Felix Dennis had everything money could buy and nothing money couldn't.
A $750 million publishing empire. Private islands where he hosted legendary parties with cocaine mountains and champagne fountains. Art collections worth more than small countries. The freedom to do whatever he wanted, whenever he wanted, with whomever he wanted.
On any given night, you might find him in his London mansion surrounded by supermodels, rock stars, and politicians, all drawn to the gravitational pull of his wealth. The parties were legendary - Keith Richards doing lines off priceless antique tables while Dennis held court, dispensing wisdom about business and life to anyone who would listen.
But in the quiet moments between the chaos, Dennis would retreat to his study and write poetry. Dark, introspective verses about loneliness, meaninglessness, and the prison he'd built around himself with money.
He also had a confession that should make every ambitious person pause:
"I have never met a happy rich person. Not one. And I've known many of them."
Dennis built Maxim, The Week, and a media empire that made him one of Britain's richest men. He lived every fantasy that money could provide. He also discovered that in his relentless pursuit of wealth, he'd lost the very things that make life worth living. His insights, later captured in How to Get Rich, reveal the brutal honesty of someone who achieved everything and found it wanting.
His story reveals the hidden psychological cost of building wealth. Every successful ascent has predictable dangers. The people who reach their financial goals with their lives intact are the ones who see the pitfalls coming.
I've watched this pattern repeat itself dozens of times. Brilliant, driven people who start with noble intentions gradually lose themselves in the pursuit of more money. The transformation happens so slowly they don't notice until it's too late.
What actually happens when you build wealth, based on what I've seen firsthand.
The Early Wealth Phase: When Everything Feels Like Survival
When you're making your first serious money, everything feels urgent. Every business opportunity could be the one that changes everything. Every setback feels like it could destroy your financial future.
I remember sitting in my studio apartment, eating ramen noodles while building my first business, convinced that once I hit six figures, all my problems would disappear. The hunger was intoxicating. I felt more alive working 80-hour weeks than I had during any comfortable period of my life.
But hunger consumes everything around it. My girlfriend at the time started complaining that I was "always somewhere else" even when we were together. She was right. Half my brain was constantly calculating, planning, scheming for the next move. Conversations became interruptions. Relaxation felt like weakness.
The cruel irony of the hunger years is that you sacrifice the present for a future that keeps moving further away. That six-figure goal becomes a quarter million, then half a million, then a million. The goalpost moves because the person chasing it changes.
Your relationships during this wealth-building phase face a particular kind of stress. Friends who lack similar financial trajectories start feeling like dead weight. You begin categorizing people by their usefulness to your money-making goals. Social events become networking opportunities. Genuine connection becomes rare because you're always performing, always selling, always on.
I watched a friend destroy his marriage during this phase. He kept telling his wife, "Just give me two more years to build this business, then we'll travel and spend time together." Two years became four, then six. By the time he had the money for travel, he was divorced. She'd found someone who was actually present.
The hunger years teach you that you can survive on very little sleep, terrible food, and constant stress. They also teach you to normalize those things. The habits you build during this phase stick around and persist when you have more money.
The Confidence Phase: When Success Becomes Addictive
Once you prove you can make serious money, everything changes. Your phone starts ringing with opportunities. People want to have coffee with you. Your opinions suddenly matter in rooms they never mattered before.
This phase is intoxicating in a completely different way than the hunger years. You feel chosen. Special. Different from all those people who "don't get it."
I remember the first time someone introduced me as "successful" at a party. The rush was incredible. People listened differently when I spoke. Conversations that had nothing to do with business somehow became about business because everyone wanted to understand "how I did it."
Success triggers the same neurological pathways as cocaine. You're getting high off the process of making money. This addiction pattern, explored in depth in Dopamine Nation, shows how achievement becomes a compulsive cycle requiring increasingly larger doses.
Success is a drug that requires increasingly larger doses. The deals that excited you during the hunger years feel routine. The income that would have thrilled your former self becomes the new baseline. You're addicted to the feeling of being someone who makes money.
Your peer group shifts during this phase, often without you realizing it. You start spending time with other successful people because they "understand the game." Conversations with old friends begin to feel frustrating because they lack appreciation for the complexity of your challenges. How can you explain the stress of managing seven figures to someone worried about making rent?
