Freedom in Simplicity: Why We Don't Regret Getting Rid of Everything to Travel

People often ask if we'll regret selling and donating everything to travel the world, especially as we grow older and are less able to explore—or if one of us finds ourselves alone, without the tangible memories of our shared home.

Before we made the decision to travel the world, we had these same questions ourselves. They prompted us to reflect on what truly matters to us. How do we each define home when it's no longer tied to a physical space? How do we balance the intangible richness of new experiences with the nostalgia for physical mementos? Our decision wasn't made lightly, but with purpose and passion. We concluded that accumulating possessions was secondary to a life lived boldly. We believe this path, while unconventional to some, is one without regrets for us. If you're considering a similar path, let’s explore why this journey can bring endless rewards without the burden of material possessions.

Why Letting Go of Possessions Can Be Liberating

A home is whatever you make of it—it doesn’t have to be a place filled with decades of memories. Instead of holding onto material things we once thought were important, we’ve embraced the idea that experiences and memories outweigh our possessions. By letting go of our stuff, we opened ourselves to a world filled with countless adventures. We digitized our pictures and other special things that hold memories but we didn’t need to hold onto the stuff itself. Those items now live in our phones that we take with us everywhere versus being hidden away in containers stored on shelves that we never or rarely look at anyway.

We often hold onto items because of nostalgia or the belief that they define our identity. However, these tangible things can also weigh us down, both physically and emotionally.

One part of our donations pile while we  downsized

Life is inherently unpredictable, and by letting go of the need for control through possessions, we become more adaptable. We’re building resilience in the face of uncertainty, which we think will serve us well as we age. In a consumer-driven culture that promotes accumulation, living minimally can feel counterintuitive. Instead, we’re learning to embrace change and trust that in a world of unpredictability, our relationships and experiences will sustain us far more than material items ever could.

Redefining Home and Creating New Memories

Right now, we’re crafting incredible experiences. What might be routine in daily life—like grocery shopping, laundry, or haircuts—becomes an adventure as we travel. Each location offers a unique twist, turning everyday tasks into memorable moments. Consider how you can find joy and excitement in the simple things when every day is filled with new experiences.

Paris fruit market, 11th arrondissement

We never know what we’re going to find when we enter a grocery store or food market in a new city. We rarely visited farmers markets in the US. But now we know we’re going to get local, in-season foods, which haven’t had to travel thousands of miles to get to us, so they’re fresher and tastier. We typically stay in an Airbnb with a washing machine, and each one works a little bit different. We make a game of trying to guess what the icons mean and we are overjoyed when we discover that there’s also a clothes dryer. When we lived more traditionally, we weren’t nearly as grateful for having a washer or a dryer. Laundry was something we had to do, and now we’re even grateful when there’s a drying rack!

Fortunately, hair grows back and wrong colors can be changed, so even navigating a haircut or hair appointment is an adventure. It’s been interesting to see what the local customs are. I never dreamed someone would color my hair by putting a sombrero device on my head, but it happened in Palermo! When you go to the same salon month after month, you miss out on experiences like this!

Building and Maintaining Global Connections

Friendships can thrive even when spread across the globe. Our relationships in the US remain strong because we continue to nurture them from abroad. But our travels allow us to form new friendships and deepen other ones. Kevin has friends living overseas that we would occasionally see when they visited the US for business. Recently we bumped into one of them on a flight to Vienna. We ended up meeting up for dinner and they gave us a guided tour of their favorite places around the city. We’ve met up with friends and former coworkers living in Scotland, Amsterdam, and London, too. And we’ve even bumped into friends who were on vacation or on work trips in Italy and France at the same time as we were! When we lived in the US, we lived in a different state from our daughter, so we only saw her once or twice per year. Now that we are living a life on the road, she’s visited us in Japan and Italy along with our yearly visits to the US. We look forward to having more opportunities to share new parts of the world with her and it’s inspiring her to want to discover more of the world on her own, too.

Chris Phin giving us a tour of Dundee, Scotland

By actively seeking out connections, whether through social media, travel groups, or casual meet-ups, you’ll find that travel enriches your life with diverse relationships. We’ve even built friendships with tour guides and servers at restaurants that we still are regularly in touch with, too!

Financial Planning and Flexibility

Financial security is important, and we approach it with mindfulness. While we still have our savings and Kevin recently started receiving Social Security, we also actively work on our travel blog and YouTube channel (subscribe if you haven’t already!). This allows us to earn money while sharing our journey, reducing the need to dip into our savings. If you’re considering this lifestyle, explore how you can create income streams while traveling. Remote or online work is limited only by your imagination. It’s okay if your previous career didn’t involve computers. It’s never too late to start something new that allows you to work from wherever you are.

If you’re interested in reducing travel costs, we know of people who have used the following organizations that provide accommodations in exchange for some type of temporary work: Trusted House Sitters provides free accommodations in exchange for housesitting pets or doing chores while the owners are on vacation; Worldpackers is a platform that connects hosts who offer farm work in exchange for accommodations; WWOOF is an international organization that provides room and board to people interested in learning about organic farming and sustainability; and Workaway, which offers volunteer experiences like gardening in an olive grove in Italy, helping on a hobby farm in Australia, etc., in exchange for room and board. Note that you need to arrange your own visa and transportation to these locations.

Living Fully Without Regrets

Kevin in a Serbia hospital after a hernia surgery

We believe in seizing the moment because we can’t know when a health problem will derail our retirement plans. Every day presents the chance to explore, grow, and live fully while we are mentally and physically capable. Don’t wait for the government to tell you it’s time to enjoy life—embrace the present and create a path filled with rich experiences.

Exploring New Horizons and Future Planning

We remain open to living differently than we did in the US. We acknowledge that possessions don't equate to happiness, and we can live on less than what we previously thought necessary or what it costs to live in the US. Even if our journey leads us away from settling down in Italy, the new destinations we discover are potential homes for us that can offer rich, fulfilling experiences at a fraction of the cost of settling down in the US.

Conclusion: Is This Lifestyle Right for You?

As you reflect on your own journey, ask yourself what truly matters. Are you ready to prioritize experiences over possessions? By approaching life with a spirit of adventure and open-mindedness, you may find that this unconventional path leads to profound fulfillment and a life without regrets.

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Peace of Mind Abroad: Choosing the Right Health Insurance as Retired Travelers