Working Overseas Could be Your Ticket to Early Retirement

Today we have a life that we could have only dreamed of. We don’t need to work anymore. We have enough money for the rest of our lives. And we get to travel the world full time. But just a decade ago, we were a regular couple living in the same city where we were born. We had a mortgage; we had a car; we had one big vacation a year. We were plugging at our mid level jobs and wondering if we were going to be doing the same old routine for the next 20 years. Basically, we were living a very standard life. 

Underneath it all, we were wishing for something else. We wanted to see the world. We wanted more than just a two week vacation every year. We wanted the adventure of exploring new countries and getting to know new cultures. 

We thought that maybe our careers could be the way to make it happen.

Perhaps we could somehow get a job overseas and use that as our way to see the world. Except we assumed that working abroad is something people do in their 20s when they have all the freedom in the world. Or that it’s for executives who get moved by their international companies. Fortunately, we discovered that that’s just not the case at all. It is possible to get a job overseas mid career and use that to get to retirement faster. 

Of course, when we first started fantasizing about getting jobs overseas, it really didn’t seem like a realistic prospect for me. I was pushing 40; I was mid career; my entire network was in one city. Quite frankly, no company that I worked for was likely to give me a fancy expat package and move me to another country. And Gillian worked in the Canadian public health care system so there was definitely no international transfer available to her.

We could have kept fantasizing about a different life forever and never done anything about it. But then a huge milestone approached: it was my 40th birthday. I realized that if we didn’t try now, it was never going to happen. We would be stuck in the same routine in the same city for the rest of our lives, always wondering if we should have taken a different path.

Of course, it would be a huge risk to gamble the lives and the careers that we’d built in Canada. What if we put in the huge effort to try to find jobs and it doesn’t work out? Or, even worse, if we move overseas and just hate it; what would we be coming back to? Do we keep our home? What about all our belongings? What about our friends and family? Is it too late in life to make such a big change? But we had to try.

Our first big challenge: figuring out which country we would try to move to. We had to focus our effort somewhere, but where to start? We didn’t just want to go to the US or the UK, even though those are great places to work. We wanted to go somewhere different enough to make the whole enterprise worthwhile. We were thinking about Asia but where could we work in English? Our second language is French but that wasn’t going to get us very far.

I was procrastinating at work one day by looking at a list of countries and the languages spoken in each one. I suddenly discovered that English is the language spoken in Singapore, a country that I had never considered before and could barely find on a map. Despite knowing absolutely nothing about Singapore, I decided there and then that’s where we’d focus our efforts. 

Our next problem: we knew no one in Singapore. We had no professional network there whatsoever. If we wanted to find jobs there we’d have to build a new network from the ground up. So we used LinkedIn. We spent our evenings trying to connect with as many executives in our respective industries as possible. And if anyone accepted our LinkedIn request, boom, they’d get an email right away where we’d introduce ourselves and ask for a call to get to know the local industry. 

At this point, everything was still theoretical. Sure, we landed a few phone calls but we were far from moving those into interviews let alone jobs. Who was going to hire us just based on a phone call? We realized that if we were going to move this thing forward, we needed to go there in person.  

Here’s where things got really interesting. We had a trip planned to celebrate my 40th by hiking up Mount Kilimanjaro in Tanzania. This was already going to be a totally grueling, once in a lifetime experience. Since we love multi-tasking, we thought why not make it a round-the-world trip? We could stop in Singapore on the way back and finally have a chance to see the country and meet the people. 

We packed one bag full of hiking gear and another bag full of suits and resumes and away we went. We spent a couple weeks climbing Africa’s highest mountain and then we dusted ourselves off and flew to Singapore. This visit to Singapore was really the turning point for us. Suddenly it was a real place with real job possibilities. And — surprise — just a couple weeks after our visit, I got an actual job offer and Gillian was close to landing one as well. 

At this point, we needed to make a decision: Were we really going to give up our comfortable lives and comfortable jobs and move to Asia?

It was extra risky because Gillian didn’t actually have a job, just some promising leads. We would be uprooting our entire lives on the back of a job contract for one of us and some follow up interviews for the other. 

But we did it. We took the plunge and went all in. We sold our car and our condo. We severed our residency ties to Canada so we would no longer be paying taxes there. We said our goodbyes and got on a plane with just six suitcases to begin a totally new life. 

Of course, landing those first jobs and moving to Singapore was just the beginning. Moving overseas was life changing both professionally and financially. We went from being in a mature economy to one that was growing much more quickly. Suddenly we had access to a dynamic job market. We had better paying jobs. And even though Gillian was still working in the public healthcare sector, she received regular bonuses, which was unheard of in the public sector back home. And we kept more of our paycheques because of Singapore’s much lower tax rate. We were able to save and invest more than ever before. 

We found that every year that we worked in Singapore was worth a few years back in Canada. Within just six years of expat life, we had reached our financial goals. We had saved and invested enough that we were financially independent. We could say goodbye to our corporate jobs and live whatever kind of life we wanted.  

Yes, we took a huge risk, uprooting our lives to move to a very far away country. But the payoff was enormous. And it wasn’t just about the money. By taking this risk, we gained the confidence to blaze our own path in life. We’re no longer people who are satisfied to follow a standard recipe. We’re willing to try something risky for an even greater reward.

Of course, when it came time to quit our jobs and begin a life of travel, we were still pretty nervous about making such a big move. How could we be sure — truly 100% sure — that we had saved enough money. You can check out the next post about what it took for us to take the plunge and finally step away from work. 

Is This the Year You Can Finally Quit?