*Our first night as full-time travelers. Milan, Nov. 21, 2022*

Two years ago today we landed in Milan, Italy, wide-eyed, giddy, relieved, and a little bit panicked. We were on the threshold of the biggest adventure of our lives. We were grateful to our long overseas flight because it gave us a breath to recover from our skin-of-our-teeth departure from San Francisco. As we snuggled under the covers that chilly November evening I practically broke out in a sweat and definitely had a pit in my stomach as my head hit the pillow. Despite being exhausted, the first thought on my mind was that I would never be sleeping in my own bed or have my own pillow ever again. Two years later, have I gotten over this fear? Absolutely. Most nights I sleep like a baby.

We spent weeks, not months or years, on our decision to be full-time travelers. Our first flight as full-time travelers happened only a month after we chose to pursue this lifestyle. It was impulsive but not quite as reckless as it may sound.

Back in 2011 we had dreams of living in London after our first European vacation. In January, 2020, I found my Italian birth mother and her family and I wondered if a path to dual citizenship would potentially allow us to live in Italy. And now in 2024, we’re celebrating being on the road full time for exactly two years. What was the path that got us here? We talk about this in our episode, You Don’t Have To Be An Expat To Leave The US, if you want to watch it now.

Could We Live in Italy?

I had a lot of conflicting information about whether I would be eligible for dual citizenship. Italy’s rules are somewhat complicated, but after getting some insights from some Facebook groups and doing a bunch of genealogical research, it seemed like it could be possible. Eventually I found a reputable company that offered a fairly turnkey solution that could help me navigate the process. It would be expensive and time consuming, but being able to fully claim my Italian heritage would be a dream come true. So far it’s taken two years and nine months just to compile all the paperwork (working steadily). We’ve spent over $8,300, and we will spend about another $8,000 (or more) before my dual citizenship has been finalized. It will be more money to for Kevin to acquire citizenship by marriage and will take another couple of years after I have mine.

Before finding my birth mother, we’d visited Italy twice. Once in 2017 and again in 2019, so we knew that Italy was a place we wanted to live if we could find a way to get there. After signing the contract to begin the dual citizenship process in February 2022, there wasn’t much holding us back. We drew up a list of criteria for the qualities of the areas that were important to us and we lined up a scouting trip to six different cities in March to get a sense of where we might see ourselves living permanently in Italy. We weren’t expecting to move immediately, but we were eager to see if we could find someplace that fit. We were conscious that the cost of living in San Francisco would most likely prevent us from retiring here.

Our first major setback came towards the end of that trip when we learned that my path to dual citizenship did not entitle us to live in Italy while the paperwork was in progress. It was heartbreaking news, but the idea of living outside the US had been fueling us for months, so we needed to do something with all that untapped energy.

Kevin’s father passed away a few months after we were married in 1983. His father was using up his vacation days before retiring when he had a heart attack at 61 years old and died a few months later. Now Kevin was approaching his father’s age, and the anniversary brought up a lot of uncomfortable feelings. What regrets would we have if we were on the cusp of retirement and illness or death claimed one or the other of us? This concern really hit home a few weeks later when I was diagnosed with basal cell carcinoma on the side of my nose. It was treatable with surgery, but it made us think hard about the impact a more serious cancer or other illness could have. With the broken insurance system in the US, we also were very aware that a health crisis could bankrupt us and crash our retirement dreams.

*Our first logo for YouTube as podcasters*

The Launch of Finding Gina Marie

In mid April 2022 we decided to launch our own YouTube channel—you can find out here how it got its name—in a video podcast format. We mainly wanted to share the joyful reunion with my birth mother and also chronicle our journey and thought process for relocating to Europe. Our first three episodes aired on April 24 and we had 42 subscribers—the sum total of every friend and family member with a crumb of tech ability who knew anything about YouTube.

Remote Work Overseas

Would our current jobs allow us to work remotely overseas? We already had been working from home during the pandemic for the last couple of years, so we booked a trip to Verona, Italy, for November so we could do a test run for how effectively we could straddle the time zones. We also started crunching numbers to see how much we could reduce our budget by living outside of the US. It seemed foolish to continue living in a place that we couldn’t afford to live in during our retirement.

