parent). The children learn to believe it is not safe to love: ‘Whomever I love leaves or is sent away. I must be unlovable or they would stay. I will not love or be loved.’”
My mentor learned to suppress his emotions, particularly intense ones like anger and grief. Only as a teenager did he find acceptance, entertaining adults at dinner parties with his intellectual conversation.
Behind the accolades, though, he was silently screaming for emotional connection. His parents treated him as a “singe savant”—a performing monkey who excelled academically but had no space for vulnerability. To cope, he turned to alcohol, sex, and drugs. Drinking was socially acceptable in his family’s world, making his descent into addiction easy.
Through sobriety, therapy, and support groups, he has finally rebuilt his sense of self. He's now learning to form authentic connections, express his needs and show vulnerability without shame.
When glamor masks pain
A client grew up with a similar father: a self-made billionaire obsessed with presenting a perfect external image to the world. To her, he became a godlike figure. At first, she felt like the “chosen child.”
But the relationship turned toxic. Her father’s temper frightened her, and her mother’s jealousy left her without support. She learned to suppress her emotions, burying her feelings under a veneer of perfection.
The result? Anxiety, eating disorders, substance abuse, and unhealthy relationships. Outwardly, she seemed to have it all: beauty, charm, and a life splashed across glossy magazines. But inside, she felt invisible.
This is the pain of emotional abandonment. While physical abandonment is often recognized, emotional neglect is more insidious—especially in privileged families where the outward picture seems perfect.
A therapist once told me that it is far worse to be ignored by a physically present parent than to be yelled at.
The double-edged sword of boarding schools
In privileged circles, boarding schools often serve as a convenient solution for emotional neglect. In "Boarding School Syndrome," Joy Schaverien, a UK-based psychotherapist, reveals the hidden trauma behind an institution synonymous with privilege and success.
“The painful experiences of boarding, for many, inhabit the shadowy realm of split-off emotions. Secretly hidden they remain unconscious until the person is emotionally compelled to explore it. The transference can be complicated by the projected veneer of sophistication and confidence."
These institutions teach children the intellectual and social skills to succeed, but they come with trade-offs. For some, like another client, Lisa (name changed for privacy), boarding school offered partial salvation. Sent to a small school in the Swiss Alps at age six after suffering severe burns while attempting to cook unsupervised—a final indication of her alcoholic mother's unfitness to parent—she found refuge there. With her father unable to step back from work, the Swiss boarding school became Lisa's refuge. While she has outwardly flourished as a successful lawyer, the impacts linger: she exercises obsessively, and one of her children struggles with mental health issues.
“There are some for whom school is better than home. In these cases, school is a sanctuary, offering relief from constant insecurity, neglect, or abuse; as one of my patients expressed it: ‘At school at least you knew where the punishment was coming from.” For this man, and others like him, boarding school was preferable to home because it offered stability which his parents, despite their material wealth, were unable to provide.”
For others, these institutions deepen abandonment wounds. Emotional neglect, systemic bullying, sexual abuse, and isolation often reinforce the message that love and connection are conditional. “The boarding school child, as we have already seen, learns not to complain,” Shaverien continues.
Breaking the cycle
I once felt "stuck" despite years of self-work. When my codependency coach suggested exploring my childhood further, I resisted. After all, I'd already completed trauma reduction workshops and shed plenty of tears.
"No, Diana. You need to dig deeper," she insisted.
Reluctantly, I attended an emotional trauma workshop in Arizona. The experience transformed me, unearthing and releasing feelings I didn't know still lived within me. I emerged more emotionally regulated and more present.
If you struggle with intimacy, vulnerability, and emotional expression, I encourage you to reach out to a licensed therapist trained in trauma work to work on your past. Please, do not attempt to do this alone or with a coach. Coaches do not have the competencies to handle this kind of work.
One of my specialties is helping clients find the right therapist for their needs. While my practice is currently at capacity, you can join my waitlist here if you'd like support in your therapeutic journey.
In the meantime… the scent of oatmeal and Cheng’s carefully folded linens still linger in my kitchen, but now they carry deeper meaning. They’re reminders of the love I received and the cycles I’m still working hard to break.
In that space between privilege and pain, I’ve found my path to real connection—and I believe we all can. One carefully folded moment at a time.
Until next week!
P.S. I write all my blog posts myself. But I use AI to help correct grammar and spelling mistakes once I've finished. Since you've taken time to read this, I think it's important for you to know.
The money taboo: Why wealth can feel ugly to those who inherit it
Part 1 of 5: Beyond the Golden Ghetto
I remember sitting around the dinner table one Christmas, back when our family still gathered for the holidays, before the big court case that ended all that.
"It takes one generation to make it, one to spend it, and one to lose it," my uncle said, his voice carrying the weight of experience.
The table fell silent.
At the time, I thought my uncle had created our wealth. Later, I learned that he had built upon the wise investments our great-great-grandfather had made. Still, his words stayed with me, a reminder of wealth's fragility and the pressures it brings.
The pressure paradox
Billie Jean King famously said, "Pressure is a privilege." And she's right—when the pressure is just right. Imagine an upside-down bell curve. On the bottom left corner, there's no pressure: no motivation, no reason to get out of bed, no drive to engage with life's challenges.
Part 1 of 5: Beyond the Golden Ghetto
I remember sitting around the dinner table one Christmas, back when our family still gathered for the holidays, before the big court case that ended all that.
"It takes one generation to make it, one to spend it, and one to lose it," my uncle said, his voice carrying the weight of experience.
The table fell silent.
At the time, I thought my uncle had created our wealth. Later, I learned that he had built upon the wise investments our great-great-grandfather had made. Still, his words stayed with me, a reminder of wealth's fragility and the pressures it brings.
