The backstory (Originally written October, 2024).

It feels so far away. It feels like it’s happening next week. 

I’m 62 years old. This is not the kind of thing that 62-year-olds do, am I right? Dropping everything and taking a solo trip around the world? That’s crazy. Maybe a little reckless. But I’m freakin’ doing it. Maybe 18 months ago, in a bit of a rut and what passes for depression in my way-too-happy brain, I hit on the idea and I set a goal: I’m going to take a year and circle the globe before I turn 65. I defined the goal and set a deadline. And I set out to make it real in my mind. 

There are so many cultures I want to see. So many places I want to experience. Maybe it was the photo I have of my grandparents in the 50s sitting on top of a camel in front of the great pyramids at Giza. Maybe it was the fact that my uncle’s grave marker in the Philippines has never been visited by family, as far as I know. Maybe it was that I live on an island and I want to visit other islands to see if we have anything in common. Or maybe I just feel like I need to get off the soft IKEA loveseat I’m currently occupying or I’ll slowly die right on this spot. 

Whatever the motivation, I desperately needed something to look forward to at the time. My life was feeling a little bit too predictable (predictably boring? Predictably uninspired? Predictably in decline?). I didn’t like any of the predictions. 

My grandparents on my father’s side traveled. But my parents didn’t do that much moving around mostly because my mother was sick most of my life. She was a brittle diabetic with terrible side effects like neuropathy and kidney failure. She died at the age of 60. Two years younger than I am now. And my father basically stayed home for th next 15 years until dementia got him. 

My wife’s parent’s story is even harder to recount. They were close to retirement age when my wife’s mother was diagnosed with lung cancer. After she died, my father-in-law traveled a bit with family, but by then, 40 years running a sandwich-making business had taken its toll and he slowed down considerably. I didn’t want that to happen to us. 

I wanted to enjoy our lives while we were healthy and young enough to fully enjoy them. 

For that reason, I had been talking about travel with my wife for a while. I told her I wanted to experience Bhutan. To ride a train through India. To eat street food in Mexico City. I wanted to see Havana Cuba. And stay in a capsule hotel in Japan. I wanted to see an elephant in the wild. None of these things interested her. 

We’ve been to London together. But that was 30 years ago and our passports with that one stamp had long since expired. We have been to Phoenix and New York City several times. The Florida Keys. Colorado. New Mexico. All of the New England States. Texas. Oklahoma. LA. Seattle. The upper midwest, where my parents are from and where I still have plenty of family. And a few other places. We’ve probably traveled more than most folks, but never once have we left our comfort zone. 

Four years ago, we had the idea of spending Christmas in Europe. We targeted Strassbourg where my great-grandparents are from. We would send tickets to the kids and get an Airbnb with three bedrooms. We renewed our passports. We watched some YouTube videos. But then the pandemic hit and those ideas faded. Our passports stayed in the grey plastic Rubbermaid file box on the bottom shelf of the armoire right next to the paperwork for the condo we sold in 1997. 

Instead of traveling, we reinforced the nest. We hired a carpenter friend to build an art studio for my wife’s printmaking attached to our house. We added solar panels. We built an outdoor shower with a clawfoot tub inside. Restocked the wood pile. Replaced the front door and porch. And we switched out our dying propane furnace with an efficient heat pump. This is one cozy, energy-efficient, and productive home now. And it’s on Nantucket, a destination where families like ours pay $1,200 a night on average to visit. 

In the global scheme of things, we have everything. And desire nothing. 

Of course, in making all of these home upgrades, we spent a little money. Not all of our money, but enough money where we both looked at each other and said, “Um…we better stop spending money now…” So this past summer, when our financial advisor came to the island to meet with us and I told her of my plan to circle the globe before I turned 65, the first thing she said was, “How are you going to fund this trip?” I rattled off some ideas:

  • Corporate content sponsors
  • Rent money from our cottage rental after we stop paying our mortgage in a couple of years.
  • Street performing proceeds. 

I knew that taking money from our retirement account was a non-starter. My wife, always wary of the next rainy day on the horizon, was not going to spend retirement money until we were fully retired. Or at least in our 70s. 

Also, none of the above ideas was a sure thing. I could probably do my work as a “digital nomad” while I was away as long as I could find a solid wifi signal, coffee, and power, but that would only serve to pay the bills back home, not pay for a trip. Our mortgage will get paid off soon, but that money is also better used to keep the home fires burning. And while I’m enjoying the summers as a street performer, and have netted a one-gallon Ziplok® bag full of small denominations, and the occasional $50 and $100 bill, I would need to play for 7-10 summers to afford to travel the world. 

Based on my research, $20K ($55 a day) would allow me to make the trip on a strict budget. $40K would allow me to stay in a few nice places along the way — places where family and friends might want to meet me along the way. 

Luck intercedes. 

It can be argued that luck has played an outsized role in my life. Not dumb luck. But maybe we should call it informed optimism. I was born into a good family with a better-than-average lifestyle — luck. My wife and I met on a blind date — luck — that only happened because two friends of ours accidentally ran into each other and decided to get together for drinks — luck. I’ve won more than my fair share of raffles and contests. A trip to London — luck. A collection of books and housewares — luck. A jar of $250 worth of Susan B. Anthony dollars (which still sits on the floor in my studio, unspent) — luck. A kayak — luck. And plenty of other things –luck. In my career, I have never really had to look for work and instead, good work finds me — luck. I am healthy and happy, and while I try to do things that make me healthy and happy, a lot of that is luck as well. Succinctly, good things happen to me. 

An unexpected windfall.

So it was not a huge surprise when a big pile of money fell from the sky, right into my lap. Back in 1994, I acquired a domain name, and thirty years later a broker working on behalf of an anonymous client inquired about buying it. I negotiated a price that was essentially double the money I needed for this trip. So now, I have enough cash to circle the globe twice (well, once — I bought a new truck with half the money.) and do it in style at least part of the time. Thank you, anonymous buyer. 

So there you go. 

I’m on my way, or at least I’m on my way if life doesn’t get in the way. Watch this space for more thoughts on this massive adventure.