That Time I Became a Reluctant Digital Nomad
The story of professional endings and unexpected new beginnings.
Some moments in life pivot us in unexpected directions – my sudden departure from Dubai was one of those.
After seven years of living and working in Dubai, everything came to a crashing end.
I had been living and working in the U.A.E. since 2010, having moved there to teach at an international school. To say it had been an adventure was an understatement! After leaving teaching to work in sales and marketing for a global educational publisher, I was ready for my next professional challenge. I took a chance on a new company that had wooed me with big promises and grandiose plans.
I’ll skip the dramatic bits, but in the end, the company folded, and so did the job! At that point, I took it as a sign that it was time to depart the U.A.E. and move on to new adventures. That’s when I decided to take some time off to recoup from this traumatic experience in the lovely country of Thailand.
I had never been to Thailand despite it being on my travel list. And now, being unemployed with endless amounts of ‘vacation days’, it seemed like a great opportunity to take an extended holiday on the sunny beaches of this beautiful country.
The best place I never knew existed
After spending a week in Phuket with my friends (who had incidentally also just left the U.A.E), I booked an apartment in Chiang Mai for a whole month – at the time, this sounded like a lifetime! I planned to go and spend a quiet and leisurely month in this mysterious Chiang Mai place while I thought about my next steps.
As it turns out, I fell in love with Chiang Mai.
This little gem of a city in the northern region of Thailand was the greatest place I ever could have landed. I was enamoured by its quaint streets, the warmth of locals, and the ease of life. There was a local traveller community I quickly became part of. While it didn’t offer the beach lifestyle of the islands, it had mountains, hiking trails and a very low cost of living.
It’s also where I was first introduced to ‘digital nomads’—a group of people working online, a concept alien yet intriguing to me.
Digital Nomad noun a person who earns a living working online in various locations of their choosing (rather than a fixed business location). (Oxford Languages)
I had no idea what a digital nomad was and although I was intrigued by how they worked, I had no desire to be one. I was in Thailand for a bit of a break before I got back into a 9-5 job somewhere else!
Of course, it didn’t take long for that month to turn into two and then three. Surprisingly, it’s not hard to fill your days with things to do when living in a beautiful and fun city like Chiang Mai. So I kept extending my sabbatical. Why not stay in this lovely little city where apartments were cheap, and the sun was always shining?
Ok, I’m ready to work now
By month three, I knew it was time for my impromptu sabbatical to end. So, I started applying for jobs and tapping into my publishing world network, fully expecting to move to the next country to start my full-time office job back in the publishing world.
Then, a funny thing happened. I realised I had become unemployable. Getting that next job wouldn’t be as easy as I had hoped.
I had all this professional experience and was very knowledgeable in the educational publishing industry, yet no one wanted to pay me a reasonable salary to do this job!
The offers I was getting from rival publishers were barely enough to cover living expenses. Or worse yet, the companies offered me jobs in Asia but no work permits. So, I decided that the publishing world was no longer something I wanted to be part of, and I turned my attention to other industries.
Initially sceptical, I slowly began to see the allure of digital nomadism as I immersed myself in Chiang Mai’s vibrant community. I thought this might just be the time to reinvent myself.
I started taking a few online courses, dabbling in social media and copywriting. I was fascinated by how many people without formal education or qualifications were making money doing all these jobs I had never considered.
Wait. Am I old?
I was reading job descriptions for roles I had no idea how to do. Feeling like a dinosaur in a world of tech-savvy teenagers, I realised it was time to evolve.
So, while I waited for this new job to present itself, I reluctantly became a digital nomad.
I can’t recall exactly when I started working online, but I’m pretty sure it was through a Facebook group where I met Claire, a travel blogger looking for someone to help her with her social media. I had no idea what or how to do this, but I sent her a message and told her I’d do it for a month if she were okay with me learning as I went.
She was, and from that, I started to see how someone could make money working online.
Despite entering into this new digital nomad lifestyle reluctantly, there were so many things to love. The daily freedom, learning new things, spending your days working from a cafe (in fact, you could actually work from anywhere as you really did only need your laptop and wifi), skipping out anytime for a massage or a swim. I met so many amazing and interesting people who were building businesses or selling services like copywriting and website design, and actually making a living. It was a revelation!
Although, not all sunshine and rainbows. Getting paid to work online and getting paid well are two entirely different things, as it turns out.
And with the upsides, there were definitely downsides. Namely the fact that as a digital nomad, by necessity, you must move around a lot. By that I mean, move countries. They call it a nomadic lifestyle for a reason!
At this stage of my life I had already lived in three other countries that weren’t my homeland, so I was no stranger to visas and work permits. But when you’re a tourist in another country, you often don’t have more than 90 days to stay. Sometimes even less!
Because, as a tourist, why would you want to stay any longer? Most people have jobs to get back to!
That meant, every 90 days, you either did a ‘visa run’ or “moved” to another country for the next 90 days.
Both were fraught with negatives.
Visa runs were what they sounded like. Cross the border into another country for a few hours, maybe a few days, and then return to the first country. This was a very common practice, but it didn’t mean that it was the right thing to do. Visa runs always came with the inherent danger that the country you wanted to return to wouldn’t let you back in. After all, if you really live in a country, you should have the correct visa.
(This is the part where I should digress and tell the story of ‘That Time I Got Detained in Bangkok Airport for Spending Too Much Time in Thailand’. But I’ll save that one for another time and another blog!)
The other option was to leave Thailand and go to another country for an extended period of time. Vietnam and Bali were two popular destinations. But this meant going to another city, finding a new place to live, meeting new people, finding your way around another new neighbourhood – in another language, no less. It was exhausting.
This is where I came to dislike being a ‘digital nomad’. I am not interested in living out of a backpack. Or moving to a new place every three months. I am definitely not interested in having to make a whole new set of friends or find my way to basic places like the grocery store. I like my creature comforts. I prefer familiarity. I thrive when I know what’s coming next.
Am I the only one that hates this?
Call me boring. Call me unspontaneous. But I may be the only person on the planet who hated being a digital nomad. The truth is, picking up your whole life to move every three months is enough to get to anyone, no matter how adventurous you consider yourself.
Because I had never set out to do this ‘digital nomad’ thing, it got old fast.
I was constantly stressed, worrying about visas, overstaying my current visa, and not being allowed back into Thailand. I had grown to love Chiang Mai and the little community I was part of, and I wanted to keep going back. But this is not how it works when you do not have a residency visa in a country!
So, in the end, I couldn’t wait to give up my digital nomad life. I was desperate for stability and consistency. And I didn’t want to worry about a visa again!
(Oops spoke too soon! Remind me to tell you about “That Time I Married an Aussie Bloke and Had to Deal with Visas Processes from Hell”)
It’s funny how life works out, isn’t it?
I wouldn’t have gone to Thailand if I had never lost my job in Dubai. I wouldn’t have become a reluctant digital nomad and learned new skills. I wouldn’t have met my friend Claire, who took a chance on me. Nor would I have met the CEO of a remote software company that helped open the doors to the professional reinvention I was looking for.
The path to professional reinvention didn’t look like I thought it would, but what in life ever does? I now call myself a marketer and happily still work remotely, but this time from my cozy home office. Ironically, the instability I hated led me to a more grounded and fulfilling life than I could have imagined.
To those that helped me get my start
I’m still friends with Claire who gave me my start in the online world all those years ago! In fact, we even ventured into a few side businesses together over the years! While she is no longer a travel blogger, she is still blogging and writing about her life as a mama and family travel. Check her out here and her travel blog here.
My friend Amar, CEO of ZenMaid gave me my first real start into the marketing world for a company. I worked with ZenMaid for four years and learned so much and will forever be grateful for this path that really honed my skills as a marketer.
