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Working as you travel

By Matt Preston

Wade Shepard is a truly global nomad. Traveling the world perpetually for his entire adult life. 50 countries across five continents in the past 11 years. Every three months Wade moves on to a new destination, a self proclaimed “Three month rule”, the difference between living abroad and travelling.

A professional archaeologist, certified English teacher & webmaster, he works as he travels and, by upbringing, a pretty good farm hand. Wade is a dedicated travel blogger on his web site VagabondJourney.com now travelling the world with his wife Chaya and their child. We tracked him down for a chat about living life on the road.

What first made you fall in love with travel?

Initially, it was probably the thrill of constant stimulation, perpetual movement, new people, new places. I realized that travel is an easy to access key to self-determination. It is difficult to truly do what you want to do in a community of people who expect this or that of you at all times, a community that seeks to put you into your little social box. The traveler has little of this to contend with — unless you stay somewhere too long haha — and can, generally speaking, do just what they want when they want to. There is a certain aspect of character that I have noticed in long term travelers: they do exactly what they want with their time, even if that means not obliging the people around them. But once you feel this sense of personal liberty, it is difficult to go back to the bounds and obligations of work, friends, and family.

I suppose travel is the perfect medicine for the misanthrope, and it is, perhaps, the best teacher of self-awareness, self-determination.

What has been the most memorable moment on your journeys so far?

I have no idea. Each day of travel produces experiences and, consequently, memories that are difficult to compare against each other. Though hitchhiking across China was rather memorable, as was excavating at Copan in Honduras, interviewing Klaus Schmidt at Gobekli Tepe in Turkey, traveling in Iraq, talking with people in Syria, being interrogated by US border control about what I was doing in Iraq –
“What were you doing in Iraq?”
“Being a tourist.”
“Tourists don’t go to Iraq.”
“Well, I want to go to all of the countries in the world and Iraq is one of them.”
– trying to walk across Tierra del Fuego and running out of money, watching my wife have a baby on her mother’s living room floor, hiking in the Himalaya on the border of India and Nepal, traveling out to the wild west of China.
There are too many stories and memories from traveling to really tell in this interview — traveler tales are perhaps best told on long nights with a never ending supply of beer.

What made you pick some of the countries you’ve been to?

They were on the path. My object is to travel the world, so I will go anywhere. I can’t say that I am drawn towards any particular region of the world, it is all good. I generally don’t pick countries that I want to go to, but regions to spend a year or so in at a time. So if I want to go to, say, Myanmar, I would pick an airline hub within the region — Bangkok — and travel in Thailand, Vietnam, Cambodia, Laos, and maybe Southern China en route to Myanmar, and take at least a year doing so.

Jumping between countries that are across the globe from each other is an expensive endeavor, so I try to keep flights to an absolute minimum. If I want to go to a particular place, I will choose the cheapest airline hub in the region to fly into and travel there slowly overland.

To answer your question more directly, I just get a little feeling, buy a ticket to the next region, and go.

Where are you now? What have you done there and what do you plan to do next?

Wade in MongoliaI am currently in the south of Mexico, having traveled this past year in the Dominican Republic, Haiti, Guatemala, El Salvador, and Belize. This was my first go at international travel with my young family. Recently, I have been working towards transforming my website into a functioning business as well as making it a direct resources for people wanting to learn how to travel the world perpetually.

My latest project on the site is doing a series of interviews with other travelers about the independent travel businesses that they engage in, as well as ways to make money on the road in order to travel perpetually. The series is being published at Vagabond Journey Independent Travel Work Series.

We all love stats. Do you have any impressive statistics from your 11 years of travel? (countries, miles covered, days on the road, etc)

Around 50 countries, as many days on the road as there are in 11 years, I have no idea how many miles that I have covered, two long distance bicycle journeys in Europe, 1 to 3 travelogue entries published a day, 200+ travel questions answered, many destination guides written, published 10+ articles in print magazines and newspapers, worked nine seasons around the world as an archaeologist, grudgingly taught English in China and some other places, was attacked by the police three times in three different countries for no good reason, got really sick once, studied in five or six countries, worked in five or six more, traded webpages for free accommodation in more hotels and hostels that I care to count, on and on.

What advice would you give to people thinking of travelling for an extended period?

Chaya shepard in IrawIt is possible and vastly easier than you probably think if you are willing to work hard and be creative. The thing about traveling perpetually is that it requires a shift in mentality from viewing travel as a mechanism to “do” places and check things off a list towards living a full and balanced life while moving about the world. When you are poised with the question of working daily for the funds to keep traveling or with having to go home, your perspective on traveling takes on new forms: as life is no longer all fun and games and long nights of drinking beer and partying, you need to engage your surroundings more fully and come up with strategies to find sustenance and resources in a foreign landscape. This is a challenge, and, once fully engaged, visiting even the greatest of tourist sites often pales in comparison.

The problem with long term tourism is that it is an extremely imbalanced way to live. Simply put, after six months of traveling quick, seeing sites, drinking in bars, having wild times, and not working towards or building anything in your life, most people tend to get bored and go home. Perpetual tourism can quickly become a perpetual race against boredom. The human mind is made to be stimulated, and after becoming acquainted with a foreign place, much of the stimulation of tourism tends to fade.

Perhaps tourism is the extreme flip side to a life of working a steady job: you work responsibly all year in preparation for a vacation where you don’t work at all. This is alright for most people until they try traveling for a year or more. Simply put, there are only so many days that you can wake up in the morning having nothing to do before some internal urge makes you crave a project, work, some type of substance to make your days seem worthwhile. It is unbelievable how many people I meet who are completely bored in the middle of long journeys. Many seem to think that there is something wrong with them or that they are not cut out to be travelers. But I don’t believe that this is true, as in most cases it is my impression that they just need to become travelers and leave tourism behind: they need to engage in a project, work, something to stimulate the mind and lend a sense of substance to their travels.

Again, the Vagabond Journey Independent Travel Work Series is about sharing ideas with travelers about ways to make money and engage in projects while on the road. For me, right now, my main project is VagabondJourney.com, and writing daily provides the impetus to engage the places that I am in and gives me the feeling of accomplishment — especially now that I am making a living off of it.

What location in the world that you have been to would you recommend to everyone?

If you want to drink beer and score I would say go to the Czech Republic; if you want to be fully stimulated and shocked, try India; if you want to start an independent travel business, Mexico and Central America are good; if you are looking for beautiful natural landscapes, go to Mongolia; if you want to be truly confused with the culture, spend six months in Japan; if you are looking to save a lot of money, teach English in South Korea; if you want to get into some truly other worldly places, try Chile; for the pure excitement of traveling, go to China.

What locations and countries are you looking forward to visiting next?

It is looking as if we are going to travel around Mexico for the duration of our visa — six months — and then travel to Colombia, Brazil, around South America.

And lastly, can you describe how travelling makes you feel personally?

Traveling has become daily life, so I suppose traveling makes me feel stimulated enough to wake up in the morning with excitement in my eyes and a drive to go out and find what the day is going to bring. Each day of travel is a new day, and, after 11 years, it has not lost its luster in the least: I still look forward to each new place on the horizon, each new face I meet, and, now that I travel with a child, each new discovery that she makes.

Travel is a practice whose obsessive qualities only grow the more you do it, I truly love traveling more today than I ever have before.

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Author: Matt Preston

Matt Preston

The co-founder and editor of the online magazine and community site, Travel with a mate. Matt is a social media guru, organiser of international travel meetups, web developer for some great travel brands and photographer.