Considering Portugal

If we couldn’t live in Italy yet, what were our other options? YouTuber creators and Facebook posts all talked about Portugal as being expat friendly with low financial requirements for a long-term visa. We dove deep into tons of research and booked a trip for September 2022 to see whether Lisbon or Porto would meet our expectations. We were excited that our travel-loving daughter wanted to join us and agreed to meet up with her in Lisbon. Although she’d been to Africa, Dominican Republic, and Indonesia, this would be her first time in Europe. We were eager to share our love of Europe with her.

One small downside to these Portuguese cities is that they are extremely hilly. After eight years in San Francisco, I was hoping to live somewhere a little flatter. Living on top of a hill in San Francisco meant we enjoyed amazing views of the Golden Gate Bridge and the San Francisco Bay, but I’ll admit to being lazy at times and didn’t always appreciate lugging groceries uphill or avoiding going out because I didn’t want to climb one of the tallest hills in town to get back home.

Downsizing For Live As Expats

We had begun the downsizing process and figuring out what we would take with us and what we would get rid of. After learning how expensive it would be to bring things like furniture and other bulky items overseas, it seemed impractical to take much with us. We decided to leave San Francisco by fitting 50 years into five suitcases. It was thrilling to prune our stuff so much, but there was some trepidation. When we left Houston, we’d already done a big culling, and shrunk down again during an intercity move in 2020. Much of what remained had special memories tied to them. We were listing items for sale, packing up donations, and trashing the junk. We thought we were somewhat of minimalists, but the more we got rid of, the more seemed to magically appear.

London?

There’s a saying, “if you want to make the universe laugh, tell it your plans.” That couldn’t be more true in our case. The news that came next caught us completely by surprise. A role had opened up in Apple’s London office that would be a lateral move for Kevin and an easy pathway to live in Europe with the valuable perk of a relocation package. Maybe we could even keep more of our stuff if Apple were footing the bill for the move. The downsizing process suddenly got a bit more complicated. We created an extra set of groupings for things we’d keep like winter clothes and certain kitchen supplies and a bit of our favorite small decor. We wouldn’t be bringing these items to Portugal on our own dime, but with a bit of padding in our budget, these additional items made sense to set aside while we waited to see how the opportunities unfolded.

*Truer words were never spoken or heard*

A few weeks later, I was summoned for jury duty and selected for a three-month murder trial, which overlapped with our Portugal trip. Committed to my civic duty, I rescheduled our travel plans to early October 2022—later than we had hoped, but still manageable.

The London opportunity required some back and forth to sort out some details and then the hiring manager went on vacation. There were a lot of unknowns and the downsizing process slowed. Considering whether to set items aside for London or scrap them because we were headed to Portugal was much harder than when we knew we only had 5 suitcases worth of space.

The Phone Call That Changed Everything

Although Kevin and I discussed the idea of working remotely among ourselves, we hadn’t broached it yet with our employers. The company I worked for was global and I was used to working across multiple time zones. They chose not to renew the lease on our downtown office space during the pandemic, so my job was already fully remote. We had several worldwide offices, including London, and I was just waiting for the right moment to pitch the idea of working overseas to my manager. And then one phone call in late August turned my world upside down. I received the unsettling news that my boss was fired, his replacement was going to be bringing his own executive assistant, and my job would be changing significantly for the next several months. I was grateful to have a job, but it was one more stress during an already chaotic time. Things became even less straightforward when my role changed. In our episode, “We’re Living In Limbo, But We Want To Be In Europe,” we break down all of our conundrums and share everything we were thinking and feeling.

Family Visits

In the midst of getting rid of our stuff, we got the great news that we’d have visitors in the upcoming months. It had been two long years of isolation due to the pandemic, but people were finally feeling comfortable leaving their respective bubbles and traveling again. We’d been living in San Francisco for nearly nine years and my elder brother and his partner were planning a visit in mid August 2022 to catch up and check out our life on the West Coast. They had been living in our hometown in Western New York and had retired outside of Phoenix a few years prior. Due to work schedules and distance between coasts, it was hard for us to see each other very often when he was working, so we were looking forward to finally hosting them. And even though we were downsizing, we tried to keep most of our decorative items in place and focus on closets and drawers. What fun is it for company to visit and for your home to not be looking its best?

