What Money Can’t Buy
The Wisdom Problem Series 6 of 7
Sixth in the series The Wisdom Problem. Begin with Essay 1 here.
I remember thinking a lot about Michael Jackson as a kid.
Not even 10 years old, playing with trucks in the dirt on a few acres outside Omaha, I recall thinking: it must be so strange to be Michael Jackson!
And it must have been. He was brilliant, celebrated, troubled, unable to rest inside his own skin.
And so alone. Who could have possibly related to his life?
I sense he deeply wanted to be loved, but ordinary human connection became inaccessible. As if the accumulation of wealth and fame had not given him more life, but somehow less.
This MJ curiosity foreshadowed a proximity-to-strangeness thread in my life: early work in the bureaucracy of Catholic Bishops, a brief and unlikely closeness with my favorite folk singer, doing farm chores with Winona LaDuke, lunch with Gandhi’s grandson, an eventual career involving uber philanthropy and the inner life of high net worth families.
That’s a peculiar path. At every step, I’ve wondered: are these people happy?
At home with the Bezoses
A recent New York Times profile of Lauren Sánchez Bezos offered an extended, sympathetic glimpse into the life of one of the world’s wealthiest couples.
The details are worth repeating. Lauren and Jeff wake each morning in their $230 million compound on a private island. They don’t touch their phones. They list ten things they’re grateful for — and can’t repeat what they named the day before. They drink their coffee from matching novelty mugs and work out an hour daily with a private trainer.
The gratitude practice, the intentionality, the shared rituals — they are cultivating connection. And yet something about the portrait furrows my brow.
Jeff Bezos was once described as “mildly awkward, faintly hermetic in Seattle.” In recent years, he has transformed his appearance and personal idiom: gym-hardened, frequently shirtless, surrounded by celebrities, the founder of a rocket company. Dr. Jacque Lynn Foltyn, professor of sociology at National University, San Diego, observed: “He believes in winner-takes-all, from Amazon and delivery to space. He’s conquered everything. And now he’s bringing it down to Earth to rebuild his body.”
The same mode of relating to the world — conquest, optimization, the relentless pursuite of measurable outcomes — turned toward self-presentation.
What is the lesson being modeled here?
It seems that a teenager’s preoccupation with appearance and popularity outlasts even the greatest business achievements and accumulation of wealth.
Does the teenager’s inner uncertainty outlast it too?
The science of flourishing
Martin Seligman spent decades studying human flourishing. His PERMA framework identified five building blocks: Positive emotion, Engagement, Relationships, Meaning, and Accomplishment.
What’s striking is how systematically the accumulation of wealth can work against these building blocks.
Relationships become distorted. When your wealth is large enough to determine other people’s outcomes (employment, opportunities, access), friendship gets…complicated. Who is present because they genuinely like you? Who sees you as a walking ATM machine? Same goes with family life. Think of your most recent family holiday. Imagine the tiniest miscommunication, competition, or past hurt amplified by the charge of extreme wealth.
Meaning — a sense of greater purpose — tends to develop through contribution, through the experience of being genuinely needed. Not as a distant donor or investor, but as a person whose particular skill and effort had a concrete impact on a shared endeavor. In this way, setting a table can be more meaningful than buying a golf course.
Engagement requires difficulty. Mikhail Csikszentmihalyi’s study of flow is the peak expression of what Seligman calls Engagement — both describe the state of being fully absorbed in something that stretches you just beyond your comfort zone. The key word is stretches. Flow requires challenge.
It’s often said that the way to build wealth is to earn money while you sleep. Nobody questions this. But has anyone considered the cost? What gets lost when our reward is disconnected from the expenditure of challenging effort within the limits of time?
Perhaps what’s lost is Seligman’s Accomplishment — the deep satisfaction of having made something, solved something, learned something through sustained effort. I’ve described this elsewhere as the joy of doing it yourself. It’s a felt sense of earned integrity and self-respect from having struggled and gotten somewhere. A garden grown. A song completed. A skill painstakingly developed.
This is not romantic nostalgia for manual labor. It is pointing at something the research consistently confirms: the path to a deep sense of fulfillment runs through effort and engagement with reality, not finding a way to bypass it.
What the PERMA framework reveals is that the conditions conducive to human flourishing are akin to the conditions that extreme wealth tends to erode.
Ironic, eh?
The stimulation trap
Maybe we got here by mistaking stimulation for fulfillment.
The very wealthy live extraordinarily stimulated lives. The finest food, the most beautiful environments, constant proximity to magnetic people, endless novelty of travel and experience and acquisition. And simultaneously, an elaborate project of maintaining youthfulness. The Botox, the trainers, the optimization of the body against the evidence of time.
What is it like to feel disappointment, failure, or grief from within a state of hyper-stimulation? Are difficult experiences allowed? Do they have space to breathe and be processed?
Or does the machinery of stimulation extract the benefits of life’s challenges? The next event, the next achievement, the next curated experience arrives quickly enough to prevent beneficial encounters with difficulty.
The collateral damage is depth of experience and the process of gaining insight.
When Bezos and crew returned from space, their responses struck many observers as weirdly incongruent with the magnitude of what they just experienced: a glimpse of Earth from space. Astronauts consistently describe it as transformative, spiritual, even shattering.
But based on the Bezos team’s reaction, you’d think someone just sank a long putt.
