Origins, Fantasy, and Paradox
First, some housekeeping to catch up on…
Podcast
I was interviewed recently by George Milton, CEO/founder of Yellowbird Foods (you know their hot sauces). We talked about running a “microbusiness,” which can be another name for solopreneurship, or just a small business with a small team. But the heart of the discussion was more about what lifestyle such a business set-up and strategy affords you. And hopefully, it can be deliver “extreme happiness” — the definition of which is all yours. I was walking the canals of Amsterdam while doing this, so my speaking quality and style aren’t the most polished… but hope you give it a listen. Of course, there’s a written list of takeaways you can just read instead. Link below:
Travel
It’s been a busy few weeks, so my long-form writing has been slow. My wife and I spent a week in Greece. Paros → Milos → Athens. It was a delayed 10 year wedding anniversary trip. And my brother and his fiancée joined us half way through. Maybe I’ll do a separate travel post on it, but it was probably the best island-style vacation of my life so far. Never thought I’d say this, but considering the ease of access, food, weather, people, culture, and history… I think it beats my previous #1 Maui. After we got back, I spent a few days with my parents who had flown over from NJ to watch the kids.
“Microbusiness”
My business (Goods Group) is growing, with new client wins hitting right as the summer ramps up. Good problem to have, but it’s necessitated some stepped up time management and prioritization. In a better place now, so more long-form to come.
Coming to America
Yesterday, my wife, our boys, and I landed in Philly from Amsterdam. We’re spending the next few weeks in Pennsylvania, New Jersey, and New York — visiting family and friends, including a longtime tradition down the (Jersey) shore.
Over on X, I’ve been sharing little tidbits and observations about America. It’s fun re-experiencing everyday life here after living in Europe for over two years. Like a kind of Tocqueville nouveau.
This is Entry #5 in my “Return to America” journal (I skipped 4 and 6—this one turned into a tome).
A Simple Framework for Understanding America
I view the current United States as a combination of three core elements, which I call:
Origins — the values formed in the places where we (our ancestors) came from
Fantasy — the reasons why we (our ancestors) came
Paradox — the strange and often dysfunctional how we try to execute on the why with our behaviors and beliefs shaped by the where
The two great texts that any American or global observer should read — to form their own nouveau-Tocquevillian view on American life — are American Nations by Colin Woodard and Fantasyland by Kurt Andersen.
Origins
Woodard channels Wilbur Zelinsky and builds upon his Doctrine of First Effective Settlement, which posits that the first cultural group to seriously settle a region ends up shaping its long-term character. Building a foundation of values, behavior, governance, religion, education, institutions, and maybe a little “old world” emotional baggage. These patterns endure for generations, even as waves of new immigrants arrive later. Immigrants assimilate into these core cultural modes over time, albeit after some temporary transformation pains.
For example:
Yankeedom (i.e. New England) was founded by Puritan Calvinists who emphasized literacy, moral conformity, collective responsibility, and covenant-based governance. That legacy still shows up in the region’s technocratic and moralizing politics.
New Netherland — centered on present-day New York City but stretching into northern New Jersey, the Hudson Valley, and parts of Long Island — was originally a Dutch commercial outpost. From the start, it was cosmopolitan, trade-driven, and profit-oriented. It laid the foundation for America’s global-facing business mindset, cultural diversity, and tolerance for pluralism (what the Dutch were particularly known for, especially in Amsterdam) — with a mostly transactional, directly-to-the-point orientation (another Dutch quality).
Tidewater was established by younger sons of English aristocrats who were boxed out by primogeniture, the system in which the eldest son inherited the family estate back in the Old World. These founders sought to recreate a version of aristocratic society in the New World. Rooted in plantation agriculture and rigid social hierarchy, the region became an early stronghold of elite governance and class-based order. Its legacy still lingers in the formal, status-conscious political culture of coastal Virginia (and, of course, in Washington D.C.) whose ceremonial design and centralized authority reflect that original cultural footprint.