*Celebrating with family in San Francisco. August 2022*

Reuniting with my birth mother happened literally the weekend before lockdown in March 2020. I had found my birth family through a 23andMe DNA test a few months earlier. She decided to travel into town to celebrate my birthday by reserving a private room in an elegant Italian restaurant and inviting her sisters, their families, and a family friend. This would be our first in-person visit since we met, and my first birthday together since I was born. Our daughter flew into town to be part of the festivities and to take home some of her memorabilia that we’d been storing for her since she left for college. It ended up being quite a bash and my 58th birthday was certainly one of my most memorable.

Fortunately, the jury trial ended before their visit, and my new manager reluctantly agreed to give me a few days off. It was wonderful to spend all this family time together after cooped up and isolated for so long.

People Don’t Quit Their Job, They Quit Bad Managers

My previous manager had approved vacation time for our visit to Portugal in early October, but my new manager was less accommodating. Even though our company offered unlimited vacation and I’d only taken off three days for family and 10 business days in March for Italy, the only way I would be allowed to travel would be if I agreed to work during my vacation on the fringes of the day. I wasn’t happy about it since I had been working extra hours alongside the murder trial, and with the job changes and everything else happening in our lives, I needed a break.

We still were anxiously waiting for news about the potential move to London and while we were looking forward to checking out Portugal, a part of us was frustrated with all the uncertainty. When we compared the idea of living in London versus Portugal, our hearts filled with the idea of London and the idea of Portugal dimmed. At the same time, as we continued to sell, donate, and get rid of things, the idea of not having things at all was becoming very appealing, especially if London were to fall through.

We were starting to seriously rethink our ideas about being expats and weighing the pros and cons of being full-time travelers. A week before heading off to Portugal, we posted our video about whether to Reside as Expats or Travel Full Time and Experience the World. We were very eager to hop on a plane and see what Portugal had to offer. Would Portugal win us over?

*Donation drop-offs and selling can be a never-ending process*

By now it was crystal clear that selling things was a slow process. We learned many valuable lessons, including that everybody wants a deal and some things aren’t worth selling for the small amount of money people are willing to pay. We found that it’s much better to donate the small stuff and focus on the items that are worth the investment of time to photograph, describe and measure, promote on websites, answer inquiries, and arrange meetups.

While we appreciated that businesses and travel were opening up and people were gathering in person, we weren’t loving seeing corporations forcing their workers back into the office, especially since productivity maintained high levels despite the challenging circumstances. Apple was one of those companies, which meant that Kevin was going to have to get very creative with handling everything he was doing alongside losing two to four hours a day three times per week commuting to and from Apple’s Cupertino offices. He was frustrate because his entire team was remote and scattered throughout the world and there was no logical reason to go back into an office. Quick tip: don’t tell a software engineer to do something illogical.

Juggling work alongside travel after a hectic and strenuous few months and a lot of burnout over my job did not provide the most conducive atmosphere for us to objectively consider Portugal as a viable place to live. If we weren’t passionate about Portugal, should we be considering it? Everything was off with our moods and our energy and our mindset. Something about Portugal was losing its gleam. Maybe it was because we still hadn’t seen it, but also the idea of traveling full time was becoming more enticing.

Up until now we didn’t have retirement for either of us on our bingo card. The idea of not having a steady income was a bit terrifying, and I have always loved working. But employment with my current company under this new manager wasn’t going to be sustainable. We were clashing too frequently and the work I was doing was unsatisfying and a step back in my career. Did I have it in me to job hunt at 58 years old? There also was the question of whether Kevin would be allowed to work remotely outside of the Bay Area when there was this push to return to office. He hopped on a call with his manager to discuss our November trip to Italy. Apple allows one remote month of work per year, so we didn’t expect any hiccups with our request. There weren’t. In fact, since he could get one remote month per year, his manager suggested that he could also work remotely during the month of January, 2023. That would be perfect for us since the month in Verona would end just a few days before Christmas break when Apple closed its headquarters between Christmas and New Year’s. That meant that we’d potentially have 2.5 months to see what life would be like outside of the US.

What Now?

Although we would have loved a pleasant surprise, neither of us was shocked that for as nice as Portugal was for a visit, neither Lisbon nor Porto knocked our socks off. Both cities were beautiful, but we didn’t step into them and feel like we had come home, which for us is an elusive but critical feeling. It didn’t help that during our six cities in Italy trip, Verona did give us that feeling, which amplified our lack of love for Portugal. We wanted to move to a place that sparked fireworks that would light up our bodies and make our hearts swell to a size too big for our chests to hold.

