[Interview #014] From getting a dream job overseas to traveling the world with pets: How burnout led to a total life redesign

This interview is part of our interview series, where we curate stories of regular people who decided to design a life they love. (click here to learn more). 

Stephanie & Gillian from OurFreedomYears.com

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1. Can you introduce yourself?

Stephanie & Gillian (S&G): Both of us were born and raised in Toronto, Canada. Just 7 years ago, we had the typical life of professionals in Canada. We had solid jobs, a condo, a car, and we spent most of the year looking forward to our three weeks of annual vacation when we could explore another part of the world. After many years of fantasizing about working abroad, we agreed on a plan to find jobs in our respective fields in Asia. 

We chose Singapore because it’s an English-speaking country; we felt that we would be better positioned to find work there versus other Asian countries. The goal was to build our careers in a dynamic market while also exploring the region. 

Fast forward to 2019: After many years of saving and investing in Singapore, we were able to retire early (Stephanie in her 40s and Gillian in her 30s). We sold everything we owned, packed up our lives, and headed off for a life of slow travel with our two little dogs.

Life design journey

2. What does a typical day in your life look like for you today? How does it differ from your life before?

S&G: Our life today is a healthy balance of routine, exploration and creativity. We feel best when our lives have structure but also leave room for spontaneity. We begin each day the same way: meditation and an early morning workout followed by a leisurely walk with our dogs. The rest of the day is a mix between exploring whichever city we happen to be and working on our creative projects. We leave room in our schedule for flexibility depending on the weather. Better to be outside hiking while the sun is shining and then inside creating content when the weather is poor. 

While we were working, our life was extremely structured and disciplined. Since we spent so much time at the office, we had to maximize every hour of the day. We woke up at 4:45 each morning so that we could walk the dogs and be at the gym by 6 am. We were at the office by 8:30 am, ate our lunches at our desks, and hoped to be home by 6:30 pm. Bedtime was 8:30 pm. Any spontaneity was reserved for the weekend and Sundays were spent getting ready to go through the entire routine again starting on Monday morning.  

3. What inflection point led you to decide to change your life trajectory?

S&G:When we moved to Singapore, we felt our dreams had come true. We were working in a beautiful, tropical country; meeting people from all over the world; and traveling to all the neighbouring countries. However, as the years rolled by, we eventually realized while expat life was all that we had hoped for, our high-pressure jobs were taking a toll.

Gillian: I knew for a long time that I wanted something more than just spending my life behind a computer but I wasn’t sure what it was. I was aware of the concept of financial independence and had even calculated a few financial scenarios. However, I knew that Stephanie wasn’t ready to give up the career she worked so hard to build.  

Stephanie: Gillian broached the topic of leading a different kind of life many times but I was so focused on climbing the corporate ladder that stepping away from work was inconceivable to me. Then I got a new job with even more responsibility and I found myself working harder than ever before. After working every weekend for an entire year, I realized that I was burnt out and needed a change. Finally, I was ready to have a conversation with Gillian about doing something different with our lives.

4. What were some of the limiting beliefs that hold you back initially?  

Stephanie: Gillian was ready from the get-go but there were two limiting beliefs that held me back. The first was my unrealistic expectation of how much money we would need in order to retire. I based my preliminary ideas not on actual research and data but on how much we were currently spending while living in one of the most expensive cities in the world. The second limiting belief was that my identity and validation in life was bound up with my corporate career. Nothing could be further from the truth!

5. What did you do to prepare the transition to this new destination and how did you do it

S&G: We took two years to transition from corporate jobs to our new nomadic life. During this time we refined our financial scenarios and agreed on our financial independence target number. We increased our savings rate to 70% through an intensive process of tracking our spending and cutting costs. We researched all the countries we wanted to visit and shaped our travel plans. We sold almost all our possessions and shipped the remaining few personal items back to Canada for storage. Finally, we ensured that our two dogs met all the animal importation requirements of the countries we planned to visit. This was an added complication and expense but well worth it for the opportunity to bring our dogs along for the journey.

