Trusting Strangers

Trusting Strangers

Do you ever put too much on your plate?

It was spring 2024, and we were busy trying to revive an old little house on the island. We'd hired local carpenters to replace the deteriorating kitchen cabinets. But painting the house, inside and outside? We could surely add that to our list of activities.

We enthusiastically started with the interior walls of the living room and kitchen. We speckled the floor generously—we were in a terrible rush. This was going to be an impossible task, I thought. First painting, then removing stains and spills, then touching up... There had to be a different solution.

Our Solution: WorkAway

WorkAway is a volunteering program where hosts ask for help and travelers offer theirs. It's about cultural exchange, learning languages, sharing experiences. We quickly created a host profile, asking for two travelers to help paint the little house for 2-4 weeks. Three hours a day, in exchange for a place to stay (the project itself).

We set up video calls with selected candidates. If it was clear they wanted peace, quiet, and nature—not nightlife and partying—the plans became concrete.

Travelers came from Spain, Colombia, Mexico, Italy, Germany, Hungary, the Netherlands, South Africa, Ukraine, and most recently, Japan. They stayed either at the little house or in our guestroom at home.

Beyond the Tasks

Besides the outlined work, we went on walks, explored the island, cooked meals together, attended picnics and parties. We became friends forever—complete strangers from countries we'd never lived in or visited.

In August 2024, two young women from the Naples area joined our growing team of travelers. On one of our first hikes together, I mentioned how people around us were clearly concerned about our high level of trust. "How do you know they're good people? You're inviting them to the island, to your house. This is an accident waiting to happen."

Guess what? The Neapolitans told me the exact same thing—but from the opposite perspective! One shared that her father strongly opposed her adventurous plan to stay with total strangers on a faraway island.

We looked at each other and shook our heads at the symmetry of it all.

Building Trust Gradually

Of course, I'm trying to avoid problems, and of course there's no 100% guarantee things will work out. We were careful at first, not overextending our invitation. But the second couple proved it could work beautifully. We agreed they'd stay for one month, with the option to extend if everyone was happy. They ended up staying for three months, transforming the small property and its garden and teaching me the latest Spanish expressions: "¡Qué guay!" They even became friends with the local neighbors, who shared fresh fish and eggs.

¡Qué guay!"

The Bumps Along the Way

Did everything go smoothly all the time? No.

There was the young man who failed to mention he was escaping dark and dreary Northern Europe, hoping to boost his mental health with sun in January. The Azores might not have been the best choice for that. "I don't know... I can't seem to get out of bed," he candidly told me with a sleepy, sad face. It was tough for everyone.

Or the fun but super messy couple who left our guestroom greasy, sticky, and smelly. I don't do inspections, you know...

The Last Volunteers (For Now)

Earlier this month, a young Japanese couple said farewell after spending six weeks with us—the last travelers on the island for us, for a while. Like the previous volunteers, they took ownership of their tasks, maintained their living quarters, and genuinely wanted to build relationships with us and the community.

The experience was one of many for them. They'd spent the last few years working and volunteering around the world, ultimately discovering that their home country was actually a wonderful place to return to—despite opposite sentiments at the beginning of their journey.

The Moral of the Story

Most people are amazing, positive, loyal guests. A program built on trust instead of conventional contracts and compensation—based on exchange—worked fabulously. The priceless bonus? Learning from global travelers about their cultures and languages while sharing our own.

It might not sound very 2025-ish, but it's happening!

The Plot Twist

Here's the irony: we were willing to trust complete strangers from across the world—people we'd only met on a video call—to stay in our home and work on our property. We did our homework, sure, but ultimately we trusted our gut and gave people the benefit of the doubt. And it worked. Beautifully, messily, imperfectly, genuinely.

Yet how often do we extend that same trust to ourselves?

I'll wait while you think about that one.

We doubt our decisions, second-guess our capabilities, and talk ourselves out of dreams before we've even googled the first step. We're happy to trust a stranger's potential but remain deeply skeptical of our own. The same instincts that helped us navigate these cross-cultural exchanges—reading situations, adapting on the fly, learning from the occasional greasy guestroom disaster—we already have those skills.

Trusting Ourselves: The Final Frontier

So if we can create something meaningful by trusting people we've never met, what could we create by trusting ourselves a bit more? This is actually one of the most common topics in my coaching sessions. That voice that says "if only I could be more confident and do the things I dream about"—it's practically on repeat for most of us.

Maybe the lesson from our WorkAway adventure isn't really about strangers at all. Maybe it's about recognizing that we're more capable of good judgment, resilience, and connection than we give ourselves credit for. (Even when we leave paint speckles everywhere.)

Struggling with self-trust? Let's talk. If this story resonates with you—if you find yourself trusting everyone except the person in the mirror—I'd love to help you explore what's holding you back. Sometimes we all need someone to remind us we're more capable than we think. Get in touch to schedule a free discovery call.

One of the special handmade gifts we received from volunteers. Grateful!