We’ve been married for nearly 41 years and we know how love feels. Knowing there would be hard times ahead, we needed a strong enough attraction to the city we’d choose that we wouldn’t want to throw in the towel at the first sign of trouble. As I look at my photos from that time and I see Lisbon’s beautiful architecture, one of the most amazing bookstores in the world in Porto, and the very charming beach town of Cascais, it’s hard to imagine that we couldn’t fall in love with one of those places, but the heart wants what the heart wants. ♥️

When we returned home, our minds were so much clearer. The job opening in London had been frozen for the near term, and while it might open up again, we opted to move forward in the way that felt the most authentic to us. Italy had been out—the digital nomad visa that’s now available was merely a glint in the government’s eye and no other visa path there could work for us. London was out—it was way too expensive for us to give it serious consideration without jobs there, and Portugal couldn’t stand up to our critical scrutiny. Although we didn’t love the idea, we reserved a small storage unit for London items like cold weather clothing and the other items we had been setting aside should the job open again in the next few months. We gave up any thoughts of bringing furniture since storing it would be impractical and risky.

Trusting Our Gut

While I’ve been known to overanalyze things to death, we’ve both always trusted our gut. We’d spent plenty of time with the numbers and logic would say that we both should keep working, become less consumption focused, and save as much money as possible. But we also were extremely conscious that we had been working our entire lives and knew we weren’t getting any younger. Thinking about the idea of health versus wealth, which tied into the concerns Kevin expressed back in March, caused us to step back and analyze our priorities.

If this was the only life we’d live, would we be okay that the best years were spent prioritizing work over family? My former roles as an executive assistant to CEOs and presidents all required me to be available 24/7. It wasn’t the type of work that allowed for much balance. My family had sacrificed a lot when weekend plans would have to shift due to a sudden deadline, or dinners would get canceled because someone missed a flight and I had to rework their travel plans, or any of the other work emergencies. How long was I willing to have misplaced priorities, especially when I was in a job with a manager that clearly didn’t have respect for me or the work I did? I had reached a breaking point and finally had enough.

We played with numbers some more and spent a couple of weeks considering all our options. Our YouTube channel wasn’t bringing in any money yet, but Kevin’s Whisky Riffs channel was monetized. It was no where close to breaking even, but it held out a promise to us that if we are resilient and open to other type of work than what we had been doing, we could make it all work. We also brainstormed alternate career ideas outside of a conventional 9 to 5. Kevin’s editing skills were improving with each video he released. I knew several people who successfully ran their own virtual assistant businesses. I had done work as a voiceover artist and had seen some colleagues get work from Fiverr and Upwork. We had money in savings and investments, and while we would have liked more, we were confident that we could hustle enough to make ends meet.

I resigned from my job in mid October and didn’t look back. Meanwhile, Kevin was getting pushback from his job and he started to think about leaving corporate America for good. Spoiler alert: Kevin quit Apple just a few weeks into our journey at the start of January, 2023.

The Ultimate Decision

*Piazza dei Martiri, Naples 2022. First stop as full-time travelers.*

We were ready to move forward. With almost exactly a month before our November trip to Verona, we decided to rejigger it. Instead of having it be a trial run at working remotely, it would be our first stop as full-time travelers.

We’d split the month between Napoli and Palermo, cities where my birth parents had family members. We wouldn’t be meeting up with any family there, but it would be an opportunity to connect with my roots and great places for a fresh start. The trip was meant to be a round trip with us saying farewell to San Francisco in mid November and then visiting my birth mother on the round trip layover in Los Angeles. We’d skip the final leg of the flight and book a one-way flight for goodbyes to family in Houston and then head to Athens, Greece for New Year’s Eve.

It was a great plan. It also meant that we really had to put pedal to the metal to clean out our apartment to meet our November deadline. We notified our building manager, who ended up being such a godsend to us. She offered to take care of dropping off donations for us and clear out anything we weren’t able to get rid of on our own. We couldn’t imagine accepting this degree of generosity, even though she would be leveraging some of the building staff to assist. She had many charitable organizations she liked to support, so she promised it wouldn’t be trouble. She notified other tenants in the building that we were giving away and selling certain things. This was a mixed blessing. Although it was great to meet some of the neighbors we never ran into and we were glad to get rid of things, it was a time-consuming distraction because people wanted a tour of our apartment and made small talk. We loved all of this, but watching time tick by made us anxious.