The confidence phase is where many people lose their empathy. When your daily problems involve tax optimization and investment allocation, other people's problems start seeming simple or self-inflicted. For those seeking a healthier approach to wealth building, The Bogleheads' Guide to Investing offers a more grounded perspective on financial growth that doesn't consume your identity. You forget what it felt like to choose between paying bills and buying groceries because those memories feel like they happened to someone else.
I've seen friends become completely baffled why their broke friends couldn't just "start a side hustle" or "learn some high-value skills." The cognitive empathy remains, but the emotional empathy fades. You remember being poor intellectually, but you can't access the feeling anymore.
The Optimization Phase: When More Money Becomes a Prison
Somewhere around half a million dollars annual income, money stops being about survival or even comfort. It becomes about financial optimization, efficiency, and abstract scorekeeping. This is where things get psychologically dangerous for wealthy people.
You have enough money to solve most problems, which means the problems that remain can't be solved with money. But by this point, money-making has become your primary skill, your main source of identity, and your default solution to everything. When your hammer is very, very good, everything starts looking like a nail.
This is where I've seen the most marriages implode. From emotional poverty instead of financial stress. One partner becomes obsessed with extracting maximum value from every decision while the other desperately wants someone who can just exist without calculating the ROI of every experience.
I know someone who makes $2 million a year who can't enjoy a vacation because he spends the entire time thinking about the opportunity cost of working instead. He's physically present but mentally calculating how much money he could be making if he were in meetings instead of on a beach. His wife eventually stopped planning vacations because his anxiety was contagious. Even noise-canceling headphones couldn't silence the constant mental chatter about missed opportunities.
This phase is also where the paranoia starts. When you have serious money, every new person in your life becomes potentially suspect. Are they interested in you or your bank account? That attractive person who seems genuinely interested in your thoughts about philosophy could be genuinely interested in your thoughts about portfolio allocation.
The mindset focused on efficiency and maximum returns that makes you wealthy starts poisoning non-financial decisions. You begin analyzing friendships for their strategic value. You calculate the cost-benefit of family time versus work time. Everything becomes calculated because calculated thinking is what got you here.
Humans aren't investment portfolios. Relationships don't follow efficiency models. Love doesn't scale. Joy doesn't grow at 8% annually. The skills that make you wealthy can make you insufferable.
The Ultra-Wealth Phase: When Freedom Becomes Emptiness
Once you have real wealth - multi-millions or more - the problems change completely. You have enough money to do anything, which paradoxically makes it harder to choose what to do. The constraints that used to guide your financial decisions disappear, leaving you with endless options and no clear path forward.
This is the phase where existential questions become unavoidable. If you can buy anything, what's worth buying? If you can go anywhere, where's worth going? If you can do anything, what's worth doing?
Felix Dennis spent years in this phase before his final revelations. He could afford any experience, any possession, any lifestyle. But experiences lose their impact when they're unlimited.
I've watched wealthy friends develop a strange kind of depression that's hard to explain to people without money. It's the depression of emptiness. When external achievements stop providing satisfaction, you're forced to confront whether there's anything satisfying about your internal world.
The wealth phase is where you discover that money amplifies who you already are rather than changing who you are. If you were generous before wealth, you become more generous. If you were anxious before wealth, you become more anxious. If you were empty before wealth, you become more empty.
But there's something else that happens that nobody warns you about. The things that used to bring you joy stop working. Before getting rich, a nice meal at a restaurant or a weekend trip felt special, exciting, worth looking forward to. After getting rich, luxury becomes normal so quickly that there are fewer and fewer things left to actually enjoy.
The private jet becomes just transportation. The five-star restaurants become routine Tuesday dinners. The luxury becomes invisible. You're constantly chasing bigger and more expensive experiences to feel the same satisfaction you used to get from simple pleasures. Even the wealthy who travel mindfully with quality gear like Patagonia Black Hole duffels or Samsonite premium luggage find that the tools don't fix the underlying emptiness.
The tragic irony is that by the time you have enough money to fund any lifestyle you want, you may have spent so many years optimizing for money that you've forgotten what kind of lifestyle you actually want. Or worse - you've lost the ability to enjoy any lifestyle at all.
