From Side Hustle to Dream Life: How We Afford to Travel Full-Time as a Family

From Side Hustle to Dream Life: How We Afford to Travel Full-Time as a Family

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We’ve been traveling full-time since August 2017. Our first 10 months were spent on an epic road trip through the United States and Mexico, followed by a temporary stay in Utah as we explored the American Southwest. We then left the U.S. for good in May of 2018 and have been a full-time travel family ever since.

In the past two years we’ve been to 22 states and 19 countries. Phew! 

 

“How do you afford to travel full-time?”

We meet lots of other permanent expats and traveling families on our travels. The #1 question we seem to be asked is, “How do you afford to travel full-time? It’s the traveling equivalent of,  “What do you do for a living?

 

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You know what I mean.

Haven’t you ever been to a dinner party among new people where the conversation inevitably begins with, “And what do you do?” It’s because (for the majority of the world not living from a trust fund) everyone does something! Comparing jobs is the default ice breaker because it’s an easy way to make connections with people. Maybe you have a skill in common, maybe you know the others’ company, maybe you have acquaintances who work together, maybe you both have long commutes, maybe you’re both thrilled to work at home instead of an office… You get the idea.

The same is true for travelers.

It’s arguably easier to make connections with fellow travelers because we already have something huge in common: We want to see the world! When one commonality is already so obvious, connections are further forged on a few supporting details.

We size each other up and consider a future friendship based on variations of the “And what do you do” criteria:

  1. Why did we each choose to travel,
  2. who are we traveling with,
  3. how long have we each been traveling,
  4. where are we based (if anywhere), 
  5. why did we leave our home country,
  6. when do we plan on returning, and
  7. how do we afford to travel. 

We have our answers to every questions down to a ‘T’.

  1. We chose to travel because seeing the world is more important to us than building a long-term life,
  2. we’re traveling as a family with one child whom we home school on the road,
  3. we’ve been traveling since Summer 2017 but out of our home country since May 2018,
  4. we don’t have an official home base (but like to stay in one place/ country for at least one month when possible), 
  5. we left the United States to see more places and expose our son to different cultures and people,
  6. we plan on returning to the U.S. by the time our son is late elementary school age, and
  7. we afford our travels by working online.

Most people may assume full-time travelers are independently wealthy to support such a “lavish” lifestyle, but that’s not true. The days of traveling being reserved for the rich are long gone. There are many different forms of travel based on every income level, and just as many ways of supporting family travel.

 

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In fact, we have yet to meet anyone living or traveling abroad who is doing so without significant work commitments. The vast majority of travelers are working some sort of location-independent job online (we call ourselves Digital Nomads). Many have even taken a significant pay cut by leaving a stable job back home in favor of an online job just for the opportunity to travel. We don’t call them lavish. We call them brave.

We are no exception.

 

How we afford to travel: The short version

So then, how do we afford to travel full-time? You can probably guess that we aren’t millionaires. The answer is that we run our own business online. Ben and I each designed product brands which we have manufactured around the world, sell primarily through Amazon, and ship to customers worldwide.

Sounds easy, right? Wrong!

Oh, if I had a nickel for every person we’ve met (in the States or abroad) who tells us, “Wow, we should get together! Maybe you could teach me how to sell on Amazon so I can travel full-time, too!” then I’d have… well, probably about $5. But you get my point: It happens a lot. And poor Ben is always so composed when people whittle the years spent developing our Amazon business down to something he could teach “over lunch.”

I really admire that guy.

 

travel full time with an Amazon business

Here’s the more complete story of how we grew our online business to travel full-time:

Ben and I initially connected over our shared love of travel and desire to see as much of the world as possible. He had been to 23 countries before we were married, I had been to 21 (not including many European travels as a child which I don’t remember.) 

One of our most memorable early dates was a Saturday spent in Charleston, South Carolina. I’ll never forget that day. We were talking about our futures over the 2-hour drive and what we each wanted out of life. The unforgettable part? We had the same answer: We both wanted to run our own businesses so we’d have the flexibility to travel.

We were married in April 2010. Seven years later we achieved our goal.

 

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Those seven years were long, though.

Ben was in a rotational position at a Fortune 500 company when we were married. He would be assigned to learn the ins and outs of a certain department in one place for a year, then switch to a new department and location. Ben was finishing his second of three yearly rotations when we were first married, so I had no motivation for finding a full-time job I’d soon have to leave. Instead, Ben and I decided to start a business which I could manage and grow as we moved around.

We bought the equipment and software to start a vinyl decal business and I set to work learning some new skills. Technology is very far from my personal strengths, and there were a lot of sleepless nights of frustration, tear-filled conversations, and even a few arguments as my stubborn brain seemingly refused to learn something new. With Ben’s help things did get easier, and I had just enough confidence in my ability to run the machine and software to start trying to sell something.

I spent a full year in the cricket-laden basement office of our North Carolina rental growing my decal design skills and testing my stickers on different products. Every surface of the house was covered in vinyl decals as I tried in vain to test, photograph, and sell the physical stickers or vector images on Etsy or our own website.

I eventually bought a heat press and heat transfer vinyl and expanded my product line to cloth items. It still took a year and a half of trying to sell everything from aprons to shadow box decals to make back our initial investment.

