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Greece’s First Digital Nomad: Why I Decided To Live And Invest Overseas

By Jacelyn Holmes

Published in Live and Invest Overseas Magazine and website:

Greece’s First Digital Nomad

a woman sitting looking out the doorway over the Mediterranean Greek Aegean sea
Enjoying the stunning views from the castle of Palamidi, in Nafplio

The new “life insurance” is getting residency in another country. The effects of the pandemic are still casting a shadow over many people… but because I had the ability to go somewhere else, I managed to avoid strict lockdowns, a mental health crisis, and economic uncertainty… There is no guarantee that world events will get any smoother. You need a backup plan—like mine. I left Canada in November 2020 and headed straight for Costa Rica, where I live part of the year… and had a plan to land in Greece to start the process of getting a residence visa.

I actually became the very first person in the world to obtain Greece’s digital nomad visa. Today, I’m a Canadian citizen, who lives between Costa Rica and Greece. I can live in three countries. I have options.

Whatever happens, I have a plan to protect my lifestyle… To me, that’s the true meaning of having insurance.

tattoo on a finger that reads eudaimonia in ancient greek


I got this tattoo to celebrate…The day I received my digital nomad visa in Greece, I got a tattoo on my finger to celebrate. It was painful. But it wasn’t as painful as the process of getting that visa… The common saying, “no pain, no gain” could not be more

true here. My tattoo reads eudaimonia. This is my favorite ancient Greek word. There’s no one-word translation in English. It’s the combination of wellbeing, happiness, and flourishing which is the ultimate goal of life… These are the virtues and values I try to integrate into my own life. They’re also the reasons why I decided to live and invest overseas. If you, too, are searching for a way to diversify your life—and feel more alive than ever—then perhaps my journey will help guide you on a path to your very own eudaimonia, here, in glorious Greece…

Your Visa Options The requirements to apply for Greece’s new digital nomad visa are pretty straightforward. It’s important to note that there are two different types: A one-year or two-year residency. With the latter, you have the option to renew and the possibility of applying for Greek citizenship. The paperwork must be done both in Greek and English, and signed and notarized by a legal representative. It is absolutely paramount that you find yourself a lawyer and accountant who understand the needs of foreigners, as well as the logistics of Greece’s immigration system. There are many people who will take your money and have no idea what they are doing… This is what happened to me.

“The First Person In The World” I showed up to the immigration offices in Athens, and the staff confidently told me that this visa didn’t even exist. OK, it was a newly launched visa program. But come on, the immigration staff should at least know it exists! I was right, and they were wrong. As it turned out, I would become the very first person in the entire world to apply for and receive this visa…I was the “guinea pig” for the whole process. I even had to educate both my lawyer and accountant on the information I had researched and learned.

My Odyssey Two weeks into the process… and after one-and-a-half-months. Do I look worn out? I wish I could tell you the process was easy… it was anything but. Still, like I say, “no pain, no gain”… I won the prize in the end. And today I enjoy my dream lifestyle…I’m telling you about my frustrations so you’re prepared—and don’t lose sight of your own goal. Dealing with insurance companies is usually not fun either… But it’s still worth it to get the benefits of insurance. The most frustrating aspect of the whole process for me, was that I was told so many different rules and guidelines—which were then changed and reinvented each time I came in to speak to someone… At this point I was basically living in the immigration office, because I was there almost every day. The staff started to greet me by first name, and others rolled their eyes when I arrived. I ended up at the top floor in front of the “man in charge” without an appointment. My manners and my sanity had literally left the building (just like Elvis). I was begging for the correct information, which would allow my application to proceed… I was determined to find the answers and have a successful application—but my tourist visa had run out and the man who was leading the dog and pony show would never admit that he had no idea what he was doing… I was now an illegal alien and the rubber walls I kept hitting had taken a toll on me. Over the course of the next few weeks, this man was exhausted by my persistence and even one time threatened to call the police to have me removed! With the help of many hugs and encouraging words from my Greek friends, freddo cappuccinos, spanakopita (Greek spinach pie), nights with strong shots of ouzo, the sights and sounds of Athens (the Acropolis is a dream), and many weekend trips to the stunning islands to blow off steam… I was able to get through this odyssey and land on top. I now truly understood all the locals’ complaints about their government’s bureaucracy… and now I was respected by the locals and my friends for seeing this experience through… I not only became a resident—I felt that I had earned the right to be called an honorary Greek. My perseverance prevailed. The officials finally stamped my papers. I was the first person in the world to go through this particular theatrical immigration process. Here’s hoping they’ve learned something, and it’s easier for you.

The Ancient Theatre of Epidaurus in Greece
The Ancient Theatre of Epidaurus

My Final Steps After my application was approved, I was told it would take three months for my visa to become official and for me to receive my residency card. In the end it took more than eight months. I decided to chance it and leave Greece, as winter was creeping in and Costa Rica was calling me. All I had was a piece of paper that said my visa was in the process of being approved. “Risky Business” was a great movie… but I was playing with a lot more risk than I realized. I was almost denied access through the Schengen Area to Costa Rica at the German border… I learned that I needed to have this document in Greek, English, and German (or the language of whatever country you may fly through) in order to be admitted through the Schengen regions. I did eventually land in Costa Rica and everything was fine. But I couldn’t help but wonder what my difficulties might be trying to re-enter Greece… In the end, there were none whatsoever. A welcoming surprise.

You Know What They Say About Lemons… I started this whole process in September of 2021, and left in December 2021 with the paper confirming my application was on file. I arrived back in June of 2022 and although I was back in Greece, I was still waiting for my actual residency card. When I picked up my card on July 31, 2022 (which also happens to be my birthday), I was told that I needed to renew my residency on December 2023. I was livid because it meant that they started counting my two-year residency back in December 2021. It felt like I just got the darn thing, and instead of enjoying it, I was thinking about the unwanted adventure I’d have to go through to renew it… Life can throw you a bag of lemons… they’re especially abundant here in Greece, where the lemons and oranges are out of this world—and trees line many backyard gardens… In fact, I have a lemon tree in my own backyard, in Nafplio, Greece, a vibrant seaside town in Peloponnese where I have finally settled. I’ve learned to appreciate the lemons.

The city and sea view of Nafplio in Greece, stunning blue waters and cliffs
Nafplio, Greece

From my sprawling terrace I can see the castle on the cliffs, casting a mystical ambience over the romantic Old Town… I have 180 degrees of unbelievable mountain views, with the crystal blue sea calling me to come for a swim and play in its diamond essence… So, I guess I learned how to make lemonade.

Despite the infamous Greek bureaucracy… It was so worth it. My life now is full eudaimonia.

Sincerely, Jacelyn Holmes Contributor, Simon Letter

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