I just spent eight days in Italy, and I did not want to leave.
Now of course, that's typically how vacations feel. By nature, they're stress-free, lighter, more full of the things that light you up.
In the small Tuscan town of Capalbio where we spent our time, breakfasts were long, lunches longer; wine that costs less than the sparkling water.
Nobody was on Slack, email.
And somewhere around day five, I caught myself checking local real estate listings, doing the math and pricing out houses in the country that we could somehow imagine ourselves living in.
But eventually, I landed back in the States, and I asked myself a dumb little question.
Why am I actually back?
The easy answer, of course, is that Italy was vacation, and I live here.
But the question stuck around for me longer than I thought.
And here's why.
A guy in Italy wanted in.
While we were there, a local entrepreneur got to talking with my sister and brother-in-law and asked them a pointed question, one you could tell he'd been wrestling with.
He’s young — wants to build something of his own, make real money, maybe have kids and a better life for he and his girlfriend. And he wanted to know, straight up: is America still the place to do that?
Is the American Dream alive, or is it just an old story we like to tell?
Here I was, sitting on the tarmac in Philadelphia, wondering why I'd ever left Italy in the first place. And a guy standing in that same beautiful country was looking across the ocean at my country, wondering if it still held the thing he wanted.
Scott Galloway said something on his podcast recently that stuck with me. Paraphrasing, but it was basically this: America is the best place in the world to make money, and Europe is the best place to spend it.
When I heard that, my whole trip clicked into place.
The entrepreneur and I were standing on opposite ends of that exact line.
He was eyeing the money side. I was eyeing the living side.
Same dream, split in half.
But it raised the real question.
If the American Dream is just about making money, that's one thing. If it's about living a good life, that's a completely different thing.
And to answer the entrepreneur, or even define the term, you have to stop and ask what it actually means.
The man who named it didn't mean money.
Turns out the American Dream isn't as old as the country; it wasn't handed down from the Founders.
A historian named James Truslow Adams coined it in a 1931 book called The Epic of America. Depression-era. Breadlines. The worst economy the country had ever seen.
That's when the phrase was born.
And, it turns out, Adams didn't just mean money.
He wrote that it was the “dream of a better, richer and happier life for all our citizens of every rank”.
Richer, sure. But also happier.
He went out of his way to say it wasn't a dream of fancy cars and high wages.
He warned – all the way back then – that Americans were so busy trying to make money that we were treating it “as a value”, and sometimes forgetting how to live.
He wrote that in 1931. Already worried we were turning it into a money thing.
Want to know what symbol he picked for his whole idea of the American Dream?
A room the country built for itself, where a janitor and a senator could sit at the same table and read the same books.
That was his American Dream. Access. Dignity. Education. The same shot.
So the man who named the thing we sometimes argue about wasn't telling us money doesn't count. He said richer. He just refused to stop there. He said better, and happier, too.
Somewhere along the way, we kept the first word and maybe started to drop the second.
So let's start where most people start. The money.
The climb became a coin flip.
Forget arguing over wages and savings rates.
Let's instead start with maybe the cleanest measure there is: do kids end up better off than their parents?
A Harvard economist named Raj Chetty ran exactly these numbers using census data and tens of millions of tax records.
He tracked how many American kids grew up to out-earn their parents, by the year they were born.
The result is brutal in how simple it is.
If you were born in 1940, you had about a 90% chance of out-earning your parents, which means it was basically a sure thing.
If you were born in the 1980s, it plummeted to about 50%.
Chetty's own way of putting it: "It's basically a coin flip as to whether you'll do better than your parents."
A coin flip.
The part of the dream we usually mean, the climbing part, went from a near-guarantee to a coin toss in two generations.
Now, that study stops at kids born in 1984. Not because anyone's trying to hide more up-to-date data. But to measure whether you out-earned your parents, you have to wait until you're about 30 and see where you landed. The 1984 kids hit 30 in 2014. Everyone younger is still mid-race.
Now, before this turns into a political thing, here's the honest truth about that data, because the drop isn't due to the economy's growth just coming to a grinding halt.
By most accounts, the American economy keeps chugging along.
And yeah, part of this is just math. It's easier to beat your parents when they're poor, and the 1940 kids were measured against people who came up in the Depression. A richer country sets a higher bar, so some slippage is automatic.
But Chetty ran the numbers two ways. Keep the economy exactly as rich as it is now and just split the gains the way we did at midcentury, and about 80% of kids would still out-earn their parents, instead of 50%.
The bar isn't the problem. The slicing is. The pie's still growing, we're just cutting it a lot less evenly than we used to.
The stuff that builds a life got expensive.
But income is only half of it. The other half is what your income has to buy.
Buying power. Inflation. Etc.
And here, both your optimistic uncle and your broke cousin could be telling the truth at the same time.
An economist named Mark Perry has been tracking the price of stuff since 2000 against wages, using government data.
People call it the Chart of the Century.
Here's the gist:
Look at the split.
Average wages beat inflation, but don’t forget, average is a slippery word. The typical worker barely kept pace, and men without a college degree actually lost ground.
But, regardless of the split, wage growth was real, and the optimists who point to it are completely right to say it. And the stuff that fills up a house, the TVs and the toys and the gadgets, it all got dramatically cheaper.
A TV that ate a chunk of a paycheck in 2000 is basically free now.
But you also have to look at what went the other way — hospitals, college, childcare, going to the doctor.
