Portugal: Matar Saudades in the Algarve (Part Two)

On lifelong friendship, my 50th birthday, and listening to my calling for home

I had invested a lot, emotionally, into my visit to Southern Portugal, the region called the Algarve. I had a vision of celebrating my 50th birthday there a few years ago, and more recently, began fantasizing about it as a potential new home. I’m forever searching for my place — nestled between the mountains and the sea, where the weather is perfect year-round, with a thriving outdoors and arts community, and does not require a tech salary to live a decent life. There are few places in the world that match this criteria. The Algarve checks the boxes.

After enjoying a solo week in Lisbon, I was joined by my friend Jamie. She was fully briefed on my future dreams of Portugal living and was up for the reconnaissance. We would roadtrip together to Lagos, a small city in the Algarve about a 3-hour drive from Lisbon. Spending a holiday with Jamie, the Portuguese may say, would be matar saudades, which translates as “killing the saudades.” In plain English, I was crawling out of my skin to see her.

When Unbound became Uncomfortable

In October 2025, when I quit my tech job, I adopted “unbound” as my word-of-the-moment. “Living unbound” meant being liberated from anyone else’s control. I would finally live with autonomy, an overused word in the corporate world to attract people to a dream job. We often hear, in leadership roles, that we will have autonomy. But it never works that way. We are always bound by corporate goals and culture. And if it is not a job that is tethering you, it is a partner, a family, a pet, an investment, or a myriad of other things.

I decided to embrace this gift of living unbound, with an intention to claim agency of my attitudes and actions -- to follow my curiosity and intuition instead of someone else’s mission, or my addiction to external validation.

250 days into my 365-day sabbatical, while in Portugal, I felt a stirring of my joyful unbound shifting to an imposing uncertain, and filling me with an undesirable uncomfortable. Unfortunately, this all came to an emotional peak while trying to have an adventure and a mini-brouhaha for my 50th birthday.

That pull I felt toward Portugal a couple years back had vanished, and I was now feeling a compulsion to leave. I arrived in Portugal with no return ticket home, and an expectation to travel for at least a month. But the discomfort was suffocating. I woke each morning with a headache and a weight of sadness, and each night I suffered eerie and agitating dreams. I wanted the comfort of home, which was a complex feeling because I happened to be in a transition between homes and, therefore, unbound from one of those as well.

Captivated by Lagos Cliffsides

Despite the heaviness I was experiencing, I tried to carpe diem. Having my best friend there helped in every way. We weaved through hordes of tourists, in and out of shops and restaurants, on the stone-tiled streets of Lagos Old Town. We enjoyed the natural butteriness of fresh seafood, paired with the local verde vino (green wine). We took a drive to the nearby surf town of Aljezur to check out newer housing developments (a future home?) and west coast ocean views.

We gazed in wonder at the iconic limestone cliffsides from as many perspectives as we could position ourselves — from the Ponta da Piedade boardwalk, where the bird’s-eye view highlighted the mesmerizing color combination of golden copper cliffs against the cerulean sea; from a sailboat at sunset, serenaded by Fado (traditional Portuguese music whose melancholic feel matched my mood), golden reflections of limestone in the blue-green sea, and new detail in the layers of the cliff rocks; from the beach, where we contemplated all the ways a crashing wave could carve its stories into a single rock; from a kayak as we paddled through the caves created by these very waves, and those layers of rocks were revealed up close as markers of geological eras.

Seasides cliffs and seastacks in Lagos

Celebrating 50 Years

I’ve known Jamie for nearly 30 years. She knows me better than most people do. She’s usually the person who I ask to decide for me when I’m in those moments of “I don’t know what to do, just tell me what to do.” Turning the corner to my 50th birthday was another moment in my life that I was grateful to share with her.

My birthday was filled with many things that I love, starting with an early hike on Fóia Summit, in the small mountain town of Monchique, about an hour’s drive from Lagos. Fóia Summit is the highest point in the Algarve, at 900m/3000 ft (still not even the starting point for the hiking trails in the PNW, but whatevs, I’ll work with the mountains available to me wherever I go).

Fóia gave expansive views of the southern Portugal coast, as well as a hazy semblance of what we believed to be Morocco in the distance. After returning to Lagos, we had coffee at our favorite coffee place along with a pastel de nata and carrot cake (because, why not have coffee and cake for lunch on your birthday??🎂), stopping at shops along the way to the beach, where we swam in the sea, and I spent quality time with my sketchbook. On the way home from the beach, we stopped for Aperol Spritzes where the bar next to us was playing Led Zeppelin’s D’yer Mak’er (LZ always brightens my spirit 🤘). After taking refuge in the air-conditioned apartment, we made a tinned fish charcuterie, with a local wine, and had an afternoon siesta.

tinned fish charcuterie, a 500-year-old bridge, Aljezur, and sketching

Going Home

I made the decision, with Jamie’s help, to follow the calling for “home” - despite not having a specific domicile - and booked a return ticket to NYC to spend time with family. Just having the ticket booked lifted the weight that I was feeling, and the nightmares eased up.

I still grieve about the original plan I had for Europe that did not manifest, but in this new way of listening to myself that I am doing, I have faith that the trip - the long bike trip, traversing many countries, suffering through mountain climbs - will happen when the time is right.

My birthday - and my time in Portugal, as it turned out - ended on a high note with another one of my favorite things, a dram of Lagavulin. Cheers! 🥃 or Saúde!, as they say in Portugal.

Live with Love. Be Unexpected. 😘

a 30-year friendship