Freedom Lessons From 18 Years Being a Digital Nomad

Established in 1350, the wonderful spa town of Karlovy Vary, Czech Republic. © 2019 Pete Sisco

Individual freedom has been a borderline obsession for me since my early youth. Stories of slavery, pogroms, and various forms and degrees of political tyranny have always fascinated me and caused me to wonder how life would have been for an ordinary person trapped in some grisly, institutionalized system of human control. Frankly, for better or worse, I think about these things a lot of the time.

Many years ago while living in Idaho the state slapped a lien on our house claiming we owed them something like five thousand dollars in state income taxes. It was completely bogus and what I considered to be a financially broke state’s attempt to find revenue somewhere. I spent some money on lawyers and accountants and the issue went away. No apology from the strong arm extortionists, of course.

That episode got me thinking, “Why am I living in a state that has an income tax when there are alternatives.” So we starting looking at the US states that didn’t have one. Not long into that process I started wondering, “Why am I even living in a country that has an income tax?” And that started me down the road to looking at other countries, including using the oversimplified but mostly valid flag theory that involves legally not really living anywhere.

I should say that there were a couple of factors that made this easier for us than for most people. First of all, since about 1996 I had been making all of my income from online sources. I was first selling e-books at a time when I had to explain what they were in order to make a sale, and I was still telling some of my friends what the internet was. Remember the “information super highway?”

The other relevant condition was all of our six kids were reaching ages where they were moving out of the house and starting their own independent lives. So Connie and I sold our home and everything in it, except our photos favorite books which went into storage, and we hit the road with one suitcase and one carry-on bag each. That was eighteen years ago. In those years we’ve spent time in nearly forty countries and lived in about a half dozen, depending on where you draw the line on living vs visiting.

Here of some of the takeaways we have garnered after nearly twenty years of living this way.

Minimalism is Incredibly Liberating

Because of airline rules, and because I don’t want to feel like a professional Sherpa all the time, our luggage is limited to about 20 kilos or 44 lbs in weight, plus what we can shove in a backpack for the overhead bins. That’s about 100 lbs of stuff for two people for two decades. The items change but the weight does not.

Our aforementioned home was in a rural area on thirteen acres, and there were several outbuildings. The home, the outbuildings, and even a storage garage a few miles away were all filled with possessions. At one point we had thirteen licensed vehicles, from cars and trucks to motorcycles and four wheelers. Amazon dropped things off almost daily. In short, we were a poster family for consumption.

So almost overnight we went from being reckless (but happy) over-consumers, to being Zen monks who meditated on which pair of shoes weighed more and therefore had to be left behind to make room for the new computer mouse and blue jeans.

But the other side of that coin was the liberation from not owning all the “stuff.” No more insurance on those vehicles, or keeping the plates up to date, or getting new tires. No more mortgage, home maintenance, car payments, and no debt. We did short term rentals of condos, hotels, AirBnB’s, cars, motorcycles, and anything else we needed for awhile. When the weather started getting bad in Germany, we’d move to Thailand. Every year was a blank sheet asking us, “Where do you want to go? What would you like to do?”

I can’t tell you how liberating that feels. And I mean I really can’t find the words to tell you. It’s one of those things you have to experience. It’s like nothing and no one has a hold on you. And that’s just an unknown condition for most of us.

There are tradeoffs to be sure. Anyone who’s lived awhile knows that life is a constant calculus of tradeoffs. And there aren’t a lot of absolutely right or wrong choices. When our kids were very young the tradeoffs likely wouldn’t have made sense for us. As empty nesters in our 40’s it was a wonderful lifestyle. But, man oh man, is it liberating.

Adapting to Change is the New Wealth

You don’t need me to tell you that we are living through a time where not just the number of changes, but the speed of change is accelerating all the time. In my view, the guy who laments that things should just be more like the 1970’s is going to have an unhappy time going forward.

Whereas, the mindset of embracing change is going to be a very valuable skill for the foreseeable future and I can’t think of a better lifestyle to build that particular muscle than being a digital nomad who deliberately plans to change his plans frequently.

