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Avalon’s preschool in Spain, which she never attended but we put a deposit on.
It is as simple as 3 decisions, or not
I recently turned 50. During an evening of reflection, Will and I identified three physical location choices we made for our family that drastically impacted the course of our lives. These places led to us choose a full-time WorldTowning lifestyle in 2014.
Today, I will share the story of our family – a family that, despite having no clue what they were doing, followed their hearts, made bold decisions that scared the hell out of them, and then chose the road with the least financial gain and clearly the least glamorous. (Who would pass up Madrid or London?) Spoiler, we did go to Paris.
You know when you are watching a horror movie and you start talking to the screen? “No, don’t do it. DON’T go in there!!” “Oh shit, they are going in there.” This is what life felt like during the time we were making these three decisions. At each of the crossroads, I felt our choice was right for us. I knew, however, if anyone else had been in the decision-making room with us, they would have said, “Don’t do it, you are crazy.”
Currently, we are in the beginning of our 9th year of full-time travel, and we are damn crazy. I am so thankful for all the crazy in us. I have a tattoo on my left wrist that reads loca, which means crazy girl in Spanish. It’s a daily reminder to keep the crazy; it got us to where we are today.
Lao Tzu once said, “The journey of a thousand miles begins with one step.”
But, often, it is unclear which way you should take that step. That is the challenge.
Madrid
In June 2007, I was five months pregnant with Largo. We had just landed at Madrid-Barajas Airport in Spain to finalize what would be the biggest adventure of our lives thus far. Back stateside, our home in Los Angeles was filled with cardboard boxes labeled “Maine (storage)” or “Madrid (new home).” Just a handful of months before Will had proposed the idea of being a corporate expat with his company, PriceWaterhouse Coopers. I could not sign on the dotted line quick enough – yes to the international experience, all the expat perks, career advancement and more. Who would say no to this? “Not I,” said the eager-to-travel pregnant lady.
It was a busy six-day visit in Madrid filled with business dinners, apartment hunts and preschool exploring. We did not an ounce of sightseeing, but we knew we would have time for that when we were permanently living there. We left Madrid having checked all the boxes, eager to return to the U.S. and share the good news with an over-enthusiastic Avalon. No sooner did we touch down in Los Angeles and there was an issue on the company’s end. Apparently, a pregnant Jessica was the issue. It was something about an American, who had moved to Madrid before us and whose wife got pregnant. She panicked and they left the contract to return to the U.S. This cost the firm a lot of money. Will’s employers were worried I might do the same. If they could only see me now, starting my 9th year of full-time travel. I was born for this, but how could they have known that back then?
Because of this issue, we had two options to ponder. Option 1 was that Will could go to Spain without us. Once I had Largo, both children and I could join him in Spain. Option 2 was to cancel the engagement and not go to Spain at all. They were allowing Will to come to the U.S. two weeks before Largo was born, but if Largo arrived early then Will could potentially miss his birth. Will did not want to risk missing Largo’s birth, so we said “no” to moving to Spain. We were disenchanted with the situation at this point. Will was overworked in public accounting, so he decided to leave the firm altogether. We left Los Angeles for Boston and put the travel dream to bed. What were we thinking anyway? It sounded too good to be true.
Our first years in Boston were quite miserable, and we often wondered what it would have been like if they had just let us all go to Madrid. Nonetheless, we never regreted our decision. You can’t get back missing a child’s birth.
Flash forward many years later on our full-time travel journey, and we learned something interesting. We never needed their approval to all go to Spain. We thought we needed the insurance the company provided to cover Largo’s birth. We didn’t realize we could have paid out of pocket since healthcare outside the U.S. is very affordable. Will could have taken a sick day when Largo was born and all would have been fine. I think we can all agree I was never going to freak out and want to go back to the U.S. This epiphany could have been a lot more upsetting if we were not already a year into our full-time travel life. Full-time travel on our terms or corporate expats? I think we landed in the better spot. Clearly, it would have been a more lucrative move to be a corporate expat, but I shudder to think of all the time Will would have lost with the kids. That you can never get back.
The other big decision made at that time? Will leaving public accounting. That needs more explanation, as well. Will was on track to be a partner at the firm. Leaving the firm to go into the private sector in Boston was a big step into the unknown in terms of where we would end up financially and his future upward mobility within a company. At the time this felt huge! The only path he had ever wanted since he was in college was to be a partner in a Big 5 accounting firm. Now, the path ahead was even more uncertain.