Three Billionaires: Different Paths to the Same Destination
To understand the full spectrum of what wealth can do to a person, consider three different approaches to building and handling money.
The Cautionary Tale: Howard Hughes
Howard Hughes inherited wealth, then multiplied it exponentially through aviation, Hollywood, and real estate. By his thirties, he was one of the richest men in America. By his death at 70, he was a paranoid recluse who had spent years without cutting his hair or nails, lived in complete isolation, and trusted no one.
Hughes's descent began with the very success that made him famous. Each business triumph increased his paranoia that others were trying to steal from him. Each romantic relationship ended when he became convinced the woman was after his money. Each friendship dissolved under the weight of his suspicion.
In his final years, Hughes lived in sealed hotel rooms, communicating only through written notes passed to assistants he rarely saw. He had billions of dollars and used them to buy the most expensive isolation in human history.
Hughes represents the extreme end of wealth paranoia - the gradual transformation from successful businessman to prisoner of his own suspicion. His biography, detailed in Howard Hughes: His Life and Madness, reads like a horror story: man gets everything he wants, then spends decades discovering that what he wanted was a prison.
The Redemption Story: Chuck Feeney
Chuck Feeney co-founded Duty Free Shoppers and became worth over $8 billion. Then he did something almost unprecedented among the ultra-wealthy: he gave it all away.
Feeney's story is about the psychology of enough. While building his fortune, Feeney watched wealth corrupt people around him. He saw friends become isolated, paranoid, and fundamentally unhappy despite having more money than they could spend in multiple lifetimes.
So in 1984, Feeney secretly transferred his entire fortune to his foundation, keeping only $2 million for himself and his family. He spent the next 36 years giving away $8 billion to universities, human rights organizations, and healthcare initiatives around the world.
What stands out about Feeney's story is how his happiness increased as his wealth decreased. In interviews, he describes feeling "liberated" by giving away his money. The constant stress of managing vast wealth, the paranoia about others' motives, the burden of endless financial decisions - all of it disappeared when he chose to have enough rather than more.
Feeney died in 2023 with a modest apartment in San Francisco and a life full of meaningful relationships. He often said his greatest joy was watching his money create positive change in the world rather than building it.
The Different Path: Patagonia's Yvon Chouinard
Yvon Chouinard built Patagonia into a billion-dollar company, but he structured his life to prioritize purpose over profit from the beginning.
Chouinard lived in a modest house, drove old cars, and spent months every year climbing mountains and surfing. When Patagonia became successful, he used the company's profits to fund environmental activism and sustainable business practices rather than upgrading his lifestyle proportionally.
In 2022, Chouinard made a decision that shocked the business world: he gave away the entire company to fight climate change. Chouinard's decision was about never letting wealth accumulate in the first place rather than giving away wealth he'd accumulated.
Chouinard's story represents a third path: using business success as a tool for meaning rather than an end in itself. He stayed connected to his original values throughout his wealth-building experience, which allowed him to avoid the psychological traps that caught Dennis, Hughes, and countless others. His approach to conscious wealth building aligns with principles found in Your Money or Your Life, which reframes the relationship between financial success and personal fulfillment.
Warning Signs: How to Know If Money Is Corrupting You
After watching people navigate these phases for years, certain warning signs consistently appear before the transformation becomes irreversible. The earlier you catch these, the easier they are to address.
You Calculate the Monetary Value of Your Time
When you start declining social invitations because they fall below your "hourly rate," you've crossed a dangerous line. Time becomes a commodity to be optimized rather than life to be lived.
I know someone who refused to attend his daughter's school play because "those three hours could generate $15,000 in revenue." He was technically correct. He was also fundamentally missing the point of having a life outside work.
Conversations Always Return to Business
You discuss sunsets in terms of real estate values. You enjoy restaurants by analyzing their business models. You watch movies while thinking about marketing strategies.
When everything becomes a potential business opportunity or learning experience, you've lost the ability to simply exist in the moment.
You Judge People by Their Net Worth
Poor people become invisible. Middle-class people become irrelevant. You only take seriously the opinions of people who've "made it" financially.
