From Debts to Successful Career and Nomadic Life – Thilini Wijesinhe

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Life is journey of constant changes, growth and learning. In this episode, Thilini shares her story on how she recover from past mistakes to building a professional career, and ultimately exchanging a lucrative pay check for the freedom to travel around the world. We chat about the mindset of riding the wave of life, and also things to consider when leaving a well paid job for a nomadic travel life. 

  • 02:00: Taking actions without regrets
  • 05:05: Maintaining a long distance relationship
  • 07:50: Transiting from travel to digital nomad life
  • 11:05: Managing others’ responses to your transition
  • 14:00: Travel style and budget
  • 17:10: Pursuing passions and ideas during pandemic
  • 23:45: Learning from our past and how it shapes the future
  • 28:05: The mindset to adapt and adjust
  • 33:28: From finance to writing
  • 38:40: How travel changes perspectives
  • 42:50: What do you miss out when being away
  • 44:30: A different phase of life with minimalism
  • 50:10: Travel and experience to really discover
  • 52:30: Tips for transiting from corporate to nomadic life



The following is an extremely summarized version extracted from the transcript of the full conversation. I strongly recommend listening to the podcast for all the valuable insights. You will also hear more detailed and contextualized stories from the guest(s), as well as pointers from me in a two-way conversation.

Hi Thilini! Please give an introduction of yourself.

I’m originally from Sri Lanka, where I grew up, study and started my financial career. I had a challenging childhood and youth, including losing both my parents. Eventually, my financial career became somewhat lucrative, but I had several problems in my personal life. So then, I emigrated to Australia through the skilled immigration program and continued my financial career in different roles. Finally, somewhere around 2018, I felt like I wanted to see and do more in life. So, when my partner was living in Texas, we decided to put our full-time jobs behind us and go traveling and use Mexico as a base. So that’s how it started.

What triggered your wanderlust, and gave you the courage to travel?

As I mentioned, I’ve faced challenges since early on in my life. So, I understood that life is fragile and finite; if you want something, you’ve got to go for it. I didn’t grow up traveling; I started as an adult. I made my first overseas trip when I was 21. I did travel a bit in Sri Lanka when my career became lucrative. But it was after I moved to Australia that I started traveling extensively. In Australia, we have a little more annual leave, but vacation days still limited us; sometimes, I had to take no pay. I talked to my partner; we have reached a stage where we were financially stable; we had no other obligations. We thought 50 years from now are we going to regret doing it or not doing it?

Did you plan to travel around the world, visit specific continents, or be free and easy?

What we thought was not to Nomad, fully, we wanted to use a base. We picked Mexico as a base because my partner was born there. It was also relatively easy for me to get a temporary residency. After we moved to Mexico, we started with South America and Central America and then we went to Europe.  Before we gave up that base, we also explored locally and just traveled for a couple of months. Then we came back and completed a road trip across the country towards the Yucatan Peninsula, where we stayed. Then the pandemic hit.

How did you meet your partner and what’s your secret tip for maintaining a long-distance relationship?

We first met online, not through a dating site, but something else. Then we met in person and realized we were on the same page. We did have a long-distance relationship; it’s the longest possible distance you can imagine.

At the time, we both had full-time jobs, so we had a permanent base. The funny part was the time difference between Sydney and Texas; one person had to stay up late and sacrifice sleep, so you can’t talk all the time. You have a specific time in the evening or morning, plus some short calls in between. You need to have other interests because if your whole life revolves around the relationship, it can be challenging. You’ve got to have your hobbies, independence, and friends. I think it’s a balance between the two, and I think what’s most important is you need an end date. That means you can’t do long-distance forever.

How did you transit from a gap year for full-time travel to embracing a long-term nomadic lifestyle?

Firstly, we planned to take a year or two off, travel, and possibly go back to work. After about a year of traveling, we decided that we liked the flexibility and freedom, so we thought about what we could do using our skills. For the following few months, I had some anxiety, and I was struggling a little bit. So, I thought about my hobbies and focused on those things; that’s how we started. It’s great we get to do what we love and travel.

If your initial plan was to take a gap year and travel freely, why did you feel the need to have a base?

We had a moving base. The reason was that I didn’t want to get exhausted from traveling constantly and having to carry luggage or backpacks throughout. I was curious about Mexico; the lifestyle intrigued me; I wanted to explore the locality, learn Spanish, volunteer, and do community work. I thought it would be helpful to have a base, and Mexico worked perfectly because of its geographic location. The plan turned to be more location-independent work and less of a digital nomad. Location-independent means we don’t have to travel; we can travel if you want to.

How did your family and friends respond to your lifestyle change?

I had seen others do it before me. My colleagues and friends in Australia thought it was a great idea. My bosses wished they could do it too, but they couldn’t because of their work commitments. So, there were a couple of concerned people; sometimes, I think the concern is genuine. But generally speaking, I think the response was positive. There were some opinions, but I learned very young not to care too much about other people. Life’s too short. I had an older colleague who told me this before I left that opportunities come in small windows; you got to take them before they’re gone. Don’t miss it; one or two years is a short time considering the human lifespan, so just go.

