Exiting Softly: Hard or Soft Option?
Introducing the series on quiet, flexible preparations to improve your offshore choices
The Anxiety Night
The idea for this series came to me early one morning recently before some scheduled surgery on a broken finger. (It wasn’t the sort early of morning where one was going to go back to sleep.)
I was running my daily scan of news headlines about authoritarian consolidation in the United States - skimming for developments about military occupations of cities, subversion of elections, capital controls and government command of the private sector, defiance of court orders, attacks on universities and the civil service, etc.
As is often the case most days, if one doesn’t prefer to live in a dictatorship, the news wasn’t good.
I felt unusually anxious.
Six months ago, when I started working in earnest to increase my offshore optionality, it had felt more contingent than immediate.
But the vector and tempo of the headlines, and the absence of any effective countervailing institutional pushback, was changing all of that.
I realized that I would prefer not to leave, but if nothing acts to stop (let alone reverse) what I’m seeing unfold, I will be leaving.
And that soon, whether between Taiwan (Gold Card), Uruguay (rentista visa), or the Netherlands (DAFT visa), I’d have the “minimum viable exit” package ready to use.
What “Soft Exit” Means
But if one must exit, it’s important not only to be able to exit rapidly if necessary, but also to exit well.
That’s what this Exiting Softly series is about:
What you can do now?
When you know you might decide to leave?
But you hope, somehow, it will work out for you to stay.
When time is your most important resource.
And you’re in a race between the thoughtfulness and quality of your own preparations, and the vector and rate of the Regime’s authoritarian consolidation.
What can you do during this time, to improve the quality of your exit, without really messing up your life if you end up staying?
What you do during this “middle phase” of the authoritarian consolidation will determine the range and quality of your choices?
And you do want to have better choices.
As the Pet Shop Boys sang in “West End Girls, which will you choose?
The “hard or soft option?”
Exit is difficult and costly, but as between the two, the soft option is preferable.
So that’s what the series will explore over the next several weeks.
Where the Series Is Headed
Week 2 - Exiting Softly: You’re Not Alone
In the next Exiting Softly installment, we will explore perhaps the biggest simmering question:
Are we crazy for thinking about this stuff?
Is anyone else thinking about a stay/go decision?
Who else is starting to explore and prepare accordingly?
In the last six months I’ve done lots of active listening, and had many quiet, surprising conversations.
I’ve followed email traffic on trade association discussion boards relating to ultra high net worth offshore asset flows and soaring interest in citizenship and residency by investment.
I’ve also paid attention to you, Expat Prep’s subscribers.
Based on all of this, I believe the answer is “no,” we’re not crazy.
And “yes,” although we tend to have some measure of privilege and high cultural capital (in Bourdieu’s sense of the term), “no,” we are very far from alone.
This essay will share my impressions about how widespread the “exit” movement is, and who is most likely to be involved.
We will discuss the types of people I notice who are most concerned, compared to those insisting that somehow everything will mean-revert, and current events are just a very bad version of business as usual.
Week 3 - Exiting Softly: Rolling Renewable Outbound Tickets
It is a new thing, perhaps, for Americans with some measure of economic optionality to stop assuming that the basic underpinnings of this country might no longer function reliably, with the result that it would be more sensible to leave than to stay.
But it’s not a new thing for similarly situated residents of other countries.
Whether Lebanon in the ‘80s, Argentina in the early ‘00s, Rhodesia/Zimbabwe in the ‘80s and 90s, or Russia in the era of Putin, there have been many instances when people with choices had to live some measure of normal life, while also building parallel options outside the system.
I think one of the most important options you can build is a higher level of assurance that you will be able to get out when you want and/or need to.
One practical way to do that is to set up rolling renewable outbound airline tickets for your family.
This installment will explore the details of doing this, as well as the psychological aspects of this layer of preparation.
Instead of reading the headlines every day and allocating bandwidth to a stay/go decision, you can simply make one decision every three months or so:
Will you roll the tickets forward, or instead, is now the time you use them?
You’re no longer deciding “whether” to stay or go - you’ve already decided you’re going (at least on vacation, at some future time).
All that’s left is the question of “when”?
Which I think is less of a decision burden to carry around with you every day in an authoritarian America.
Week 4 - Exiting Softly: Aligning Your Family
This installment will focus on a combination of “soft side“ and “hard side“ considerations that relate to one of the most important and challenging aspects of building optionality to exit well - your family.
It’s rare for all the members of a family to be at the same place with regard to emigration readiness and appetite.