Did even this rarest of human experiences become somehow trite — absorbed into a life so stimulated that even the view from space was, ya know, pretty cool?
The NYT journalist asked Lauren whether the couple ever wonders about the effect their life has on others. The question slid away unanswered. Lauren spoke of wanting to give everyone flowers. Of spreading joy into every room she enters.
Those are not bad impulses.
But some moments require a different quality of presence — the willingness to ask “how are you?” and patiently listen to a meaningful, meandering, uncertain answer. The ability to hold space for the broken heart of a loved one without rushing to fix it. A freedom from the need to be clever and camera-ready. It’s hard to hold that kind of awareness in a hyper stimulated life.
This stimulation trap is not only a billionaire problem. It is the organizing logic of the attention economy that most of us swim in daily. The scroll, the notification, the algorithmically curated next thing, the coffee and then the more coffee.
We have all grown weak in the capacity to be nourished by what is freely given rather than purchased or performed.
A child knows the difference instinctively — the absorption of playing in dirt, the complete sufficiency of a good stick.
Our culture conditions this abundant enoughness out of us.
What the trees know
I like to hike. On a recent outing, I’d been moving at a good pace for a while — focused on physical exertion, climbing higher, letting my monkey-mind thoughts swing to and fro — when something shifted.
I quietly and suddenly dropped into an awareness of my own basic awareness: the immediate, felt experience of being on a path, breathing in a beautiful environment.
It happened without my trying. The cognitive chatter fell quiet, and what remained was something calmer and more expansive — a state I recognized but hadn’t sought.
In that state, I could literally sense the aliveness of the trees around me. They felt present the way another person is present in an elevator, but without the awkwardness. I felt fondness for them. Love, even.
It was simple, really. I was feeling the aliveness that is shared by all living things — that people and animals and plants have, but that no manufactured thing can simulate.
I smiled, thinking of how the trees were not performing. They were not managing an impression. They were simply doing what they do — converting light into life, exhaling what I need to inhale, inhaling what I exhale — without the need for validation.
And that is a kind of freedom.
In this same way, the ground of human wellbeing is not stimulation. It is not the accumulation of positive experiences. It is something more like the direct, felt sense of being alive and present in a world that is also alive and present. Sensing the dappled warm glow of light through leaves, the quiet hush of wind high in the branches, the breath moving in and out. Interdependence felt rather than theorized. The trees are breathing and so am I, and we need each other for that to be true for any of us.
This did not require a subscription. The light didn’t give me a 15% discount on my first order. The wind didn’t want my email address.
This experience cost nothing. It is abundantly available. It requires no compound on a private island, no private trainer, no novelty mug. It requires only enough interior quiet to receive it — which means enough freedom from externalities that the miracle of being alive can register from the inside out.
That freedom is harder to access when you are overstimulated. When your attention is perpetually monetized — by social media, by the entertainment economy, by the architecture of a life organized around generating and sustaining an image.
Being a maker has the same quality. The joy of doing something with your hands, of learning a skill slowly and imperfectly, of making something that didn’t exist before. It returns you to a relationship with reality that is not mediated by money or virtual transactions or the opinions of other people.
It also points to the dignity of work. There is beyond-monetary value of an economy built on effort and productivity that do not extract human wellbeing or nature’s integrity.
When you are simply engaged with something undone, getting incrementally better, occasionally delighted by your own progress, the satisfaction is deep and specific.
This is not luxury. It is fulfillment.
Try this
Do you want to try accessing this state right now? Here’s a simple practice.
Recall a time when you were genuinely fulfilled. Not just succeeding, but fulfilled and flourishing.
How old were you? Where were you? Who was present? Let the sensory details come back slowly: what you would have seen, heard, smelled. Let them surface in your memory, in your body. Roam among them. Let them linger.
Now see if you can regenerate the physical sensations of that time — the warmth, the openness, the posture. Use your imagination. Let it show on your face.
Hold that for thirty seconds. Make it 2X more intense. 5X!
Now sustain the sensations, but let the memory recede. Marinate in the sensations.
Notice the state you are in.
That’s you, right now. It was never somewhere else.
It’s available to you right now.
The paradox of wealth and what it reveals
My point is not to shame Lauren and Jeff, or anyone in a context of wealth.
I’m pointing at the paradox that the experience of extreme wealth tends to undermine the experience of genuine flourishing. That is consequential for the wealthy, and for the rest of us too.
Some AI proponents envision a “workless” future where humans have lots of free time. Even if that’s possible (plenty think it’s a pipe dream), it sounds a lot like the reality of living in wealth.
Would anyone flourish in that future?
Instead, could AI help humanity enjoy both wealth and radical self-acceptance? A repair of broken relationships? A way to find joy in differences?
I think it’s worth mentioning MacKenzie Scott here. She has given away roughly $26 billion, largely anonymously, with few conditions. She married a high school teacher. She appears to have reorganized her life post-divorce.
I don’t know her interior. But her choices appear structurally more aligned with what the research suggests produces flourishing — contribution, relationship, meaning over stimulation.
What does all this reveal about all of us who aren’t wealthy? What we reward, what we support, what we celebrate, what we strive for, what we hold up as the image of a life well lived?
That is where the final essay is headed.
Next week: the last essay — a theory of change and what each of us might do with it.