Why We Traveled Long Term

On July 8, 2019, my husband and I set out to travel the world for a year… with our two kids. People thought we were a little crazy. Do I blame them? No. What is that adage, “A vacation with children is called a trip”. We knew that it would take mental strength and a lot of deep breaths. But we also knew that it would be worth it for our family. We just didn’t realize how worth it.

Before today I have never listed exactly why we wanted to travel long term. Not in any sort of formal method. Sure, we built our Travel Values (more about Travel Values and how to design yours in my book How to Travel the World: Long Term Travel Planning). We were clear on what we wanted to get out of the experience. But the reasons that led up to taking the leap kind of just swam around our heads. Until now. With the clarity and confidence of hindsight, I’m going to share the 5 reasons why we sold (almost) everything and traveled long term as a family.

Our Life Pre-Travel

Let’s travel back in time to the Hiltons of 2017 to give you all a frame of reference on what life looked like…

You know that Talking Heads’ song, “This is not my beautiful house… This is not my beautiful wife… Well, how did I get here?”. That’s what my inner monologue sounded like most days. Trent and I were married, had one child and then another, and became very settled in our lives. Gone was the young guy who cycled cross country with his 4 friends. (That’s a story for another day!) Gone was the young girl who traveled internationally to visit any and every friend living abroad. We were rising within the ranks at the same company, working more than ever, seeing less of each other and our kids. It didn’t happen overnight, but we did eventually pick up our heads and wonder “How did I get here?”

That was until I read about a family of six who had traveled the world for a year. I had always dreamt of selling everything to travel long term. But, honestly, I gave up on that idea once we had kids and starting thinking that a trip to Target was the highlight of the weekend (of course, dropping hundreds of dollars there per visit). 

But in a moment the dream of traveling long term wedged itself inside my head. I began thinking about it constantly and finally worked up the nerve to share my far-fetched plan with Trent. We pondered it many nights after putting the kids to bed. You can probably imagine the questions that we asked ourselves. Maybe you’re asking yourself the same ones! “Shouldn’t we just save money and travel when we retire?” “Would the kids get anything out of traveling while they’re young?” It took a lot of convincing Trent. And then sometimes Trent would have to convince me. We were happy where we were in life. But we also knew that if we pushed ourselves out of our comfort zones, there were so many experiences out there that would change us forever. 

After a month of serious conversations, we committed to a year of travel over drinks one night. We were giddy with excitement and bewildered by what we were actually saying. The next year was filled with saving for our trip, selling our home, holding 5 garage sales to sell (almost) all of our belongings, and saying goodbye to friends and family. We whittled down everything to one vehicle and an 8’ x 5’ x 7’ U-haul box filled with our belongings. And then set off to see the world!

The Reset Year

We called it our Reset Year and that’s exactly what it did. Our lives look completely different than they did pre-travel. (Pandemic or no pandemic, we have made a lot of changes.) One day I will devote a post to the ways our lives have changed. To sum it up in one sentence, we are able to spend time on the things we enjoy doing. We spend more time as a family, in a new town, and are soaking up our kids before they get old, less cute (ha!), and leave us for their own adventures.

So as I sit at the end of this journey, I’m going to share the reasons we decided to take it at the beginning. Maybe you’ll see a little of yourself in our story. Maybe it will inch you closer to taking the leap into long term travel. Or to start that business. Or to live whatever dream tugs on your heart.

Before I list our reasons, let me take a moment to try to find my words around privilege and how it shaped our ability to chose this life route. I am no expert on the impact that privilege has had on my life. But I am learning. What I know is that while many different decisions went into living a life where we were able to make this shift, I was provided with excellent options to choose from because of the privilege that comes from the color of my skin. Whether or not to leave a job where my talents were valued. Whether or not to sell my home which was purchased with the help of a loan which we easily qualified for. I’m learning how my white privilege has shaped the choices we’ve been able to make in life. I’m learning to recognize it and not overlook it.

The 5 Reasons Why We Traveled Long Term

We had a lot of dream destinations

Yes, this is as obvious as it sounds. There were so many places that I wanted to see in the world. (My dream destination is still long, or even longer than before!) I used to pour over maps as a kid, planning imaginary trips. Reading books like National Geographic’s “Journeys of a Lifetime” was a normal activity for me. When I lived in New York, which feels like another life now, I used to babysit the children of Wendy Perrin, Condé Nast Traveler’s legendary travel writer. After I put the kids to sleep, I would sit in their living room, homework on the coffee table, and just stare at a huge map of the world on their wall. There were pins all across the world where Wendy had traveled. I was inspired.

