About Me, and What My Journey (and this Blog) are About
I am a mid-50s (mostly) retired real estate attorney. For several years, I have been pondering when and how to retire and move on to a new phase in my life. I spent more than 30 years working at my law firm. I love the people, and often really liked the work. But it was stressful, and I have several heart stents to prove it. And after 30 years, the ratio of things that I enjoyed and things that drove me crazy in my job had swung way too far towards the “drove me crazy” end of the spectrum.
But it wasn’t like I could simply stop working and expect my savings to support me and my family for the rest of my life. I lived in Southern California, and things were expensive. Health care is expensive. Food is expensive. Housing is expensive.
And what I really want to do in my retirement is travel. A lot.
It didn’t take any advanced math to understand that I could not quit working, maintain my household in California, pay for health insurance, and expect to have money to travel. The math would never work. So it was time to figure out a plan that would work.
The first idea was to move elsewhere in the United States, since almost anywhere is less expensive than Southern California. But the math still didn’t work. It wasn’t even close. I was looking at trying to survive on around $6,000 per month, give or take. And insurance – heath, car, and life – was going to eat up more than half of that. Add in housing costs and basic food, and I’m out of money. No travel. No expensive outings. Heck, there wasn’t going to be money left to go out to dinner – and my wife and I rarely cook.
Over time, I reached the conclusion that there was only one realistic way I could retire, travel in my retirement, eat out without worrying about the cost of every meal, and not spend every day pondering when I would run out of money.
The answer was actually fairly simple, even though the idea seemed at first pretty extreme: I would have to sell our house, sell or get rid of most of our stuff, and stop trying to maintain a home in the United States while traveling around the world. Instead of travel costs coming out of a vacation fund (that I couldn’t afford due to all my “regular” expenses that would exist regardless of whether I was “home” or not), travel costs would become my regular living expenses.
Fundamentally, by giving up my home in the United States, I could eliminate the “double” cost of housing that I’d experienced during my entire career any time I traveled away from home – paying my mortgage in California plus my hotel wherever I was on vacation.
So I had a concept, and at least conceptually, it made sense. But there’s a lot more to it. I have a wife, two college-aged kids, aging parents, and all my friends and other family members in California. I have preexisting medication conditions that make health insurance more complicated. I don’t speak any other languages (unless you count four years of high school Spanish almost 40 years ago). And I have a 30-year career that includes clients who depend on me.
So here I am, mostly retired and about to embark on the journey of a lifetime. My wife and I leave for South America January 14, 2026, and we plan to live outside the United States for years – at least until we turn 65 and are Medicare eligible. Lots of planning has already happened, but there is lots more to do. And there are more unknowns than I can even count.
This website is intended to chronicle that journey. I hope to post about my retirement process, including the financial and logistical issues that come along with what I’m trying to do. I will also post about our travels, where we go, what we do, and what it costs. For now, we have a roadmap for 2026, spending time in South America, Mexico, and Europe. After that, who knows. We may gravitate towards the “slow travel” movement, staying places 1-3 months at a time, and remaining nomadic for the foreseeable future. We may find a place we love, and seek a residence visa for a year, or two. After that, we’d need to decide whether we found a long-term home, meaning we’d need to think about permanent residence and, potentially, dual citizenship, or whether we want to move on and try something else.
I have ideas of what I think makes the most sense for me. But I’m not sure I’m right, and I’m definitely not sure that what seems right for me will end up being right for my wife and the rest of my extended family. Time will tell. In the meantime, I’ll be documenting things along the way, and hopefully using this blog as a jumping off point for a YouTube channel covering the same topics.
I hope you’ll come along with me on this journey.