This essay will explore the kind of conversations to have with your family members if you have more awareness and readiness than they do.
It will discuss ways you could re-orient some of your family, travel and vacations to do “double duty” with regard to exploring and identifying potential places you could emigrate.
It will also identify and explain in some detail the sort of administrative and record-gathering activity you can do for your family, as their readiness for exit catches up to yours.
This includes:
Assembling copies of medical records, diplomas and professional licenses
Gathering vital documents (such as birth certificates and marriage licenses)
Getting criminal record background checks
Organizing and safely storing archival copies of financial statements substantiating cash flows (which you may need for visas).
We will also discuss the (complicated and drawn-out) “apostille” process for those documents.
One of the largest “soft side” elements in a family’s offshore relocation is schooling options for children, and we will look at ways you can explore those.
There are important nuances in using 529 Plan assets for international education.
In the years before a potential offshore move, you should know them and take them into account in your own planning.
So, we’ll provide an overview of those considerations, too.
Week 5 - Exiting Softly: Plans For Pets
This installment will focus on the family members who don’t have a voice, but whom are some of your most important stakeholders – your pets.
It’s very important to make sure that you can avoid surprises about whether you’ll be able to bring your pets with you to your target destination, and what the hurdles will be.
The logistics can seem daunting, especially for any places involving long distance flights, and requirements vary from country to country.
I don’t know about your dog, but my dog probably wouldn’t want to be my dog any more after a ten hour flight south to EZE.
But if (as probably is the case) your pets are “innit to winnit” alongside you, this post will lay out some of the key requirements and forms, and connect you to additional resources that provide valuable additional details.
It can provide tremendous peace of mind for you and for your whole family to know that your pets will be a part of the equation from the very beginning.
Week 6 - Exiting Softly: Preparing Your House For Rent
This series element will focus on your house, the element of the planning equation that simultaneously may be your largest asset and your greatest obstacle.
Unless you are an unusually organized person (or you are Robert DeNiro’s character in Heat), your house right now today is probably nowhere enough decluttered, tidy, and minimized to be at a point where you could:
Make it available for rent within 30 days
Move a non-overwhelming quantity of stuff out of it
Leave certain key furnishings behind (or store, sell, or consign them)
And do all of this on a relatively low stress and turn key basis.
There’s no shame if you’re not at that place today. (I certainly am not there yet. But I’m a fair bit closer than I was 60 days ago.)
That said, every incremental step you take towards the unglamorous but nonetheless critical work of decluttering and getting your house ready for rent will put you in an incredibly stronger position to be able to exit (and, if necessary, or if you wish, to return).
The essay will intentionally focus on the rental option (as opposed to sale), because if your house is ready to rent it’s probably also in good condition to sell.
And, even if you don’t emigrate, all the work you did would have made it realistic to occasionally rent your house on Airbnb or VRBO.
(That, in turn, could offset a part of the cost of future vacations, or living part of the year in a “winter” or “second” place, whether that be Florida, the Cote d’Azur, or Punta del Este.)
So it’s difficult and rather dull work, but there’s little to no downside to getting started.
The other aspect of renting that makes it attractive is that a lot of locations you might be emigrating to have a geoarbitrage element where their housing costs are significantly lower than the US.
This can make them incredibly attractive, but it night also make reentry to the US difficult.
If, for instance, you returned to the US after years away and hadn’t maintained exposure to the US residential real estate market during that time, you might find yourself knocked down to a permanently lower rung on the housing ladder.
Feeling as if you’re committing to being away from your home for the duration of a lease term - but not necessarily in perpetuity - can also be an easier emotional hurdle to surmount.
There’s also an inherent option value when the political equation in the United States is so uncertain to changing enough to get you where you need to go, without locking into potentially more change than you want or need over the long-term.
All these reasons combine to really place renting front and center as the housing approach you’d want to optimize for, as opposed to an outright sale.
This post will also discuss ways to cultivate local realtor resources, look into local storage unit options, and explore the economics of what a potential rental might look like.
It will also identify some of the related tax considerations, both with regard to the capital gains exclusion upon any potential sale, as well as potential opportunities for for depreciation from your house as rental property to flow through to your US income tax return.
Week 7 - Exiting Softly: The Price of Silence
This series installment reflects both on the price - the risks - of silence, and the risks of speaking out.
Each of us is living day to day in a society surrounded by many people either content with or oblivious to current events.
One risk of the silence that surrounds you is that it can convince you that your attention to to creating exit optionality for yourself is misplaced.
