My conversation with a wealthy friend

The empathy gap that's tearing America apart and blinding us to our demise

I had my mind blown yesterday.

I was having what I thought was a friendly text exchange with a friend about the housing crisis. Then he dropped a bombshell: A mailman shouldn’t be able to buy a home because it’s a “pathetic career.”

The conversation had started innocuously enough.

My friend (let’s call him Jonas) is a TV producer who lives in L.A. I had casually mentioned how much harder it’s become for average Americans to achieve basic milestones like homeownership compared to our parents’ generation, or even our own experience as Gen Xers. I acknowledged the luck inherent in our well-timed birth: we came of age during an era of greater economic mobility and opportunity. I didn’t think my observations were controversial; they seemed pretty self-evident.

But Jonas saw things differently.

Where I perceived systemic economic shifts that have made traditional paths to prosperity increasingly difficult, he saw moral failure. Where I recognized the advantages we’d enjoyed simply by being born when we were, he attributed all outcomes (and failures) to individual character and work ethic. Where I acknowledged the gap between inflation on the ground vs inflation based on government “data,” Jonas insisted that wages are rising faster than the cost of living.

Throughout our conversation his comments reflected a bizarre disconnect from economic reality.

He repeatedly claimed that anyone struggling in America in 2025 simply isn’t working hard enough. At one point, I shared a job posting from a major Chicago law firm to show how even educated, white collar professionals are struggling. The position — requiring five years of experience — paid $85,000-$120,000 annually.

Here’s the reality: unless they’re from an upper class family, any competitive candidate will carry an average of $300,000 in college and law school debt, translating to at least $3,500 monthly in loan payments (significantly higher if you made the mistake of attending an Ivy League university). After taxes, take home pay maxes out at $7,300 per month. Subtract loan payments, and you’re left with $3,800 for rent, utilities, food, transportation, and out-of-pocket healthcare expenses in one of America’s most expensive cities.

“Good luck saving $60,000 for a down payment,” I pointed out. “In the 20 years it will take you to scrape it together, home prices will have doubled.”

The math behind my Chicago law firm example should have been sobering for anyone paying attention. But that’s when I realized Jonas’s contempt for the bottom 99% wasn’t limited to mailmen; it extended to anyone who couldn’t navigate the new economic reality with the same ease that we had experienced decades earlier.

He insisted that lawyers are part of the “top 1%” — and if they can’t afford homes, it’s their fault. Never mind that the average salary for an American lawyer ($176,470) is well above the median but nowhere near the $730,000-$800,000 threshold for the top 1%. He was off by a factor of four, yet doubled down with unshakeable confidence.

“And you’re not going to make that same salary for 20 years,” he insisted. “Obviously, you need to move upwards and compete. If you fail, that’s on you.”

The assumption that salary progression will level the playing field completely ignores the reality that career trajectories — in the legal profession and elsewhere — have fundamentally shifted since we graduated decades ago. Law firms are increasingly outsourcing document review to lower-cost markets and corporate clients are demanding fee caps that squeeze profit margins. Moreover, AI is not only automating tasks that once required junior associates, but also threatens to eliminate jobs for less skilled white collar work like customer service, data entry and even market research.

I’m a lawyer who’s practiced for 20 years. When I tried to explain how much harder it’s become for my own family to make ends meet, Jonas deployed what I call the “Third World Dodge” — praising his father’s caregivers from Guatemala and the Philippines who can “make it work on $300 per month for groceries,” while characterizing white and black Americans as “lazy” by comparison. (As someone who is half-Asian and half-white, Jonas repeatedly used his own identity to justify a harsh social Darwinism).

$300 per month for groceries in L.A. Wrap your mind around that.

This cynical sleight of hand dismisses legitimate economic concerns while weaponizing immigrant desperation against American workers. It’s a particularly insidious form of victim-blaming that avoids engaging with actual cost-of-living data. It also ignores a reality I recently wrote about: our dysfunctional economy relies on progressively cheaper sources of labor to sustain itself.

“Seriously,” I challenged him, “I want you to go to the grocery store, buy $300 worth of food that you claim will last a month, put it in your cart and show me the receipt. Until I see this, the ‘$300, no problem’ claims simply aren’t believable.”

Crickets.

Throughout our exchange, Jonas consistently framed economic struggle as moral failure. The unemployed are “lazy.” Those who can’t save for down payments lack “discipline.” Working-class Americans who expect to earn a decent income without working three jobs are “entitled.”

The cruelty is breathtaking. When you dismiss systemic problems as individual character flaws, you lose the ability to understand or address the actual forces shaping people’s lives.

What makes this mindset particularly maddening is that Jonas lives in a city where the consequences of extreme inequality are literally outside his front door. His neighborhood isn’t immune to Los Angeles's homelessness crisis, rising crime, or home invasions. The economic desperation he dismisses as personal failure surrounds his multimillion-dollar neighborhood.

But this isn’t the America Jonas and I grew up in.

We were raised in middle-class families. My parents weren’t college educated and worked for L.A. County; his father was a teacher and his mom was a homemaker. Our families lived in homes they owned and bought in their early-to-mid 20s. Yet even on their modest income, our parents were able (with some sacrifice) to send us to private school. After we graduated, Jonas went to Harvard; I attended Princeton and Harvard Law School.

Since then, the economic mobility that defined previous generations has been systematically dismantled. Wages have stagnated while costs have skyrocketed. The $72,000 in student debt I carried would now be $709,000 to attend the same schools. The social contract that promised hard work would be rewarded with stability has been shredded.

