Overcoming Obstacles to Traveling While Working as a Digital Nomad

Updated May, 2018 Stuck in a rut or feeling like life is passing you by? Wishing you were traveling instead, but feeling like there’s no way to make it happen until retirement? We were in the same boat when we decided it was time to make our dream of traveling the world a reality. It’s been a few years ago now since we started this journey. We couldn’t quite retire yet, but we realized that if we found a way to work from anywhere, then there was really nothing preventing us from making the leap to being “digital nomads” (one who travels the world while working online using wireless internet, smart phones, Voice over IP, and cloud based applications). If you’ve been considering the same thing but don’t quite know how to get there, you’re not alone. It’s a matter of overcoming your fears and the challenges.

“Your greatest dreams are all on the other side of the wall of fear and caution.” –Unknown

As we’ve traveled and spoken to people who want to do the same thing, we’ve found that there are five fears or challenges that you need to get past in order to take the leap to full-time travel while working.

Fear #1: “I can’t possibly afford such a thing!”

If you attempt to treat becoming a digital nomad as though you’re going on a long-term vacation, then no, most of us can’t possibly afford such a thing. The trick is to go where the cost of living is less than where you are now, and to live like a local instead of a tourist. To illustrate, here is a sampling of cities from nomadlist.com that have a cost of living of below $1,350 USD per month.

Ho Chi Minh City (Saigon), Vietnam:  $864 Kiev, Ukraine:  $1,340 Chiang Mai, Thailand:  $1,038 Cancun, Mexico:  $1,250 Denpasar Bali, Indonesia:  $770 Lodz, Poland:  $1,291 Ploiesti, Romania:  $1,183 Antigua, Guatemala:  $1,176 Quito, Ecuador:  $1,154

Compare these to a few cities in the US and Canada (all in USD):

Toronto:  $3,036 Calgary:  $2,770 Vancouver:  $3,315 Ottawa:   $2,215 Seattle: $5,935 Los Angeles:  $4,215 Houston:  $3,949 Jacksonville:  $2,583 Raleigh:  $2,850

Need more convincing? Check this out.

Fear #2: “I still need to generate income. How will I ever do that?”

It’s definitely possible, but you need to open your mind to the possibilities. There are a number of legitimate ways to earn an income from anywhere. Think about making your current job remote, teaching classes online, learning a new skill such as programming or medical transcription, or taking a job with a company that hires remote workers. These are just a few of the possibilities. My advice is to simply make the decision that you are going to become a remote worker by such and such date, then determine the best way to get there. If you try to do the process in the reverse, it may never happen.

Fear #3: “How will we leave the things we love?”

You might be wondering how you’ll stay connected with family, friends, your company or even your favorite entertainment. By embracing technology, you really don’t need to “leave” much behind at all. With a bit of pre-planning, living in another country shouldn’t be any different than living in another city in the same country. Using technology, you can have video chats with family and friends for free, you can keep your local phone number and have it ring anywhere in the world, and you can stay connected with the office as though you were in the building next door. At the same time, you can monitor your home (if you still have one) or that of a loved one and you can even keep up with your favorite programs, movies and sports teams.

Fear #4: “What about the house, the car, and 30 years worth of accumulated possessions?”

It’s always amazing to me how many people don’t feel they can make a move because they’re too entrenched with the things they’ve accumulated over the years. It can be totally overwhelming to look around your house and see nothing but mounds of stuff. But sooner or later you need to address it, and the longer you wait, the longer you put off having complete flexibility to travel.

“Time is at once the most valuable and the most perishable of all our possessions.” ~John Randolph

 There are at least two big reasons to start clearing out your stuff: According to Francine Jay, “Miss Minimalist”, our stuff holds us captive in three ways.

Physically – the more stuff, the less nimble we become Psychologically – too much stuff weighs on our spirits and makes us feel heavy and lethargic Financially – stuff can enslave us via debt

Jay and Lea in Paris


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If you’re serious about hitting the road, then at some point, you just need to start the process of downsizing to a couple of suitcases. Here’s how we did it.
  • Start decluttering and stop buying new stuff!
  • Sell or rent the house
  • Eliminate, eliminate, eliminate
  • Eliminate some more
  • Then, store anything you can’t bear to part with
  • As you continue on your journey, you’ll eliminate even more

Fear #5: What about health and safety?

Health safety are serious concerns. But one thing you should keep in mind is that…

The reality of the situation in a country or city is usually far better than the perception you and others have of it.

Let’s take healthcare, for instance. Here is how the World Health Organization ranked health systems around the world. Notice where both the U.S. and Canada fell in the rankings. What this means is that you can find good healthcare – even better healthcare – away from home.  As for safety, do your research before you go by checking either the US State Department’s Alerts and Warnings and/or Canada’s Travel Advice and Advisories. And no matter where you go, take the usual precautions. Here are the “rules” we live by:
    • Leave the flash and bling at home
    • Stay alert
    • Blend in
    • Use a taxi app or Uber
  • Don’t travel alone at night

There’s nothing like overcoming something that scares you so much. Nothing feels better.” ~Laura Wilkonson

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