6. Once on the journey, what were some of the biggest wins you realized? What were challenges you had to face along the way?

S&G: Although there were many positive changes, two big wins stood out. First, the experience of landing in a new country and discovering its people and culture was just as exciting as we hoped it would be. And it was something we had the privilege of repeating every month or two as we moved through different countries. Second, we were thrilled to connect with the larger community of early retirees and nomads. It was really rewarding to make new friends as part of our new life. 

The biggest challenge that we faced is the one that everyone is currently facing: all our plans ground to a halt with the onset of the global pandemic. One day we were blissfully discovering Florence, Italy. Not too long after, we found ourselves on a rescue flight back to Canada, sheltering in place for months on end. Although this was a massive disruption to our plans, we are grateful for the opportunity to spend time with our families in person. 

7. What did the people around you (friends/family/colleague…) think of your plan to take on this new life? 

S&G: Our friends were surprised and impressed by our news to retire early and travel the world. Our families were proud that we had the financial wherewithal to make our dream happen. After watching us leave Canada mid-career to start a new life in Singapore, they expected us to follow it up with an equally exciting plan. 

Cost of living

8. How much yearly expense did you have before and after this change in lifestyle?

S&G: Before we discovered the concept of financial independence and we’re spending freely in Singapore, our annual budget was embarrassingly high. Take the monthly rent of our two-bedroom apartment in Singapore of $3,000 USD and extrapolate from there. Fortunately, we began tracking our spending and eventually decreased our cost of living by 40% prior to retiring (including moving to a much cheaper apartment!).

Once we began our nomadic life, we were pleased to discover that it was just as inexpensive as we hoped. Our monthly living expenses are typically less than what our rent alone was in Singapore, depending on the country we’re based in. We have videos outlining our cost-of-living for a number of destinations on our YouTube channel.  

9. What strategies have you used to reduce your expenses? And what strategies have you used to fund your lifestyle?

S&G: Our main lever for reducing our expenses in retirement is geo arbitrage. Our travel itinerary includes a focus on low cost-of-living countries, particularly those in Eastern Europe. We also travel slowly, so we can take advantage of long stay discounts with Airbnb. If we do end up in high-cost countries like Canada, we can further manage our budget by eating at home more often, something which we enjoy anyway.

In order to fund our lifestyle, we’ve built up a portfolio of investments including both equities and fixed income. These provide a return — essentially passive income — that covers our living expenses on an ongoing basis. For equities, we hold a slice of the global stock market in the form of a low-cost index fund. For fixed income, we hold syndicated mortgages, which provide us with exposure to the real estate market without the complication of owning real estate ourselves. 

Lessons, tips & advices

10. Some of our readers think that you have to choose between a nomadic lifestyle and living with your own pets. You guys have shown a path where both can be possible. What would you say to people that think it is not possible and what recommendation do you have for them?

S&G: Traveling with a dog is a lot of extra work and usually adds expense but it can be truly worthwhile if you want to see the world with your best furry friend at your side. Being with our two dogs on the road ensures that we travel more slowly, maintain healthy routines, and get enough exposure to green spaces and hikes. 

However, the complications are many. We have to pay more for travel as many budget airlines don’t allow pets. Each country has its own pet importation requirements that need to be researched in advance. Also, we also have to reach out to multiple AirBnB hosts in each destination to ensure we find an apartment that allows pets. 

That said, we wouldn’t travel any other way. We really enjoy exploring new countries with our two dogs and having them with us spark conversations and connections with the locals we encounter. We have a recent video (click here) that shares the lessons we’ve learned from traveling with two dogs:  

11. If you had to do it again, what would you do differently?

S&G: One thing we would have done differently is to plan less of our travels in advance. For the first six months of our journey, we booked a lot of it in advance and then we felt stuck when we needed to make last-minute changes. As full-time travelers, we’ve learned that we need to be more flexible so that our plans don’t keep us from responding to changing circumstances, for example when our family needs our support back home or if there’s a major crisis like there is now.