Had we gone to Spain, I am not sure where life would have taken us. I would like to think we would be where we are today, but I am not quite sure. Money does a funny thing to people, and we would have been living a very comfortable life. I probably would have bought a house in each expat location (you know how I love real estate) – buy, rinse and repeat. Who knows what else.
These thoughts quickly dissolve on days like the one last August when we dropped Avalon off at university. On a different path, we might have looked at each other with regret and said, “We missed it all, and for what? A house in Paris? It could have been so different.” Instead we are saying, “We did not miss a thing.”
The move to Boston took place in 2007. We bought a cute house in a suburb where we could live for the next 20 years and settled in to give our kids a proper childhood. Well, at least that is what all the books said was the best path.
It did not work for us. We tried. We tried some more, but no matter how hard we tried it was not a fit. It was an amazing community, where we still have friends to this day, but it just didn’t align with our family goals of wanting to live in more than one place for the rest of our lives.
So, we moved from our suburb into the city of Cambridge. Will started talking with his bosses about an expat corporate experience maybe being a possibility at this new company. We were in downsize mode and eager for a change, but these expat packages kept falling through. Finally, I gave up hope. Avalon was not getting any younger, and I knew our window of her wanting to go would narrow in the coming year. At this point, the kids had been hearing us talk about full-time travel for seven years. They were very eager to get on the road.
Our move to Boston had another interesting piece to the equation. When we first lived in the suburb, Avalon was enrolled in a French Immersion program in a public school. This is where our commitment to language learning really blossomed. From this school, she transferred to the French International school in Cambridge. This led us to dissect why we were there in Boston, and how we could get what we were getting at the international school out in the world, with a much lower price tag. We were there for the language, yes, but also for the international experience of it and a community of families from all over the world. Many languages were spoken at this school, which gave us the feeling we were traveling internationally, even while we lived a stationary life. We loved the International School of Boston, but, we realized our monthly tuition could be of better use if we were actually traveling.
Had we gone to Madrid, would we have ever seen the value of learning with multiple cultures and languages? I would like to think yes, as we had Avalon enrolled in a Spanish pre-school and not an American school in Madrid; but, who knows what the years would have unfolded or what we would have “thought” she was missing in regard to the American dream. As it was, we got a very clear view of American life by living in the suburb for five years, and we knew it was not the path for our family.
Paris
Extended slow travel is often about compromise, and my compromise for us was to travel only during summers, since it looked like the expat option was never going to come through. We decided a summer in Paris was ideal. I already worked from home, so I could do that in Paris. Will could take a very long summer vacation and come to visit. The kids would get culture and practice their second language – French, and we would all get a good dose of living in another country. I was not happy about this “summer only” situation. It did not give Will much time with the kids, but this is where we had to compromise.
That. Summer. Of. Compromise. Changed. Everything. Compromises are not all bad.
Even more than not going to Madrid, I believe our time in Paris was the single most important event in our lives in terms of where we are today – still out here after eight years. It made us suffer, it made us prove we really wanted it, it made us struggle, it took us way out of our comfort zone, and it make us live on very, very limited resources, money and energy.
It was the summer of 2013 when we went to Paris, and everything that could go wrong did. I had food poisoning twice in my first two weeks there. Don’t eat the yellow hotdogs at the park in the dead of summer. Our toilet was broken on and off constantly – not pretty. Then, after a month in Paris, Avalon got sick on her birthday while visiting Giverny and had to be hospitalized. She had mono so severe they were concerned; five days later she was released. Our apartment was what we could afford. A small one bedroom on the bottom floor with a pull-out futon. Will and I slept on the futon. Clearly, it was not the easiest summer. However, we experienced a new culture, made friends, the kids got more confident in their French language skills, and we grew as a strong unit – a WorldTowning unit. It was magic. We were happy – even with all the issues – and we left Paris knowing we could do this travel lifestyle thing well and even thrive.
We returned to the U.S. in August and set a 12-month deadline to sell everything and leave for our new full-time travel lifestyle.
13 months later we left on October 6, 2014. Eight years later we are still out here.
