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      • Chitré, Panama
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      • Las Terrenas, The DR
      • Pisa, Italy
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      • Home
      • Countries

        Top Destinations:

        Whether you’re looking for fun and sun, a peaceful retirement, or the chance to earn some extra income, you’ve got a real world of opportunity open to you… In short, we’ve done our best to narrow down your best options, but only you can decide the right country for you.

        • Spain
        • Portugal
        • Panama
        • Belize
        • Colombia
        • Cyprus
        • Mexico
        • France
        • Montenegro
        • Browse All Countries

        Best For:

        • The Best Places To Retire
        • Health Care Abroad
        • Cost Of Living
        • Investing in Real Estate
        • Establishing Residency
        • Gun Laws In The World
        • English-Speaking Countries
        • Safest Places For Retirement
        • Best Places In Latin America
      • Budgets

        How Much Will It Cost You To Live Overseas?

        The only honest answer is, we have no idea. And neither does anyone else. The only one who can answer that question is you. Here’s the most important thing to understand about budgeting your new life overseas…

        Super Cheap

        • Chitré, Panama
        • Santa Marta, Colombia
        • Phuket, Thailand
        • Dumaguete, The Philippines

        Cheap

        • Medellin, Colombia
        • Boquete, Panama
        • Kyrenia, Cyprus
        • Hua Hin, Thailand
        • The Algarve, Portugal

        Affordable

        • Valencia, Spain
        • Cascais, Portugal
        • Las Terrenas, The DR
        • Pisa, Italy
        • La Rochelle, France
        • Mazatlán, Mexico

        Luxury

        • Ambergris Caye, Belize
        • Kotor, Montenegro
        • The Panama City Beaches
        • Paris, France
      • Resources

        Global Living

        • Living & Retiring Overseas
        • Raising A Family Abroad
        • Foreign Residency & Citizenship
        • Offshore & Diversification

        Making Money

        • International Real Estate
        • Banking
        • Employment
        • Investing

        Follow Us:

        • Meet Our Experts
      • Real Estate

        Join our Weekly Newsletter
        Overseas Property Alert

        Sign up for our weekly newsletter to receive expert insights on the best international real estate investment opportunities.






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          PANAMA CITY, PANAMA

          June 18-20, 2025

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          Valencia, Spain

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          Home Lifestyle

          Chart Your Own Pioneer Lifestyle

          How To Chart Your Own Path As A Pioneer

          by Lief Simon
          Jul 14, 2023
          in Lifestyle
          0 0
          A cowboy

          iStock/cgbaldauf

          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 Dream

          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.

          Start Your New Life Today, Overseas






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            The City v. Country Divide

            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…

            Pioneer Lifestyle: How Does This Relate To Expat Life?

            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…

            In short, 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 signature

            Lief Simon

            Editor, Offshore Living Letter

            Share87Tweet54
            Lief Simon

            Lief Simon

            Lief Simon has lived and worked in 7 countries on 5 continents and traveled to more than 75 countries. His real estate investment career began with a $5,000 down payment on a three-flat building in Chicago. Less than three years later, Lief sold the building for a leveraged return of 3,000%—$150,000 in profit after closing costs and commissions.

            From there, he turned his attention overseas and has bought property in 24 countries including France, Croatia, Portugal, Ireland, Belize, Spain, Argentina, Cyprus, Romania, and beyond. Thanks to his decades-long career as a global property investor, Lief has built a multi-million-dollar portfolio that includes rental properties, significant land holdings, and 7 personal residences.

            Lief has established residency in 3 countries and acquired a second passport from Ireland.

            In 2008 Lief and wife Kathleen Peddicord made the most important investment of their lives—a 215-acre oceanside finca, known as Los Islotes. There, on Panama’s largely undiscovered Veraguas coast, they’ve installed underground electricity, water, and internet and built a forever family home that sits at the heart of their ultimate vision: a gold standard private residential community for those in search of a true safe haven escape.

            Lief’s latest book, “Cowboy Millionaire—The New American Pioneer,” collects all the wisdom he has learned in three decades of living and investing outside America.

            He offers advice on international diversification in his twice-weekly Offshore Living Letter and monthly Simon Letter dispatches. For real estate investment opportunities, check out his monthly Global Property Advisor service.

            If you’d like to meet Lief in person, join him for one of our upcoming in-country conferences. You’ll find further details here.

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                  HOME

                  Top Countries

                  • Spain
                  • Portugal
                  • Panama
                  • Belize
                  • Colombia
                  • Cyprus
                  • Mexico
                  • France
                  • Montenegro

                  Best For:

                  • Health Care Abroad
                  • Retirement Living
                  • Cost Of Living
                  • Investing in Real Estate
                  • Establishing Residency
                  • Gun Ownership
                  • English Speakers
                  • Safety
                  BROWSE ALL COUNTRIES

                  Budgets

                  How Much Will It Cost
                  To Live Overseas?

                  Super Cheap

                  • Chitré, Panama
                  • Santa Marta, Colombia
                  • Phuket, Thailand
                  • Dumaguete, The Philippines

                  Cheap

                  • Medellin, Colombia
                  • Boquete, Panama
                  • Kyrenia, Cyprus
                  • Hua Hin, Thailand
                  • The Algarve, Portugal

                  Affordable

                  • Valencia, Spain
                  • Cascais, Portugal
                  • Las Terrenas, The DR
                  • Pisa, Italy
                  • La Rochelle, France
                  • Mazatlán, Mexico

                  Luxury

                  • Ambergris Caye, Belize
                  • Kotor, Montenegro
                  • The Panama City Beaches
                  • Paris, France

                  Resources

                  Global Living

                  • Living & Retiring Overseas
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                  Store

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