Did you have a pre-plan budget in mind before leaving?

Roughly, but nothing specific. We thought we had enough money not to work for two years or even a little more. Mexico is a low-cost location, so the money goes further. We didn’t have a strict budget, but we were careful. We didn’t go to expensive restaurants and splash our cash. Instead, we stayed in mid-range hotels instead of backpacker hostels. A couple of times, we rented cars when we traveled, and in Mexico, we went on road trips. We prioritized how to spend money based on our likings and requirements.

What is your typical travel style?

When we were on the Pacific Coast, we made short trips of two to three weeks. Then we left that base and traveled for two months. Then we came back, and we went on a shorter trip to Cuba and Belize.

Have you found the pandemic a good opportunity to start writing?

So, I used just to write; I have some financial background and technical knowledge; maybe I could start writing. So, I offered my services directly to a few people and got started like that. Now, I am working on a couple of other ideas. So, it was a hobby that I was able to monetize.

Has the pandemic allowed you to pursue your passions?

Yes, exactly, that is precisely the point because we were caught up in our daily lives. Ideally, it would be best if you got started in your business before you quit your job. That is the ideal way, the less risky way, but for me, I was too entangled in daily life that I would never have got around to it.

I wanted to travel, and I wanted to become an entrepreneur. Then I lost the only family member I had early on, and things were not possible. So, I put my dreams on hold and continued working and sorting other personal issues. It went from one thing to another to another. The more you progress in your career, the harder it gets to leave, to quit. My dreams and all those fun things were falling behind.

Was the financial industry a busy and competitive lifestyle?

When I was younger, I used to have long hauls and very stressful jobs early on in my career. But later in my career, it was comfortable and not too stressful. Maybe I was getting a bit bored or not living the best life I could. I was thinking about working for 35 more years and then retiring. What if I had done something else?

Do you think your real passion was always in writing?

I do, definitely. I am entrepreneurial; I am working on many other things, and I’ve always had that mindset. I studied commerce in school and enjoyed it. I do like financial markets and trading and watching financial instruments fluctuate; that was fun. But, on the other hand, I think I was not too fond of the nine-to-five structure, lacking flexibility. There are still so many rules and regulations; you can’t just go off work; it doesn’t work. But, on the other hand, when you’re doing location-independent work, you can take your laptop and go and work anywhere.

Can you talk to us about some of your past experiences?

I was just young and dumb, and I should handle things better. Hindsight is a wonderful thing, I would tell my younger self I should have done X Y Z, but at the time, I didn’t have that capacity. It is a very stressful time because I was living in Sri Lanka, and my earnings were far less than in Sydney, and it was a much weaker currency. It taught me many things starting from handling stress, but it also highlighted more anxiety. Finally, I realized that I couldn’t continue the same way, I had to make some changes, and I had to get out of it. I wasn’t planning on spending the next 20 years getting out of debt; it had to happen quickly. So I restructured some debt, restructured the expensive ones. Before leaving, I was able to sell my car and pay off some of my debt. When I went to Sydney, I was employed relatively quickly. I did have to make sacrifices. Even though I was earning enough, I learned to live with flatmates. I learned how to allocate money to do what I like. I liked to travel, so travel was something I splashed on. At every stage of our life, we make our decisions based on our information and understanding. It’s sometimes not fair for us to look back later and judge ourselves, saying we should have done X, Y, Z. You’re not in the same situation anymore.

Do you think your growth mindset made it easy for you to transition out of your job to a nomadic lifestyle?

There’s always a way. As humans, we can underestimate our potential and abilities. Some people tell me they want to do this or wish they could do it. So, if you want to do it, and for whatever reasons it’s not possible, then take steps towards it. What do you wish to be doing ten years from now? There’s no point wishing; life just flows. The worst is worrying about finding another job or something else. But you can always find a way. It’s not as courageous or as risky as it sounds, especially today. As we live in an online world, there are so many opportunities. If you can get creative, you can always do something and make money. Still, time, opportunities, and experiences may not come again. The real risk is not taking those chances or those experiences. Also, the stresses of risk and change can come whether you like it or not. The pandemic caused many things to change. Many of those so-called steady jobs became unsteady, and many things happened, and people have to adjust to them as they had no choice. Sometimes, we rise to the occasion only when we are in difficult situations.

Has the pandemic caused many businesses to close, and then new ones take their place in Mexico?

Yes, and also back home in the village I grew up. People who lost their jobs in factories making clothes are now stitching masks and doing other things to put food on the table. I think people back home have started understanding that things aren’t as stable as they thought, and anything can happen. We could be here today, and something could happen tomorrow. So, we have to live to the fullest and be joyful now and not wait for something to happen in the future. As a result, people have stopped to think about what really matters. Is it chasing money or spending time with your loved ones and doing what you love?

Have you noticed much difference moving from the financial industry work to the writing world?