Deep South was seeded by slaveholding English elites from Barbados who imported rigid class structures, racial hierarchies, and a plantation mindset. That inheritance still shapes attitudes around race, labor, and centralized authority in the American south today despite a devastating civil war
The Midlands (e.g. Pennsylvania, New Jersey) were built by Quakers and German pietists who were practical, tolerant, and decentralized. To this day, the region tends toward moderation, pluralism, and intense commerce.
Greater Appalachia was settled by Scots-Irish frontiersmen who valued clannish loyalty, independence, and armed self-defense. These were traits forged over centuries fighting the Romans, the English Crown, and rival clans from their perch in the borderlands and Highlands. That original ethos still fuels much of America’s populist, anti-establishment reflex. Today, this culture dominates a broad swath of upland America stretching from western Pennsylvania and the Appalachian Mountains, through West Virginia, Kentucky, Tennessee, and the Ozarks, and into parts of Texas and the lower Midwest.
And so on. The point is that America is not a cultural monolith. It’s an uneasy federation of inherited belief systems that arrived from wildly different origins. If you want to learn more about the origins of the other “nations” Woodard outlines — like El Norte, The Left Coast, The Far West, New France — go check out the book. It’s a fascinating framework for understanding America.
Fantasy
Meanwhile, Fantasyland explains a different layer — one that complements the Zelinsky/Woodard model in my view. Andersen researches and explains (hilariously) the fantasies that brought us all here… the highly specific why behind each group’s migration.
For example, the Tidewater region may have attracted second sons excluded from inheritance back in England, but it was the specific promise of gold that got them on the boat. Jamestown was founded in 1607 by the Virginia Company of London, which was explicitly a for-profit joint-stock venture. Investors back in England expected returns in gold, silver, or other valuable exports. There were even early promotional materials hyping the region as a potential source of vast mineral and financial wealth.
Sadly for all involved — initially at least — there was no gold. Eventually, tobacco emerged as a viable cash crop but only after a decade of famine, disease, and mass death. Jamestown was a purely speculative play. It was like the SPAC of its day. Only after centuries have we built various origin myths and Disney movies around it.
In Puritan New England, the fantasy was purely theological. They weren’t moderate Anglicans seeking tolerance, but religious extremists trying to build a holy commonwealth. Dissent was rarely if ever tolerated. They believed God was actively “clearing the land” for them by wiping out Native populations by divine intervention (it was, of course, smallpox and other diseases which had already ravaged the region for upwards of 100 years before they arrived). They saw themselves as the new Israelites.
Fantasyland explains the specific calls to action or events that actually nudged all the nations Woodard explains into existence. Yes these were migrations but they were also collective leaps of wild faith. Boarding a wooden ship in the 1600s was the equivalent of launching a mission to Mars. Half the Mayflower passengers died before even reaching land.
In both Jamestown and Plymouth, few settlers even knew how to farm. These weren’t seasoned agrarians from the English countryside. They were mostly gentlemen, craftsmen, indentured servants, urban laborers, and in some cases, low-level criminals. Many in Jamestown were from the lower rungs of English society or the idle sons of the Old World aristocracy unfamiliar with manual labor and unprepared for frontier survival. Some even refused to farm altogether, considering it “beneath their station”. In Plymouth, the Pilgrims were educated and devout, but not exactly agronomists. They struggled with the local soil and climate and depended heavily on help from the Wampanoag during their first year (hence the more kid-friendly Thanksgiving narrative we’ve all come to know and love).
It just underscores the insanity — the intense fantasy — of our origin stories. They were spiritual gambles, imperial experiments, or high-risk corporate ventures… made by people who often lacked even the basic skills to survive. Sound familiar?
So, by synergizing the work of both Woodard and Andersen, we start to see that fantasy was the only true common denominator across all these founding nations — the fantasy of gold, the fantasy of building a new Israel, the fantasy of a better, self-made aristocracy.
Yes, fantasies can come true. That’s what makes them powerful.
But they are fantasies nonetheless.
