A Feeling I Kept

Every morning, I walk down to the beach with Leo.

Leo is a dog of considerable charm and zero humility about it. Within minutes of arriving, he has introduced himself to everyone within a fifty-foot radius, and I am meeting their owners. This is how I have made many of my friends in Ericeira, the small surfing village on the Atlantic coast of Portugal, where I have lived since 2021. Leo leads. I follow. It's working out well for both of us.

I've officially entered my 60s. I hate saying it out loud. But these days, I start my work day at 1 p.m. That gives me plenty of time to enjoy coffee with friends or do yoga in the morning, both of equal importance. It's a great way to start the day. I live thirty-five minutes north of Lisbon in a place where surfers paddle out into waves that would kill me, and I watch them from the shore with complete admiration and zero desire to join them.

I am also a career coach. And I want to tell you something that took me most of my adult life to understand fully.

Sometimes the most deliberate thing you can do is hold onto a feeling — even when you can't explain it, even when it seems impractical, even when a global pandemic boxes up your dreams and shuts the door.

I know, because I held onto one for decades. And it brought me here.

It started with a Portuguese boyfriend while working on a cruise ship.

I was in my late twenties, working on what Berlitz had rated the number one cruise ship in the world. Five-star plus. The kind of ship where the dining room staff were Europeans — Portuguese, Italian, Spanish, French — who took the service of a good meal as seriously as any art form.

We spent the summer months sailing through Northern Europe and Russia. Grey skies. Cool air. Beautiful in its own way, but heavy. And then in early September the ship turned south, toward the Iberian Peninsula, toward home for much of the crew.

I will never forget the mood shift when we pulled into Lisbon harbor.

It was as if the sky opened. The light was different — that particular golden Portuguese light that painters have been trying to capture for centuries. The crew, who had been professional and efficient all summer, were suddenly alive in a different way. Laughing louder. Moving lighter. We were in their world now.

So that Portuguese waiter boyfriend wanted to show me his city. He was warm, enthusiastic in the way that people are when they're showing you something they love — he got a rare evening off and took me ashore.

We walked through neighborhoods I couldn't find on a map. We ate pastéis de nata still warm from a bakery. We stood at little bars and drank small glasses of red wine with plates of local cheese and meat. And then, late in the evening, he took me down a narrow staircase into a small underground bar where a guitarist and a fado singer were performing.

Fado is not exactly uplifting music. It is the music of longing — saudade, the Portuguese call it, that beautiful untranslatable word for a melancholy love of something absent. We sat on pillows on the floor. The room was small and warm and close. The singer began.

I didn't understand a single word.

I felt every one.

Something landed in me that night that I didn't have a name for. It wasn't about the boyfriend — he turned out to be less remarkable than the city, as people sometimes do. It was about the feeling of being somewhere that felt, inexplicably, like it had been waiting for me.

I filed it away. Life continued. The ship moved on.

That was 1993.

For the next twenty-plus years, I built a career. Communications professional turned executive recruiter. Career coach. Military reservist. Author. Conference speaker. I founded Linsey Careers in 2008 and specialized in placing senior marketing and communications leaders. I was good at it. I worked hard, made a good income, and I loved the pace.

Portugal lived in the back of my mind the way a song does when you can't remember the title — surfacing occasionally, then disappearing again.

In 2013, I decided to find out if the feeling was real or just the romanticism of youth. I booked a solo trip. My first solo trip, as it happened — no small group tour, no travel companion. Just me and an Airbnb in Lisbon and another in Cascais, a coastal town I remembered loving from a day trip off the ship years before.

I won't lie — I didn't love being alone in an Airbnb. No front desk, no recommendations, no one to talk to. I am, it turns out, a person who likes people, and traveling solo is a skill I had not yet developed. But Lisbon is forgiving to the lost and curious. You can wander and find exactly what you need.

One night I went to a fado restaurant. A more touristy one this time, with dinner and a show. I was seated alone at a small table in the corner, away from everything, as one apparently is when one dines alone at such places.

I looked at my overpriced dinner. I looked at the small stage. I looked at an empty table for two directly in front of the performers.

I picked up my plate and moved.

The waitress scrambled to catch up with the rest of my things. I sat down and watched the musicians tune up. And that was when the evening changed entirely — as evenings in Lisbon tend to do when you stop waiting for permission and simply move your plate.

I won't tell the whole story here. But I will say that by the end of the night, I had been invited to join a table of four Portuguese men, one of whom turned out to be a fado singer and another of whom owned the place. They were harmless and funny and kind. When the restaurant closed, we stayed. The guitarist — apparently one of the best in Portugal — played privately for our small group in an empty room.

The feeling from 1993 came back. Stronger this time.

I flew home to Seattle knowing two things: I was moving to Portugal someday, and solo travel gets considerably better when you're willing to move your plate.

Next: When a doctor's appointment changes the timeline — and a vision exercise in Hawaii changes everything.