Trent and I were lucky enough to take three international trips within our first 8 years together. But when I thought about our track record so far of traveling abroad approximately once in every 3 years, I realized that we would probably see only 10 of the sites on my list before we retired. In the big picture, seeing ten of your must-see destinations is amazing. It’s just that the number made me a little sad. Travel is a big source of happiness for our family. We don’t spend or get a lot from other areas of our life. And so I wanted to invest more time, energy, and money into what brought us joy.

The idea of seeing more of the world continuously gnawed at me. Much like the little egg in the book What to Do with an Idea. This children’s book might have been the final reason that led me to take the leap, sell everything, and set out on this journey. (Buy the book for your kids, and then secretly read it yourself at night while you plot the next great chapter of your life.) I started to daydream about my idea, feed it time and energy, and then just like in the book “My idea changed right before my very eyes. It spread its wings, took flight, and burst into the sky.”

We wanted to change careers and do something on our own

After 30 combined years in the restaurant industry, we were itching to go out on our own. Trent and I were both directors at the same restaurant company and we’re constantly brainstorming ideas of what our own restaurant would look like. But we were so focused on the day-to-day that our ideas didn’t progress, well, beyond ideas.

One day, I drove into work listening to Ina Garten on the How to Be Amazing podcast. (Gosh, I miss this podcast.) In it, she describes her transition from owning the successful store, Barefoot Contessa, in the Hamptons to her rise in food fame. She was struggling with figuring out what to do next while still running her store until a therapist friend gave her some advice. Her friend told her, “Type A people think that they can figure out what they’re going to do next while they’re doing something and they can’t. The only way you’re going to change your life is if you stop doing it. And you get really bored.” That advice has stuck with me for over five years. Sometimes you’re lucky enough to hear exactly what you need to hear when you need to hear it.

I’ve always been the type of person who is so invested in whatever they’re doing. If I’m working on something, my work thoughts don’t stick to a time clock. I don’t ever fully, mentally check out. For better or worse. Which meant that I brainstormed about work on runs, driving to and from work, at dinner. I didn’t have the mental space to dream up my next work chapter until I, in fact, got really bored. Traveling long term gave us the space to redefine what we wanted life and work to look like. Upending our lives made it really hard to sink back into old patterns. Which has made all the difference!

We wanted more family time

After a year and a half of being together 24/7, it’s insane to think about how much time we used to spend apart. I love my alone time. Both Trent and I are introverts and need alone time to recharge. And there was a time or two that I longed for my old work commute and solo time. But I would take a lack of alone time to the guilt I was feeling about being away from my kids longer and longer each year. We usually averaged about 30 days/year spent together as a family of four. We often worked weekends and opposite schedules to balance childcare. In the end, we made the wrong kind of sacrifices during those early years. Bigger paychecks for more responsibilities and less time together.

Choosing to travel for a year was such a relief for that guilt. It felt like we were making up for lost time while the kids were still young. It wasn’t perfect. The kids sometimes got on our nerves. We drove them crazy. The allure of our phones and iPads sucked us away from time together more than I’d like to admit. But we spent more time together than ever. We know each other’s routines in and out. We have little family inside jokes that make no sense to anyone else, yet are so special to us. All of the struggles in life pre-travel were totally worth it to have this time.

We wanted to be involved in our kids’ schooling

We traveled when our kids were about to turn 5 and 8. Little sponges ready to soak up everything around them. We loved to teach them through experiences on the road, but we also knew that this could be a formative year for their fundamentals. We poured hours into school with the kids. We watched every step as Livy learned how to read and write. We saw T’s skills grow with one-on-one time. T had struggled to keep up with school in the years before. I had begun to wish that we had started him in Kindergarten a year later when he was about to turn 6 (he’s an August birthday). When I asked the school about the possibility of holding him back, they said that they didn’t do that anymore. Honestly, I didn’t want him to suffer just because a school wants their stats to look good. So we used our travel year to strengthen his skills and then had him repeat the same school year when he returned to school this past fall. You could take every other benefit away: the travel, the family time, all of it. If the benefit of T being in the right grade is all that we gained from our year, it would have still all been worth it.

We learned how short life is

The couple of years before we traveled were hard on our families. We lost four family members in 2017, including Trent’s mom. People our age around us were being diagnosed with cancer. A family friend passed away just after retirement. We had never really encountered death as we had before that year. The cliche saying “Life is short” became more tangible than ever. I said before that we questioned traveling with our young kids and thought about traveling long term once we retired. But it felt uneasy to put such big dreams on hold for a time that isn’t promised. I feel so incredibly lucky that we were in a place to make the leap into this adventure when we did.

If you’ve gotten this far… thank you. I’m impressed and I’m grateful for you! I hope that a piece of my story resonates with you. And I hope that whatever idea lives in the back of your head begins to grow and suddenly becomes part of the world.

Do you want to learn about how to plan for long term planning? Check out my book How to Travel the World: Long Term Travel Planning.