This mental filter gradually cuts you off from most of human experience and wisdom. You start living in an echo chamber of other financially successful people who all think the same way.
You Can't Enjoy Simple Pleasures
A good meal requires Michelin stars. A vacation requires first-class everything. A night out requires VIP treatment. Regular experiences feel inadequate because your standards have inflated beyond reason rather than being objectively worse.
This is the hedonic treadmill in action - you need increasingly expensive experiences to feel the same level of satisfaction.
You Develop Paranoia About Others' Motives
Every new person becomes suspect. Every invitation gets analyzed for hidden agendas. Every compliment feels like manipulation.
While some caution is warranted when you have significant wealth, chronic suspicion isolates you from genuine human connection and creates a lonely existence.
You Lose Touch with Normal Financial Reality
You become completely perplexed why people can't just "hire help" for problems you find inconvenient. You forget that most people make financial decisions based on necessity rather than optimization.
This disconnect makes it impossible to relate to the vast majority of human experience and slowly chips away at your empathy.
The Hidden Truth About Rich People: Dark Secrets Nobody Talks About
I heard about a tech billionaire who spent $50,000 a month on cocaine during his company's IPO.
Think about that for a second. Fifty grand. Every month. On drugs.
When asked why, he said something that should terrify anyone chasing wealth: "It was the only thing that quieted the noise in my head about losing everything."
This guy had more money than he could spend in five lifetimes, and he was using a drug that cost more than most people's salary to cope with having too much money.
Substance abuse among people making over a million annually is three times higher than everyone else. These people get addicted to plastic surgery, shopping, sex, gambling, and work itself at rates that would horrify you beyond just cocaine and alcohol.
There was another case of a woman who became addicted to cosmetic surgery after her divorce settlement made her worth half a billion. She spent two million in six months trying to "fix" what wealth had broken inside her. The surgeries were about feeling something, anything, other than the emotional numbness that extreme wealth had created instead of vanity.
The pharmaceutical game among the wealthy is insane. Adderall to work 20-hour days. Xanax to sleep. Ambien when Xanax stops working. Antidepressants that cost more per pill than your lunch. Private doctors making house calls with briefcases full of Schedule II drugs, no questions asked.
What's disturbing is how normal this becomes. Wealthy social circles discuss their "performance enhancement" cocktails like middle-class people talk about coffee. Having a "house pharmacist" becomes a status symbol.
How Wealth Destroys Empathy
Wealth literally shrinks the part of your brain responsible for empathy. This neurological change, combined with the psychological patterns described in The Mindful Millionaire, shows how money fundamentally alters human connection.
UC Berkeley did brain scans. As income increases, the medial prefrontal cortex - the area that helps you understand other people's suffering - gets smaller.
They ran experiments where people played games for money after being primed to think about wealth or poverty. Those who thought about wealth were significantly more likely to cheat, lie, and steal from other participants. Even for trivial amounts.
The most troubling part? They followed the same people for 15 years as they got richer. The researchers documented measurable decreases in empathy and increases in what psychologists call "dark triad" traits: narcissism, manipulation, and psychopathy.
Wealth creates sociopaths rather than just attracting them.
The Mental Health Crisis Among Rich Kids
Rich kids are more depressed, more anxious, more suicidal, and more addicted than children from any other economic background.
These are kids who go to the best schools, get the best healthcare, and have access to every opportunity money can buy. Their depression rates are three times higher than normal. Suicide attempts are two and a half times higher. Substance abuse is four times higher.
The damage comes from knowing they'll never achieve anything that wasn't bought for them instead of earned. They develop what researchers call "achievement anxiety" - paralyzing fear that any success is illegitimate because of their advantages.
Many also develop trust paranoia early, learning to question whether friends like them or their family's money. They describe feeling like they're constantly performing, constantly being evaluated.
One Harvard study followed billionaire children into adulthood. Seventy percent described feeling "fundamentally empty" and "purposeless." Most said their greatest wish was to lose their family's money so they could discover who they really were without it.
The Mental Health Shadow System
The ultra-wealthy have access to psychiatric care you've never heard of. Discrete therapists who make house calls. Private facilities that look like luxury resorts. Experimental treatments available only for cash.