Happily this outlook rubbed off on our kids and at one time our family was living on four different continents simultaneously. Three of our kids have already married people from other countries and cultures and I consider all of us richer for it. When the day comes that real adversity is imposed from above, they already see a half-dozen escape routes.

Most People Everywhere are Wonderful

I don’t want to sound Pollyanna, but the honest truth is that “foreigners” everywhere we’ve been are literally just like you and me. We lived in communist China, which has a dreadful government bent on maximum control of everyone, but our Chinese neighbors in our apartment community would gather daily with their kids and watch them run and play. The adults would chat and laugh with each other and they always enthusiastically waved and smiled when they saw us walking around the community.

They worry about their kids’ education, they worry about their own health and their retirement. Contrary to what politicians would want you to believe, they don’t spend their day thinking about how to undermine capitalism, how to “destroy our way of life” or how to harm people on the other side of the world in any way. They couldn’t care less. Conversely, when have you ever made a New Years resolution to harm someone in Asia? When have your and your partner ever sat at the kitchen table discussing ways to disrupt life in Egypt? It doesn’t happen. Virtually everyone has a live and let live attitude toward other people.

Politicians are constantly selling the fiction that “the world is a dangerous place,” mostly because organizations like the CIA, MI6, FSB, and others work constantly to make it dangerous for anyone who won’t obediently live under their domination. But the real truth might be closer to a world with eight billion potential friends and customers who all have to cope with a nation state that constantly makes enemies for them.

Respect is the Universal Currency

This brings me to another very helpful observation we’ve made over the years. I only speak English but I’ve learned to say please and thank you in maybe a dozen languages. It helps to know the equivalents of sir and ma’am as well. Of course, I butcher pronunciations and have an obvious foreign accent, but making the sincere attempt shows respect for where I am and for the person I’m addressing and is a tool of connection.

Tourists are notorious for declaring that certain places like Paris have rude people working in service jobs. But imagine running your own antique store in Dallas, Texas and having a Chinese woman barge through the door and start barking Cantonese at you while gesturing around your store. Who’s really the one being rude?

Respect is the universal currency and you can carry a big bundle of it everywhere you go. Respect opens doors. Respect makes friends. Respect is win/win.

You Are Seen As a Tax Cow

Personally, I’ve been through the immigration systems of the US, Belize, Ireland and the UK. I’ve also looked deeply into a few others. Other than Belize, it was very obvious in every case that a country’s principle interest in me is money. If you’re as cynical as I am your first response might be “Of course!” And you might even believe there are good reasons to focus on that. And perhaps there are.

But few things bring this fact into bold relief the way trying to legally enter a country does: they want lifelong tax cows. It very clear that every country’s principle focus is on how much they can extract from you annually and how secure those sources are. Every piece of paper submitted is an exercise in financial compliance and living inside a prescribed box. In short, all your wealth has to be in a place where it’s easy for the nation state to grab anytime it declares a justification.

I mention this because most of us are basically oblivious how interconnected the systems of payments, direct deposits, approved banks, approved brokers, and regulated pensions are inside every country. All the money - and I mean all of it - runs through the fingers of politicians who reserve the right to take it when they say they need it.

Living largely outside of this system for 18 years has made us keenly aware of how everyone is forced to conduct their financial affairs; tax cows living on a farm so they can be milked daily. Glorious national anthems about freedom notwithstanding.

You Need to Create Your Own Freedom

In many ways our time in history is very similar to everyone’s in the last few thousand years. We are born into control systems we didn’t create, with rules we didn’t make or agree to, and we can’t truly change or control any of it.

While some of us want to directly work to help make those changes possible for ordinary people, most just want to run their own lives as best they can with the time they have. If living life on your own terms is a priority in your life, you might want to consider the freedom of being a digital nomad.

The C19 pandemic did a lot to awaken the world to the possibilities of living like we have for two decades. Many countries now offer Digital Nomad visas in some form but it’s still very possible to operate without one, as we always did.

Until we have the technologies of global human freedom, the best most of us can do is to find the cracks and crevices in the authoritarian control systems that want to lock us inside the farm, and to instead live on our our terms in the few ways that are still legal. Because real freedom - complete control of your own life and property - is very illegal everywhere.