Meet Jane, The Insurance Agent Who Gave Up Career, Marriage, And Condo To Be A Digital Nomad

Immigration has become a hot topic in the past year. But thus far, the discussion has mainly been centred around foreigners that choose to come to Singapore. But what about the other side of the picture? In this ‘Singaporeans Abroad’ series, we share with you the stories of locals who—thanks to living in a globalised world—have found success in different corners of the globe, whether financially, romantically, or for the pure joy of adventure. 

Recently, we brought you the Singaporean working with refugees in Syria, and the Singaporean who moved to Australia to become a land developer.

Now, we bring you Jane Tor Ying Le, the Singaporean who had it all: the career, car, and condo. But after her marriage fell apart, she decided to leave it all behind and start a new life as a digital nomad. This is how her journey began.

My name is Jane, and I’m a digital nomad. I’m far from living what most Singaporeans consider to be a “successful life,” but success to me means being able to unlearn those toxic benchmarks of what happiness looks like. Success to me means living a life I’m proud of. Success to me means having an individual thought process, not manipulated by society or family. It took me a long time to realise I didn’t want what most of my friends wanted, and it took one year of backpacking in 2020 to realize I thrive the best in situations where I’m physically and mentally challenged. 

I used to have what most of my friends wanted. I went to a good JC, then I studied politics at NUS. About 4 years ago, I got to the point where I was earning about $7000 a month in an insurance career. I had a husband who was an airforce pilot, I lived in a condo, had a car, had everything that I thought would make me happy. Except it didn’t. They were good goals and dreams—but they weren’t mine. 

In 2016 when I won top case count in my insurance company.

3 years ago, I quit my insurance job and travelled to China to learn about businesses there. It was then that I realized how small our bubble is in Singapore. 

My marriage was also not doing well. We had very idealistic visions of what love is. I now believe that you receive what you are putting out into the universe, and at that time, we were giving each other what we were looking for. Eventually, we learned that’s not the best foundation on which to build a relationship. If you get into a relationship to nurse your own wounds or to fill a gap in you, it can be toxic. So within two years, it all fell apart.

It was a very powerful wake up call for me because I realised I had gotten myself in this situation. There was no one else to blame but myself. 

May 2018 wedding ceremony.

In an attempt to nurse a broken heart, I left Singapore in January of 2020 to go on a one month backpacking trip to Mexico. Covid was exploding all over Asia and Europe, and against all odds, I decided to stay out of Singapore. 

It was the best decision I could have made, because the energy in Mexico didn’t allow me to be down. And because it was the first time I solo travelled, I was forced to get out of my comfort zone. I didn’t have time to be sad. I met so many amazing travellers with whom I shared my story, and every time they would share something of their life too. Speaking to others about their pain helped me deal with my own. 

There was one Australian woman in Mexico who really inspired me to change my life. She has been travelling for 12 years, and the more she backpacks the more she wants to do it long term. When I met her she was running an Aussie cafe and giving haircuts.

When I asked her why she was travelling for so long, she said: “I come from a first world country. In Australia, the minimum wage is high enough that I could always go back, get a decent job and live a decent life. I probably won’t be super happy but I wouldn’t be suffering either. Look around you, besides you and me, everyone comes from a developing country. If they can make it work, why can’t you? Anytime you want, you always have a home to return to.”

That’s when I realised: I need to stop worrying about my future if I’m not even enjoying my present. Like that, I decided not to return to Singapore.

Building a makeshift shelter in Chacahua, Mexico.

I went to Europe and I picked up volunteering opportunities so I could continue traveling while reducing expenses. I worked in exchange for food and a bed—I was a babysitter, worked in a hostel in Albania, and did construction work as the only girl in the team. One month became one year. One year has now become an indefinite amount of time. 

During the first lockdown, I spent 5 months in England doing light construction work and helping out with chores. It was the most liberating few months of my life. I was “working” 25 hours a week in exchange for a bed and all meals provided—money was not really the point of work. 

I did the chores I was given because I really wanted to. I took every job as a way to learn a new skill. I got upgraded by mowing with an entry level mower to a diesel powered one, and that day, I mowed the lawn with the biggest smile on my face. I had earned this ‘promotion’. For those few months, I spent so much time gardening, weeding, playing with chickens, pigs, one horse and a few dogs, and I cooked so much with my host family. Every other week, we had bonfires, something Singaporeans don’t really get to experience.

Raising chickens in the UK. This one is called Paulie.

