Such a great topic (and solution). I swear those of us out there posting all the gradients of "Living the Dream" -- the ups, the downs, the doldrums -- carry a heavy load. As if our luggage is packed with all the folks who "wish" they could too...wish they could "up and leave" (as if any of us have floated away on the wind so easily, without pining and planning and stressing and booking and all-the-things, ha!). But the ever-present reason (dare I say excuse?) holding them back keeps them seat-belted into that travel armchair, watching from the sidelines, hollering, "Please keep sharing your journey" as they live vicariously. I hope all who truly desire an adventurous, hell-even just a low risk/predictably safe, life of travel figures out the rules they play by are all made up. Not to say there aren't responsibilities; just to suggest that so many are held back by imaginary boundaries that, if crossed, they'd find that life goes on and really, no one cares all that much. No one is fussed. The hamster wheel spins whether you're on it or not. Here's to breaking boundaries, to the coveted escape. Circle that date, y'all! See ya in the wild world.
There really is a moment where a dream either becomes décor… or a decision.
You’re right — every nomad started as a dreamer. No one wakes up mid-flight over the Atlantic thinking, “Huh. How did this happen?” There was a whisper first. Then a plan. Then an uncomfortable conversation. Then a ticket purchased while slightly nauseous.
I’ve lived both sides.
At 53, when I chose this life, there were plenty of raised eyebrows. People quietly wondered if we were making a mistake. We had adult kids, aging parents, a house, responsibilities. We weren’t 25 with backpacks and nothing to untangle.
But here’s what I’ve learned: The shift from dreamer to doer isn’t about bravery. It’s about clarity.
Once you’re clear on what you’re optimizing for — time, health, curiosity, autonomy — decisions start to line up behind it. Not magically. Logistically. Spreadsheet-ly. Conversation-ly. Sometimes painfully.
I agree with you on circling a date. Deadlines create gravity. But I’d add one layer: before you circle the date, define what you’re actually leaving for.
Adventure? Reinvention? Simplicity? Escape? Those are different engines. And they fuel very different journeys.
Because becoming a doer isn’t just about departure. It’s about sustainability. The “after” matters as much as the launch.
So to answer your question — yes, I’m a doer. But I’m also a recalibrator (is that a word?). We still adjust. We still renegotiate. We’re about to spend six months in South America starting later this year — and even that is a designed chapter, not a permanent identity.
My question back to you: Have you ever circled a date that didn’t lead where you expected — and had to redefine the dream midstream?
That pivot space between dream and reality is often where the real work happens.
Either way, I love that you’re nudging people toward movement. Just… with eyes open. 💛 Kelly
Such great feedback Kelly. I’m actually writing my next post about how I’m not courageous at all—rebellious, yes.
And to answer your question about circling a date on the calendar. Sure, things changed between the circling and the doing. The circling, though, is a step. An intention. An easy button to the next difficult thing. It’s not an end-all. It’s a beginning.
Lot's of good points here! Whenever I have someone say to me that "I want to do what you're doing," I say to myself "no you don't." When I ask what's stopping them, there's always an excuse, mostly around the fear of leaving their current life behind.
Such a great topic (and solution). I swear those of us out there posting all the gradients of "Living the Dream" -- the ups, the downs, the doldrums -- carry a heavy load. As if our luggage is packed with all the folks who "wish" they could too...wish they could "up and leave" (as if any of us have floated away on the wind so easily, without pining and planning and stressing and booking and all-the-things, ha!). But the ever-present reason (dare I say excuse?) holding them back keeps them seat-belted into that travel armchair, watching from the sidelines, hollering, "Please keep sharing your journey" as they live vicariously. I hope all who truly desire an adventurous, hell-even just a low risk/predictably safe, life of travel figures out the rules they play by are all made up. Not to say there aren't responsibilities; just to suggest that so many are held back by imaginary boundaries that, if crossed, they'd find that life goes on and really, no one cares all that much. No one is fussed. The hamster wheel spins whether you're on it or not. Here's to breaking boundaries, to the coveted escape. Circle that date, y'all! See ya in the wild world.
Such a well-written capture of the misguided American (retirement) Dream! Yes, let's go!!!
Chris, I love the clarity of this.
There really is a moment where a dream either becomes décor… or a decision.
You’re right — every nomad started as a dreamer. No one wakes up mid-flight over the Atlantic thinking, “Huh. How did this happen?” There was a whisper first. Then a plan. Then an uncomfortable conversation. Then a ticket purchased while slightly nauseous.
I’ve lived both sides.
At 53, when I chose this life, there were plenty of raised eyebrows. People quietly wondered if we were making a mistake. We had adult kids, aging parents, a house, responsibilities. We weren’t 25 with backpacks and nothing to untangle.
But here’s what I’ve learned: The shift from dreamer to doer isn’t about bravery. It’s about clarity.
Once you’re clear on what you’re optimizing for — time, health, curiosity, autonomy — decisions start to line up behind it. Not magically. Logistically. Spreadsheet-ly. Conversation-ly. Sometimes painfully.
I agree with you on circling a date. Deadlines create gravity. But I’d add one layer: before you circle the date, define what you’re actually leaving for.
Adventure? Reinvention? Simplicity? Escape? Those are different engines. And they fuel very different journeys.
Because becoming a doer isn’t just about departure. It’s about sustainability. The “after” matters as much as the launch.
So to answer your question — yes, I’m a doer. But I’m also a recalibrator (is that a word?). We still adjust. We still renegotiate. We’re about to spend six months in South America starting later this year — and even that is a designed chapter, not a permanent identity.
My question back to you: Have you ever circled a date that didn’t lead where you expected — and had to redefine the dream midstream?
That pivot space between dream and reality is often where the real work happens.
Either way, I love that you’re nudging people toward movement. Just… with eyes open. 💛 Kelly
Such great feedback Kelly. I’m actually writing my next post about how I’m not courageous at all—rebellious, yes.
And to answer your question about circling a date on the calendar. Sure, things changed between the circling and the doing. The circling, though, is a step. An intention. An easy button to the next difficult thing. It’s not an end-all. It’s a beginning.
Chat soon!
Chris, I love that — rebellious, yes. That tracks. 😉
And I agree with you about the circling. It’s not the destination. It’s a declaration.
The date doesn’t guarantee the outcome. It signals willingness. It’s a quiet line in the sand that says, “I’m moving.”
Things will change between intention and execution — they always do. But without the circling, there’s nothing to adapt. No direction to refine.
I like how you frame it: not an end-all. A beginning.
That feels honest. 💛
My last day of work before I officially graduate (Im a teacher) from school, finally :) is Dec 18/26 and off I go!
A perfect day to start!!!
Lot's of good points here! Whenever I have someone say to me that "I want to do what you're doing," I say to myself "no you don't." When I ask what's stopping them, there's always an excuse, mostly around the fear of leaving their current life behind.
Always. Usually it’s family. But it’s always rooted in fear.