originally published May 4, 2014

It only took 14,465 days for me to figure it out, but I think I finally know what I want to do when I grow up. No, it’s not writing; that’s my fall-back option if the real dream doesn’t pan out. Don’t get me wrong – I enjoy plucking fancifully at my keyboard like a squid with a brand new marimba. But all that arrhythmic finger-tapping can be exhausting. Also, it gets in the way of my finger-drumming along with Rush’s “YYZ”.

No, the answer wafted sensuously into my think-holes this morning on a breeze of sweet euphoria and buttery revelation. I want a vocation that simultaneously provides no measurable improvement to the world around me while enabling me to try the best regional food and liquor around the globe. Something with only the vaguest of schedules, yet with a built-in excuse to disentangle myself from unwanted invitations whenever necessary. I’m craving a career that would inspire envy and drive in my younger self – a true calling steeped in long, lazy stretches within the regal realm of unending liberation.

I want to become a perpetual traveler. Is that too much to ask?

There are two variants on the perpetual traveler philosophy. The first is rooted in the freedom of not being a resident of any nation. It’s an expression of pure anarchy, or as pure as one can muster on the friendly side of local laws. One must still adhere to regional rulebooks, but without having to pledge fidelity to any bureaucratic system. The bastions of authority may still dictate the impenetrable limits of your actions, but they don’t own you. To put it existentially, you are adrift – truly disconnected from the rigors of permanent residency. You never vote, and you are tethered to the ramifications of politics by nothing more than the sponge-cake strand  of your whim. Sounds pretty, doesn’t it?

The other philosophical impetus that can scoot a soul into the perpetual travelers’ lounge is purely financial. There are certain obligations that come with citizenship and numerous elbows nudging at the soft flesh of your bank account wherever you are considered a resident. Those can all be eliminated – or at the very least tempered – by the perpetual traveler who cautiously plots his or her affairs.

It should go without saying that the first step in becoming a perpetual traveler – in particular if you want to do it right – is procuring a sizeable fortune.

If you have a lot of money, the most ethical thing to do is to pay a lot of taxes. An effective society will distribute a portion of the wealth from its most affluent citizens to ensure a functional system that provides for all its citizenry. The perpetual traveler will cram their ethics into the overhead bin, pop in their earbuds and enjoy the in-flight movie – to hell with their “effective society” because really, they don’t belong to one. A person can live in many nations for a number of months without becoming a resident, and therefore without having to pay taxes to actually help out those places.

You don’t want to leave home? No problem. You can renounce your Canadian citizenship and still live in Canada for up to 182 days a year without being a resident. If your home base is in the US, you can only be there for up to 122 days before Uncle Sam shows up with his hand in your pocket. Most countries in Europe will allow you plant your tuchus for three or six months every year without any tax obligations. The perpetual traveler isn’t spending the bulk of their days in an a departure gate, popping from third-world cesspool to fourth-world slum; they can pull this off in the cradle of modern civilization.

You’ll still need to pick someplace to call “home”, meaning your legal permanent residence. This is going to take a bit of work; most countries won’t offer you a passport simply because you asked. You’ll want to focus your energies on finding a tax haven, a place that will impose the fewest taxes and reveal next to nothing about your financial affairs to any curious international party. These are small but wealthy nations who don’t really care what you earn or where you earn it. Someplace with at least one foot in the modern, connected world, but without the threat of revolution or political instability.

Luckily, a number of those places have palm trees and plenty of sun. You’ll be laying the pseudo-foundations of owning property there, but don’t let that suppress your sense of adventurous roaming. This domicile is little more than a technicality. It’s the Residence Flag in the Five-Flags Theory of perpetual traveling.

Oh yes, there is a theory at work here.

The first flag is your citizenship. If you aren’t ready to say so-long to your home nation, grab a dual-citizenship somewhere where non-residents don’t get taxed. Africa is chock-full of nations like this. Some of them aren’t particularly stable, which could muck up your plans down the line, but you might be able to score a passport from one of these places without even having to visit. Given the relative lack of five-star hotels and the bevy of life-snuffing diseases in Africa, you might prefer this.

Flag #2 is the place where you’ll make your money. You’ll want to set up your business in a nation separate from your citizenship and your legal residence. Again, pay close attention to how much dough the government will siphon from your earnings. Or, take the easier route and be ludicrously wealthy. I recommend this as the best course of action.

Your third flag is your residence (which we’ve already covered), and the fourth is the place where you keep your assets. This may seem excessively complicated, but think about it – you’re from one place, you live in another, earn your money in another and store your goodies in yet another. No tax collector on this planet is going to bother figuring out your obligations, and if you’ve scouted out the right locations to begin with, they won’t even try. That leaves us with the fifth flag: your playgrounds. These are the nations where you’ll spend your time – your six months in Canada, your four in America, or if you’re looking to expand your worldliness, just throw a dart at a spinning globe and check the local limitations for visiting without being a resident.

It sounds like a magical lifestyle. Unfortunately, it isn’t a simple flip-switch for a poor working schlub like myself. But it’s something to strive for, an end-game truly worth the effort it will take to arrange all the details. It’s certainly an idea to look forward to, on that fateful day when I finally grow up.

If that ever happens.

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