When my husband Shayne and I sold nearly everything we owned to travel the world full-time, we thought we were ready for anything. We had spreadsheets, backup plans, a carefully managed budget, and, as two adults in our 50s, decades of experience behind us.
What could go wrong? Turns out, plenty.
Over the past two and a half years, we’ve lived in more than a dozen countries and traveled thousands of miles. We’ve hiked to waterfalls in Bali, wandered the streets of Barcelona, and eaten our way through Thailand.
But we’ve also made mistakes that cost us time, money, and more than a little peace of mind. Some were honest slip-ups, while others came from overconfidence, but they all taught us lessons we’ll never forget. Here are five of the biggest mistakes we’ve made.
Overplanning made us feel burned out
At first, we packed every destination with nonstop activities. Sunrise temples, food tours, museums, waterfalls, cultural shows — we didn’t want to miss anything.
But within a few months, we were running on fumes. The pace was unsustainable, and on some days, it felt like we weren’t even enjoying ourselves.
These days, we travel more slowly. We leave room for naps, long walks, and spontaneous days with no agenda.
Some of our best memories now come from lazy mornings and quiet moments, not the things we planned, but the ones we stumbled into.
We underestimated how hard it is to build a real community
We assumed full-time travel would mean constantly meeting fascinating people and forming deep connections around the globe.
Although we’ve met plenty of kind and interesting travelers, most friendships are fleeting, shared over a meal or a few days before everyone moves on. We didn’t expect how lonely it can feel to always be “the new people.”
Now, we intentionally choose places with digital nomad scenes, coworking spaces, and expat meetups. In Vietnam, for example, we love that locals and expats gather for weekly street-food tours and surf lessons.
It takes effort, but building community on the road is possible. We just had to actively seek it out.
One time, we misread our visa and had to change plans at the last minute
When traveling to Vietnam, we completely misunderstood how our visa worked and accidentally arrived in the country on the day it expired.
Immigration let us in, but warned us we had to leave almost immediately and apply for a new visa. We scrambled to book a last-minute flight to Cambodia and ended up paying a fine.
It was stressful, chaotic, and expensive. Oddly enough, though, our visit to Cambodia became one of our favorite unexpected adventures. But now, we double and triple-check visa rules and requirements ahead of time.
We’ve also let our guard down
In Paris, Shayne had his crossbody bag slung around his back while boarding a crowded metro train. Seemingly within seconds, his phone was gone.
It was a rookie mistake, and we knew better, but sometimes travel lulls you into a false sense of security.
That one slip-up cost us days of frustration replacing his device and updating accounts, not to mention a chunk of money.
Even seasoned travelers need to stay alert, especially in busy cities and transit hubs.
Choosing accommodations with zero walkability made exploring more difficult
When we started traveling full-time, our first stop was Bali. We booked a picture-perfect villa with sweeping ocean views and dreamy Instagram potential. What we didn’t realize, though, was that it was over an hour away from the nearest town.
It was beautiful, but it made everyday activities like walking to cafés, exploring neighborhoods, or talking with locals nearly impossible.
Now, we prioritize location over aesthetics. Being able to walk out the door and explore a neighborhood, find a local market, or grab lunch at a street stall makes us feel like we’re actually living somewhere, not just passing through.
Despite the bumps in the road, traveling full-time has been incredibly rewarding
The mistakes we’ve made haven’t just taught us how to travel smarter. They’ve reminded us to stay humble, adaptable, and patient with ourselves.
We’ve learned to slow down, embrace the unexpected, and let go of the need for every day to be perfect, because no matter how experienced you are, travel always has something new to teach you.
And often, the detours become the best parts of the journey.
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