Making the Transition (or, How to go From Wage Slave to World Traveler)

Some people say that the hardest part of traveling the world is acquiring the mindset that nothing else matters as much as the journey. Possessions are nothing more than additional baggage, and baggage does nothing but weigh you down, slowing your enjoyment and detracting from the overall experience. The actual journey to the place where you reduce your consumption of unnecessary extras and transition from 9-to-5 slave into someone who no longer lives by a daily routine takes a major shift in priorities, not to mention complete dedication and commitment into becoming a new person who no longer views a singular city as their home. And for many people, that shift in priorities brings to light one of the greatest challenges you will face in your transition from slave-to-the-clock into a location independent digital nomad and international vagabond: fear.

Photo (c) T.W. Anderson

Human beings fear change. This is an undeniable fact. In some cases it is justified. Such as when you are learning how to swim for the first time, and you are terrified of the water because you don’t believe you can survive the experience. In others, it is simply a way of thinking that is born out of years of brainwashing regarding the way things are “meant to happen”, the way things are “supposed to be”. The American Dream, working the 9-to-5 job, buying a house in the burbs, having a cozy family with a few kids, driving the latest car, having the latest gadgets, the nicest house on the block, the best-landscaped yard, the “My Kid Is On The Honor Roll” bumper sticker, and the hope that one day, when you are 60 years old or so, you will have your house paid off, the kids’ college tuition taken care of, and you will finally have the time to buy a boat and travel the world with your spouse/significant other.

What if you could do all of that now, instead of waiting until you are 60+? What if you could change everything that defines you as the person your workplace and social status want you to be, and transform yourself into a world-travelling expat who makes their home wherever in the world they want it to be, with total and absolute freedom to do what they want, when they want, without anyone telling them what time they need to get up, be at work, go to bed, have dinner or prepare for a commute to work?

What if you could finally become the person you have always wanted to be: a globe-trotting wanderer who explores the nooks and crannies of the planet at their leisure, enjoying international investment opportunities and economic strengths, taking in exotic sights and sounds and flavors and cultures and peoples, all the while indulging in the one thing most human beings have forgotten how to do: live life.

“Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma – which is living with the results of other people’s thinking. Don’t let the noise of other’s opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.”~ Steve Jobs

Making the Change

Breaking away from the 9-to-5 grind is a calculated transition, and one that–while anyone can undertake–takes careful planning and some forethought. It’s certainly much easier to do if you are someone who is flying solo, or if you are already established as one of those who work remotely via a laptop in whatever your chosen profession is, but it is entirely feasible even if you are someone who is married, attached to a significant other, have a traditional job in a brick-and-mortar location, or even someone who has children and an entire family unit to think about. However, it is not something you can simply jump right into without any forethought or research.

The absolute first thing you need to do before you jump ship and leave your life of drudgery and slavery behind is to research which cities or countries you would like to live in. This is as important as finding countries that have a lowered cost of living because even if you are cutting your costs in half by moving to a specific place, if there is nothing there for you to enjoy, what’s the point of going in the first place?

With that in mind, it is vitally important to pick destinations that speak to your heart. There is no point in going to a country if you aren’t going to enjoy the surroundings or feel at home. If you are a beach fanatic who prefers year-round toes in the sand, a mojito in your hand and the surf lapping at your heels while you kick back and enjoy the combination of sun and sand, places such as Cancun, Mexico or the Bahamas are what you are looking for. Or, if you prefer your winter months filled with skiing the slopes of Bansko while you keep yourself warmed with a bottle of Burgas 69 or your summer months hiking and camping in the rugged outcroppings of the Rhodopes bordering Greece, then Sofia, Bulgaria is a great choice.

Another thing to consider before taking the plunge is making sure you pick cities that have the infrastructure to support you if you are a working professional, or if you are someone with special medical considerations or a family in tow, for example. Choosing cities that have quality medical services, educational facilities and modern amenities are certainly a pre-requisite for many travelers, and rightfully so. While there is a lot to be said for adventure traveling, the whole point of moving and living abroad is to enjoy the same amenities as you did back home, simply at a drastically reduced rate and in a place where you can rest assured that the infrastructure is already in place.

It’s ok to head off into the middle of the mountains, the jungle or on a remote island for weeks or even months at a time if you enjoy that sort of thing, but if you are a working professional, someone with children who need a school system or an elderly individual with a heart condition, you need to know that you have access to the same facilities you did back home. Most people who are looking at setting up foreign residencies need to know that everything will be in place for them to make the transition with as little stress as possible. After all, the whole fear of change in some cases is justified; if you are someone who needs all the amenities a big city can offer, you need to be sure you are looking at countries who have cities which can give you what you need. While it might sound like a great idea to head to Mexico to live for 6 months (or more) out of the year, there is a vast difference between living in Palenque or one of the outlying pueblos versus Mexico City or Cancun.