They're treating conditions most people don't know exist beyond what you'd expect. "Acquisition anxiety" - compulsive need to keep making money even when you have more than you could spend. "Loss paranoia" - overwhelming fear that everything will be taken away. "Achievement dysphoria" - inability to feel satisfied by accomplishments.
There's even something called "wealth dissociation disorder" where people become emotionally detached from their own lives because the gap between their material reality and emotional reality becomes too great to process.
Private psychiatric hospitals in Switzerland and the Caribbean charge $100,000+ per month treating these conditions. Most people have never heard of them.
Why Rich People Have Higher Suicide Rates
Rich people kill themselves at higher rates than everyone else. These deaths rarely make news because families use their wealth to keep details private.
What makes these suicides particularly tragic is timing. They often happen during periods of peak success rather than crisis. The realization that achieving everything you thought you wanted hasn't brought satisfaction can be psychologically devastating.
One private investigator told me that in 20 years, he's investigated over 200 suicides among the ultra-wealthy. In almost every case, the person had recently hit a major financial milestone - selling a company, reaching a net worth goal, completing a big acquisition.
"They get to the top of the mountain and realize there's nothing there," he said. "That's when the despair becomes overwhelming."
How Generational Wealth Destroys Families Forever
There's a saying in every culture: "shirtsleeves to shirtsleeves in three generations." The pattern goes deeper than losing money. Wealth systematically destroys the human qualities that created it in the first place.
Generation One: The Builders
The first generation builds wealth through hunger and sacrifice. They remember struggle, have clear motivation, and work ethics forged by necessity.
The process of accumulating wealth changes them. The qualities that make them successful - single-minded focus, willingness to sacrifice relationships for goals, viewing everything through cost-benefit analysis - gradually make them shitty parents.
First-generation wealth builders often become emotionally unavailable. They're so focused on building security for their families that they forget to actually be present with their families. The kids get every material advantage but lack emotional connection and moral guidance.
Generation Two: The Inheritors
Children who inherit significant wealth face psychological challenges their parents can't understand. They grow up with every material need met but often lack purpose and accomplishment.
Seventy percent of wealthy families lose their wealth by the second generation. The loss goes beyond financial.
Second-generation family members develop "inherited guilt" - the sense they don't deserve their advantages. This manifests as reckless spending (trying to get rid of the money), self-destructive behavior, or complete paralysis around life decisions.
Many struggle with "achievement anxiety" - fear that any success is illegitimate because of inherited advantages. This leads to either compulsive overachievement (trying to prove worthiness) or complete avoidance of achievement (afraid of succeeding for the "wrong" reasons).
Generation Three: The Destroyers
By the third generation, connection to the original struggle is completely severed. These individuals grow up with no understanding of money's value, no work ethic, and no purpose beyond consuming what previous generations created.
Third-generation wealth produces "affluenza" - complete inability to understand cause and effect, consequences, or personal responsibility. These individuals often destroy family wealth, relationships, health, and any chance at genuine happiness.
The Vanderbilt Meltdown
Cornelius Vanderbilt died in 1877 as America's richest man, worth about $185 billion today.
His children began the decline by using wealth as a weapon against each other. They built competing mansions, threw increasingly extravagant parties, and treated money as scorekeeping rather than a tool.
The second generation dissipated the fortune through lifestyle inflation, poor investments, and lack of business skills. They inherited money but not the drive or values that created it.
The third generation accelerated destruction through addiction, divorce, and spectacular business failures. By 1973, when 120 Vanderbilt descendants gathered for a family reunion, there wasn't a single millionaire among them.
The real tragedy was lost people rather than lost money. The family tree is littered with premature deaths, broken marriages, and individuals who never found purpose despite starting with every advantage.
The Kennedy Pattern
The Kennedy family shows how wealth creates self-destruction patterns that persist across generations.
Joseph Kennedy Sr. built the fortune through ruthless business and political maneuvering. His single-minded focus on success created a family culture that prioritized achievement over emotional health.
The second generation faced enormous pressure to live up to expectations while dealing with moral complexity of inherited wealth and power. The assassinations were tragedies, but family struggles with addiction, reckless behavior, and premature death continued long after.
