by Shawn Roberts
I have worked inside some extraordinarily expensive homes.
Homes with wine cellars larger than my first apartment. Homes with hidden doors, imported marble shipped across oceans, and refrigerators sophisticated enough to probably qualify for voting rights in certain states. I’ve stood in kitchens worth more than entire neighborhoods I’ve lived in while in college in Arizona.
And every once in a while, usually late in the day when the owners loosen up a little, somebody asks the question.
“So what do you think?”
What they’re really asking is whether I’m impressed.
Sometimes I am.
Beautiful craftsmanship is beautiful craftsmanship. A hand-cut dovetail joint still deserves admiration whether it’s inside a billionaire’s library or an old fishing shack. Skill is skill. Vision is vision. There’s nothing noble about pretending otherwise.
But wealth gets harder to define the longer you work with your hands. Because eventually you start noticing something strange. The happiest people are almost never the ones trying hardest to look rich.
Real wealth has a completely different feeling to it.
You notice it in the old couple drinking coffee barefoot on a weathered porch they paid off thirty years ago. In the fisherman whose truck frame is rusting out from putting in at Children’s Beach for the past decade, but whose children genuinely enjoy being around him. In the carpenter who owns three good tools instead of thirty shiny useless ones. In the woman who somehow knows every single person at the grocery store and still has time to ask how their mother is.
There are people on Nantucket worth fifty million dollars who seem spiritually exhausted. And there are tradesmen and landscapers with sawdust and sand on the floorboards of their trucks who stand together at Fisherman’s Beach and laugh like kings. That contradiction fascinated me long before I had words for it.
Growing up around extreme wealth gives you a strange perspective on human nature. You learn very early that money amplifies people more than it changes them. Generous people become more generous. Insecure people become impossible. Calm people grow more comfortable. Narcissists simply purchase larger stages for themselves.
Money solves many problems: anybody pretending otherwise is either lying or has never struggled financially. A warm house in February matters. Health insurance matters. Being able to buy groceries without anxiety matters. But beyond a certain point, wealth becomes psychological rather than material. And psychology is where things get interesting.
Some people own beautiful homes. Other people are owned by them. You can feel the difference immediately.
There are houses so immaculate they almost feel medically sterilized. Nobody sits in the living room. The kitchen looks untouched by hunger. Perfect white couches stare out toward the harbor like museum installations. Everything is expensive, yet nothing appears fully alive.
Then there are homes where the floors creak, dogs wander through sandy kitchens, coffee mugs collect near the sink, and the porch furniture never quite matches. Somehow those places feel infinitely wealthier. Not because they cost more—because people actually live there.
A carpenter notices these things.
You start understanding that ownership and stewardship are completely different concepts. Some people buy houses as trophies. Others care for them like living organisms. The first group worries about resale value. The second group worries about whether the place still feels warm during a storm. Only one of those people understands the home.
The island teaches this lesson constantly.
Nantucket itself is a strange collision between enormous privilege and brutal reality. Billionaires may arrive on private jets, but eventually everybody still ends up standing in line at the Steamship when the weather turns bad. The Atlantic remains the final authority here. Salt air corrodes everything equally. Pipes freeze without caring about your stock portfolio. A northeast gale can humble almost anyone.
That keeps certain truths alive.
You can always tell the people who understand the island from the ones merely consuming it. The people who understand it move differently. They respect weather. They know the ferry schedule by heart. They wave at Five Corners. They own practical jackets instead of fashionable ones. They don’t panic when plans change because they already understand that coastal life runs on negotiation rather than control. That kind of adaptability is wealth too.
So is competence. Modern society wildly underestimates the emotional security that comes from knowing how to do things yourself. A person who can repair his own roof before a storm sleeps differently than one completely dependent on calling someone else. A person who can cook, grow vegetables, navigate by instinct, or remain calm during a power outage possesses a kind of ancient prosperity that never appears on financial statements. Competence reduces fear.
And fear, more than poverty, is what seems to imprison most wealthy people I’ve encountered. They fear losing status. They fear aging. They fear discomfort. They fear being irrelevant. They fear stillness.
You see it in the architecture sometimes. Entire homes designed around distraction. Home theaters, game rooms, bars, spas, gyms, entertainment wings. Massive houses built almost defensively, as though silence itself might become dangerous if given enough empty space to settle into.
Meanwhile, some old carpenter sits on a five-gallon bucket watching a sunset with a beer and feels perfectly content.
Who is actually wealthier?
The older I get, the more I think freedom may be the purest form of wealth available to human beings. Freedom to sleep deeply. Freedom to speak honestly. Freedom to disappear for an afternoon without needing to prove productivity. Freedom to sit quietly on a dock without scrolling online. Freedom from constant performance.
That last one is becoming rare.
Modern life pressures people into branding themselves endlessly. Everybody is curating an identity now. Wealth especially has become theatrical. Entire lives constructed around appearing successful to people whose opinions don’t actually matter.
But carpentry strips away performance very quickly. Wood does not care about your social status. A board is either level or it isn’t. A roof either leaks or it doesn’t. A porch either holds weight or falls into the scrub oaks and sand.
Physical reality is refreshingly uninterested in ego.
Maybe that’s why tradespeople often develop a different relationship with money. After enough years building things with your hands, you start valuing solidity over appearance. You become suspicious of surfaces designed only to impress. You also realize how temporary ownership really is.
I have renovated enough historic homes to understand that none of us truly possess these places permanently and found enough coins, newspapers, letters behind fireplaces to know their stories. We borrow them for a while. We repair them. We damage them. We leave fingerprints behind.
Then somebody else arrives and repeats the process.
The houses outlive almost everybody. So do ships. So do islands. So do certain stories.
In the end, I don’t think wealth is measured by square footage, investment accounts, or how expensive your kitchen appliances are. Those things may indicate financial success, but they say almost nothing about whether a life feels meaningful once the noise dies down.
A carpenter’s definition of wealth is simpler.
Good work. Useful skills. People you trust. A body still capable of labor. A few close friends. Enough time to notice sunsets. Enough humility to keep learning. Enough resilience to survive winter. Enough perspective to know that no amount of money can buy back lost time.
And maybe, if you are truly fortunate, a weathered old porch somewhere near the Atlantic where you can sit at the end of the day listening to the wind move through the cedar shingles, feeling rich in all the ways that cannot be photographed.