Cultural Understanding

“When you travel, remember that a foreign country is not designed to make you comfortable. It is designed to make its own people comfortable.” – Clifton Fadiman

You cannot afford to be culturally ignorant. If you wince at the thought of a 15 year old being able to legally drink, if you cringe when you hear about people in small villages eating the brains of monkeys, if you think that the menus in restaurants in foreign cities should be in English and you want the televisions at the restaurant to show American football instead of real football….you, my friend, have a long road ahead of you before you can successfully make the transition into living like a local in countries around the world.

Respect is a two-way street. You expect foreigners to respect your holidays, speak your language and follow your rules and regulations when they are in your country, so it is only natural that you do the same for them. If you walk into a foreign country with a chip on your shoulder about how you are from a “superior” world power, you will find yourself on the short bus to dissatisfaction, because every aspect of your trip is bound to be plagued with footnotes of you continually complaining about how “nothing is like it is back home”.

The whole point to living like a local in foreign destinations is to take advantage of their cultures while at the same time enjoying the drastically reduced cost of living that allows you the opportunity to improve your quality of life. But if you cannot look past the cultural differences and you continually look down your nose at the locals because of their traditions, society and culture, you should never have left your home country in the first place.

Cultural understand is perhaps the absolute most important aspect of making the transition into a location independent digital nomad. The old saying, “When in Rome, do as the Romans do,” is absolute valid and correct. You are on their turf. Their rules apply. Learn their language, follow their rules, celebrate their festivals, immerse yourself in their culture.

Appreciate Time for What it Is

“Your true traveler finds boredom rather agreeable than painful. It is the symbol of his liberty-his excessive freedom. He accepts his boredom, when it comes, not merely philosophically, but almost with pleasure.” – Aldous Huxley

“To my mind, the greatest reward and luxury of travel is to be able to experience everyday things as if for the first time, to be in a position in which almost nothing is so familiar it is taken for granted.” – Bill Bryson

Your everyday life is the buzzing of the alarm clock, the morning routine, the commute to work, the 9-to-5 grind, the 40 hour work weeks, the two weeks of paid vacation per year, the mortgage, the car payment, the credit cards, the health insurance, the car insurance, the gas for the car, the cable payment, the cell phone payment, the taxes, the limited number of sick days per year you are allowed to take before you lose your job, the stress over missing an extra day of work when your spouse/significant other really needs you but you can’t miss another day because you need the income so desperately, coming home and only having the energy and time to take a quick shower, eat fast food, lay on the couch for a couple of hours before you need to get to bed and repeat the exact same routine over and over and over.

My everyday life is getting up when my body tells me it’s time. I lay in bed pondering whether or not I should go to the beach today, hike the mountains, head off into the jungle, spend a few hours at a cafe, wander the parks or plazas or maybe work out and do a little bit of work on the laptop. I get up, I make some coffee, I check my emails in between intervals while I work out, I take my time preparing a healthy breakfast, never once looking at the clock (I haven’t worn a watch in years, and I haven’t used an alarm in over 4), doing a little bit of work while I cook. I settle in to only work for a couple of hours, then I look out the window and see what kind of weather it is today before I finalize my decision on beach, mountains, jungle ruins or cafe. I decide I’ll head to the beach for a few hours, after which I’ll catch a late lunch/early dinner at my favorite cafe and spend a couple more hours there before I come home, take a shower, have a nap, wake up, call a few friends, see what they are doing, and decide whether or not I want to head to a local culture event with some local dancing, or maybe a moonlit walk on the beach, or a midnight hike in one of my favorite parks or canyons. Eventually, I feel sleepy and I decide to call it a night. I don’t know what time it is, only that my body is telling me I need sleep. I come home, crawl into my bed, and I sleep softly, soundly, uncaring of what tomorrow might bring. When I awake, I lay in bed pondering whether or not I should go to the beach today, hike the mountains, head off into the jungle, spend a few hours at a cafe, wander the parks or plazas or maybe get a little bit of work done on the laptop….

If you had to compare the two, which do you think is the lifestyle every person on this planet wants to live?


If you are looking for something more hardcore and are ready to get started actually living the lifestyle (or looking for additional ways to increase your prospects abroad as an expat), The Expat Guidebook is the ultimate guidebook for all levels of expats, from beginners all the way to the professionals who have been on the road for a decade or more, plus Marginal Boundaries has several immersion guides available for various cities in the world, based upon my experience living in those destinations, establishing residency, opening bank accounts and starting various businesses, including the ones I run now.

About the author: T.W. Anderson has been traveling since 1999 and living abroad full time as an independent international citizen since January of 2008. He has established residency, opened businesses and lived long-term in four different countries and visited over 20 since first starting out. He is the founder of Marginal Boundaries, a company dedicated to cultural immersion and long-term, slow travel as a permanent expat. He is the author of The Expat Guidebook as well as immersion guides for Sofia, Bulgaria; Bogota, Colombia; and Cancun, Mexico. For more information on how to live a life of continual travel on a passive income, visit