Digital Nomads
(Millennials & The New American Dream)
by Jett Dunlap
Recently, I was on the phone with a close friend—we’ll call him Mr. Fish. He’s in his early forties and living with his parents; a situation shaped as much by economic forces as by his own choices. We both fall into the category of Elder Millennials: caught between the sardonic yet pragmatic edginess of Gen X and the disillusionment that defines so much of our generation.
Mr. Fish and I have always been different, but one of the starkest contrasts is our relationship with money. I live by a strict financial code. I haven’t been to a movie theater in six years or a theme park in the past ten. My wife and I never dine out. You know those annoying people who tell you the annual cost of your daily Starbucks habit? That’s me. If I buy something, I sell something else. I maintain an equilibrium with my ’stuff footprint’. As a backpacker and rock climber, I think about possessions the same way I think about gear: I carry only what I need. If I want something new, something old has to go.
I learned early on, after helping clear out the homes of deceased relatives, that possessions aren’t only physical clutter—they take up space in your mind. I watched friends and family fight over the material scraps left behind by those they loved; relationships fracturing over dining sets, watches, and old jewelry. The whole thing left a bad taste in my mouth. Think about it: the nicer the things you own, the more likely people are to fight over them when you’re gone. I’d rather leave behind my words and my work—something meaningful, not a pile of objects to argue over.
That may sound pompous, but it’s actually quite freeing. I’ve never inherited anything, and I never wanted to. I’ve seen people waste 10 to 15 years of their lives consumed by legal battles and resentments over things that ultimately don’t matter. That’s the weight of ownership—the burden of inheritance that Boomers and Gen X cling to like some form of immortality. But for me, letting go of that expectation wasn’t a loss. It was an escape.
Mr. Fish, though, sees ‘things’ differently. After a decade with his ex, he had amassed a lifetime of belongings—objects that carry deep personal meaning. His attachment wasn’t about hoarding; it was about preserving memories, maintaining a tangible connection to his past. But when he mentioned he was paying over $300 a month for a storage unit, my instinct was to call him out for what I saw as a phenomenal waste of money. I couldn’t help myself:
“So you’re telling me your stuff has an apartment…
and you’re still living with your parents?”
I can be a bit of a jerk sometimes, but we have that kind of friendship (I hope).
That joke stuck with me though, because he’s not alone. A quick Google search showed me that Millennials spend upwards of $900–$2,200 a year on self-storage. This isn’t just a Mr. Fish problem. It's become a generational reality.
The Reality Millennials Inherited
In 2025, Millennials will be in their late twenties to mid-forties—the first generation in modern American history where homeownership is out of reach for many, and fewer are choosing to have children. At the same time, they carry more student and credit card debt than any generation before them. The cruelest irony? Millennials are the most educated generation in history, yet those degrees haven’t translated into the financial security they were supposed to bring.
Often, older generations push back by citing misleading statistics that suggest Millennials have accumulated more wealth than any other generation. But if you remove the billionaires (the Zuckerbergs, the Waltons, the Altmans), the reality is much bleaker. It’s like saying an entire neighborhood is wealthy because one guy won the lottery. The median Millennial is nowhere near the financial standing of Gen X or Boomers at the same age.
So when people ask why Millennials aren’t having kids, the answer often isn’t ideological. It’s likely mathematical.
It’s not that we don’t want families; it’s that we’re expected to build them on sand. In my family, none of my adult siblings have children. In my wife’s family, none of her siblings have children. Among my closest friends, the ones who do have kids either inherited wealth or received significant financial help from their parents.
This isn’t a coincidence.
It’s a pattern.
The Baby Boomer Time-Money Illusion
A big disconnect between Millennials and older generations goes beyond just wealth—it’s the very concept of time as an automatic asset.
For Baby Boomers, time literally meant money: they bought homes in their 20s, and by the time they reached their 40s or 50s, those homes had doubled or tripled in value. Their companies invested for them, and in them. They put their money in blue-chip stocks that grew effortlessly. The mere act of existing long enough meant their net worth increased.
But for those of us who don’t own hard assets—who rent, who never had the option of a lifetime job with a pension, who didn’t get in before housing costs exploded—time doesn’t work the same way. It doesn’t reward us for patience.
For Boomers, aging meant gaining wealth. For Millennials, aging means a rising cost of living with no automatic built-in financial gains.
Many of us, at the age where Baby Boomers were seriously planning for retirement, are still trying to figure out where our next paycheck is coming from.
Rewriting the American Dream
For my wife and me, the answer was adaptation. We’ve spent the past decade living in a “tiny home”/RV on a plot of land in Northern Los Angeles. Not because we’re chasing an aesthetic, but because renting in L.A. would have drained us financially, and buying a “starter home” in our neighborhood would have cost more than $800,000. When given the choice between struggle and suffocation, we chose… neither. We built something else.
In doing so, we learned skills we never would have acquired in a traditional life. We built our own office from the ground up—the very space I’m writing in now. We learned full electrical, plumbing, and carpentry work. We restored vehicles and fixed machines that other people had thrown away, selling them for a profit. We designed a self-sustaining home where our shower feeds our irrigation system, and our solar power keeps us off the grid.
We didn’t set out to live this way because of some grand vision—we adapted, because adaptation was the best choice in an ever-changing world.
Our generation was in school when September 11th happened, graduated into a collapsing job market during the Great Recession, and entered our ‘prime earning years’ just in time for a global pandemic. At what point are we supposed to believe stability is real?
The Pioneers of the AI Age
Millennials have been conditioned by crisis after crisis. But what comes next will make everything before it look like the warm-up act.
AI won’t just disrupt blue-collar labor. It will gut the credential and managerial class, technologists, the finance sector, the knowledge workers—all the people who thought they were untouchable.
The off-grid livers, the digital nomads, the van-lifers—whether we knew it or not, we were training for a future that’s coming faster than anyone realizes. What started as a workaround—avoiding rent traps, cutting expenses, living with less—may have actually put us ahead. While many of our friends are locked into mortgages that eat up 80% of their income, we’ve built lives with lower overhead, greater flexibility, and fewer dependencies on a system that has never really worked in our favor.
A creative mentor of mine once said in a toast:
“May you live in interesting times.”
It’s an English expression that always felt like it fit my generation perfectly. We have lived in interesting times.
However, it turns out it may be a mistranslation of a traditional Chinese curse. In that context the expression is ironic, as “interesting” times are usually times of trouble.
When I found out that it may have been misinterpreted, I was even more inspired. Trouble is often interesting—and we are a generation built on adaptation. We share little with the generations before us, but we blaze the trail for the ones that will follow.
And if adaptation is our greatest strength, then maybe it’s time to start applying it everywhere—even to the way we think about the things we hold onto.
If you learn nothing else, please learn this: your stuff isn’t throwing you a party in that storage unit. Sell it! Trust me, you’ll feel lighter.