The exact things you need to build a stable life and climb a rung blew past both wages and inflation.
So here's the summary: The stuff that fills a life got cheaper. The stuff that builds one got way more expensive.
We added years. But mostly sick ones.
There's one more scoreboard that's worth looking at. Because we all hear it quoted often.
"We live longer than ever." And we do. That's true.
And unequivocally, I think, that should be a good thing.
But I always wondered. Longer, okay. But is it better?
Welp, a Mayo Clinic study in 2024 compared lifespan, how long you live, to healthspan, how long you live in decent health, across 183 countries.
The US has the widest gap in the entire world. Americans now spend about 12.4 years, on average, alive but in poor health at the end of life.
And here’s an absolutely scary stat. Between 2000 and 2019, American men gained about 2.2 years of life expectancy. Healthy years went up by 0.6.
We added time… we just added most of it as sick time.
Remember Adams's word? Better.
He didn't necessarily say longer.
A life can get longer and worse or emptier at the same time, and on this measure, that could be what we've done, it's just so hard to say.
The part no chart measures.
So far this sounds grim, and I don't want to be dishonest in the other direction.
Because there's a whole layer of the American Dream that doesn't show up on any of the charts above, and many of us live it every single day.
In a lot of the world, you can't just decide to start a company on a Tuesday and have it registered by Friday. Here you can.
In a lot of the world, your daughter doesn't get the same shot as your son. Here, on paper and mostly in practice, she does.
In a lot of the world, you grease a palm to get a permit or a court date or a fair hearing. Here, mostly, you don't.
Our institutions are slow and messy and they can drive you up the wall, but they mostly work, and they mostly aren't for sale.
The vote. The courts. The right to say anything you want about your own government without a knock on the door. Women owning their careers and money and choices. The freedom to fail at a business and go instantly start another one.
We treat all of that like background music, but it's not.
For most of human history, and for most people alive right now, that is the dream.
The money stuff is what you get to argue about after you already have the freedom stuff.
The one thing we actually lost.
But there's one piece of Adams's vision we've genuinely lost, and it's the piece he may have cared about the most. The reading room. The shared table. The whole idea that a janitor and a senator could sit in the same room and belong to the same country.
I hate the fact that we’ve sorted into corners where the other half of the country isn't a neighbor with a bad or differing opinion, rather, they're the freaking enemy.
The share of us who call the other side flat-out immoral has jumped in just the last decade, and you can feel it in every conversation that brushes against politics, every public square, and every corner of social media.
But also important to point out, for the record, we have actually been much worse!
Any Civil War historian will tell you today's fights pale in comparison to a decade that killed 620,000 people. We’re not there.
But Adams never said the Dream was the absence of a war or plain old catastrophe, he said it was the room, the same table, the same shot.
And if you judge the Dream by the people believing in the same table, the same shot, then things aren’t looking great.
In 2017, almost nobody under 30 said the dream was out of reach for them.
By 2024, about a third did.
And the number, not unsurprisingly, is worse for those in lower income brackets, without college educations.
The people who are supposed to be chasing the dream are the ones deciding that maybe it's just an old story, passed down with nostalgia, but no longer really relevant to them.
There used to be a formula.
Speaking of nostalgia, I keep thinking about my Dad.
He grew up poor, served in Vietnam, barely ate out until adulthood, saved every penny, ground through eight years of school, and bootstrapped his way into the middle class as a dentist.
When I was a kid I asked him once why he loved it.
Why he "chose" dentistry.
He kind of snickered, but didn’t BS me for a second.
He looked up and said, basically, "I didn't love it. But back then, there were three ways a poor kid could get ahead. Lawyer, doctor, or dentist. Becoming a dentist was just the shortest path."
That was the whole plan, and to my Dad's credit, that was a solid plan.
The formula was simplistic by design. Study hard, graduate high school, save every dollar you made, go to college. Get a job or build a business.
Do that, and you'd land in the middle class, upper middle, if you were lucky.
Follow the steps, get the result.
Can you say that anymore?
That linear path my Dad walked, the one with a map and a feeling of guarantee, is mostly gone.
The out-earn-your-parents coin flip proved it.
Nobody can hand a kid that clean a formula today and mean it.
You have to define your own dream now.
But here's where I land, and it's what I'd tell the Italian entrepreneur if I were still there.
The dream isn't dead. But it is not easy to see.
Nobody's going to tell you which of the three jobs is the shortest path, because there aren't three jobs anymore, there are a thousand, a million, and most of them didn't even exist when my Dad picked his.
The guardrails are gone. So is the work-hard guarantee.
But what's left is still the chance; the shot at a fuller life, on mostly your own terms, that a lot of the world still doesn't get.
My Dad knew exactly what he wanted and walked a straight line toward it.
Today, the straight line may be gone, but you get the choice, the freedom, and a country that still, for all it’s problems and flaws, let’s you bet on yourself and start over when you lose.
You have to define your own American Dream now, and then you have to go grab it.
That's harder than a formula. But I'll take it. And my guess is, so would the guy in Italy.
I know this version of the American Dream reflects the advantages I had, many of which were never available to everyone and still aren’t. This is one person’s view, not the whole story, and I’m aware that for a lot of people, this moment feels far more precarious than hopeful.
If you liked this, you may like my 2025 Year In Review (on idle time, work, money, health, and relationships).
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