And this draw to fantasy requires a certain kind of person. Someone willing to risk everything on an imagined future. For better or worse, that fantastical orientation embedded itself into the country at large, across all of Woodard’s nations, thanks to the Doctrine of First Effective Settlement.
But this leads us to the third core element: paradox.
Paradox
When you build a culture based on fantastical origins, you can get outcomes that are both astonishing and self-defeating. America is full of energy, invention, and unyielding belief in an incredible future… but often relying on systems that are fragile or completely contradictory with their stated values.
Some examples?
The most dynamic, wealth-generating economy in the world — with one of the weakest social safety nets among developed nations
The most advanced medical/pharma technology and research infrastructure — paired with some of the worst public health outcomes and embarrassing obesity levels.
A country founded on liberty — yet with the largest incarcerated population on Earth
A society obsessed with freedom and self-determination — yet governed by layers of obscure bureaucracy, credit scores, and invisible red tape
A nation that glorifies entrepreneurship and innovation — yet 9 out of 10 working adults cling to W2 jobs, ask for permission to live their lives via an HR portal, and quietly hope not to get laid off
And when they do get laid off, there’s no real safety net — no employment courts to adjudicate the rationale for the layoff and whether it was necessary.. and no severance guarantees. Just a “quick minute” email from HR, a COBRA form, and good luck
A culture that celebrates reinvention and mobility — yet is deeply constrained by geography, NIMBY zoning laws, licensing regimes, and guild-like credentialism
A global empire that distrusts its own institutions
A meritocracy that runs on inherited networks and class signaling
These are structural constraints rather than random externalities of innovation and action. They’re what happens when you try to build an Atlantic-to-Pacific continental system of institutions, laws, and norms to deliver on various competing fantasies from various places of origin. It is supremely dysfunction.. not by design but by circumstance. There’s nothing right or wrong about it per se… it’s just how it is.
Castles and Knights
One of the most enduring American fantasies, in my view, is the belief that each of us can carve out our own little fiefdom on this Earth.
Begone with Old World feudalism. We’re not beholden to kings or queens. We’re free individuals, staking our claim in a vast untapped landscape... first mostly geographic and now mostly economic. A plot of land we can develop and enjoy as we please, a career where we can bounce around and explore new industries, our own business where we decide what meetings to take and when, a belief system or set of zany personal interests we develop all on our own. Whatever we can fence off as ours.
Most Americans have never experienced the cultural contrast because most have never lived abroad, but this ownership-like perspective is relatively rare in a place like Europe, citizens of which still carry feudalistic conceptions of work, class, and day-to-day civil organization. Of course, some may take issue with this, but it’s my personal opinion based on my lived experience so far on both sides. Note I say relatively.
But who defends our American fiefdoms?
Not knights in shining armor, but lawyers… some of whom become lobbyists and politicians.
America is the land of litigation. Every broken rule, every minor accident, every interpersonal slight… prepare your lawyers to battle mine. Lawsuits are just another frontier of commerce. Perhaps another way to extract value from misfortune.
Take corporate and political lobbying… itself not unique in the world, but its prominence is. The “lawyerization” of America is driven by its decentralized system and First Amendment protections. In Europe, lobbying is about 1/4th the size — in terms of dollars spent — despite having 100 million more people. And in places like Japan or China, lobby-like influence flows through informal or state-controlled channels. Our pluralistic tradition — the origin nations we talked about from Woodard— plus revolving door between government and industry amplify lobbying’s impact on American society… far unlike in more centralized democracies like in Canada. This reinforces our political and cultural dysfunction because entrenched interests often drown out ordinary “common” voices. In fact, there may not even be a “common voice” at all. While lobbying — basically just “lawyering up” for large groups — is our protected First Amendment right, it can also undermine equal representation and fostering distrust in the very governments and systems we created for ourselves — hence more paradox.
