Pausing to Reflect (February 11, 2026)
It sounds amazing, doesn’t it? Spending a full year abroad. And while this trip has turned out much different than I had originally imagined, it is truly special in so many different and unanticipated ways.
Bill, Elena and Violet in our rental car: Longest ride so far: 10.5 hours
Resilience & Overcoming Obstacles
This trip almost didn’t happen … several times. As you can imagine, planning for a year-long trip is challenging and can, at times, feel next to impossible. Picking the destinations, deciding where to stay, figuring out the order and sequence of where to go and what to do when you get there. It’s challenging enough to do this for a 1 or 2 week vacation, but for 52 weeks there’s just a new level of complexity I’ve never faced until I attempted to plan this trip.
I had imagined that I would be doing this planning with Violet. After all, this originally her gap year between high school and college. And it started out that way. I rolled out an old fashioned paper map of the world and asked her, “So, where do you want to go in the world?” Her top choice was Japan followed by “Europe” (but not any particular countries) except Spain which she was excited to visit. Beyond that, she was open to anywhere and anything.
That’s a great attitude to have, but doesn’t help much with the actual planning or narrowing down where to spend our time. I spent the better part of a year doing the “heavy lift” of considering various different plans and options. Several times I felt overwhelmed by just how big this trip was and how little confidence I had in planning it.
Trusted House Sitters
Having spent time talking with my friend, Nathan Blah, I was excited to learn about Trusted House Sitters and it sounded like the perfect solution to my problem. In exchange for taking care of dogs, cats and other animals (which both Violet and I love to do) we could stay in someone’s home. Nathan has mastered this platform and has lived as a digital native for more than a year primarily using this platform.
In reality, however, I was never able to make it work for me. Despite signing up for the premium tier, getting endorsements and following the guidelines, there were only two sits that aligned with our travel plans and we were not selected for either of them. I haven’t given up. I still have four more months of travel and would just like to do a single sit for the experience and to recoup the membership fee. If it doesn’t happen, however, I’m still glad that I tried this approach. On paper, it’s a really great deal and I love the concept. I think if we end up spending any more time in the UK or Australia, I’ll have better luck as the platform is more mature in these specific parts of the world.
What It’s All About
Today, I’m sitting on the porch of a gorgeous AirBnb looking out to the ocean and taking it all in. This is my view:
Porch view from Pohara, New Zealand (one of many great views)
The only thing on my mind is remaining fully present to what’s here right in front of me. Should be easy, right? These are amazing views and I’m so lucky to be here in February. Right now, back home in Port Washington, NY, they are experiencing one of the coldest winters of record. It’s February and here in New Zealand, this is summer.
Despite all of this, it’s easy to “get lost” in my own mind about what’s next. In another week, my son Will is flying out from New York to join us in Auckland. This will be the first time my whole family is together as part of this World Tour.
Last night, Elena and I decided on our next destination: Fiji. We spent a couple of hours going through AirBnb locations and landed on one we think is best for the four of us. After that, who knows? Like I said, this trip is evolving in ways I hadn’t imagined. Originally, I was just planning for Violet and me to travel together. Now it’s all four of us. I love this change, to be sure, and it impacts where we stay and what we choose to do together.
We may end up backtracking a bit in Southeast Asia. My original plan was to head to South Korea, Hong Kong and China. After Fiji, we may go back to Vietnam, Thailand, and will most certainly return to Japan.
Ease & Flow
I share all of this as an anchor for myself to remain in “ease and flow.” As I plan out “what’s next” I am committed to staying present to the incredible beauty that surrounds me everywhere I go. I love this adventure and I trust that I can handle anything that shows up as part of this World Tour. Truly, I have let go of any attempt to “control” this trip and am learning to embrace the uncertainty of it all. This is a powerful life lesson that I’m capturing here so that I may return to it when the uncertainty grows well beyond my comfort zone.
I can’t tell you where we’ll be 30, 60 or 90 days from now. I accept that this is an adventure of a lifetime and I’m fully “in it.” At some point, Elena, Will and/or Violet may choose to return back to New York and that decision will have a ripple effect on the plans made. Best to enjoy what time we have all together and see where this journey takes us.
