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3 Things I Wish I’d Known — Growing As A Digital Nomad

I blame my friend Wei. If she hadn’t pushed me to apply for that job in Africa, I likely would have returned from my brief stint as a remote worker while down at Hacker Paradise in Costa Rica, and gone back to the normal job. So from the bottom of my heart, thank you Wei! 🙂

Over the last three years, I have worked as a freelance web developer and location independent entrepreneur. I have visited five of seven continents, eaten way too much food (I’m looking at you, Phở 🍜), walked more than I drove, and met countless amazing people who have all shaped me in different ways.


Above: Tour of all things dim-sum with my AirBnB host in Hong Kong (and chicken feet 🐔 ).

My life during that time has been nothing short of an amazing and humbling learning and growing experience. I’ve been places and done things that I can’t imagine the “old Kevin” having done.

I am truly fortunate to be able to do what I do and hope that I can continue to see more of the amazing things this world has to offer in the coming years.

Here are three biggest things that I’ve learned whilst being a digital nomad:

Lesson 1: Making money online is easy. Making money online is hard.**

Confused? Making money online is easy. The barrier to entry is low. Ridiculously low.

  • Got an internet connection? ✅
  • Got some skill/product that people want? ✅
  • Got a way to get paid? ✅

Congrats! You’re all set to start earning money online!😎💰 But…

Making money online is hard. That same ease of entry lends itself to a more crowded marketplace. The competition is stiff for remote work, especially if you want a salary comparable to Western standards, and you will have to do a little more work upfront.

That not to say that it’s impossible to make money online or that all the jobs pay terribly. Instead, just as with interviewing for a ‘real 9–5 job’, you must distinguish yourself to employers/clients and stand out above some of the noise. Show them why they should hire you!

Managing business tasks, like opening a bank account or filing taxes, things that would be simple at home, can present challenges when you are location independent. These issues are becoming more manageable thanks to the growing number of digital nomads running location independent businesses to turn to for help and advice and to government initiatives like Estonia’s e-Residency program.

Lesson 2: It takes work to maintain connections

“Well duh, Kevin. Of course it will take work to keep connections back at home. Tell me something I haven’t read somewhere else.” It might sound obvious to you, but until everything in your previous life and all your family is half a world away, it might not mean the same thing or truly sink in.

Many people have written about the loneliness that digital nomads can succumb to while on the road. It’s easy in the beginning to get swept up in the newness of the traveling. You’re meeting new people and seeing all sorts of exotic sights. You might hardly think about home.

After while, be it several months or several years, things can change. You find yourself with a sense that that life back home has been moving on without you or you might feel more and more detached from it when you return. It can be a shocking revelation to realize that you can no longer associate with home, and yet are left, in the present, with nothing that might take its place either.


Above: My go-to quick lunch in Cần Thơ —Bánh bao

Lesson 3: Finding a purpose to your travels and work is a HUGE game changer.

I was feeling really burned out working as a location independent entrepreneur after almost three years. There seemed to be no point to it all of working, other than to make money in order to pay the rent/bills, to eat, and to keep traveling and put off getting a ‘real job’. Business issues were hanging over me all the time from regulatory things to client work problems. Even travel had gotten old too. New places were often more about just checking off boxes. Pretty white sandy beaches started blurring together.

I was ready to throw in the towel…

The catalysis came about quite accidentally, but prompted a massive shift in mindset and began to turn things around for me completely. I had decided I wanted to start a new business, in order to diversify away from the consulting and agency work I was doing. I ended up coming up with something that was of a hybrid between a for-profit and NGO. I’m excited to be working on the logistics, setting it up, pitching investors, and then hopefully watching it grow.

Having something meaningful to work towards and motivate you is rocket fuel for enacting positive change. I went from a depressed, scarcity mindset driven outlook, to actively trying to cultivate a more abundance oriented mindset.

I can’t take all the credit. It was also partly due to meeting my girlfriend. We are opposites in many ways, but she helps to keep me from veering too far out into the left field. The two of us are traveling together now, keeping an eye out for new places that check off all our “boxes”.

What makes a home? Do I see myself settling down in the world and where? How does home fit into the location independent individual’s life? Can we design a digital nomad life that isn’t centered around Instagram? How can location independent entrepreneurs build businesses with purpose and impact while still making a living?

These are all the sort of things that I want to examine further and aim to write about in the future. Of course along way I’ll also write about things like how I travel, make money, and other topics pertinent to the location independent entrepreneur and digital nomad.

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