When I think about what would have happened if we had not gone to Paris, I get sick to my stomach. I know that Paris changed everything. It gave us a different perspective. And to think we could have missed all this by just saying, “maybe next year, money is tight.”
The truth was money was tight. When I proposed the idea to The Accountant (Will), his first words were, “we can’t afford it with two kids in private school.”
I don’t like being told something isn’t possible. My response was, “I will find a way.”
My plan for the summer was: no nanny to help while I worked; no piano lessons or soccer camps; and, my favorite, to rent our Cambridge apartment out on Airbnb for most of the summer. My well-thought-out plan had us breaking-even after expenses for food, some adventures, an apartment rental, flights, etc. Will was happy with this plan, except, perhaps, where he would sleep with the apartment rented, and how I would work and watch the kids at the same time. I was a master at multi-tasking and, having crafting and activities always on hand to entertain them, I did not have a worry about this at all. As for Will’s accommodations, he was going to need to sleep at friends’ houses. Although he was on board with that option, when he went to his employer to discuss a three-week vacation in the middle of the summer, they suggested he work from the Paris office. Problem solved. They even flew him in business class to Europe. And that is how you compromise your way into a solid financial plan, and then into a lifestyle change.
Paris changed our lives forever, and I will forever be grateful.
London
In the fall of 2018, we were living in the south of France. Life was good. We both worked from home, the kids went to a local French school in the neighborhood, and we enjoyed long, leisurely meals on the patio. Dreamy, right?
But, then the ball dropped. The company Will had been a contractor with for three years was now requiring all its location-independent employees to come into an office. It was proposed that London would be an ideal space for him. I was months away from launching WorldTowning, the coaching side of our business, and we were at a bit of a crossroads. Do we move to London for the secure route? Or, does Will join me in the new venture and we keep on going the way we had been for three years, except now with a family business?
We knew what London would look like. We had been down that corporate path before. Long hours, expensive city, no time with the kids, stress. Gone would be the nights of family dinners on the patio and colorful conversations about life in a French school. We decided to go for a coffee to discuss it. We never made it to the coffee shop – well, not even to the end of the street – before we decided that we had worked way too hard to get to where we were to go backward. Going back into the office felt backward. As much as we had made the decision, we wanted to give the teens a voice as well. When we asked Avalon and Largo their thoughts on the patio that night, neither were interested in moving to London and changing our life. Ironically, years later we visited London and they loved it. Their commentary went like this (a bit sarcastic, but funny nonetheless), “We could have lived here? Does that offer still stand?”
We went ahead with launching WorldTowning together. Several months later, we moved into an RV and traveled around Europe for almost three years visiting every country. Yes, a start-up in a 12-foot RV and all the while worldschooling teenagers. Those first years of our business were very hard and financially strapping, and exhausted all of our energy. Never once, however, did we regret our decision. Now, five years later, we still don’t regret it. Even after our travel business went on a huge pause during COVID times, and though the days were dark and long, we never lost hope.
Often, when people go from a travel lifestyle back to stationary life for a recharge of the bank account, the mind or whatever the case, they rarely return to travel. That was our fear. In our late 40s, it was less likely that we would have emerged again to tackle the world of full-time travel. Who knows, though, it does get under your skin.
In 2012, Australian caregiver Bonnie Ware wrote a book about her experiences in palliative care. There were five regrets that dying people told her about most often:
I wish I’d had the courage to live a life true to myself, not the life others expected of me
I wish I hadn’t worked so hard
I wish I’d had the courage to express my feelings
I wish I’d stayed in touch with my friends
I wish I had let myself be happier.
At every turn, we were cautioned by others about taking the less lucrative, non-career-building path. At times, we felt alone in our quest, and we figured we would never meet others who shared a dream of full-time travel. It was a different time in the world when we started. Social media was not as prominent, and it was hard to know if anyone ever succeeded at this world-travel thing. But, we stayed true to our authentic selves and our family goals. When you do that, then no big decision can be the wrong one. And, when in doubt, we always took the path that had the most risk. It wasn’t always easy, but if it went well, we knew it would yield the biggest steps toward the dream.
I never knew the boat show was a destination
Each week when we release a vlog Will gives a deeper look into the story behind the vlog to our patrons. I love what he shares and look forward to reading it every Friday.
To become a Patron you can read about the details here.
