When Privilege Dresses as Character

Monopoly is commonly remembered as a fun family game, but it began as an economic model. Its earliest version, The Landlord’s Game, was designed by Lizzie Magie and patented in 1904 as a way of illustrating anti-monopoly ideas associated with Henry George. Only later did it evolve into the familiar commercial version associated with Charles Darrow, which Parker Brothers mass-marketed in 1935.

In a strange way, that history already contains the whole theme of this essay: a system designed to expose structural inequality is now remembered as a game about personal skill.

And Monopoly itself has also been used to illustrate something very similar. Psychologist Paul Piff became known for a series of rigged Monopoly games in which one player was randomly assigned structural advantages: twice as much money, double salary for passing Go, and two dice instead of one. As the games progressed, the advantaged players tended to grow louder, more dominant, and more convinced that their success reflected strategy rather than structure. Piff’s broader peer-reviewed research points in the same direction: privilege does not merely shape outcomes, but often profoundly reshapes self-perception.

To me, that is almost a perfect miniature of upper-middle-class tech-bro ideology: the fantasy that they obviously got where they are through grit, discipline, and hard work. But is that really the full story?

Take Jeff Bezos. Yes, Jeff built. Of course he built. But lots of people build. Lots of people work obsessively hard. Some work so hard they go broke trying. The differentiating factor is often not effort, but the margin for error around effort. Bezos’ parents reportedly invested nearly $250,000 in Amazon in 1995 — an early family cushion that most founders will never have, before we even get to networks, confidence, and the kind of background that makes further financing imaginable rather than absurd.

And so that I’m not only picking on a white man, let’s pick on a white woman too. Taylor Swift can obviously sing. She clearly has presence. But many girls from country towns can sing and have presence. What they usually do not have is a family with the capital and industry proximity to materially de-risk the beginning of a career. Billboard has reported that Swift’s father held about a 4% stake in Big Machine, while Music Business Worldwide, citing a subscription agreement it said it obtained, put that early investment at $500,416.66. That does not cancel talent. It simply means talent was accompanied by capital, proximity, and protection — the very conditions most others lack.

These examples matter not because privileged people are vain, but because their biographies become public myths. And those myths train everyone else to misread the system they live inside.

I remember a girl I met at university who started talking about being some kind of vice–Miss of a province. I tried to be polite, congratulated her, and then in a moment of honesty — or maybe because she sensed from my vibe that I was “from the same world” — she felt the need to tell me what it actually was. She said, “Come on, you know how this works.” Then she explained that the parents of the selected girls had met in some restaurant and effectively bid for the positions: who would be Miss, who would be Vice-Miss. Everything else was stage acting, because everybody already knew which place daddy had bought, and the audience vote meant nothing. It was just there to create the illusion of community validation: so many people voted, therefore she must be valuable.

But why all this effort? Not just ego. Rich people are usually not that stupid. The point was the pinned Instagram photo from the award ceremony, and above all the social proof: Miss Province 2023. Social proof as story. Social proof as brand. Social proof as leverage in negotiating collaborations.

In my previous essay, I wrote about simplifications and symbols — why they work, and why we keep falling for them. And the answer is simple. In an overload of information, once a person arrives pre-packaged with social proof, the mind takes a shortcut: “Okay, people seem to agree she’s attractive, she also seems nice enough, I can give her a follow.” None of it has to be true. But it is a very beautiful illusion.

And that is what these bought symbols really do. They do not merely decorate a life. They make advantage legible. They turn family capital into a public aura that looks organic from the outside.

The parent buys the title so that the daughter will finally begin doing something, even if that something is as trivial as becoming an Instagram model, moving out, turning herself into a project. And the deal is simple. Other people are supposed to buy into the story so that she can keep living her small comedy as if it were destiny. Poor people often do not realize how much effort wealthy people put into manufacturing the image of bottom-up uniqueness: “I’m just like you — I just worked hard” or “fate happened to choose me.”

All of that just to build a light life. A life of brand deals, stories, vlogs — advertising whatever can be advertised to people who still work normal jobs inside the system.

I’m especially sensitive to this kind of bullshit because I grew up inside that upper-middle-class atmosphere myself. Not on that scale, of course — a small town, a still-developing Poland, born only six years after communism collapsed, so that status did not mean what it means now, nor what it means in the West. But later I lost it. Or rather, my whole family lost it, sliding into bankruptcy just as I was entering adulthood. Because of that, I have that unusually rare perspective of having lived on both sides.

I know what kind of cloud people float on when they have privilege and a wide margin for error — when the world feels full of possibilities because so many doors are quietly open in advance. And I know what it’s like on the other side, when 60–70% of your income goes to housing, when you live in a permanent squeeze, without any real safety buffer, without room for mistakes. It is one thing to choose discomfort as exploration, and it is another thing to actually be trapped inside it.

What makes the whole thing ugly in a deeper way is not merely that the board is already bought up. That part is banal. The uglier part is that people have somehow been sold the mythology of individualism and the self-made self, which allows the people I’m describing to stage their little comedies however they want.

That is what individualism does to us. The board is already owned, yet people keep believing that if they just outrun the next person, they too might become owners instead of workers.

And this fantasy survives on stories exactly like the ones above: radically incomplete stories designed to tell people that everything is possible if you just want it badly enough. For most people, the practical result of believing this is nothing. Masses of people wake up early every morning, want very badly, and work very hard. That is not extraordinary in the world of working people.

The trap is almost perfect because even when someone really does change class, they usually will not say, “I entered at the right moment, in the right technological cycle, and caught a rare wave.” They will almost always write themselves a different story: “I worked hard, I sacrificed, I deserved it.” And the system loves showing such a case back to everyone else: “Look, it worked for someone, so stop complaining — clearly it can be done.”

But what actually separates us is much simpler than all that moral theater: not all of us were given the same number of dice rolls, and not all of us started from the same square. Even I, despite losing almost everything, including my family home, still carry a huge dividend from the social and cultural background I once had. It still gives me chances in life, because someone once took me to different places, showed me parts of the world, signed me up for various activities, widened my horizon, paid for extra lessons. Those things do not disappear just because money later does.

And there is nothing wrong with someone saying, “You know what, I had it easier. A lot was invested in me.” A clip used to circulate in the Polish internet in which a girl living in one of the most expensive apartment buildings in the country was asked by a journalist, “How did you do it?” and she answered with one sentence: “Mom, Dad.” To me, that is perfectly fine.

After all, who wouldn’t want to give their child that kind of start — enough money, status, and insulation that they could do what they want, where they want? There is nothing wrong with money. Nothing wrong with status. Nothing wrong with beautiful things. The problem begins when advantage puts on the costume of virtue and asks everyone else to mistake it for character.

That is the real confusion here. Privilege itself is not the scandal. Every parent wants to help their child. The scandal begins when structural advantage is retold as moral superiority — when having more capital, more protection, more access, and more room for failure gets translated into a story about discipline, courage, and exceptional inner worth.

That is the same mistake the advantaged players make in the Monopoly experiment: they are given more starting capital and more room for movement, and then slowly begin to mistake structural advantage for character, discipline, and personal merit.

I’m not sure I have a positive ending here, because all of this is rooted in human egocentrism, while behavior is constantly shaped by structural pressure as well. But much of it would become more bearable if people with privilege could simply put their ego in their pocket, say “Mom, Dad,” and then try to make themselves useful instead of building elaborate myths about their uniqueness. Maybe that is utopian. Or maybe I’ve managed to persuade at least one such person that this is both more honest and, in a strange way, more freeing.