“We have money, but not enough to survive a massive mistake.”
That line came from a couple planning a second home in Europe. Most of the people who write to me say some version of it. They’ve decided they want an option abroad. They’ve read the visa guides and the forum threads. What they don’t know is what to do first, and what a wrong first step costs.
Here is what it costs. A residency filed before the tax plan can make you a tax resident somewhere you never meant to be. A house bought before the estate is sorted can leave your children two probate systems and a bill from each. Health coverage dropped too early can leave you uninsured in your sixties. In one plan I worked on, the mistake we caught was worth $22 million.
Almost every one of them is a mistake of order, not of country.
What Borderless Living is
Borderless Living is the order of operations for building the life you want abroad without wrecking the life you’ve built. I call it the Sequence: residency, tax, money, property and health care, in the order that keeps each decision from undoing the last. Before the move, and in the first years after it.
Done in that order, the move gets quieter. You know which decision comes next and why. Your spouse sees the whole plan instead of a pile of open tabs. The lease gets signed after the tax residency is settled, not before. And then the life arrives: a second home that feels like home, mornings that belong to you, a guest room the grandkids actually use, and a way back to the US that stays open whether you ever take it or not.
Why I write it
I’m building the same second base. My household is working through an Italy, Ireland and US part-year plan toward two homes, and my own Italian citizenship-by-descent claim is on hold behind the Tajani decree. I’m a few steps ahead of you, not above you, and I write about my own missteps as I make them.
Before this I was a DoD policy official during the Global War on Terror, and I’ve spent my career on risk: what breaks, in what order, and how to see it coming. My analysis has appeared on NBC and the BBC and in The Washington Post and Forbes. Now I plan these moves for families, and I sell nothing else. No commissions, no residency programs, no real estate. When I tell you a plan holds, nobody is paying me to say so.
What paid subscribers get
A paid piece every week that settles one step of the Sequence: what to decide, what it depends on, and what to leave alone until it’s done.
Once a month, a piece for readers who’ve already moved: the first year of tax residency, the US accounts that close on Americans abroad, health care as you age, the estate across two countries.
The monthly live Q&A, plus the archive of every past session.
The members’ Discord, where readers who are planning and readers who’ve landed compare notes.
A growing library of BSI country profiles, 16 countries now, with more added every month.
Annual subscribers also get The Long Memo, my publication on what’s really happening to America and what it means for you, at no extra cost.
What free subscribers get
One piece a week on a costly mistake and where its fix falls in the order. It’s enough to see the ground. The paid pieces are where the order itself lives.
Founding Members
Founding Members fund this work directly, at $2,500 a year, billed annually. It’s for readers who want Borderless Living to exist and are willing to put real money behind keeping it independent. Everything in paid comes with it, and so does a thank-you: a Departure Briefing each membership year, where I look at your whole situation and show you exactly where it breaks. Borderless Concierge, my advisory firm, delivers it under its engagement terms and data practices, which you accept before it starts. Take it or skip it; the membership stands either way.
What readers say
“Deeply valuable to those of us who are SERIOUSLY considering leaving and have consulted attorneys but do not know all the pieces to leave legally, successfully and with dignity.” (Erica Baravik-Munsell)
“I like to think that I’m a reasonably capable person but have found this task daunting, especially on what’s likely a short timeline, and I appreciate any tidbits I can glean from your publications.” (Karen)
“My wife and I want to continue our journey to seriously consider options for emigrating in 2027 or 2029.” (Walter)
“Experienced insight and suggestions are extremely valuable. These, here on Borderless Living, may be the best I’ve come across.” (Evan)
A note on advice
Nothing here is individual legal or tax advice. It’s the order of operations and the tradeoffs, so you walk into your lawyer’s and accountant’s offices knowing what to ask.
If you’ve decided you want an option abroad, this is where you build it, in the right order.
Where to start
These run in Sequence order. Start at the top.
Update:
Borderless Living also now has a Discord server - free & paid membership access.
When you subscribe, details will be emailed to you. :)
This strikes me less as “travel writing” and more as a survival manual for the new century. I appreciate how it reframes leaving not as escape but as practice — sovereignty as something you build, not buy. It’s a stark message, but maybe starkness is what wakes us up.