Third and fourth generations have been marked by addiction, legal troubles, and self-destructive behavior that repeats despite access to the best everything money provides.
What Gets Inherited
What passes down in wealthy families goes beyond money. Psychological patterns that become increasingly destructive.
Emotional unavailability gets inherited when wealth-focused parents fail to provide emotional support. These children grow up unable to form secure attachments, which they pass to their own children.
Entitlement gets inherited when children grow up with unlimited resources and no understanding of consequences. They raise their children with the same lack of boundaries.
Paranoia gets inherited when children watch parents treat every relationship as potentially transactional. They learn to question others' motives, which isolates them and makes genuine connection impossible.
Most destructively, meaninglessness gets inherited. When parents derive identity primarily from wealth accumulation, children struggle to find purpose beyond consumption. This existential emptiness passes down until entire family lines lose any sense of meaning.
The Psychology Behind Wealth Worship: How They Sell You the Money Dream
The idea that wealth equals happiness is the most successful con job in human history.
The Manufactured Dream
The advertising industry spends $700 billion annually convincing you that happiness can be purchased. Every ad creates dissatisfaction with your current situation and suggests buying something will solve it.
Financial services spend billions more convincing you that constant wealth growth equals security. Investment companies, banks, and insurance providers profit from your financial anxiety and feed it with messages about never having enough.
The self-help industry built a $12 billion market around promising that the right mindset will make you wealthy and therefore happy. Authors, speakers, and coaches profit from selling the wealth dream even when they know it doesn't deliver satisfaction.
The Social Media Trap
Social media weaponized wealth worship by creating platforms designed to maximize envy and status competition. Instagram, LinkedIn, and TikTok profit from your dissatisfaction by showing you carefully curated versions of others' success. For those seeking to break free from this digital manipulation, Digital Minimalism provides practical strategies for reclaiming your attention and values.
The algorithms specifically show you content that makes you feel inadequate. Research shows people who spend more time on social media report higher financial anxiety and material desire, regardless of their actual economic situation.
Dating apps gamified relationships around wealth indicators. Tinder's features, Bumble's verification, and specialty apps like Raya create markets where financial status becomes the primary screening for human connection.
The Productivity Scam
The most sophisticated part of the conspiracy is packaging exploitation as virtue. "Hustle culture," "entrepreneurship," and "productivity optimization" are presented as moral goods rather than systems designed to extract maximum economic value from humans.
The "rise and grind" movement convinces people that 80-hour weeks build character rather than destroy lives. Young people are told that sacrificing health, relationships, and mental well-being for wealth accumulation is "paying dues" instead of being exploited.
Business schools, conferences, and "thought leaders" profit from teaching people to streamline themselves like machines instead of live like humans. The personal development industry exists to convince you that you're never productive, driven, or ambitious enough.
Who Really Wins
Banks profit from your debt and investment fees. Advertisers profit from your dissatisfaction. Employers profit from your willingness to work excessive hours for future rewards. Politicians profit from your focus on economic issues rather than quality of life.
The conspiracy succeeds because it promises happiness is always one more achievement away. Happiness is available right now, with what you already have, if you can resist the psychological manipulation designed to convince you otherwise.
Felix Dennis understood this intimately because he was part of it. His media empire profited from selling people dreams of wealth and status. But in his final years, he recognized the damage this mythology does.
"We sell people the idea that money will save them," he said in one of his last interviews. "Money can't save you from yourself. And if you lose yourself chasing money, there's nothing left to save."
How to Build Wealth Without Losing Your Soul: The Redemption Protocol
Redemption is possible, even after wealth has done its psychological damage. The process requires brutal honesty about what you've lost rather than just celebration of what you've gained.
Step 1: Honest Inventory
What relationships have been damaged by your pursuit of wealth? What parts of yourself have you neglected or abandoned? What activities brought you joy before money became your primary focus?
Write this down. Actually write it down. Think about it rather than just thinking about it. The act of putting these losses on paper makes them real in a way that thinking about them doesn't. A quality journal like a Moleskine Classic notebook or a Rocketbook Smart notebook can make this process more meaningful and permanent.
Step 2: Intentional Reconstruction
This means actively rebuilding the non-financial parts of your identity that wealth accumulation destroyed instead of giving away all your money (though some people choose that path).
