Fortune Favors the Prepared

I think there’s a saying about “fortune favoring the prepared.” If such a saying doesn’t exist, well, it does now.

This idea came to me on a recent flight back from the Portuguese island of Madeira (be on the lookout for my story in the July issue of International Living magazine; Madeira is beyond superlatives).

I’d spent time with two retired couples from the US who recently moved to Madeira, in large part because of the political decay that is now endemic to America, and which is tearing America apart at the seams, in some ways no different than the OG Civil War. (Case in point: The recent showdown between the federal government and California over migration, which has seen chaos erupt in LA.)

Just to be clear here, one of the two couples I met in Madeira comprised died-in-the-wool Blue voters; the other voted for Trump three times. So this is an entirely apolitical issue.

It’s an issue that goes back to that opening paragraph above: Fortune favors the prepared.

What I’m getting at in today’s dispatch centers around the mood of the moment in America: Fear.

The great bulk of the country is clearly hunkering down, fearful of what’s coming socially and financially. Retail giant Target recently told Wall Street to expect slowing sales across the entirety of 2025. Colgate, the maker of toothpaste and other such products, said the company has experienced a sharp slowdown and expects a poor 2025 outlook.

Kraft Heinz, a bunch of automakers, Best Buy… they’ve all cut their sales forecasts because the American consumer just isn’t showing up for the game.

Even McDonald’s, the godfather of cheap food, recently reported a 3.6% decline in US same-store sales. When the purveyor of Happy Meals is struggling, you know the American consumer is retrenching.

Which speaks to the idea of fear.

Americans don’t know where the economy is headed under the current administration, and are increasingly worried that direction is south. They don’t know what will come of the social discord that’s fraying the fabric of the country.

Frankly, it’s not just Americans.

I can tell you from living here in Portugal, and from my recent travels across other parts of Europe, that a lot of non-Americans are worried too. They’re fearful that a bad moon is rising over America and that the global economy and global society will suffer.

And, so, people are retrenching. They’re shutting down spending and hoping to weather the storm that’s clearly on the horizon.

Some, however, are taking action… which is really what I want to talk about.

They started prepping for this moment a few years ago. It’s not that they necessarily expected this moment to arise. It’s just that they recognized that this moment was possible and, so, they set about building a plan.

I was recently chatting with a friend in Uruguay who is one of the country’s leading immigration attorneys. And he told me his firm is seeing bang-up business right now—Americans (many of them Trump voters) who are popping down to the South American nation to buy land and to seek residency.

Why? I asked him.

“They see increasing turmoil at home,” he told me.

I asked an acquaintance at a Portuguese visa agency what she’s seeing, and her comment was quite similar. Lots of Americans are calling and wanting to chase Portugal’s D7 retirement visa, the D8 digital nomad visa, or the Golden Visa offered by investing a minimum of €250,000 in certain types of projects.

Over at Henley & Partners, one of the largest migration consultancy businesses in the world, the company has seen a 183% increase in enquiries from US nationals looking for second passport and residency visa options.

And it all goes back to the idea of preparedness.

I know lots of Americans are rightly worried. They’re hunkering down, uncertain of what’s next. I get that. Makes sense.

Yet on one level, it’s the wrong approach.

This is the exact moment to take action.

All those Americans locking in land purchases and visas in Uruguay… all those Americans securing whichever visa they need to live legally in Portugal… they started planning long before today.

They didn’t just wake up one day in 2025 and say, “You know, honey, we should get online to buy us a visa to live in Uruguay.”

No… they started planning a year ago, probably two or three years ago. One of the couples I talked to on Madeira—a couple from Michigan—had been thinking about moving abroad since reading stories in International Living back in 2015, and they began earnestly chasing their goal about two years ago.

The crush of other Americans just like them aren’t pursuing visas and second passports as a spur-of-the-moment notion.

They spent time figuring out where they think they’d like to go to escape whatever craziness befalls America. They whittled down their list based on all kinds of personal criteria tied to tax rates, visa requirements, local weather, lifestyle wants, etc.

And as the craziness began to emerge this year, they put their plans into action. Now, they either have the “Welcome to Country X” documents in their hands that they need to pick up and rebuild their lives somewhere else, or they are well on their way to securing those documents.

To be sure, not all of them are moving. Many are staying right where they are—at home in the US.

But they saw the wisdom of building a Plan B into their lives.

Just in case…

It’s their “Break Glass in Emergency” escape hatch.

Maybe they never actually use it.

Or maybe political, social, and financial life sours so markedly in America that they see no other option but to, well, break the glass.

Which means that, here at the very bottom of today’s dispatch, we come to the real point: Start thinking about a Plan B.

Really. Start now.

I know you might be scared at the moment, uncertain of where America really is going. You reflexively feel the urge to husband your resources. To batten down the hatches.

However, on one level I want you to resist that urge.

Start working now on a Plan B. Start thinking about what you would do if America really does devolve to such a degree that the country you love is no longer the country you recognize. Again, this has nothing to do with what color you bleed politically. As the Trump-supporting couple in Madeira told me over lunch one afternoon, “You have to be in the right huddle,” in America today. “You have to pick political sides.”

As the liberal couple told me, “The chasm [between left and right] is the literal definition of ‘irreconcilable differences.’”

This is about your future life.

Will you be prepared if a decaying situation turns bad… and then turns worse?

Or will you find yourself stuck in a situation you don’t want to be in, and unable to escape quickly?

You might never use Plan B.

Then again…

You’ll be happy you have it in place, just in case.