Thanks for this piece. I got a great deal of inspiration from it because there's a voice in my head that tries to berate me for not having the money/status. Your point about optionality is huge.
I've worked jobs that have no career through line except for food.
I homeschool my kid as a 100% single dad.
I am having g to reinvent myself hard-core after moving to canada 9 mos ago, and dealing with all you mention... housing, medical, income, refinement of a pluralistic strategy that is highly adaptable. (Sometimes too much so).
What im hearing from you piece is that by intentionally reducing my systemic dependence, i paved the way for walking away from the states on my timeline and with a coherent, if flexible plan.
The what comes next is always a question. Just getting here (overcoming the inertia of the easy/entrained) is more of a milestone than I give myself credit for.
I moved to France last year. One important thing to know about remote work is that it too is tied to jurisdictions. Most remote positions for larger firms are 'US only,' which removes a lot of potential optionality. The best option is to find a smaller firm who is able to just 1099 you, then build up a trust relationship first, so that when you move, as planned, it's just a matter of managing the time difference.
I have lived half the year in Italy for the past 10 years. I started a business preparing US tax returns for expats. I came back to the U.S. 3 years ago when I became a grandmother, but I still own property in Italy and I go for a few months. It needs work and Jm contemplating whether I want to keep it up, but something tells me to keep this option open
We are retired and speak Spanish and live in a van traveling South America but remain domiciled with our pensions in the US. It’s worked so far. I can see a time when capital controls and bank controls trip us up. All I can hope is we are dead by then. So far so good. We change countries every 90 days as permanent tourists in our camper van. Cheers from
I’ve been following you for 8–9 months now, after desperately searching for what to do and how to prepare as this nightmare started coming into focus. This piece is both heartbreaking and strangely affirming—I see myself clearly in two, maybe three, of these categories.
After months of fighting for optionality, I’ve come to realize how incredibly difficult it is to build even the beginnings of a bridge out. What’s ironic is that I’ve lived abroad before. I’m not afraid of culture shock, of losing my “American” identity, or of being a permanent foreigner. I actually loved that part.
What’s hard is realizing how entrenched I am now. Even if—when—this reaches my own front door, there are too many people who rely on me for me to simply leave. If I go, it’s not an exit—it’s an abandonment of the ship.
So my new plan is a lifeboat. Something small and imperfect, but real—figuring out what we could carry with us to survive a few months, somewhere we can work and live while we figure out what comes next. It would be a total restart, possible a “safe place” sabbatical, but it’s still an option.
Well FWIW I do consultations with subscribers. Reach out if that makes sense and we can discuss a short call to decide if I can be useful to you. I spend my time in consultations compressing and clarifying so that the challenges are considerably less daunting. In any event, thanks for reading.
William... This lands because you’re saying the quiet part out loud — without trying to rescue it or fix it.
“Infrastructure rather than identity” feels like the real unlock here. Once the spell breaks, the job stops being a referendum on your worth and becomes a tool you can use (or outgrow) on your own timeline.
Also loved the image of the commute as a costume change. That recognition — of how much energy goes into appearing purposeful — explains so much of the exhaustion people feel, even when nothing “hard” happened that day.
Curious what you think comes after the parallel economy phase. Using the system is one thing; building a life that doesn’t require so much pretending feels like the harder, quieter work.
I like the way you break it all down, but as someone who has spent much of his adult life living outside the US, you make it sound more daunting than it actually was for me. Most of us who live overseas as expats learn the ropes pretty quickly, and the complications are quickly simplified. You plug into a local network and people tell you the life hacks that you need. Problem solved.
Finnegan, it’s up to you now. Everything is privatized: Today’s clipsClose the cover on the CIA World Factbook: The spy agency announced Wednesday that after more than 60 years, it is shuttering the popular reference manual. More: NBC News
I have a friend who has spent the past ten years moving his business and family to Canada from the US. It’s not been easy, but he’s stuck with it and is finally meeting success. My friend is very smart as well as determined. From his experiences, I’d suggest that the difficulties outlined by William A. Finnegan are, if anything, understated in this generally valuable article.
This piece goes great with a Substack article by Kirsten Powers, who wrote about how unhealthy we are in the US of A. And why she lives in Italy much of the time. Note: Her husband's work requires them to spend some time in their HOMELAND.
Thanks for this piece. I got a great deal of inspiration from it because there's a voice in my head that tries to berate me for not having the money/status. Your point about optionality is huge.
