The Breaking Point

"Something has to change."

Those were the words I said to my 19-year-old son on a cold February evening in 2026. Within a few hours, we had decided to sell our house, erase years of debt, help him build a life of his own...

...and I would move to Portugal.

For three years, I had worked four jobs – one full-time and three part-time – trying to make ends meet. Trying to find a balance between providing for me and my son – two cars, the occasional vacation - and paying the bills – including four surgeries in 2 years. It was a losing proposition. Not only was I not paying off debt, I was getting deeper in it.

My boy and I just before that fateful night.

Narrowing my Choices

It was November 2024 when I first really started thinking of leaving everything and starting over in a new country. I had been researching Costa Rica as a vacation spot for a while, so this was the first country I looked at seriously. It had a great remote worker visa, and the cost of living outside the touristy areas seemed very affordable.

The rainy season from May to November made me hesitate a bit. I’m very affected by the presence or absence of sun, and I’m sure the Ticos have ways to work through this, but I believed it was an important point to consider. But there was something bigger calling me away from Costa Rica.

I’ve been drawn to Europe for as long as I can remember. My first European vacation was to England when I was 25. Since then, I’ve traveled to Ireland, Switzerland, France and Norway. There are several things that stand out to me every time I travel to Europe. Unlike America, there is not a fast-food restaurant on every corner. People are out walking around constantly – I live in Louisville, KY, and there are only a few areas of town where you can get around on foot. People just look healthier.

If it’s going to be Europe, it must be France. I joined some friends on a bicycling trip in 2021 from Geneva, Switzerland to Annecy, France. 5 days, 150 miles. When I rode up to Lake Annecy in Talloires, I felt like I had arrived home. The beauty of this pristine lake, the Alps in the distance, even the overcast skies, felt right to me.

As the months were going by and Jack was in his last year of high school, I began to look at France as my landing spot. This was around the fall of 2025. I had a friend who lived in Carcassonne. She and her husband had moved there from Kentucky several years ago. Looking through her social media posts, she seemed so happy. I reached out to her, and we set up a call. Could her reality be anywhere close to what she was posting?? Turns out…it was. She and her husband had settled well into their life in France, their daughter was attending university nearby, and they could not even imagine returning to the US.

I began to investigate the visa process.

Then Came February

Two things happened in February 2026.

One, I finally reached a financial breaking point. I had robbed Peter to pay Paul for so long that I was backed into a corner. I could not physically work more than I already was. I had no money left on (all) my credit cards. And still the bills were coming in. I was in a very dark place, struggling with real depression for the first time in my life. My son, Jack, wasn’t doing much better. He had been broken up by his long-term girlfriend, lost his first job out of high school, had a rollover car accident that could have killed him and was struggling with what to do now that he had graduated.

When I sat down with him, he said he knew things needed to change. He knew how bad things were. He said, “I can’t be happy, if you aren’t happy.” And I said, “Well, I can’t be happy, if you aren’t happy.” So, we made a decision. We were going to make a real change.

The second thing that happened around this same time is that I began to doubt my visa application for France. But really? I just doubted myself. I had “lost” my house, I felt as if I had failed as an adult and a single parent.

Selling my house didn't feel brave. It felt like admitting defeat. I wondered if everyone would think I'd failed.  But eventually I realized something important: Staying exactly where I was would have been the real failure. It’s so very difficult to change.

Back to the drawing board. I began researching (again!) remote worker visas in countries that had a low cost of living. No matter the criteria I put in, Portugal came back at or near the top of the list, time and time again. I narrowed my research to Portugal and loved everything that I was seeing.

Rent was cheaper. Groceries were cheaper. No car? No problem!  

They have a fairly straightforward remote worker visa. It has beaches, big cities, mountains and small towns. There is a big American expat community. I would prioritize integrating myself into whatever community I moved, but it would be nice to know there are other Americans around.

Oh, and one other thing. Portugal is drop dead gorgeous. The view of Porto from the Douro River will blow you away. The rocky outcrops along the beaches of the Algarve. The hiking trails and waterfalls in Madeira.

Portugal, it is.

I mean, will you just look at this beauty?!?!

Packing Up and Moving On

The house sold in three weeks. The debts have since been paid off. Jack has moved into his apartment and is working at UPS (it’s practically a rite of passage to work at UPS as a teenager if you are in Louisville).

In addition to selling the house, I sold almost everything in it. I own no furniture. I have two boxes of family memories. I have a hella lot of shoes. I’ll pare those down later. I still have a ton of Christmas decorations that need to be whittled down, as well. My whole life went into a 5’x9’ storage unit.

And I’ve never felt lighter. It’s just stuff. The things I kept are only things that really mean something to me. Family photos, a yak bell from my Everest Base Camp trek, paintings from Africa. Items that tell the story of my life.

This is all that's left!

Now at 55, I’m couch surfing for the first time in my life at a dear friend’s house for the summer. This fall, I move to Portugal.

For a year? For two months? Forever? I don’t know. I am giving myself the grace to change my mind at any time. Maybe Portugal becomes home.

Maybe it doesn't.

But after years of surviving, I'm finally choosing hope over fear.

One thing I've learned through years of solo travel is that sometimes the biggest adventure isn't climbing a mountain or crossing an ocean. Sometimes it's giving yourself permission to start over.

In my next post, I’ll tell you how I narrowed Portugal down from an entire country to one city. Things did not go as planned.

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