The Wealth Illusion, When Having More Feels Like Less

Loss is not the first step. It starts out with plenty, so much so that even the joy gets stale. At first, you are unaware of it. A five-star suite no longer feels opulent. Nothing new is sparked by a new car. An additional zero on the account only adds more distance.

Freedom is supposedly brought about by wealth, and it does. However, it also frequently brings with it a more subdued burden: a gradual, increasing detachment from daily life. Many ultra-wealthy people, especially those who have been wealthy for over ten years, are now attempting to return to normal life—not as a gimmick, but as a means of regaining their sense of groundedness.

They’re not looking for luxury. They are paying for their economy flight. They are making reservations at rustic hostels. They are learning how to make their own dinner or cut wood. Recently, a Manhattan investor told me, almost sheepishly, that he traveled upstate alone on Amtrak only to sit with strangers and purchase a $12 sandwich from the cafe car. He remarked, “It made me feel like myself again.”

Although the motivations differ, their emotional foundations are remarkably similar. The hedonic treadmill, as defined by psychologists, is the theory that as income rises, expectations rise at the same rate, and the joy that comes from material gains decreases proportionately. The second week makes a larger house feel smaller. A high-end purse becomes the backdrop. The excitement fades.

The fear of exposure, rather than poverty, is equally urgent. Many wealthy people talk subtly about their anxiety, not because they are poor, but rather because they are afraid of being distrusted. It feels riskier to be in a relationship. One could consider gifts to be bribes. Conversations have underlying meanings. A discreet philanthropist revealed that she keeps her activities a secret from new acquaintances “because I never know what they’ll want from me.”

Many people seek anonymity as a result of this perceived loss of authenticity. They are drawn to environments where status is unimportant. where no one shakes hands and then Googles their name. They seek moments of connection that seem spontaneous and unplanned. They therefore change, sometimes drastically.

A tech founder moved into a modest craftsman bungalow in Portland, giving up his $20 million home. He told a local journalist, “The first night I slept there, I felt more relaxed than I had in years.” There was a change in the silence. The room seemed human-sized. Three HVAC systems did not filter the air.

This isn’t a kind of pain. Selective discomfort is what it is. the kind that people voluntarily pay for. It is intended to shock the system—to feel something again—much like a silent retreat or a cold plunge. There’s a reason why “simplicity” is now the main selling point of a lot of upscale retreats. Silence is what they sell. Time. simple food. Make eye contact.

I once strolled through a high-net-worth individual-only minimalist retreat in Arizona. Cell phones were prohibited. There were no TVs, mirrors, or minibars in the rooms. Nevertheless, the attendees, many of whom were founders and senior executives, appeared genuinely relieved. A retired venture capitalist in her 60s told me it was the first time she hadn’t considered her balance sheet in years.

The simplicity is about control, not style. A life with fewer choices becomes very appealing when everything is carefully chosen, promoted, and optimized. You start asking, “What can I let go of?” instead of, “What should I upgrade?”

For the ultra-wealthy, minimalism is not a sacrifice. This is a recalibration.

I asked a private wealth manager I spoke with what trend he saw most among his more recent clients. “They’re scared,” he stated. “Of meaninglessness—not of markets.” I was reminded of that statement. We frequently believe that having money protects one from existential angst. However, he clarified that money frequently makes it worse.

Rich people frequently bargain the hardest—not because they are stingy, but rather because they are out of control. Someone on Reddit brought up the fact that wealthy people will tip a cabbie $2 but spend thousands on fine dining in one night. Anchoring is more important than quantity. having a sense of control over the transaction. being regarded as astute rather than stupid.

But as the cost of disconnecting becomes too evident, that mindset gradually starts to erode. Many people start subtly investing in relationships rather than profits. Legacy, not leverage, is their top priority.

Because of this, a lot of people are now drawn to giving in ways that seem impactful and instantaneous. donations that are anonymous. initiatives driven by the community. mentoring. Interestingly, they don’t always want their name to be displayed on a wall. Instead of their title, they want their presence to have meaning.

As I thought about this, I recalled something a friend of mine said to me after he sold his business for eight figures. After going off the radar for a few weeks, he eventually rejoined his local volunteer group, which he had joined prior to his success. He remarked, “They knew me as a guy who cleaned the sidewalk, and I liked that version of myself.”

I was surprised to hear that statement.

The idea that wealth causes misery is not paradoxical. It’s that unchecked wealth causes distortion. And many are now taking conscious steps to reintroduce friction in order to correct that distortion. to experience moments once more. to not have your days controlled by portfolio updates.

Old sneakers are worn by some. Others prepare all of their own food. Many deliberately hide their way of life. Some people still have cracked iPhones. These are reminders, not affectations.

A new type of luxury has surfaced in recent years, one that prioritizes presence over performance and transparency over polish. People desire to be perceived as human once more. Not merely “rich,” but stable, trustworthy, and well-known.

It’s amazing that the same individuals who previously paid for exclusivity are now paying for inclusion. Not in private clubs, but in important discussions. They long for environments where no one evaluates their value.

And maybe they’re discovering something surprisingly uncommon in that peaceful return to the norm: peace that can only be chosen, not purchased.