Dose #1 Embarking on the Digital Nomad Journey

Hello from Sunny ☀️ San Francisco!

You know, creativity often comes when you're doing everyday things, like walking your dog, waiting for your food at a cafe, or simply sitting in the park with a book. For me, it happened when I was sitting in a pizzeria eagerly awaiting my Chicago-style deep-dish pizza 🍕, and that's when I started writing this.

This is my first attempt at writing after a long hiatus. So I’ll introduce myself first.

I am from Sri Lanka. A beautiful tropical island in the Indian Ocean. I am a Digital Nomad. Two years ago Dulitha (my husband/best friend) and I moved from Colombo to a beautiful beach city called ‘Hiriketiya’ in Sri Lanka. We lived there for a few months before deciding to start living as Digital Nomads.

I studied law but I am a self-taught startup program manager. My expertise is building community relationships through startup programs and partner collaborations. In simple terms, I love working with people (especially founders) with diverse backgrounds.

When I moved to Hiri I didn’t have plans. After 3 months of break, I wanted to start working again. But I was not ready to go back to 9-to-5 or in-person work. Remote work was a non-negotiable for me for a couple of reasons but the most prominent one was that I wanted to live a slow life.

So it’s been 2 years since I started working remotely while travelling. I have worked remotely on 3 Startup programs (Accelerators and Incubators) with 3 different program teams while nomading through 10 different cities.

I write this Newsletter to share lessons I learned on this journey as a professional and who knows maybe an entrepreneur one day.

So let's dig in!

Who is a Digital Nomad?

This is a frequent question I get.

Well, It depends on who you ask.

For me and Dulitha, it’s a lifestyle. Working while taking trips to different cities in the world. Our home base is Sri Lanka and we travel to different cities in the world to explore while working remotely. Since both of us have our own companies and projects, you can call us Nomadic Entrepreneurs.

We choose to live in a city between 1 to 3 months. Duration mostly depends on the type of visa we get but there are other reasons we factor in when we decide on a location. (this is a topic for a different day)

Travelling and Working at the same time: Isn’t it fascinating?

It definitely is a fascinating thing to do. I always loved watching others taking trips abroad and living vicariously through them. Starting off as a digital nomad was not an easy task; financially or emotionally. But it’s something anyone and everyone can do with proper planning.

There are pros and cons to being a digital nomad. I would call them Motivations and Challenges.

Motivations for me are;

• Freedom: The desire for autonomy over my work schedule and environment. I work from our Airbnb apartment, coffee shop or a coworking space depending on the type of work I do or the weather of the day.

• Exploration: A passion for exploring new destinations, cultures, and experiences. Getting to make beautiful memories with nature and people. Watching Sunrise from the Annapoorna mountain range in Nepal to Sunset Scooter rides in Phuket are beautiful core memories I made as a result of exploring.

• Work-Life Balance: Aiming for a holistic work-life balance that encompasses travel and personal development. I learnt many things about myself that I would not have realised if it wasn’t for the constant travel and planning. When I was working I never took breaks during weekdays. I learnt how to take breaks and not feel guilty for taking them. The trick is to acknowledge the break as a break.

As with everything else in life, there are challenges I face;

• Connectivity Issues: Ensuring stable and reliable internet connectivity can sometimes be a challenge. Especially if you don’t choose the right phone carrier to get a SIM. It is important to be aware of how connectivity works in different parts of the cities you travel to. Do your research first and ask the community.

• Time Management: Balancing work, travel, and leisure requires adept time management and self-discipline. I use Akiflow and Google Calendar to make sure that I don’t miss meetings or deadlines I have committed myself to. It’s a work in progress.

• Legalities: Navigating through various countries’ visa regulations and taxation laws necessitates careful planning and compliance. I use Notion to create a comprehensive plan for each country we visit to and use Google Drive to upload all the necessary travel documents. Since I have a Sri Lankan passport, it’s one of the most challenging things to do, but what comes after is worth the effort.

Thinking about being a Digital Nomad: Where to start?

When we started nomading, we were unsure of whether to continue doing it or not. We had a permanent lease for an apartment in the city, I was in a decent place in my career, and we had made friends and lifestyle choices that needed our constant attention.

When I think about how we did what we did, there is only one explanation for it.

We took a calculated risk.

Instead of starting big, we started small.

Instead of moving to a different country, we moved to a city that we are familiar with.

We did our research about the lifestyle using community forums, blogs, articles and real-life experiences.

Some of the questions we found answers to are;

1. What kinds of places do we prefer to live in? Like shared living spaces, hotels, living in a van, or having our own apartments?

2. What are the essential things we want in a place when we decide to live there?

3. What daily schedule do we feel good with?

4. How do we like to relax or take short breaks?

5. How much money do we need each month to feel comfortable?

You’ll have your own set of questions depending on your priorities in life.

Well, easier said than done of course.

But that’s where you can start.

Start small and figure out the nitty gritty of the Digital Nomad lifestyle for yourself.

I’m planning to continue writing about being a digital nomad covering travel tips, productivity hacks and remote work lessons.

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