Those jobs taught me that the life I thought I enjoyed in Singapore was not actually for me. All I need to be happy is a good sunset, to be close to the sea, to surf, and to connect with good people. I also realised how little I need materially as I just kept shedding luggage weight the more I travelled. 

When I came back to visit Singapore for two months at the start of 2021, I couldn’t adapt. I was so happy and free the whole year, but the minute I arrived in Singapore I felt like I re-downloaded all the stress, worries and concerns most Singaporeans have. My entire headspace just went nuts from everything that was going on. I felt detached, and I would find myself in conversations my friends were having and I’d think, “Why am I here? Why are we talking about things that don’t matter to me at all?”

I love Singapore, and I love my country, but if I can’t feel at home there, then where can I feel at home? I felt sad because I knew I would no longer be able to fit in, at least for the time being. So I bought a one-way ticket to Croatia, and here I am now.

Van tripping around Scotland.

I live a digital nomad life, working remotely for a Singapore Edu-tech company. While I live in Zagreb, I regularly move around to different coastal towns and other cities. I intend to work as a nomad for the next few years at least. Now that I’ve tasted the freedom … it will be hard to go back to being plugged into the Matrix.

Finding a company that would let me work remotely was a testament to me that if you live life the way you want it to, things will fall into place over time. I took about a 50% pay cut, but considering how expensive life in Singapore is, it still works out better for me this way.

Despite me being happy, there is of course a lot of judgment from people. One of my mum’s friends had recently written a whole article for Lianhe Wanbao about how her friend’s daughter (i.e. me) gave up a good life and a marriage to become a hippie. She was worried that I was getting older and that I wasn’t on the right path in life, so she was basically writing asking how to confront my mum about this. Luckily my mum stopped her from publishing the article and told her that she believed I was resilient, and that it was up to me to live my life how I wanted to.

While I actually don’t mind people calling me a hippie, I wish I could tell them that if you’re not living life the way you want to, then a lot of the decisions you make are based on what you think you should do, not what you want. That’s how people wake up at 40 and realize they lived their last 10 years clueless, and ask themselves how they got here. I see that with people my age too in fact. There are so many people who are lost, even young kids and people in their early twenties.

Showing my parents around Croatia.

I know many people who are in the same situation as me, with no real obligations to stay in Singapore and have always wanted to venture abroad but hold so much fear that they will be ‘lagging behind’ in society if they put their careers on hold for even just a few months. 

It’s also so sad that people care so much about what others think of them—reputation is everything in Singapore (and around the world too.) When you’re young, it’s who is on the VIP list in the club, or who is in the box by the DJ. At F1, are you invited to the after-party or the after-after party? Then when people go through divorces or any other difficult situation, we don’t talk about them. We only talk about the good things—like the 100,000 dollar wedding this or that person had, but we don’t talk about the divorce that came after that. 

Even when I was talking about my divorce it was shocking to people. They would say, ‘how can you talk about this so publicly? Aren’t you embarrassed?’ And I thought, if I have to sit through you reposting your wedding photos month after month, why can’t I speak about something that equally impacted me?

To wrap it up, yes—I’m 29, divorced, working in a completely different industry than I started with, I no longer have the car or condo, but I’ve never been happier in my life. I remember owning so many material things and spending more because I had more earning power, but none of them ever made me feel fulfilled. In fact, the more I owned, the more empty I felt.

Growing up, we weren’t given many choices. We weren’t even told that we can choose to not make a decision right away. We weren’t introduced to the idea of a gap year, which I am happy to hear now is being encouraged in some institutions. Our educational system creates unrealistic goals of what studying hard can get you.

I want to tell people out there, to live a life they want. To live a life that they will be happy with after the next 2 decades. I want to inspire more Singaporeans to journey out, go slow traveling, really face their fears and conquer them. I think as a small and mighty population, we have a lot of power to do more good in our societies and in the world. But when we stay in our bubbles of security and comfort, we remain selfish and unkind to each other, we remain indifferent and self serving. 

Of course, I’m not saying that’s true of all Singaporeans. I know that Singaporeans are full of heart, full of joy and many are just trapped in a vicious cycle of wanting to live up to expectations and obligations. I’m just saying that it’s time for us to face these limitations we put upon ourselves and allow us to make our own decisions. 

You can follow more of my journeys on my blog here.

Do you know any Singaporeans with interesting experiences abroad? Let us know at And if you haven’t already, follow RICE on InstagramSpotifyFacebook, and Telegram.

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