Written by our very own seasoned Digital Nomad, David Heiling.

A World of Experiences

Traveling the world gives you experiences you are unable to have while sitting at a home office or in a cubicle at your company-paid desk. But that doesn’t mean it’s a full-time vacation or constant walk in the park, far from it. You need to make money to survive and research nearby attractions, neighborhoods, restaurants, markets, barbershops, fitness centers, bike rental businesses, and much much more. Every time you relocate to a new city, town, or village, you start from scratch.

I’ve met people from six different continents from my three years on the road and have made friendships that will undoubtedly last a lifetime. During my travels, I have stayed at hostels and hotels, on boats and in tents. I’ve slept on a bed with 20 pillows big enough for 10 people and on the streets of Delhi, India.

I’ve traveled to 56 countries in the last three years, and here are the most common questions I get asked by locals and fellow travelers:

What do you do?

This question tops the list, and it’s not even close. When I used to meet people in hostels and told them about my journey, they would often be amazed at how I could make money while traveling. I told them I was an editor and a travel consultant for small startup companies, both located in California. I would often be met with a confused glance.

“You’re not in California, though.”

I explained to them that I was a remote worker and that I could effectively do those two different jobs from the comfort of my pajamas. As long as there was an internet connection, I could continue working those jobs to make money and fund my travels. Because the American Pacific time zone was often very different from my current timezone, sometimes I would have to work some funky hours to peek my head into a meeting. Otherwise, as long as my work was done before my deadline, I was good to go. Currently, I work as a freelancer after both of my jobs were lost to COVID-19. I help other small businesses with copy-writing, social media marketing and management, SEO, and content strategy. I make my own hours and take my own clients. Bonjour from Paris!

So you’re a digital nomad, then?

In the simplest terms, yes, my lifestyle fits into the definition of digital nomadism. When you think of a digital nomad, you may picture someone with a big pair of noise-canceling headphones and a laptop computer on the beach somewhere sipping a martini as the sun sets. I’ve never fulfilled that exact scenario, but I have been able to work while on an African safari, during a week-long surfing class in Portugal, and from the island of Santorini in Greece. I work out of coffee shops, co-working spaces, public WiFi areas, and even, once, in a club.

Is your family wealthy?

Many people along my journey assume I must be a trust fund baby or received a sizable inheritance as soon as I turned 18 years old in order travel like this full time. My simple answer to the above question:

No.

I have received exactly $0 from my family members while on the road for the last three years. That doesn’t mean my family doesn’t love me or support my decisions; I just am not financially supported by them in any way. I’m nearly 30 years old and have decided how I want to spend my time. My family hails from a small town in Wisconsin, not at Buckingham Palace.

What is your favorite place you’ve traveled to?

When I tell my new friends I have been to over 50 countries, they want to get the inside scoop on which place is the best. For me, this is an impossible question to answer because all the places I have traveled to are important to me for a specific reason. Many of the places are not comparable, so it is hard to narrow down a favorite place.

Here are some of the places that I tell people have made a specific mark on my heart and soul:

● Budapest, Hungary - where I met my partner.

● Split, Croatia - where I started my journey.

● Varanasi, India - where I was utterly overwhelmed by spiritual emotion.

● Marrakesh, Morocco - where I found beauty in chaos.

● Nairobi, Kenya - where my childhood dream of seeing a lion in person came true.

● Batumi, Georgia - where I found serenity on the sea.

Why did you start this journey?

It’s a valid question: Why would you give up your security, your relationship, and the stability of a permanent working position to go traveling for a while? It’s hard to explain, but let’s call it an innate need I didn’t know I had.

I felt extreme boredom and no sense of purpose while working as a journalist for a small newspaper in North Central Washington from 2014-2017. I worked in a basement with no windows and no hope of career advancement. I punched the clock six days a week and routinely didn’t arrive back home until after 2 a.m. I had two weeks of paid time off and felt as though the world was passing me by. I would spend my free time planning extravagant trips worldwide to see how I could most effectively use up my vacation time. I would virtually explore places I figured I would never get to. When I told my partner at the time my thoughts, she laughed it off as some ridiculous fantasy.

I felt as though American society had put me into a box. My life was supposed to go like this:

Finish university
Get job
Get partner
Adopt dog
Get married
Buy a house in the suburbs
Have children
Put up a white picket fence
Die

I rejected this idea and decided I wanted to live life my own way. So I quit my job and booked a one-way flight.

Where are you from?

No matter where you are or who you are talking to, people want to know where you come from. Before my trip, I read about some Americans telling everyone they met that they were Canadian to avoid trouble. I say I am American to everyone.

Some people are honored to meet an American; others scoff at me and mumble under their breath. Nobody knows where my town in Wisconsin is, though, so I usually say… “Near Chicago.”

How old are you?

When I started my journey, I was 26. Many of the travel friends I met had just finished high school and were on their gap year. This made me feel pretty old, and when I got asked this question more and more often, I started to wonder if I was getting a bit too old for hostels. Currently, I am 29, and I have no plans to stop the journey. Mostly my partner and I stay in Airbnb rentals for a month or more at a time and enjoy living as locals wherever we are.

How do you pick where you’re going next?

Pre-COVID-19, my partner and I would play a fun game. We would research places around the continent or around the globe that we could afford to live for the foreseeable future. We would add up how much the flight would be and make sure it was within our budget. We would go on Nomad List and research locations, activities, transportation, food, religion, architecture, and more. After we got the full picture of what living in that place would entail, we would each select our top three favorite places. Next, we would jointly rank our destinations 1-6 and give each a corresponding number of entries.

For example, if the following were our top choices:

Lisbon
Istanbul
Prague
Copenhagen
Berlin
Paris

Then Lisbon would receive six entries; Istanbul would have five; Prague four, etc.

Finally, put all of the entries into a hat and pick your next destination. Pretty fun, right?

What is your No. 1 bucket list destination you haven’t yet seen?

I actually like this question because most of the people I tell the answer to are like… why? My No. 1 bucket list destination is to get to Antarctica. To be able to see the islands of South Georgia and step foot on the seventh continent of the world, to me, is the ultimate adventure. I’d love to go during blue skies when penguins are flipping around in the water, watching icebergs float by. Imagine the silence.

Whenever the time comes, I’ll be ready with my camera in hand.

Want to make the leap and become a remote worker or a freelancer like David? Have a look at this offer. You might just find the job of your dreams…

Questions I Get While Traveling The World As A Digital Nomad.