The pressure paradox
Billie Jean King famously said, "Pressure is a privilege." And she's right—when the pressure is just right. Imagine an upside-down bell curve. On the bottom left corner, there's no pressure: no motivation, no reason to get out of bed, no drive to engage with life's challenges.
As pressure rises, so does performance. This is the "sweet spot"—where challenge feels manageable and motivating. It's here that people thrive.
But beyond this sweet spot, the curve dips. Excessive pressure—rooted in shame, guilt, or impossible expectations—causes performance to falter. On the far right, individuals become so overwhelmed they can't perform at all. Depression, isolation, burnout, substance use, and emotional paralysis take hold.
This curve illustrates the paradox of privilege. Too little pressure, and individuals lose their sense of agency. Too much, and they crumble under unrealistic expectations. The key lies in finding that middle ground where pressure motivates but doesn't overwhelm.
The weight of inherited wealth
For individuals from wealthy intergenerational families, finding this sweet spot proves particularly challenging. The pressures they face are complex, compounding like interest in a bank account:
Isolation breeds difficulty finding friends who understand without judgment.
Privacy and trust issues create emotional walls of constant wariness.
Societal judgment demands proving one's worth and humility.
Self-worth struggles when wealth defines identity; and when well-meaning parents shield children from consequences.
Frequent international moves foster rootlessness, severing ties to place and community.
Mental health suffers as isolation and money enable addiction.
Conformity pressure clashes with some modern values.
Identity confusion taints achievements.
Financial decisions loom large despite advisors and planning.
Legacy expectations stifle personal dreams.
Yet, these pressures are symptoms of a deeper issue—the emotional foundation often missing in families.
The missing foundation
While many focus on identity and purpose—Maslow's higher needs—emotional safety must come first. Wealth often masks neglect through outsourced attachment, i.e. institutions and nannies.
Consider the four-year-old Russian girl in Gstaad who arrived each day alone to daycare by taxi. Her defiant behavior and tendency to run into traffic signaled deep distress. When her father, yachting in the Mediterranean, was contacted, he merely berated the teacher. In less privileged circumstances, social services would have intervened.
These historical attitudes have shaped a cultural legacy of secrecy and shame around wealth, a legacy still alive in modern-day interactions.
Historical legacy
Shame around wealth runs deep. Tokugawa Japan ranked merchants lowest. (Interestingly, it ranked samurai at the top (yay!), followed by farmers and craftsmen.)
Medieval Christianity prohibited usury and condemned profit. Consider the biblical quote: “It is easier for a camel to go through the eye of a needle than for a rich man to enter the kingdom of God.” The "eye of the needle" was a gate in Jerusalem—to pass through, a camel had to kneel in humility and shed its bags, symbolizing attachments and character defects.
Even America's Gilded Age aristocrats' disdain for "new money" created secrecy around wealth that persists today. Emotionally damaged inheritors avoid engagement while nouveau riche miss key values for preservation.
Today’s reality
At a Newport party 20 years ago, an older man—who "never worked a day in his life"—sneered and said "I'm so sorry" when a family member announced his new job as an analyst at a prestigious real estate firm.
Just last week, a client, whose family fortune vanished through "misadventures and delusions, bad investments, carelessness," and who congratulated me for "having the courage to speak about this taboo" is now rebuilding his wealth. I am confident that through his industry and resolution, he’ll succeed and I root for him.
By the way, I mentioned last week that while I’m currently all booked up at the moment, I’m opening up a handful of spots to work with new clients at the start of the new year. I wanted to let you know that if you’re not already on the waitlist and this is something that you might be interested in, here’s the link to get yourself on the waitlist now.
Besides strained relationships, how money should be spent, saved, or given provide fertile ground for friction.
At 13, I discovered a book left by a British houseguest and read it in one day. It was called Class: A Guide Through the American Status System by Paul Fussell. The book confirmed what I innately knew that showing too much wealth was considered “declassé.”
But it’s not just it’s display. There is a more insidious aspect to wealth that undermines health. It’s called hyper-agency.
Hyper-agency—wealth's ability to avoid all friction—erodes resilience, as Dr. Paul Hokemeyer writes about. After my Gstaad neighbors fled rainy days by private jet, their house manager confided to me that the couple seemed perpetually miserable, seeking external solutions to internal problems.
Historical wisdom
Some historical figures recognized wealth’s dangers.
Michel de Montaigne’s father sent his young son to live with peasants, teaching simplicity and humility before returning to the château. This grounding influenced his later essays on how to live a meaningful life.
Similarly, in Confessions, Leo Tolstoy admires the common peasants he encountered in Russia. He found meaning in peasants' groundedness and resilience—qualities that eluded the elite of the day.
These lessons remain relevant. Shielding children from hardship and simplicity doesn’t prepare them for a meaningful life. Instead, it disconnects them from experiences that build self-worth and resilience.
This explains why rags-to-riches stories resonate: struggle fosters growth or antifragility.
The path forward
A man of simple beginnings, Benjamin Franklin, wrote about his favorite 13 Virtues—temperance, silence, order, resolution, frugality, industry, sincerity, justice, moderation, cleanliness, tranquility, chastity and humility.
These virtues remind us that wealth need not define us—it can be a tool for growth. For example, industry and resolution can counter feelings of isolation, while frugality and order provide a framework for managing wealth responsibly.
Breaking taboos and to the horror of my friends, we used to discuss money as well as sex and politics at table. Mother taught more than checkbook balancing; she stressed only spending interest and not touching capital. Money in the hands of a woman was even seen as insurance against an abusive marriage. I later learned through experience that attachment bonds prove stronger than wealth.
The privilege paradox requires finding motivation's sweet spot—where pressure energizes rather than paralyzes
.
Money isn’t good or bad—it just magnifies the shame or willingness that’s already there.