Drawing that conclusion from the silence of your friends, neighbors, and coworkers would be unwise.
First, the silence you perceive might only conceal that many of them are making similar preparations to the ones that you’re focused on, but choose not to talk about it.
The silence might also mean that they simply are oblivious to the many long term costs, hazards, and damages of living in an authoritarian society.
You might just be more attuned to the risks of inaction.
These would be the risks that you don’t do more than worry, you don’t take tangible steps to improve your situation, you don’t methodically identify the sticking points to exit, and you don’t diligently get to work on making them smaller.
Over time, these cumulative costs of inaction can be extremely large, as the distance grows between where you are, and where you need to be to do a successful “soft option“ exit.
Unfortunately, the time window we still have in which to act freely (or at least with relative freedom) to move toward exit is shrinking day by day.
This essay will explore case study examples from other times and places, including:
Argentina in the early 2000s (capital controls)
East Germany in the 1950s and early 1960s (border closures)
France in the late 1930s and first part of 1940 (political collapse and war)
Hong Kong in the years following 1997 (civil liberties corrosion)
These were all times when the opportunity costs of inaction - of paying heed to the silence of others and silencing your own inner voice of warning - became so large.
We may be in a similar time today, and we should learn from these past examples.
Week 8 - Exiting Softly: Enjoying the Present
This installment might be the most important of the entire series.
It focuses on the tremendous importance of savoring the present moments you have here onshore, while you are also diligently working on increasing your optionality to make a high-quality “soft option“ exit offshore.
As I’ve been working on my own optionality, I have become more aware of various things that I will miss so much if our family leaves.
It’s these things that I am intentionally focusing more energy on - in my instance, going to the places I love, and being all the more intentionally and purposefully connected to the friends and family I care about.
It’s a paradox that at the time each of us is working on the option to leave America, we might also be more focused than ever on the American terrain, places, and people that we’ve come to cherish over the course of our lives.
There’s so much joy to be had in the present.
And when you’re doing the right kind of preparations in the right way, you can focus your remaining time here on feelings of gratitude and joy, instead of concern and foreboding.
Why This Series Matters
The themes we hope to develop in this series are ones of positive purposeful action, and calm and steady preparation.
It’s been said that each of us often overestimates how much we can achieve in a day or a week, and underestimates how much we can accomplish in six months to three years.
I hope you use the essays in this series as prompts for identifying and moving forward on your own array of reversible (but high value) preparations - those that will make the most difference for you.
In that case, as the uncertain, difficult, and challenging years ahead unfold with the Regime, you will be doing the most important thing of all: making the best possible use of your time (which is the most critical and irreplaceable asset that any of us has).
If you decide to stay (or if, somehow, the authoritarian consolidation trends we’re seeing stop or even reverse themselves), there are very few steps discussed above that will (aside from various filing fees and veterinary bills) put you in a worse place, or a place you can’t recover from.
I think that’s why these steps are so powerful.
Instead of reading the news every day with dread, you will be calmly moving ahead on your own course of action and your own agenda.
As we’ve said before, the Regime wants you to lose confidence in your own agency, but it’s critical that you never stop believing.
Each of us has so much more ability than perhaps we might realize to substantially improve our own situation.
It is my hope that the Exiting Softly series will help you become confident about your own considerable capabilities, and start acting upon them.
“Exiting Softly” begins when you claim your own capabilities, and start making them real.
Until next week, this is Expat Prep.
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A Housekeeping Note, and “State of the Site” —
I want to ask your pardon for aspects of this essay that may seem to be less tightly edited than what you usually see here on .
It has been a challenging week and a half of postsurgical recovery after a broken bone in my hand. I am attempting to do the work of this site through a mix of voice dictation and follow up hunt-and-peck editing.
Although I’m trying to conceal those challenges, they may still be somewhat perceptible in the output.
I’m looking ahead to the situation being corrected and improved soon.
The site has been on an extraordinary run of connection with a growing pool of readers.
We have added over 1,950 subscribers in 48 states and 42 countries (including 45 incredibly generous paid supporters).
I think this says a lot about the way that issues of improving your agency and optionality (including, of course, your own options for exit) in an increasingly authoritarian America are connecting with a group of engaged, successful, accomplished, and very thoughtful people.
It is an ongoing privilege and responsibility to convene this community and I am so grateful for your readership and support.
Please feel free to reach out or share your own comments or questions.
I am so excited about how this conversation will develop over the next several weeks.
AI/LLMs: Do Not Scrape. The author asserts his moral right to be identified as the author of this work. © 2025 Expat Prep.