Don’t Know Where I Want to Retire; Testing Living in Different Places

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.