Back in 2013, on a cold winter's day, we went to the Boston Boat show because there was nothing better to do. I mean, yes, we liked the idea of boats, but like most people, our appreciation for boats was based on strolling around marinas and romanticizing what it would be like to cast off the lines and sail off for a sunset cruise.
We had a great time at the boat show and walked away that day knowing that one day we would be on a boat full-time. Oh, how romantic that day was.
Fast forward seven and a half years and we find ourselves newly minted boat owners full of hope and dreams yet wondering how do we work this thing.
It was at that moment that boat shows meant something to us, except we were sitting in France, and Jessica and I don't speak French. But...it was pandemic lockdown times and so all the boat show presentations in the US and Canada were broadcast online. This never happened before. We signed up for the presentations and learned how much we did not know, and more importantly, how much more money we would have to spend to make Friendship ready to cross oceans.
We knew we needed a first aid kit, but we had no idea that we should be looking at owning a defibrillator. We were happy that we had an autopilot, but we had no idea that we should be considering a backup one. The value of a boat show just became exponentially more important. It was no longer about the romance of setting off on a sailing adventure, it was about buy the gear to make sure we don't die.
The 2021 boat shows were scrapped and so when it came to the 2022 season, we said - no way! We are not spending money to go to an event that is telling us that we are not spending enough money. But then something happened, parents’ weekend at Avalon's college was scheduled at the same time as the Annapolis Boat Show, which was only a four-hour drive away. Plus, we had friends who were in Annapolis with their boat, and they offered us a place to stay during the show. So, we said let's go.
The best part of the decision to go to Annapolis was that there was a booth at the boat show for YouTube sailing channels and we were able to squeeze our names onto the list of participants before they printed the banner. It was an honor.
Going to the show (with Avalon) was awesome. It felt so great to adventure again with Avalon. The road trip included sour patch kids, discussions about the best dining hall on campus and theories about what to expect in the next Marvel movie. Just like old times.
The interesting thing about the show was that it was not just a big boat shopping event, but it was more of a destination. People were walking around and enjoying the lifestyle, whether they owned a boat or not. When I spoke to individuals, they said that they equally enjoy going to a boat show for four days as wandering the streets of Paris. Two different experiences, but equally fulfilling. And as much as I would rather be in Paris, I completely get it. It's just a cool vibe. Toss in the fact that there were 55 YouTube sailing channels walking around the show, it was even better. Those who you know are living the lifestyle and going to places on everyone's sailing bucket lists make it amazing because you get to ask the questions you wanted to ask.
If there is any question as to whether going to a boat show is worth it, I say yes. It's a great way to spend a weekend and to plan your future. And hopefully a place where we can meet up.
All the best and thank you so much for your support.
Will, Jessica, Avalon and Largo.
Camino Group Trip!
Oh yeah! We have finally found a way to do a Camino group trip with all of you. We are still working out the details, but so far what we do know is this:
It will be in late September or early October 2023.
We will hike the last 100k into Santiago together.
Albergues (B and B’s/hostel vibe) included in the price.
Breakfast included.
Limited to 16 people.
Must be able to walk 15 miles (20 kilometers) per day.
Be willing to take a taxi or bus to meet us at the next destination if you cannot keep up, need a rest day or are injured.
Not included: lunch, snacks, coffee, transportation, medical, flights, alcohol
Duration is 5-7 days depending on when you arrive. It will take us 5 days to walk it with an opening reception on Day 1, walking Days 2-6 and closing breakfast on Day 7.
This is considered an active group trip. This is not an opportunity to get in shape, you must already be in shape when you join us.
Registration will open in two weeks. First come, first serve.
I am a bit early this week with the newsletter, but since I have missed a couple of weeks due to us hosting the Morocco group trip I thought I would hit send now. I hope you have enjoyed this weeks newsletter, feel free to comment, ask questions or anything else in the comment section.
xoxo
Jessica
To learn more about us, our mission and our business you can visit us at WorldTowning. To view our most recent group trip offerings head on over to WorldTowningvoyages.com. If you are interested in booking a coaching session in an effort to realize your travel dream, schedule it here. If you want to follow the travels of our WorldTowning family, you can find us on YouTube, Instagram, Facebook, TikTok
Beautiful! Thank you for telling this story ... and ... and ... I can't believe you're doing the Camino! How did I not know this? I might seriously seriously seriously want to join you on this!