What I Have Learned Being a Digital Nomad For Over 20 Years

As a freelance writer, I’ve spent over two decades living the digital nomad lifestyle. I’ve lived mostly in Thailand working remotely, started and sold two businesses, and have spent over 15 years working as a freelance writer. For the past three years, I’ve been living and working from the beaches of Pak Nam Pran in Thailand. It’s a sleepy little resort town that attracts kite boarders from around the world, myself included.

Since I began this lifestyle in 2002, living remotely has become easier by multitudes. In my first house outside of Bangkok where I created my first online business I couldn’t get a phone line to connect my dial up modem. Now, I can find my next job while scrolling my phone on the beach. No doubt, things are easier now, but that doesn’t mean it all comes naturally for digital nomads just starting out.

In my twenty years of living as a digital nomad, these are the takeaways that stand the test of time.

READ MORE: Chiang Mai Digital Nomad Travel Guide

Enjoy the Place You’re Living

One of the most puzzling situations to me, still after twenty years of living remotely in Thailand, is how many foreigners continue to live abroad despite the fact that they constantly complain about the weather, or the food, or the driving. Being a digital nomad is supposed to be about the freedom to live anywhere, so if you find yourself living in a city, country, or culture you just don't like, don’t be afraid to admit it and move on. I lived very happily for ten years in Kanchanaburi, Thailand and then one day decided I had had enough of the place, so I packed up and went traveling for a year.

Of course, you don’t have to or even should enjoy everything about your new home, but know that it’s not going to change to accommodate your preferences. Finding the right place at the right time is the key to making it work, and the ability to pull up stakes and move on when it stops working for you is what being a digital nomad is all about.

Keep Your Expenses Low

The low cost of living abroad draws many people to this lifestyle, but over the years I’ve seen people lose their judgement and build bad spending habits. As a freelancer, I am careful not to overstretch myself and to have at least several months of cushion in the bank for when things go sideways. This helped during the pandemic when I lost my regular monthly gig and all the work I had set up in the months previous in just a few days' time. Thankfully, I had a one-year buffer saved up.

Take Advantage of the Systems Already in Place

Something that took me a while to learn because of my natural stubbornness is that you can take advantage of systems that are already in place to make your life easier. Being a digital nomad is all about gaining independence by taking advantage of a low cost of living, but I’ve learned that if someone else has figured out a good hack, then you should use it. Not everything has to be DIY. Taking good advice will save you time, money, and frustration. This could mean using a local lawyer to simplify your visa applications or an agent to find a place to live, the small fee will be well worth the time and frustration saved.

Get to Know the Locals

When living abroad, it’s easy to gravitate towards niche communities of expats and settle into a bubble that could keep you from discovering all your new home has to offer. Mixing with your neighbors in everyday life lets them know you as a person, helps you develop your language skills, and builds a network that may come in handy if you ever find yourself in a pinch.

Personally, I love shopping at the fresh markets, not only because there are always unexpected discoveries, but also because by being there frequently, the merchants get to know me. This has the knock-on effect of when I see them at a local restaurant and they introduce me to their friends who may end up waving to me in the street. Suddenly I'm no longer a stranger-stranger but a familiar stranger who may be a friend one day.

Learn What the Laws Actually Are

This should be a no-brainer but I have seen and heard foreigners in Thailand giving each other advice on both law and custom based on nothing but age-old expat gossip. For instance, some people will say that working remotely is illegal in Thailand, when it is not. It should be as simple as a quick google to find out what the laws actually are and how they are to be interpreted.

In countries like Thailand, just knowing the law isn't the end-all and be-all though. In many instances, the local culture trumps the law no matter what. I once found myself in a land dispute over a couple of meters with a neighbor; the boundary was clearly marked and I wouldn’t give in. In the end, I wound up on the bad side of all my neighbors for a while and was even ordered to have a wall constructed by the village headman. He had no official position, but all the respect of the village. In the end I should have just let her have the two meters.

Even with a few bumps along the road, there’s probably never been a better or easier time to be a digital nomad than right now. For me this lifestyle has been the best way to live for the past twenty years and I have no plans to change course in the decades ahead.