I was working not in consulting but in investment analytics and funds management. The comfortable six-figure amount in Australian dollars and the transition for me now are what I used to feel anxious about. When you’re doing something creative, like writing, you have to focus. You have to learn how to handle distractions and how to focus on work. I won’t let money stress me because I think I’ll always figure it out, and sometimes those thoughts do occur. But I decided to keep going, and now I have to keep going and make it work. I have no regrets. I’ve done everything I wanted to do in life. I’ve learned to chill out with my writing and use simple language, and drop the big words I’m used to using. It’s a process; we know as we go every month, we get a bit better or improve or get quicker.

Has travel changed your perspective on how you see other cultures?

Yes, I learned so many things from traveling. One is that as humans, we are not as different as society has made us think. In every country you go to, people have the same complaints, wants, exact needs, and problems. So, in a way, I found it very endearing that we are so similar; it’s nice that you can connect with people. Media portrays things very differently from what you see in Mexico; I found it very eye-opening. I learned that people back home move on with their lives, and sometimes friends move on; it’s just life. I learned to appreciate every moment, especially nature; it makes you realize that you’re just a speck in this vast universe. So, what are all these problems and anxieties? I don’t mean to diminish the problems of the world; there are huge problems. But sometimes, we also tend to worry about ridiculous things that we shouldn’t. I think the pandemic made many people realize that you shouldn’t waste time on unseen things.

Do you feel that you miss out on things with your friends back home due to your new lifestyle?

Yes. I keep in touch with my friends, but there are time differences, and people are busy. They have their lives, jobs, and families. Sometimes people move on, and they don’t have the time to coordinate things. I also learned young to accept that phases of life end, and then you go to the next stage of life; that’s just how it is. There are many friends I miss. Maybe we’ll have more great times in the future, after the pandemic. But we used to have the best possible times together, and that’s what matters the most. It’s like a happy nostalgic memory while I also missed them. I think the same about my father, it would have been great if I had him more into my adulthood, but we had the time we had; that’s just how it is.

Did you consciously think that you were starting your next phase of life when you decided to quit your job and go on this trip?

I didn’t spend much time contemplating it because I was so busy trying to organize everything, which was a nightmare while working. I worked up to one or two days before I left, so there was a lot to do. I viewed it as the next step following many different episodes in my life.

I sold my car and goods; I didn’t want to put things in storage. I didn’t take much with me; I felt so free. I used to have a shopping problem, and I thought it would make me happy. But they weighed me down; the things I’d worked hard to buy were baggage. I packed myself into a few bags, and I suddenly felt so free; it was terrific.

What are your plans and are you going to stay in Mexico?

Right now, I think that’s our only choice; I was lucky to have got a temporary residency. I had thought about going to Sydney. But I just went ahead and got it, and thankfully, for now, I can continue to stay. I also have worker rights here because temporary residency doesn’t come with work rights. So now I’m free to do whatever I want. The plans are to travel domestically; we have traveled quite a bit locally. When things open up, we will start going overseas again. I prefer having a base and location-independent work to nomadic because it’s less tiring and gives a little stability.

I love it here; there’s so much to do, and there’s pretty much everything. The healthcare system is sound. I was able to learn Spanish; I would say I’m semi-fluent. It has worked for me; I haven’t had any safety incidents. There are areas in the country and states that are considered unsafe, but we haven’t personally had any incidents. I’m not saying bad things don’t happen; they do, but sometimes things get exaggerated in the media.

If people are looking to go into the lifestyle, what are some things you would recommend before quitting your job?

I’d say have a financial buffer. If you are thinking of going for a while, then make sure you have a budget. That way, you won’t get stressed when you’re getting started in your business or freelancing. You don’t have to worry about every dollar you have. Second, while working, I would say get started with your freelancing or your side business. I know sometimes there are compliance rules, and it’s not allowed depending on what it is. But if it is unrelated, it shouldn’t be a problem. That way, you can get a head start. And the third one, I think, is that planning and all that is good, but think about how you would feel when you’re years old. If you look back, will you believe I wish I did that, or I’m glad I stayed, but don’t live in limbo?


Book Your Flight

I usually use a combination of 2-3 of the following search engines to find cheap flights: Skyscanner, Momondo, Google Flights

Find Your Accommodation is my usual platform for finding accommodation options as they have one of the largest selections. Hostelworld is great for booking hostels. For more private or long term accommodation, Airbnb is my go-to platform.

Travel Insurance

Travel insurance is important for to protect yourself against unforeseen circumstances. I usually look at a few insurance companies depending on my travel needs.
  • SafetyWings for Travel Health Insurance
  • IMG Global for added Insurance when doing activities outside of usual coverage
Packing for your trip? Check out the packing list for ideas on what to bring

For more travel resources, check out my resources page for best platforms and companies to use when you travel.

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Welcome To NomadsUnveiled
This is Rax. For over a decade, I have traveled to over 60 countries - from a budget backpacker to a business traveler, expat and then a digital nomad. You can find insights and perspectives from myself and other world travelers that will inspire your journey of discovery.


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