I've worked jobs that have no career through line except for food.
I homeschool my kid as a 100% single dad.
I am having g to reinvent myself hard-core after moving to canada 9 mos ago, and dealing with all you mention... housing, medical, income, refinement of a pluralistic strategy that is highly adaptable. (Sometimes too much so).
What im hearing from you piece is that by intentionally reducing my systemic dependence, i paved the way for walking away from the states on my timeline and with a coherent, if flexible plan.
The what comes next is always a question. Just getting here (overcoming the inertia of the easy/entrained) is more of a milestone than I give myself credit for.
I moved to France last year. One important thing to know about remote work is that it too is tied to jurisdictions. Most remote positions for larger firms are 'US only,' which removes a lot of potential optionality. The best option is to find a smaller firm who is able to just 1099 you, then build up a trust relationship first, so that when you move, as planned, it's just a matter of managing the time difference.
I have lived half the year in Italy for the past 10 years. I started a business preparing US tax returns for expats. I came back to the U.S. 3 years ago when I became a grandmother, but I still own property in Italy and I go for a few months. It needs work and Jm contemplating whether I want to keep it up, but something tells me to keep this option open
We are retired and speak Spanish and live in a van traveling South America but remain domiciled with our pensions in the US. It’s worked so far. I can see a time when capital controls and bank controls trip us up. All I can hope is we are dead by then. So far so good. We change countries every 90 days as permanent tourists in our camper van. Cheers from
Paraguay.
I’ve been following you for 8–9 months now, after desperately searching for what to do and how to prepare as this nightmare started coming into focus. This piece is both heartbreaking and strangely affirming—I see myself clearly in two, maybe three, of these categories.
After months of fighting for optionality, I’ve come to realize how incredibly difficult it is to build even the beginnings of a bridge out. What’s ironic is that I’ve lived abroad before. I’m not afraid of culture shock, of losing my “American” identity, or of being a permanent foreigner. I actually loved that part.
What’s hard is realizing how entrenched I am now. Even if—when—this reaches my own front door, there are too many people who rely on me for me to simply leave. If I go, it’s not an exit—it’s an abandonment of the ship.
So my new plan is a lifeboat. Something small and imperfect, but real—figuring out what we could carry with us to survive a few months, somewhere we can work and live while we figure out what comes next. It would be a total restart, possible a “safe place” sabbatical, but it’s still an option.
Well FWIW I do consultations with subscribers. Reach out if that makes sense and we can discuss a short call to decide if I can be useful to you. I spend my time in consultations compressing and clarifying so that the challenges are considerably less daunting. In any event, thanks for reading.
William... This lands because you’re saying the quiet part out loud — without trying to rescue it or fix it.
“Infrastructure rather than identity” feels like the real unlock here. Once the spell breaks, the job stops being a referendum on your worth and becomes a tool you can use (or outgrow) on your own timeline.
Also loved the image of the commute as a costume change. That recognition — of how much energy goes into appearing purposeful — explains so much of the exhaustion people feel, even when nothing “hard” happened that day.
Curious what you think comes after the parallel economy phase. Using the system is one thing; building a life that doesn’t require so much pretending feels like the harder, quieter work.
– Kelly
I like the way you break it all down, but as someone who has spent much of his adult life living outside the US, you make it sound more daunting than it actually was for me. Most of us who live overseas as expats learn the ropes pretty quickly, and the complications are quickly simplified. You plug into a local network and people tell you the life hacks that you need. Problem solved.
Finnegan, it’s up to you now. Everything is privatized: Today’s clipsClose the cover on the CIA World Factbook: The spy agency announced Wednesday that after more than 60 years, it is shuttering the popular reference manual. More: NBC News
Well luckily I’m up to the task… lol.
The Fact Book was an interesting project., but most of the information contained within it is available in other sources.
The classified version of the “Fact Book” was considerably more entertaining.
I can imagine
I have a friend who has spent the past ten years moving his business and family to Canada from the US. It’s not been easy, but he’s stuck with it and is finally meeting success. My friend is very smart as well as determined. From his experiences, I’d suggest that the difficulties outlined by William A. Finnegan are, if anything, understated in this generally valuable article.
Interesting.
This piece goes great with a Substack article by Kirsten Powers, who wrote about how unhealthy we are in the US of A. And why she lives in Italy much of the time. Note: Her husband's work requires them to spend some time in their HOMELAND.