Borderless Living

Borderless Living

The Sequence

When One of You Wants to Go

The partner who won’t go is usually right about something. Here’s how to find out what, before anyone sells, buys or signs anything.

Borderless Bryan's avatar
Borderless Bryan
Oct 22, 2026
∙ Paid

“What if we’re lonely and broke in the wrong country, missing the grandkids, and then it all goes back to normal here?”

Someone planning a move asked me that question this year, and it is the most honest sentence I’ve read about leaving. Every fear in this business is in it: money, loneliness, family, regret.

And it is almost never the sentence of the person who writes to me first.

Of the households who filled out my planning questionnaire this year, four had the same shape. One partner wrote in. The other was the holdout. The partner who writes is usually ready, or close to it, and has the research to prove it. The partner who doesn’t write is the one asking the question above, and the one the plan will live or die on.

If you’re the one reading, here is the argument of this piece in a sentence: the holdout isn’t your obstacle. They’re your early-warning system. What follows is how to treat them that way, what the disagreement is usually about once you take it apart, what not to touch until it’s settled, and what the life looks like when a couple gets this right. The worksheet that goes with it is attached.

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