Travel as a lifestyle centerpiece?
Why Jamie and I are trying to travel 4–8 weeks a year
Working 45+ years with 2 weeks of vacation a year and then retiring.
That idea makes me feel like…
There are too many exciting things to see, do, and experience. I get really depressed thinking about slaving my life away in jobs until I’m old and have time to do the things that I want to do. But only for a short while. And, in all likelihood, in sub-optimal health.
I’m drawn to all kinds of alternative lifestyles that maximize time, flexibility, and adventure. Of course, I need to be able to pay the bills, and I want to live comfortably, but I’m always looking for ways to do this unconventionally. Because conventional American work/life balance isn’t doing it for me.
Tiny houses are something I research compulsively. The idea of simplifying your life to the point where you can choose the work you love and the adventures you desire because your expenses are so low appeals to me greatly.
Unfortunately, most of the tiny houses I like are on wheels, not a foundation, and that makes living in them illegal in most places, including Boise. I’ve approached the local Planning and Zoning office multiple times over the years to see if I could make this work. No dice. (Not that Jamie would go for this though…)
I first heard about this idea from Tim Ferriss, probably in the 4 Hour Workweek. The concept is that you design your personal and professional life to allow for “retirement experiences” while you’re still young instead of waiting until you’re old. For example, you could take several months off work every few years to explore, learn, and pursue passions.
I love this idea as well. But easier said than done, right? This stuff costs money, and most normal jobs aren’t okay with you peacing out for weeks at a time, let alone months.
Travel isn’t the only thing I would want to do during mini-retirements, but it’s probably the biggest thing.
I studied abroad in college, and it changed my life.
I was in Norway for a semester, and because it was so goddamn expensive, my friends and I travelled elsewhere in Europe constantly. I probably visited close to a dozen countries that spring. And in the summer, I lived in Amman, Jordan for 6 weeks.
Yes, I saw the sights, collected many Instagram-worthy photos, and ate some great food, but the biggest value was the people I met, the conversations I had, and ultimately, the mind-stretching that happened. I became more empathetic, less judgmental, and more confident. I realized different didn’t have to mean bad. Given my background, I needed this really badly.
When I returned, I knew I didn’t want my study abroad chapter to be my last significant international experience. Jamie also studied abroad and shared this perspective. As we graduated from college and started our careers, travel was always in the back of our minds. When could we do more, in a big way?
Travel for a year?
For a long time, we considered quitting our jobs and exploring other countries for a year. We’d been inspired by others that have done this, and it seemed doable if you planned well enough. A couple years ago we got fairly serious about it and started researching.
Eventually we realized that constantly moving from place to place for a year sounded exhausting and unmooring, so we shifted to finding a “home base” somewhere else where we could integrate, learn the culture, and take smaller trips from there. We were thinking pretty seriously about Cuenca, Ecuador.
We started considering all the logistics. What to do with Wookiee for a year, renting our house, pausing all of our friendships, and of course dealing with being jobless. It’d be extremely disruptive, and not something that would be easy to replicate a few years later, since it would require us to coordinate quitting and finding jobs. Also, the complexities of adding kids to this mix was discouraging. So, we tabled it.
Meanwhile, I started a company.
It was an analytics consulting company, and the idea was helping cool organizations that normally couldn’t afford these types of services. Between myself and my network of volunteers and subcontractors, we helped dozens of organizations, but one in particular really made me think about travel differently.
Though the project we helped them with was fairly routine, they intrigued me. As someone that’s curious about education, parenting strategies, and international experiences, this school grabbed my attention.
I loved what I saw on their website. Learning other languages from an early age, routine international travel, ecological learning, international baccalaureate accreditation — the program looked amazing. And then I checked the price tag. About $20,000 a year, per kid. 🤯 Uh, never gonna happen.
Even if I could afford that in the future (<5% chance), I don’t think I like the idea of all my kids’ school friends being from wealthy families. Diversity matters a lot to me now, and public schools are way better at that. I started wondering if it were possible get the benefits of a program like this another way?
Do it yourself?
What if the whole family traveled together every summer, so kids wouldn’t lose the stability of friends and activities during the school year. And what if travel revolved around backpacking for the most part — that’d check the ecology boxes while still giving access to surrounding towns and cities. It’d also cut down on costs since you wouldn’t need to pay for as many hotel stays or traditional tourist experiences.
I did some quick math. Depending on a lot of factors like destination, length of time, number of kids, etc., a trip like this could cost on the order of $7,000-$15,000. For the whole family!
It seemed like the best of both worlds. 1) You get the stability and grounding experience of a public school education. And 2), you get special knowledge and experiences from other countries, cultures, landscapes, etc. And the whole family gets to benefit from it! And besides the learning, I can’t think of a better bonding experience for a family. Not only is this concept way cheaper, but it seems way better. Jamie loved the idea.
Great! Fantastic. But what about money?
Though the theoretical cost of the trips seems manageable, the job factor would be tricky. How do you hold down jobs that don’t mind you being gone for 4–8 weeks in the summer every year, but that also pay decently well, and have growth potential? Therein lies the challenge.
My first thought was being a teacher. Checks the “summers off” box, but doesn’t pay much (but maybe enough). My next thought was being an entrepreneur with a business that prioritizes flexibility. Then again, some conventional jobs could stomach unpaid time off in the summer if you’d proven yourself indispensable, and it’s not their busy season. Or, if one parent had a remote job, they could work some during the trip, to minimize disruption for the company while still allowing for the family adventure.
This seems to be the biggest puzzle to figure out.
Flexibility is king.
I realized that the ambitious idea of designing a life that allows for 4–8 weeks of travel annually seems achievable, but to make it sustainable, we’d have to choose compatible career directions. Luckily, Jamie and I were already on paths that could probably work. She’s a highly valued employee at a flexible organization, and her job’s slow in the summer. And I can probably be an entrepreneur with a flexible business or a remote worker. ✅ ✅
Let’s put the plan into action!
We’d been talking about this often and had started working out logistics, so I was thinking, “When do we start?!”
Jamie and I were hiking when I made my pitch.
“You’ve been talking about doing the Camino de Santiago for years. We have our big lifestyle design project pretty well worked out. Let’s start this year!” At first Jamie felt that it seemed too soon. Too much, too fast. Maybe next year.
But I doubled-down and made the case that this year is perfect — there’s probably never going to be an easier year to try this out. I kept at it until I was repeating myself. Jamie wasn’t sold, but she heard me out. She consulted her peeps, and after some feedback and reflection, she decided she was game! She got her boss’s approval, we blocked our calendars, bought tickets, and things were in motion.
We leave this week.
The Airbnbs are booked, the gear is bought and tested, our Wookiee plan is set (thanks Dad!), and we’re prepping the house and yard for a 6 week absence. In a matter of days we’ll be walking the 500 miles from France to Santiago de Compostela along the northern route through the Basque country.
Initiate crazy travel experiment.
It feels great to be acting on this crazy idea, and I’m excited to see if it feels right and we want to continue with this lifestyle approach. Time will tell!