• At 55, I thought I would have already figured out where I want to retire in the next few years.
• Instead, I've been living out of suitcases and housesitting in different places to see what I like.
• I still don't know where I will retire, but I do have a much better idea of what I want — and don't.

I always thought I'd be settled somewhere for good by age 55, with a comfortable home, established garden, and chest freezer in the garage.

But after growing up in the San Francisco Bay Area, raising my kids in Seattle, and becoming an empty nester, I realized I had no idea where I wanted to settle down.

For the first time in more than 20 years, I suddenly had the freedom to choose where I wanted to live.

So at 52, I started housesitting in exchange for places to stay so I could travel without depleting my savings. I quickly realized how much I enjoyed the nomadic lifestyle and how this gave me the opportunity to test out places I might eventually want to live in.

After a few months, I liked it so much that I gave away almost everything I owned, put the rest in storage, and decided to do it full-time.

That was almost three years ago. Since then, I've lived in dozens of cities, towns, and remote islands, from northern Washington to the southeastern coast of Mexico's Baja California peninsula.

Housesitting has changed my mind about what I thought I wanted

I typically stay in each home for two weeks to three months at a time, which allows me to get to know a new place without signing a lease, buying a house, or committing to a community.

Instead, I chat with locals, visit the library and grocery store, explore nearby nature trails, and try to imagine what it would be like to live there.

I ask myself a lot of questions: Can I tolerate this climate? Do I feel able to connect with this community? Could I live without whatever thing this place might be missing … which is sometimes as simple as my beloved Trader Joe's?

Throughout my stays, I've learned new things about myself and what I really want.

For example, I'd long pictured myself settling in a city since I've spent most of my life in major metropolitan areas.

So, I was thrilled to book a housesitting job right across the street from my old high school in San Francisco. I couldn't wait to walk the same streets I did in my youth and revisit my old haunts.

But the nostalgia wore off quickly, and a $105 street-cleaning ticket reminded me of the hassles of city life. I realized that a noisy, crowded, expensive city isn't where I want to settle after all.

These days, less traffic, more green space, and a slower pace feel more like my style.

After that stint in the city, I went to the other extreme and booked a multi-week housesit on a remote Pacific Northwest island where the closest grocery store was a ferry ride away — long enough to require ice packs and a cooler to get my frozen food home before it defrosted.

At first, I couldn't imagine staying there for more than a few weeks, but I quickly fell in love with the solitude and have returned several times.

I realized that being surrounded by water, going days without talking to another person, hearing owls hoot at night, and watching a mother deer and her fawn wander across the yard made the extra effort of island life worthwhile.

I was willing to plan errands around the ferry schedule and give up some of the conveniences I'd always taken for granted for that kind of peace.

Turns out, I'm more open to living in a remote place than I expected.

Now, I'm rethinking what it means to settle down — and if I'd even stay in the US

I'd also never even considered moving abroad until I booked a five-week housesitting gig for an American woman who had retired in La Paz, Mexico.

I felt inspired by my client's willingness to give up familiar comforts and conveniences to risk starting over in a new country in search of the life she wanted.

Although I'm not sure Mexico is where I want to settle, I loved my time in the Sonoran Desert and haven't ruled out retiring outside of the US. This experience helped me learn what living abroad was really like and realize I'm more capable of making that jump than I ever imagined if it's what I ultimately choose.

After trying out more than 50 locations in three years, I still don't know where I eventually want to retire. But I know I want to be somewhere I can walk in nature, enjoy some solitude without feeling isolated, and engage with a community when I'm ready for company.

Above all, I'm searching for a place that makes me feel at home — even when I'm visiting for the first time.

• I was living with my boyfriend when we broke up, and he suggested that we stay roommates.
• After looking into my options, I realized that living together might be the best financial move.
• It was awkward at first, but acknowledging the situation and setting boundaries helped.

I met my ex in Spain, on a warm October night in 2024. He approached me as we were both walking home from a boxing class and confidently started a conversation.

About two weeks later, we went on our first date. A few months after that, we took our first weekend trip together. In April, he surprised me with a key to his home. By June, I'd moved in.

Our relationship was built on genuine care for one another. Throughout our relationship, we always sought to support each other's well-being and growth. Of course, we had bumps here and there, but they were never significant enough to change our respect for each other.

That's why, when we agreed to break up in August because we saw our lives going in different directions, I wasn't at all surprised that we found a way to continue living together.

We broke up, but I stayed at my ex's house

Under normal circumstances, I would've moved out as soon as possible. I've always believed that you can't start to heal from a breakup until you cut all ties and communication with your ex.

So, I bought the boxes, tape, and bubble wrap, started looking for apartments, and began packing.

But then two weeks later, I lost a freelance contract that contributed a significant portion to my income. This, coupled with the fact that I was already in the middle of a lengthy visa process to make Spain my long-term home, only added to the stress of going through a breakup.

Seeing the distress I was enduring, my ex sat me down and suggested that I continue to live with him until I was able to get back on my feet again.

My first thought was that people would think I was out of my mind for choosing to live with an ex. Then, I started weighing the pros and the cons.

If I stayed, housing would be one less thing I'd have to worry about … but every day, I would have to see someone I'd just broken up with. Worst of all, I'd have to treat my ex like a roommate, as if we didn't just spend the past two years in an affectionate relationship.

If I decided to move out, I wouldn't have to see my ex every day, and I could focus on healing my broken heart alone — but I'd be in a tough financial situation.

Unlike my ex — who's lenient and open to pulling some extra weight when I can't make rent or contribute 50/50 on utilities — I knew that a landlord wouldn't necessarily care about my personal situation once the first of the month rolled around.

I chose to keep living with him.

At first, there was an adjustment period

Those first few weeks were awkward. We'd already had separate bedrooms because of my ex's insomnia, but the changes to our routines and interactions felt foreign.

Instead of getting a text inviting me to come cuddle with him on Sunday mornings, my phone remained silent. Instead of getting ready and walking to the gym together in the afternoon, I started going in the morning.

Instead of sitting down to have dinner together, we ate at different times in different rooms. Whenever we saw each other, we would force a smile, say hi, and go our separate ways.

We didn't acknowledge the strangeness of our situation until one moment broke down the barrier. I was used to having crying sessions in my room, but this time, one snuck up on me while I sat in the living room. The stress of my breakup, finances, and living situation had just built up too much.

My ex was passing through the living room when he saw me crying and gently asked if he could give me a hug. I nodded.

This interaction prompted us to finally discuss the elephant in the room (well, house): Living with your ex is weird. Simply addressing the situation and talking about how we were both coping instantly made it feel a little bit lighter.

We found a new way to live together

What followed was a conversation about how we wanted living together to look like. We knew we were doing something unusual, which was daunting, but also meant we were free to make our own rules.

Our first decision was to stop acting like strangers. Barely acknowledging each other's existence just didn't work for us, so we welcomed a level of friendliness into our new relationship.

Then, we decided we'd continue offering each other a certain level of emotional support. My ex recently took a leave of absence from work to heal from burnout and contemplate his next career move.

Meanwhile, I was struggling to find full-time work and sustain the life I was building abroad. Being there for each other when one of us needed a listening ear felt important.

Lastly, we agreed not to cross any lines that would confuse the other person. We weren't in a romantic relationship anymore, so we decided that any affection beyond a friendly hug would be prohibited.

With this, our living situation went from something that felt unbearable to something that works for us. In the next few months, I plan to save enough from my freelance work to move out. Until then, I'm happy knowing I have a home, even if it's with my ex.