I was feeling more frustrated than ever at being unsuccessful for so long when Mustache Mayhem hit. Don’t you remember when mustaches were everywhere? Well, I decided to make a last-ditch effort with our business. I heat applied a large mustache across two pillow cases for beard-obsessed customers to place on their beds.

And they sold. Well.

After almost two years of daily effort I’d finally stumbled onto something people actually wanted: decorative pillow cases.

Over the next three years Ben helped me perfect and expand this new product line. We eventually changed our application process completely, added tons of new styles and sizes, outsourced our own pillow cases out of custom fabric, and even began selling the pillow inserts.

Around our fifth anniversary our pillow case empire was out-earning Ben’s corporate job + benefits. That felt good.

Ben earned an MBA at night while I was building our business, and he eventually left his job to use his new business knowledge to bring our products to Amazon. It took around a year of constant trial and error on his part to become an Amazon expert, but his diligence eventually paid off.

We were finally a team, running our own business together and dreaming of traveling full-time.

Once we knew we could survive on our Amazon income alone we set our sights on ways to expand the business and leave our home offices. Ben found a few outside manufacturing sources to manage different products and packaging, and I continued to create new designs.

Once our U.S. manufacturing site and a few hard working employees were in place we experimented with the full-time travel life by spending a summer in Montreal, Canada. It became my favorite place in the entire world. That summer our son attended a French daycare, Ben ran the business from our AirBnB, and I spent my days wandering around Montreal and learning how to bake croissants. We had a set schedule of when we’d stay home and when we’d explore, and found that a travel/ work life balance was not only possible, it was something we really did want full-time.

Experimenting with life away from our home and business center was crucial for us. We’d come to love the city of Ben’s last rotation. Traveling abroad meant giving up the house we’d renovated into our dream home, wonderful friends, nearby family, and a fun city with activities we loved for the opportunity to see the world. It may sound like a no-brainer, but the decision to commit to a nomadic lifestyle wasn’t actually that easy.

It still pains me to think about the stable life and friendships we left behind, but we know we did the right thing.

Today Ben runs the day-to-day operations of our business by overseeing our Amazon ad campaigns, tracking sales and ordering new products and supplies, most of our social network marketing, making new product listings, communicating with our different manufacturers and employees, and so on. He’s also developed a second product brand of safety athletic accessories and manages other people’s Amazon stores. I’ve mostly given up on the pillow case business, instead working full-time on this, our travel blog, as a means of diversifying our income and chronicling our time abroad.  (Doesn’t quite sound even, right? :D) 

 

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The Digital Nomad Travel/ Life Balance

Our business does well enough for us to take time off when we want to, but for the most part, it follows the model of earnings according to effort.

Quite simply, when we dedicate more time to our businesses we earn more money. But we didn’t give up our dream house and good friends to work like fiends and make as much money as possible. We decided to live abroad as digital nomads to actually see and experience the world.

We balance our travel and work life as well as possible, working hard during set hours then enjoying the rest of our time to sight see and experience new places. Sometimes the scale tips one way or the other- a crisis with work causes us to spend a few days at home working while we arrange play dates for our son, and sometimes we only have a limited amount of time in a new country and work is put off for a few days.

We found the most success by following the same daily schedule as much as possible: working during the morning while our son is on play dates or doing school work, then going out for lunch and spending the rest of the afternoon exploring our area. This schedule allows us just enough time to maintain and slowly grow each business while still enjoying the place we’re visiting.

 

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Issues do arise when forces outside of our control cause our business to drop or when we’ve put off time-consuming business updates for too long. We try to minimize it, but the truth is that sometimes work needs to come first. For instance, Ben went to two Amazon conferences in July and was overwhelmed with new ideas to implement to grow our storefronts. It took a month for him to find enough time to dedicate to actually whittling down that to-do list. And when Google released an SEO update in June 2019 my website traffic tanked, and I had to work furiously to try to resolve the issue and get back into Google’s good graces.

It happens.

We realized that “fast traveling” to new countries every month (or less) and working for a couple of hours every morning was unsustainable. We started looking for a home base abroad where all three of us could settle into a routine which would slow down our pace of exploring long enough to dive deep into work projects we’d been putting off.

We found a temporary home in Medellin, Colombia, where we lived for four months. While there our son was enrolled in a bilingual school he loved, we found a 3-bedroom apartment to rent with two office spaces, and we were able to spend a more dedicated amount of time working each day than ever before.

We will continue to fast travel through South America until spring 2020, when we’ll head to Europe. We plan to continue traveling full-time as a family for at least 1-2 more years, but will probably need another temporary home to settle into work for another season. Who knows?

We wanted flexibility, and we got it!

Being the master of your fate… It’s a stressful, rewarding, wonderful thing.

 

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Follow our journey as a full-time travel family!

Thanks for your interest in us, and thanks for your interest in the world! We need more people like you who are interested in experiencing other cultures. Social media is making our world smaller and smaller, and it’s becoming more important to know, respect, and befriend people from new places.

It can be really scary to pick up your life and head into the unknown (believe me, we know!), but, ultimately, we believe the growth that comes from travel is the best hope humanity has for the future.

Send a message to info@theobriensabroad.com with any questions at all on how you can travel with your family, too. We desperately want to help more families make the leap!

If you’re interested in full-time family travel or becoming a digital nomad but not quite ready to make the leap, that’s ok, too! Follow our travel journey on Instagram and Facebook in the meantime for some inspiration!

 

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