What separates the people who say they want to move abroad… from the people who actually do it?
In this episode of Now What?!, I sit down with S.A. Grant (Boss Uncaged) for a powerful conversation about the nomad mindset, navigating big life changes, and leaving a trail of breadcrumbs for future generations.
Grant’s story takes us from Trinidad to the U.S. to the Netherlands, with stops in Barcelona, visa loopholes, and a few chess-like moves along the way. More than a relocation story, this is a conversation about becoming the kind of person who does the thing.
? What We Talk About
? The Nomad Mindset — why the desire to move is wired into human history
? DAFT vs. Skilled Migrant — how stacking visas creates resilience for expats
? Legacy Breadcrumbs — how books, podcasts, and even casual stories create impact across generations
? Indirect Influence — why kids don’t “listen,” but they always “hear”
? Worst Book Ever — why starting with imperfection is the key to creative freedom
? Advice for the 8-Year-Old (at any age) — how to find your wavelength people
? Key Quotes
“America is great… but the world is greater.” – S.A. Grant
“Kids don’t listen, but they hear. Indirect influence is often more powerful than direct advice.” – Bradley
“We wanted to live abroad, so we kept saying it, planning for it, and when the opportunity came, we aligned and did it.” – S.A. Grant
? Episode Highlights
- The Barcelona spark that turned a vacation into a relocation strategy
- Why chess moves, not chance made their family’s Netherlands move possible
- How family history of migration shapes our present decisions
- The role of background inspiration—from motivational tapes to Dean Martin singalongs
- Why writing your worst book first may be the secret to finally becoming an author
? Listen & Subscribe
?? Apple: https://podcasts.apple.com/us/podcast/repossible/id1358802479?i=1000728412226
?? Spotify: https://open.spotify.com/episode/4k2u6LgkgnP0FoTlEG6fgO?si=2tqdl88LQyW1pXSkds6ItQ
?? Castos: https://repossible.castos.com/episodes/re470-now-what-from-the-us-to-the-netherlands-with-sa-grant
? Connect
? S.A. Grant: https://bossuncaged.com
? Bradley Charbonneau: https://repossible.com
? Learn more about the Worst Book Ever workshop: https://repossible.com/wbe/
? Final Thought
Not everyone who dreams of moving abroad will actually do it. But maybe you will.
And if not you, maybe it’s your nephew. Or your daughter. Or the “8-year-old in the background” who just needs to overhear that it’s possible.
That’s the beauty of these Now What?! conversations: they ripple beyond us.
So… what’s your Now What?!
[ https://youtu.be/V7jT0Sh9eSc ]