What a transition this has been since getting the land he and I adore mutually on his radar, in Trump’s first presidency, and subsequently turning up with only hand luggage in late 2020 to create a new life.
Honestly, I can’t remember how he ended up on my radar, but once invited onto the Good Morning Portugal! show and podcast, “Jaime Olley”, as locals might call him, distinguished himself as a man with useful and inspiring things to say on ‘mindful migration’.
Speaking from his own experience and with a deep and persistent interest in human potential, he became the morning show’s ‘Mr Rogers’, sharing moving and meaningful insights, which included how migration is akin to the stages of any relationship or love affair.
A psychotherapist, and formerly a US Navy sailor, schoolteacher and hairdresser, he’s happy these days to go with a simple “Hello, I’m James, and I’m An Old Guy in Europe”, by way of an intro, as I discovered when digging deeper for a recent Resident podcast interview. But I was looking for more, which you’ll also discover in what follows, as I took the opportunity to probe further into why this American elder chose Portugal as his home, and to see how it’s all working out for him.
I began by reminding him about something I’d heard said on the YouTube channel he’s started since settling here – that this last Christmas was the fifth he’d celebrated Portuguese-style. “Time flies in some ways and rolls at its own pace in others,” he answered, observing the odd way time works, but adding: “Saying ‘fifth Christmas’ out loud hit me. Wow, five years already!”
But what was it before that, I continued, that prompted his move, which thankfully has been such a good choice and, in many ways, passed so quickly – as time does when you’re having fun?
“For the full story, I’d point people to my YouTube channel’s first five episodes as they cover everything, but for the condensed version … I was approaching retirement after careers as a public-school teacher, a hair stylist for nearly 20 years, and then a psychotherapist for about 15 years,” he began by way of explanation.
“Around 2016, I felt unsettled in the United States. Political and social unrest played a role, but it was deeper, internal too. My Navy service had opened my eyes years earlier. Seven months overseas in the Western Pacific on an aircraft carrier showed me there’s a whole world beyond America. I’d absorbed the cultural arrogance that ‘the US is the best place, so why leave?’ But reality hit differently.
“I’d lived for 20 years in Santa Cruz, California, but rising costs priced me out after grad’ school and licensing as a psychotherapist. I asked myself: ‘If not here, where?’ I researched online for places Americans retire to abroad. Initially, Central America appealed; Costa Rica, being English-friendly and US dollar-based. But the humid rainforest climate near the ocean wasn’t for me,” he revealed.
“Europe felt culturally closer with Western roots, and familiar enough without a completely alien language or system. I assumed it was too expensive for retirement, but Portugal kept ranking high (even number one some years) in those lists. I focused on the west coast, ocean vibe like Santa Cruz. Portugal fit: affordable, English somewhat accessible in expat areas, mild climate, and beaches.
“I Googled Portugal’s coast and zeroed in,” James recalled, whilst noting: “People back home often had no idea where Portugal was. Some thought Central or South America. Many Americans I knew had limited geography knowledge beyond their state and little interest in world news unless it hit home personally.”
I wondered what drew him specifically to Ericeira at first, and how the move evolved from internet research into a reality, and James shared that this beautiful town matched the Santa Cruz feel he knew and loved, with its surf-town vibe, ocean-focused and relaxed.
More generally, Portugal exceeded expectations. The people, safety, food, healthcare. “It’s welcoming,” he shared. “Bureaucracy exists, but it’s manageable compared to the chaos I felt in the States,” James continued, who has since moved from the surfers’ paradise further north to Espinho, which has a different “coastal charm”.
The story of how he found his first home here is heartwarmingly Portuguese and radiates a sense of the magic and wonder that seems to be the hallmark of his unfolding Portuguese adventure. You can hear it in my full-length interview with him, including how he landed on his feet further up the Atlantic coast too, like the icing on an already very satisfying cake.
As well as finding out about James’s ‘special sauce’ when it comes to the best recipe for a fulfilling move, I also asked what inspired him to start and continue with his YouTube channel, week after week, with 84 episodes under his belt at the last count.
“It’s evolved naturally,” the ‘Old Guy’ explained. “I started sharing my experiences honestly: the good, the challenges, the everyday realities of expat life as an older guy. Viewers seem to connect because it’s real, not a polished sales pitch. I cover practical stuff like visas, housing, culture shock, joys of simple things like fresh food or walking the beach. It’s therapeutic too, keeps me engaged, connected to others making similar moves.”
But perhaps most importantly, I asked him what advice he had for other Americans, or anyone, considering the leap and moving to Portugal.
“Do your homework, but don’t over-analyze into paralysis,” he responded wisely. “Visit first if possible. Be open. Portugal isn’t perfect, but the quality of life, especially for retirees, is hard to beat. Learn some Portuguese; it opens doors. And embrace the slower pace; it grows on you.”
Of all the many people I have spoken to about moving to Portugal, I deeply admire James’s blend of the logical and spiritual, which seem to have brought him such a simple yet profound happiness here. Others can certainly learn from his holistic approach that lacks the stressful intensity of being too rational about such a big change, yet mindful and intuitive enough to let Universe work its magic, as it did for this old guy who moved to Europe.
Hear James’s full-length interview with Carl for The Resident Podcast here and see him on the Good Morning Portugal! with his further insights around ‘mindful migration’ as well as the ‘Portuguese bird of the month’ feature.
Read Carl Munson’s previous article: Feast on the food of love in 2026