*One of the small subsets of our donation process*

We still had so much to resolve. Kevin’s manager started to dig in regarding his return to office and threatened to cancel his remote month if he didn’t stick to the required three-days-in-office schedule. The timing of this couldn’t have been worse, since Kevin had a lot of stuff to downsize and very little time to get it done.

The overwhelm I was feeling was palpable. I hadn’t really regained equilibrium after quitting my job and the amount of work that needed to be tackled would frighten anyone. Coordinating sales and meetups for pickups and continuing to photograph and post items for sale felt never-ending. People who were supposed to show up flaked out. Someone who was supposed to buy our entire living room set, which was barely a year old, changed his mind the morning of the pickup. And then a couple arrived to meet a delivery truck for our dry bar decided they wanted other items but only if they could renegotiate everything. We wasted an entire day with them nickel and timing every item they wanted and then waiting and sorting out their truck that showed up without a permit.

By this time in the process, we were only a few days away leaving and allowed people with big pickups to come into our apartment to look at some furniture. While it was great they wanted additional items, they took forever. It was more disorganized than we intended and we accepted rock bottom prices just to get rid of things. It actually ended up feeling very icky because we were over a barrel regarding timing and that empowered people to offer prices that we never would have accepted under other circumstances.

Those last few days were awful. The pantry was still full and there was too much food in the freezer and fridge—even up until the last day. We wanted to get rid of some items more intentionally, like having friends take 60 bottles of wine and nearly 100 bottles of whisky. There was camera and podcasting equipment that Kevin wasn’t able to unload, and he still owned three expensive guitars. We had no interest in keeping these things, but we wanted a say in what happened to some of it, so we made the hard decision to put it all in a storage unit and deal with it along with the “London” items. We set a goal to return to San Francisco sometime in 2023 and either it would be because we were relocating to London or visiting friends, family, and donation spots to unload the rest of these items.

We were hours away from our flight and we needed to leave for the airport, but Kevin still had more to boxes to drop off at the storage unit. He obviously wasn’t thinking it through and told me to leave with our suitcases and he’d meet me at the airport. Thankfully, I was clear-headed enough in that moment that I realized it would be a horrible idea. Instead, our Hail Mary pass was to arrange a pickup service to meet our son at the apartment and he’d direct them to our storage unit. Never in our lives did we ever expect that we’d be scrambling until the very last moment during our last day living in the U.S.

Our building manager’s name is Hope, which is perfect because she offered us so much hope in those last days and hours before our departure. She reassured us over and over again that she was fine to handle everything. Never in our lives, or nightmares, would we imagine leaving so much stuff for someone else to handle, but we’re so grateful for all she did for us. She was inspired by our dreams and wanted to do her (large) part in helping us realize them and we’ll be forever grateful.

Want to Avoid Our Pitfalls? Check Out Our Downsizing Video Series

*Give yourself plenty of time to downsize. It takes longer than you think!*

We learned SO much from what we did and didn’t do, but our mistakes are to your benefit. We put together an entire downsizing series to help others streamline the process. You can check out our full series of downsizing videos here and download a checklist from our website to help you map your plan so you aren’t scrambling at the last minute. You can use these tools even if you’re just downsizing for retirement and not getting rid of everything for a life of full-time travel.

We were additionally grateful for the long flight to Europe so we could catch our breath, decompress, and celebrate the magnitude of what we accomplished. Was it pretty? NO. Was it a messy process? YES. Do we regret anything? Sure. We wish we finalized our plans sooner. We wish we wouldn’t have had to leverage Hope’s generosity. But otherwise, our additional learnings are in our videos. You can reach out to us and we will answer any of your questions and we’d love to hear your own stories of downsizing on a deadline in the comments!

What’s the one regret we don’t have? It’s embarking on this life of full-time travel. We’ve met incredible people in our two years of travel. We’ve visited 21 countries excluding the US since we started traveling full time, stayed in 33 hotels, 48 Airbnbs, and a river cruise cabin. We’ve been on 56 flights, 39 trains, at least 2 buses, and rented 7 cars, all in the US, oh, and 2 camels. And in all these places and spaces, we’re having the time of our lives.

Happy On-The-Road Anniversary to Us