Leaving America E1: Should You Stay or Should You Go?

Deep Dive with Shawn

What if you could escape the endless news cycle, afford healthcare without a second mortgage, and actually use your vacation days without guilt? Welcome to "Leaving America," the limited series where we're diving into why a record 40% of Americans are now considering life beyond US borders, why so many are actually taking the leap, where to go, and how to get there.
This isn't just daydreaming anymore. From Mexico granting 11,000+ residencies to Americans in 2022 to Portugal's exploding expat communities, the exodus is real. But why now? What's changed to make millions reconsider what was once unthinkable?
In this first episode, we're taking you inside the political exhaustion driving many to seek more stable democracies, where election cycles don't feel like existential threats. You'll hear shocking financial comparisons – like trading a $900,000 Los Angeles home for a $200,000 Portuguese villa, or swapping a $3,500 New York apartment for a $500 Mexican casa. And the healthcare reality? That $18,865 American childbirth versus virtually free delivery in countries with universal coverage speaks volumes.
Through conversations with immigration attorneys, tax experts, and Americans who've already made the move, we examine the stark differences in work culture, community connection, and overall quality of life. As one expat puts it: "It's the best opportunity to reinvent yourself outside the Witness Protection Program."
But we don't sugarcoat the challenges either – from navigating visa requirements to understanding that yes, the IRS still wants its cut no matter where you live. This isn't Emily in Paris; it's real life, just somewhere else.
Whether you're seriously planning your escape or just curious about what's driving this modern American migration, subscribe now to explore whether leaving might actually be the most patriotic thing you could do – voting with your feet for the life you deserve.

Featuring:

Karen McCann

Daniel Tostado

Matt Wilson

Adrian Leeds

Aaron Martin

Tim Leffel

Xanthe and Dana

Heather Mason

David Lesperance

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Music:
Majestic Earth - Joystock

Chapters

1. Introducing Leaving America (00:00:00)

2. Why Americans Want to Leave (00:03:04)

3. Political Division and Democracy Concerns (00:12:56)

4. Cost of Living and Housing Crisis (00:21:16)

5. Healthcare Systems Comparison (00:28:59)

6. Work-Life Balance Around the World (00:34:02)

7. Reality Check: Challenges of Moving Abroad (00:41:41)

8. Tax and Legal Considerations (00:43:51)