12. What advice do you have for others who are considering going through a life design exercise?

S&G: Never stop experimenting to find the lifestyle that works for you. We’ve learned so much about ourselves and our needs and preferences since we started this journey — and we continue to learn with each new destination that we travel to. By experimenting with new landscapes or city sizes or accommodation types, we are continuing to refine our formula of what makes an optimal life for us. 

13. What is one resource (blog, podcast, book beside your own) you recommend for those that want to design their own life?

S&G: We would love to share the blog that inspired us to hit the road with our dogs. The Ramble, by fellow nomad Gigi Griffis. She has been living and working nomadically across Europe for several years with her dog and has published cost-of-living summaries for all her destinations.

Looking ahead

14. What is next for you?

S&G: We’re currently in Canada while waiting out the global travel bans. We plan to return to Europe in the next couple months, although we expect that our approach to travel will change dramatically in light of COVID. We imagine that our slow travel will become even slower and that we will spend two to three months in each country.

15. Is there anything I may not have asked that you would like to share with us?

• We had the misfortune of retiring just six months before a global pandemic and a major market crash. This is every early retiree’s worst nightmare and certainly gave us more than a few anxious moments. While we never could have imagined this particular scenario, we were ready with a risk mitigation plan, which included an emergency fund (handy for rescue flights back to Canada), a year’s worth of living expenses in cash and total investments that exceed 25 times our annual expenses.
• Our advice for anyone considering early retirement during these unprecedented times is to take a very conservative approach. Better to work longer and save more versus being in the position of selling off investments at a loss to fund your living expenses. 

Rapid-fire questions

We like ending every interview asking some fun rapid-fire questions for our guests.

What is your superpower & why?	We are go-getters. We like to set our sights on big, ambitious goals and then pursue them with everything we have.
What is your favorite travel destination & why?	After traveling to over 40 countries, it’s hard to pick a favourite. That said, we really enjoyed our recent trip to Turkey and would love to go back. The Turquoise Coast in particular is an area of the world that we were quite unfamiliar with and found to be beautiful and welcoming.
What’s something you can never live without?	Our two dogs, Jasper and Huxley. They make every place we travel to feel like home.
What’s the best piece of advice you’ve received?	It’s more of a mantra that we live by: Anything is possible.

Thank you so much Stephanie & Gillian for sharing your transformational life design journey with us. It is quite inspiring to see how far you’ve come in just a few years! As for now, we hope that travel will resume quickly and safely from Canada so you can get back to your nomadic journey! And if we do happen to cross paths, please let us know. 

Our Bottom Line

Here are the main lessons we took away from this interview with Stephanie & Gillian:

• Lesson 1 – Most 9-5 doesn’t lead to fulfillment in the long run. When Stephanie and Gillian decided to live their dream by moving to Singapore, they “felt [their] dream had come true”, before their high-pressure jobs reminded them they had more room to grow. This actually led them to think bigger about the life they could design for themselves and led them to the journey they recently started by becoming full time nomadic.
• Lesson 2 – Long term travel with your furry friend is possible. Stephanie and Gillian have been able to travel from Asia across Europe to Canada with their two dogs and are proving once again that we tend to have limiting beliefs that prevent us from living our ideal life. Another example of a limiting belief that some people might have when it comes to travel that isn’t actually true. 
• Lesson 3 – Always have a backup plan. When Stephanie and Gillian left their lucrative jobs to start traveling the world with their pets they had no idea that a pandemic was going to hit the globe 6 months later and that they would have to jump on a rescue flight from Italy to safely get back home. But by having thought about a risk mitigation strategy (a fancy set of words to say they have thought about backup plans) they can still move forward with their lives and don’t have to worry about running out of money or being stuck indefinitely in a place. A situation that unfortunately a lot of people that aren’t in a position of having enough money set aside are suffering right now. 

Do you want to share your story?

Sometimes we need to hear about others making unconventional decisions before we can have the confidence to make our own. If you have (or are on a path to) an unconventional journey to improve your life that has a nomadic component to it and is interested to share it, please reach out to us as we would love to consider your story for our blog.