One of the wealthiest people I know spends every Saturday morning coaching little league baseball. He's terrible at it, the kids don't know he's rich, and it generates zero income. But it keeps him connected to a part of himself that existed before money became his primary identity. He travels to these games with a simple Peak Design backpack, carrying only what matters for that moment.
Another friend takes "poverty vacations" once a year where he travels with just a backpack and stays in hostels. He wants to remember what it feels like to worry about small amounts of money and connect with people based on shared experience instead of financial status because he has to. He keeps his travel documents organized in a simple Bellroy travel wallet - functional quality without ostentation.
Step 3: Build Humanity Protocols
A successful entrepreneur I know has what she calls "humanity protocols" - specific practices designed to counteract the dehumanizing effects of wealth:
Every month, she volunteers at a homeless shelter to remember what actual problems look like instead of to feel good about herself. Every quarter, she spends a week living on minimum wage to remember what financial stress feels like. Every year, she gives away enough money that it causes her genuine financial anxiety.
These aren't feel-good exercises but mental maintenance designed to prevent the gradual erosion of empathy and perspective that wealth typically causes.
Step 4: Practice Strategic Giving
One of the most counterintuitive discoveries about wealth is that giving it away is often harder than making it.
When you've spent years or decades optimizing for accumulation, the muscles for distribution atrophy. Many wealthy people report feeling genuine anxiety about giving away money, even when they have far more than they could ever spend.
Chuck Feeney solved this problem by giving away his wealth secretly and systematically over decades. Even he admitted that the psychological transition from accumulator to distributor was one of the most difficult challenges of his life.
Start small but start now. Give away enough that you feel it, but not so much that it creates genuine hardship. The goal is rebuilding your capacity for letting go instead of financial martyrdom.
Step 5: Create Money-Free Zones
Designate specific times and spaces where financial concerns are off-limits:
Family dinners without business talk. Vacation days with zero work communication. Hobby time that generates zero income. Friendships that exist independent of business value. A phone lockbox can help enforce these boundaries by physically removing the temptation to check messages during designated personal time.
These zones protect your non-financial identity and remind you who you are beyond your net worth.
The key is building these practices before you need them. By the time you realize you've lost touch with your humanity, it's much harder to find your way back.
Dennis's Final Warning
Felix Dennis spent his final years trying to undo the damage his wealth accumulation had done to his humanity. He gave away hundreds of millions to charity. He focused on poetry and environmental conservation. He tried to rebuild relationships that money had complicated.
"I would have been much happier as a moderately successful poet," he reflected near the end of his life.
His story doesn't have to be your story. The people I know who've built wealth without losing themselves share certain characteristics. They treat money as a tool rather than a scorecard. They maintain relationships that have nothing to do with business. They remember what it felt like before they had money intellectually and emotionally.
Most importantly, they regularly step outside the wealth-building world to remember what normal life feels like. They volunteer with people who have real problems. They maintain friendships with people who don't care about their net worth. They engage in activities that have nothing to do with optimization or efficiency.
Dennis's warning was about what the pursuit of money can do to your soul if you're not careful.
Money is a powerful tool that can enhance almost every aspect of life. It's a terrible master that will consume every aspect of life if you let it.
The question isn't whether you should pursue wealth. The question is whether you can pursue wealth while remaining the kind of person you want to be.
Dennis spent his final years writing poetry about islands - the private islands he owned, and metaphorical islands of isolation that wealth had created around him. His poems were haunting meditations on loneliness, regret, and the price of getting everything you think you want.
In one of his final poems, he wrote:
"I am the richest poor man alive,
Surrounded by gold, drowning in fear,
Having everything, possessing nothing,
Wealthy beyond measure, bankrupt of joy."
His story isn't a warning against ambition. It's a reminder that success without humanity is just elaborate failure. This theme resonates throughout Viktor Frankl's Man's Search for Meaning, which explores how purpose transcends material circumstances.
You can reach for the sky. Just make sure you remember how to come back down to earth.
Because the view from the top is only meaningful if you're still yourself when you get there.
The climb doesn't have to cost you your soul. But it will, unless you actively decide otherwise.
Every step of the way.
The choice is yours.
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