Chart Your Own Pioneer Lifestyle

I’m a big fan of the “Yellowstone” franchise.

You might have seen me write about it before.

Last Christmas, I was in Paris with my family. I had seen all the “Yellowstone” episodes and eagerly watched the prequel series, “1883,” starring Tim McGraw and Faith Hill.

The second “Yellowstone” prequel, “1923,” with Harrison Ford and Helen Mirren, had just been released.

I discovered it wasn’t available on Paramount+ in France—and that nearly ruined the holidays.

All the series—especially the prequels—are old-fashioned Wild West stories, with cowboys and Indians and lots of horseback riding and gunfights.

But the series are also a deep exploration of the American Dream… and what you might call a contradiction at the heart of the American Dream: the desire to be free versus the desire to live a comfortable life…

The American frontier, the Old West, was in many ways the perfect representation of freedom… the moment of greatest freedom in the history of the human race, in the minds of many…

For the American settlers traveling west and building lives for themselves, there were few laws, no government supports—little interference, even, from other people… just man and the land. Almost endless landscapes waiting to be tamed.

In the original “Yellowstone”—set in the modern day—John Dutton, played by Kevin Costner, fights to preserve the vast, vast ranch his ancestors founded in Montana—to maintain the old-style cowboy way of life his family pioneered, against the encroachment of cities and tourism and, well, more and more people…

This tension between a city and a country way of life is at the heart of the franchise—and, you might say, at the heart still of the political divide in America…

In “1923” (set, of course, in that year) there’s a funny scene where the cowboys head into town and a vendor is selling some brand new conveniences—washing machines and refrigerators. The cowboys can’t understand the purpose of these things. It will save time, the vendor explains—and then you’ll have more time for leisure. The cowboys are more interested in sticking to their old ways of doing things—the way of life they know and sometimes love—than trading in their traditions for convenience…

At another point in “1923,” Harrison Ford’s character imagines how wonderful life would be if there were no cities—just man free in nature. A businessman explains that cities are the future: in the countryside you merely survive against nature—bracing winters and digging holes to use as a toilet… in the city, man is the master of nature: water flows from the tap and light comes at the flick of a switch…

The voiceover in “1883” warns us that cities have weakened us as a species. In the city, there are fewer consequences to your actions… you won’t sit down in the grass to pee and get bitten by a snake… you don’t have to keep wolves away from your campsite… you become weak and you can’t fend for yourself.

These are the tensions “Yellowstone” sees in American life between freedom and comfort… urban v. rural… tough v. soft…

And it’s true, old-style rural life offers a very different set of freedoms to the freedom a city offers. In the wilderness, you have freedom from people; the freedom to make your own way; build something entirely new where nothing was there before. But you have to have the toughness and the skills to do it.

Rural freedom is the freedom to chart your own path as a pioneer…

The city offers a different kind of freedom… freedom of choice. An abundance of choices for entertainment, food, and lifestyle… freedom from want, with modern conveniences like delis on your doorstep…

But that essence-of-freedom you feel when you stand on the edge of a mountain and yell into the void… that’s not something you’ll find in a city.

In many ways, this city v. country divide still lies at the heart of America’s political divide: the liberal city-dwellers who want freedom from want and need; to be free of the need to provide for themselves (as our ancestors did), thanks to modern conveniences and government protections… to live that comfortable life.

And then, that older American ideal of freedom that still holds sway in the heartlands… the individual fending for themselves against the frontier.

Why am I delving into a popular TV show like this in a newsletter about offshore opportunities?

Well, like I say, I’m a fan.

But, I’ve got to say, when I think about those two ideas of freedom the show sees in conflict… the sovereign individual v. the freedom of a life where everything you want is at your fingertips…

With expat life today, you don’t have to choose between them. Both of those freedoms are possible. Indeed, they’re combined and fused together. The expat is both a pioneer and has the option to have every comfort at his fingertips…

In “1883,” the character of the Captain explains to a group of immigrants who are in his charge—he’s leading them from Texas to Oregon—that they are pioneers, and all there is, is the journey, till they get to where they’re going—and the journey is treacherous…

We see how perilous it can be, with the simple act of crossing a river… a task that risked death in the time before bridges…

For the characters of “1883,” there is the grand adventure of pursuing a new life on the frontier—but with that comes the risk of death in nearly every moment: wolves, snakes, raging rivers, bitter cold, and beating sun (and little to safely drink)…

I think of today’s expats and those of us who go offshore as the new American pioneers… we’re looking for adventure and freedoms beyond those we had in our old lives…

I started living overseas and investing offshore three decades ago, because I saw it would give me a life far more interesting—with far more opportunities—than I would have if I just stuck to my own backyard…

But today’s American pioneers (we expats and overseas investors) can enjoy the adventure of the pioneer lifestyle, without the same perils—all of the good and none of the bad.

Take the life I live myself… I get to be a cowboy in Los Islotes in Panama, where we keep horses and the wide open spaces rival anything in “Yellowstone”…

But I also, I have to say, enjoy city life and its conveniences and opportunities to enjoy culture and the best restaurants—and I get to enjoy that in Panama City or, especially, when we spend time in Paris…

For today’s American pioneer, the whole world and all its opportunities are our frontier…

So, “Yellowstone” has got it right that this rural and urban divide is at the heart of political conflict in America…

But those of us who are true American pioneers today, we aren’t constrained by one idea of freedom or the other—we want it all.

We want to build something brand new (build up our wealth; create our own community, like I’ve done at Los Islotes); and we want to enjoy modern comforts—easy travel; cosmopolitan luxury…

When you think beyond the divisive terms on which American life is lived today… when you decide you want more than that—you want it all… the world becomes your frontier… and offshore living is the life for you.

Stay diversified,

Lief Simon
Editor, Offshore Living Letter