Now take the summer camp my wife and I signed our boys up for this week. There are pages of liability forms… dozens of checkboxes. We've never seen anything like it after countless sports and activity camps in Europe. In the Netherlands, most camps have no forms at all. Maybe a contact number or a single quick waiver. There’s a more fatalistic, almost stoic view of risk over there. Things go wrong sometimes and nobody’s lawyering up because a kid fell off the slide. There’s even a playground in Amsterdam made entirely from discarded construction debris. Wooden pallets. Literal rusty jagged nails waiting for an arm or a leg to rip open. Kids running around barefoot too.
Parents just shrug. “It’ll teach them to be careful.”
Absolutely mind-boggling to a parent who grew up in America. “Lawsuit waiting to happen,” right? How many times have you uttered that phrase in your American life?
That’s Europe’s paradox — seemingly less control and more trust on the day-to-day street level. No micro-managing rules or policies written by lawyers and lobbyists. More personal responsibility. Yet…. isn’t personal responsibility what defines America? Isn’t Europe the “nanny state?” You’re telling my it’s reversed? Paradox aplenty.
In America, the freedom fantasy gets filtered through a compliance maze, again paradoxically.
You’re free… but also pre-liable for anything bad that might happen.
Free… but operating under 87 layers of policy written by people afraid of being sued.
Free… but sign here first!
So this brings me to my first 24 hours here
My first interaction was with a police officer at the airport, who playfully joked that he’d arrest me for throwing something in the garbage can he happened to be standing next to. It was innocent — we both laughed — but also an immediate reminder of the extra and ever-present policing we have here compared to most other places.
And yet we’re so free, right?
Personally, I want to know we’re being protected. But I’m not sure I want to see heavily armed police officers with military-grade rifles posted next to garbage cans. Because now I have to physically approach both the officer and the garbage can to throw something away. Horrible vibe, really. The freedom to throw away my kid’s candy wrapper requires a quick negotiation with the Department of Homeland Security.
Then it really hit me at Wegmans yesterday. The store is an American Castle (literally... it has a castle-like steeple) — a living shrine to the abundance of American agricultural and commercial power. Miles of aisles. Cheese from ten countries. Gigantic strawberries (probably GMO, I assume?). It reminded me of that famous Gorbachev visit — when Soviet leaders toured an American grocery store in the late ‘80s and were stunned.
“If the people back home saw this there would be a revolution,” one reportedly said.
And yet... the place was nearly empty. A few retirees, a handful of stay-at-home moms. No young men, no fathers, no workers in their prime. All that abundance sitting on ice and under fluorescent light — waiting. Waiting for the working crowd from the “big city” or locked into Zoom calls to clock out and flood in later that evening. Everything is timed. Everything is scheduled.
Yet another paradox in America. We are free, but we all run on clockwork.
Then came the most bewildering interaction of the day.
Pennsylvania’s alcohol laws. You can buy beer with your groceries — but only in a special section. It has to be a separate transaction. And you can’t buy more than 192 ounces at a time. (That’s 16 beers, in case you’re wondering.)
So I go to check out. They ask for ID. I’m visibly almost 40 years old. Greying beard. Oily, slightly wrinkled skin. The exhausted look of a father trying to keep his son from leaping out of the shopping cart. Any person with a functioning brain knows I’m over 21.
But the clerk isn’t allowed to use their brain. Making matters worse, because I gave them a non-US ID, they needed a manager to come approve it. The manager was probably 20 years younger than the clerk. I made a light comment about the absurdity. They both chuckled.
“We know you’re obviously over 21,” they said. “But this is the policy.”
Just another paradox. A society that celebrates innovation, disruption, breaking the rules. Silicon Valley. Risk capital. Rapid iteration. The move fast and break things culture that gives us trillion-dollar companies, rocket ships, and self-driving cars.
And yet… a grocery store where two people are afraid to verify that a grown man is allowed to buy a six-pack because they might violate protocol. Because if they “break the rules,” they might get fired. And if they get fired, they lose their health insurance, their reference, their housing. So instead, they follow the script, ignore their own judgment, and call over a manager.
That’s the real fear in America.
It’s fear of the very system we built for ourselves. Fear of breaking our own rules.
And yet… we are free.
