1 Year and 7 Countries Later

In addition to feeling pseudo-famous for five minutes, being interviewed by a local Montreal news station about our travel lifestyle could not have been a more perfect way to celebrate our first travel anniversary.

(Check out the news segment and article: Millennials are the new target market of Canada’s tourism agencies.)

It was a great opportunity to reminisce about our decision to leave our possessions behind in order to work and travel around the world. Here are some questions friends, family members and the occasional stranger have asked us along the way:

Is it like “Eat, Pray, Love”?  


In our case, we aren’t on some existential, let’s-go-find-ourselves, happiness-seeking kind of journey. We just really love traveling and don’t have a preference for traditional office work environments.

We also wanted to spend more time together instead of only weeknights and weekends. That being said, I think we got more than we bargained for in our Barcelona studio.

Let me tell you, living in a 100 square foot studio with no windows for an entire summer was like marriage boot camp. If there were things we didn’t know about each other before, we know them now.

This experience has also been quite transformative in that it helped us embrace our third decade of life with newfound confidence and open-mindedness.

If you would have told me when I was younger that I would turn 30, only own what I could fit in one suitcase, get my first tattoo and dye my hair teal, I would have said, “Surely, you jest!”

Why did you decide to do this?

Venice, Italy 2016

It honestly came down to a very simple question made during a trivial conversation.

I was visiting my family in New Orlean, and there happened to a big jackpot for the local lottery. Some friends and family were buying tickets and talking about what they’d do if they won.

So, I asked myself, “What would I do if I won the lottery?”

Like a lot of people, my answer was that I would travel the world. That moment, that was my game changer. I never buy lotto tickets, so waiting to win the lottery was not feasible.

I realized that if that is truly what I considered to be an ideal life, maybe I could try to make it work on my own non-lottery terms

When I returned home, I asked my wife how she would feel about traveling while working virtually, and she was open to the idea. Now, one year, seven countries and almost a dozen cities later, we are hooked and have no plans of stopping any time soon.

If you didn’t win the lottery, how do you afford to travel so much?

Barcelona 2015I am completely dumbfounded when I see articles with fanciful titles like “Quit Your Job and Travel the World.” No judgement. Good for that person!

In my case, I didn’t want to only take off for one or two years. I wanted a lifetime of travel. For that, I knew I needed a job in order to afford to travel around the world. We decided to take the digital nomad approach. I teach English online, and my wife is a virtual assistant.

One of the lovely AirBnB hosts we’ve met along the way is also a travel aficionado. He prefers to work seven or eight months without a break and then take off for two months to travel. There are plenty of other creative options.

Another consequence of not winning the lottery (sigh) is that we have to be extremely mindful about how we spend our money. It’s only been a year so far, but we already fancy ourselves the Suze Orman of travel budgeting.

Thanks to savvy traveling and hardcore budgeting, we have been able to save more money while traveling this past year than we ever have in the past. 

Why do you stay in a city for months at a time?

Rome, Italy 2015We enjoy this kind of slow travel because we prefer feeling like temporary locals instead of tourists.

A common misconception is that people who work and travel like us are always on vacation. We work 5-7 days a week at odd hours to accommodate our clients’ time zones. And, as independent contractors, if we don’t work, we don’t get paid.

Isn’t it overwhelming not knowing where you are going to go next?

New York, US 2016At first, it was nerve-wracking not having our future planned in the typical 5-year and 10-year format. But now, as long as we continue saving for the future, we are okay with just planning for the present – a “live for now, save for later” mentality.

One of the other takeaways we have had from this past year is realizing what a privilege it is to work and travel. We get to be virtual ambassadors for cities around the world and inspire others to visit cities they may have not previously considered.

How do you pick the location?

As for travel planning, we are inspired by travelers and digital nomads that we follow on Instagram. We will often ask them directly for advice about what cities have the best amenities, like public transportation and reliable internet.

We have found that the digital nomad community online is quite impressive, resourceful and eager to share their travel wisdom.

How can I do what you’re doing?

Barcelona, Spain 2015Firstly, we absolutely love being digital nomads. That being said, it’s time for some real talk.

What you see on social media are curated, aesthetically-pleasing highlights of a person’s life. Remember that for every serene beach photo someone posts, there are many moments before and after that shot that weren’t as peaceful.

It’s not a bad thing, but it is important to be aware of it. For example, I didn’t post a picture of my tear-stained face as I dealt with some personal health issues. We didn’t post a picture of us panicking when the company my wife worked for shut down overnight during our second month abroad.

Also, traveling and working remotely might seem glamorous and exciting in theory, but it is not without sacrifices.

Being away from family for months at a time can make your heart ache. Seeing your friends’ babies grow up on Facebook is not the same as hearing them squeal with delight as you impress them with your peek-a-boo skills.

In no way am I trying to dissuade you. Consider this a friendly reminder that life doesn’t stop being real while you are traveling. On top of that, you also won’t have your usual network of support to help you through some of the tough moments.

Sentimental reasons and romanticized notions aside, maybe you prefer to spend your hard-earned money on tangible things, like a new car or a nice pair of shoes.

So, if downsizing your entire wardrobe to what you can fit in a suitcase makes you feel like you’re about to experience a tiny panic attack, perhaps this particular path is not for you (or you could always get a storage unit for your other stuff).

Maybe you just want to travel more, not necessarily 365 days a year. Or maybe, just maybe, you don’t even like to travel that much (gasp). And that is ok.

My two cents: you do you. Take some time to think about what makes you happy, and find a feasible way to create your ideal life. Your future self will thank you.

My gift to my future self is living life so I never have to think, “I wish I would have…,” but instead say, “Can you believe you did that?”

Yes, I can, future self. Yes, I can.


Thanks for reading all the way to the end! Now that you’ve come this far, check out some of our other articles:
Life Lessons of Losing My Job While Traveling Abroad
It’s All Fun and Games Until Someone Gets Diarrhea

We Work Remotely — And You Can Too?
On Space: AirBnB Pearls of Wisdom
Travel Tip: Upgrade Your Stay


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