When I worked as an entertainment lawyer, I watched my consulting rates at NBC Universal, Paramount, and Disney remain virtually stagnant for seven years while our household expenses — not new expenses, mind you, just existing ones — skyrocketed. In real terms, I was no longer getting ahead, but I was surviving. And I was one of the fortunate ones.

When I explained this reality to Jonas, he flatly refused to acknowledge that inflation has meaningfully impacted most Americans’ purchasing power. If you’re struggling financially, the solution is simple: work 60-70 hours every week for 20 years until you can afford a home. Never mind that this wasn’t the expectation for our parents’ generation, or even for us when we started our careers.

“Do they think working less than 60-70 hours per week is for some reason beneath them?” he asked dismissively, as if it’s perfectly reasonable to expect people to sacrifice two decades of their lives working punishing hours just to achieve basic housing security.

“You do realize that’s not the message we’re getting from the people we vote for?” I told him. “They keep telling us the American Dream is still possible, even for a mailman.”

“Of course they’d never say that in public,” he retorted, “because you need every DOPE to vote for you. That’s the nature of the game.”

It was a depressing and heartbreaking conversation. (It also struck at the heart of a Note I posted yesterday: I’m finding it increasingly harder to connect with people I thought I knew well).

But here’s why I’m sharing this anecdotal exchange.

While Jonas’s $10-12 million net worth makes him wealthy by most standards, his portfolio is literally pocket change compared to the billionaires who influence politics and policy. Yet if his attitude toward economic struggle is any indication of elite thinking, it could explain a lot about why America is failing so many of its people.

If someone at Jonas’s relatively modest level of wealth exhibits such contempt for struggling Americans, one can only wonder what the truly elite might think about the rest of us. What goes through Jeff Bezos’s mind? What is Bill Gates thinking? What about private equity managers swallowing retailers, veterinary clinics and food and beverage suppliers? Or the tech bros building acres of AI data centers that devour scarce energy resources while sowing the seeds for mass unemployment?

Certainly Jonas isn’t representative of all wealthy people or members of the elite class. But when you understand this mindset — that economic struggle equals moral failure, that the poor are undeserving by definition — it provides fascinating insight into how policies that gut the middle class might have originated. What if we’re not constituents to be served, but instead obstacles to be managed or disposed of? What if we’re not just expendable in economic calculations, but even contemptible?

What if the elite class doesn’t just have different interests than working Americans, but literally view us as a different species? Less intelligent, less disciplined, less worthy of basic dignity and security.

I’ve known Jonas since we were in 7th grade, and I’ve valued our connection through the years. He was my “running buddy” when we were both cutting our teeth on careers in L.A. Even after I drifted to Montana, I tried to find common ground despite our differences because staying tethered to people I’ve shared formative experiences with matters to me. Yet as he’s aged I’ve seen something unpleasant and unsavory slowly emerge in him — and it’s increased in direct proportion to his “success.”

His perspective is especially puzzling because he isn’t a sociopath. I’ve seen him show genuine compassion in other contexts. Jonas has mentored underprivileged kids, helped friends through difficult times, and demonstrated real empathy when it comes to individual suffering he can see and understand. He has deep love and affection for his parents and has spent extraordinary amounts of money for their care.

Yet when confronted with systemic economic hardship affecting millions of Americans he’s never seen or met, that empathy completely evaporates.

It’s replaced by a cold social calculus — an “us” vs “them” mentality that sorts people into deserving and undeserving categories based on their occupations and bank account balances, casually dismissing human worth based on career and economic outcomes. Perhaps when you have multiple caregivers and live in a $3.5 million dollar home it becomes easy to believe that anyone who is struggling or not successful simply isn’t trying hard enough.

And maybe this is how wealth corrupts: not by making people evil, but by creating psychological distance from the lived experiences of others. Maybe wealth allows people to internalize ‘success’ as a reward that affirms their superiority and assuages any lingering guilt.

Our conversation crystallized something else I’ve been sensing for years: the complete breakdown of social solidarity in America. As the ship we all share takes on more water, we should be working together to patch the gaping holes before it disappears beneath the waves. But if the wealthy have climbed into lifeboats without looking back — convincing themselves that anyone on our sinking vessel chose to remain and deserves to die there — then the rest of us are left to face this storm alone.

And what becomes of America, the home we helped build together and that once held such promise and potential?

This isn’t just about economics. It’s about whether we’re a society or just a bunch of people competing for resources. Jonas’ worldview suggests the latter, a Hobbesian nightmare where compassion is weakness and suffering is always deserved.

If there are people with this mindset who control the levers of power, then it could explain what we’re seeing around us now: crumbling infrastructure, declining life expectancy, a toxic food supply, widespread despair, and a political system that serves only the wealthy. A society groaning under the weight of its impending collapse, yet pointing fingers and remaining blissfully ignorant as it happens. Deluding ourselves into thinking the whiff of smoke we’ve caught is a BBQ down the street, not flames devouring our home.

Understanding the mindset of people like Jonas could be crucial if we want to grok why America is failing so many of its people. Our predicament might not be solely the result of incompetence or “misguided” policy. It might be the result of a ruling class that has the power to influence and shape our future — yet convinced itself that economic value is the true measure of human worth.

Until we reckon with the fundamental cruelty of this mindset, we’ll keep wondering why decision makers plot courses that deprive us of basic human dignity. We’ll remain baffled that the richest nation in history somehow can’t provide basic needs for working people.

But the answer might not be so complicated. It could be that people with the power to change things often don’t — not because they can’t, but because they refuse to believe the rest of us deserve better.