How to Retire Early and Travel With Your Pets (Stephanie and Gillian’s Story)

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This is the latest interview in a series featuring digital nomads talking about their lives and lessons (click here if you want to be interviewed). The goal is to help demystify the process of making money online, wandering the world, and living an unconventional life!

Stephanie and Gillian are a FIRE (financial independence, retire early) couple who decided the 9-5 wasn’t working for them. Now they travel the world full time (slowly) with their two dogs.

Welcome, Stephanie and Gillian!

Introduce yourself! 🙂 Who are you? What did you do for work? And what is your nomadic story?

We are both originally from Toronto, Canada, where we spent the majority of our careers. However, after many years of fantasizing about working abroad, we decided to take a huge risk with our careers and lives and move to Singapore.  

We chose Singapore because it’s a dynamic, English-speaking country where we thought that there would be lots of opportunity for personal and professional growth. While we really enjoyed our six years in Singapore, we eventually felt burnt out from our high-stress corporate jobs. 

In 2019, after many years of saving and investing, 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. 

And we’ve been traveling full time ever since. Despite the global pandemic, we’ve traveled to Poland, Ukraine, Turkey, Italy, Greece, Croatia and Malta. Our stays in each country have ranged from a short stop of two weeks in Lviv, Ukraine to four months exploring Turkey including Istanbul, Faralya Fethiye and Kas. 

Stephanie and Gillian

Please tell us your detailed FIRE story!

When we first moved to Singapore to work as expats, we felt like we had made all our dreams come true. We were working in a beautiful, tropical country. We were meeting people from all over the world and traveling to all the countries in the region. 

However, as the years rolled by, we eventually realized that our high-pressure jobs were taking too much of a toll. We were locked into a trap of high earning and high spending and couldn’t agree on what our future might hold. 

Finally, after a very stressful year of work, we were ready to come up with a new vision for our future. We chanced upon some blogs that outlined the steps for becoming financially independent and suddenly we realized that we could have a different path for our lives.

With that, we started a journey of sharply reducing our expenses, investing the difference and planning our future as full time travelers. Since we already had a strong foundation of savings to build on, it only took a couple years to go from the discovery of FIRE to setting out on our adventure.

What do most people not understand about retiring early?

For us, retiring early just means that we don’t need to work at salaried jobs anymore; we have enough money to support ourselves for the rest of our lives. However, we retired when our careers were just peaking and we still have many productive years ahead. So even though we’re retired, we enjoy challenging ourselves and being industrious. Retiring early doesn’t mean that we’ll be sitting on a beach for the rest of our lives. Instead, it means that we are now free to pursue all our interests and passions. 

Please tell us the story of starting and growing Our Freedom Years! 

We knew that we would need a substantial project to help us transition from full-time work to full-time retirement. Launching Our Freedom Years gives us the satisfaction of creating something that other people enjoy. We’re constantly learning new skills and stretching our brains. And it helps us stay connected to the larger financial independence and travel communities. That’s probably the biggest benefit of our creative project: all the new friends we’ve made over the past year of having a YouTube channel. 

However, to anyone starting a YouTube channel and blog, our advice is to consider the time commitment. Our channel requires four days of week, between conceptualizing videos, shooting, editing and promoting. We’re thrilled with how our community has grown over the past year but it definitely takes a substantial effort to scale up.

Stephanie and Gillian

What inspired you to start nomading? And how has nomading changed your perspective on life?

We love to travel. We love exploring new landscapes, food and history. We love the feeling of landing someplace new and experiencing a culture for the very first time. And since we both love reading up on history, we really enjoy getting a first-hand experience visiting historic sites, museums and galleries. 

We always felt constrained trying to fit our adventures into one- or two-week vacations. When we realized that we would be able to retire early from our careers, we knew that travel would be the focus of our new life. 

Our perspective on the world had already broadened quite a bit after living in Asia for six years. We developed a real appreciation for how individualistic Western culture is in comparison to family-oriented, collectivist Asian cultures. However, we feel even more enriched by the past year of being full-time nomads. We’ve seen a lot of hardship and poverty during our travels, particularly among refugees in Greece and Turkey. It’s made us feel very grateful for all the privilege we’ve enjoyed in our lives and it’s also inspired us to increase our charitable giving.  

What are the 2-3 favorite places where you’ve lived/traveled to and why?

We would choose Turkey for the amazing food, history and value that the country offers; Croatia for the easy-going lifestyle on the Dalmatian coast; and Italy for the food, architecture and culture.  

What advice would you give to someone who’s thinking about nomading?

Our advice is to do the one thing that we overlooked. When we headed off for our new life of early retirement and long term travel, we didn’t know anyone in the financial independence and nomad communities. Of course, we had been reading many blogs and listening to podcasts during our research but we weren’t active members in any forums. 

We waited until we were actually on the road before connecting with others. This meant that our first months on the road were a little quieter than we would prefer. We would encourage anyone thinking of this path to take the time to find your tribe in advance and build connections in that community. There are online communities and forums for just about every demographic and interest group. One starting place is the Choose FI Community ecosystem, which offers a range of geographic and cohort groups on Facebook. 

Stephanie and Gillian

Four of the biggest barriers to people nomading are debt/student loans, owning a pet, having an apartment lease, or owning a home: if you had any of these when you started traveling, how did you address or think about these issues and what advice would you give to other people with a similar situation?

We are very fortunate to be traveling the world with our two little dogs, Jasper and Huxley. Traveling with a dog is a lot of extra work but it’s well worth the effort if you want to see the world with your best friend at your side. For us, traveling with our dogs comes with a lot of benefits: we spend more time in each destination; we maintain healthy routines; and we spend lots of time outdoors.

That said, there are many complications and additional expenses if you want to travel internationally with a pet. 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. 

Still, we wouldn’t travel any other way. Having our dogs with us makes every new destination feel like home. We have a recent video (click here) that shares the lessons we’ve learned from traveling with two dogs.  

For someone interested in retiring early, what’s the best advice that you would give? And what books, podcasts, thought leaders or other learning resources do you recommend?

You can get started by simply tracking your expenses. It’s a small step but one that opened so many doors for us. 

We discovered how much fat there was in our monthly spending that could be cut out. It also helped us understand our core living expenses, which paved the way to deciding on our financial independence number. This is the amount that we needed to save and invest in order to quit work and live on the returns for the rest of our lives.

For anyone interested in learning the basics for becoming financially independent and retiring early, we have a free 7-day course available loaded with tips, exercises and suggested resources. 

If you only had a few minutes to live, what are the most important life lessons that you would share with the world?

Career success does not necessarily equal personal fulfillment. It didn’t matter how long or hard we worked at our jobs; there was always something missing from our lives until we took control of our finances and our future. Now we are in charge of our time and our lives and we don’t need to look to a salaried job for validation. 

What’s the best purchase you’ve made under $100 in the last 12 months?

We purchased a subscription to Alomoves for $20 a month. Since the onset of the pandemic, we’ve really missed going to a gym every day. Alomoves offers a range of excellent yoga classes so we’ve been able greatly improve our daily at-home workouts. 

How can people learn more about you and your work?

Join us at Our Freedom Years on YouTube for a new video every Sunday. You can also find out more about us on our blog  and Instagram @OurFreedomYears 


Lauren is a freelance journalist from Seattle. She travels the globe in search of the best grocery stores, bouldering gyms, and snorkeling locations. Her mission at Freedom Is Everything is to help others make the transition into location-independent lifestyles.