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From 9-to-5 to Anywhere: Start Here
PLUS: 2025 guide to expat taxes, 4 places to find work abroad over 50, how one woman teaches and travels.
The Unretirees
August 03, 2025
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We’re in the Florida panhandle this week spending time with friends. The weather is hot and sticky, and the conversations are deep and soulful—the kind you can’t rush.
This morning I sat outside with a close friend who had just turned 50. She asked me what was bringing me joy in my marriage right now.
I told her that Matt and I are at our best when we’re on a great adventure.
Right now, living in Portugal, every single day feels like an adventure. And our marriage is better for it.
She smiled and said, “We want to do something like that someday.”
It got me thinking: if someone is in a location-dependent job right now and dreaming of more freedom—more time, more flexibility, more purpose—what would I actually tell them to do?
Here’s the practical plan I would give them: