Stephanie & Gillian — this is such a grounded, generous look at what freedom actually looks like once the novelty wears off and the life begins.
What struck me most is how intentional your choices are now. Not chasing novelty for its own sake, but returning to places that already feel like friends (Oaxaca, CDMX), then staying curious enough to let Georgia re-route you entirely when plans fell apart. That train-and-minivan odyssey felt like the real heart of the year — not the hike you planned, but the one that showed up instead.
And the volunteering section stayed with me. It’s easy to romanticize post-work freedom; much rarer (and more honest) to show how purpose often deepens when time is no longer scarce.
Also: the Canaries arrival after that journey, dogs and all — that exhale at the end felt earned.
Six years in, this doesn’t read like escape. It reads like arrival, again and again, in different forms. Thank you for sharing the texture of it — not just the highlights.
Here’s to 2026 continuing to surprise you in the best ways!
Hi Kelly - Thank you so much for your very thoughtful comment! We have found that the post-work journey continues to be interesting on all fronts. It's been a true privilege to have the time and freedom to explore this chapter of life.
Also, I have been meaning to mention how much I've enjoyed reading your content. I've read many, many travel and early retirement blogs over the past few years and find that you have a very unique, self-reflective take on the retirement/travel journey. I'm looking forward to reading more!
Coming from people who are actually living the post-work chapter (not just writing about it), that means a lot. I’m glad the self-reflective layer is landing, because for me the inner shifts have been as interesting as the geography.
I’ve loved following how you’re exploring this season too. It’s a rare privilege, as you said — and a fascinating one. Looking forward to more overlap as we all keep figuring it out. 💛
What a fun year you and Gillian had! I enjoyed reading the full retrospective, you travelled quite a bit in 2025. Now that you’ve been getting used to a mix of home and travel, what would you say is your ideal ratio of each? Sending you two and the pups greetings from San Diego - happy New Year! - Jessica (and Justin)
Happy new year to you as well! Glad you enjoyed it! The ideal ratio of home to travel is very much under debate in our household. Certainly each winter will have a few months of slow travel (more than a few if I win the debate!) and we’re also planning a couple dog-free getaways each year. It’s a work in progress. 😊
Haha I lived in Montreal for 4 years and I fully understand why you'd want to plan longer winter escapes ;) And for sure, life is flexible and I'm sure you'll have fun adapting the balance of home base and travels. We're aiming to be fully nomadic for a few years at least, then buy a home base and find more balance. If only our friends and family didn't live in expensive southern California! Looking forward to your next newsletter with updates on the Canary Islands.
Stephanie & Gillian — this is such a grounded, generous look at what freedom actually looks like once the novelty wears off and the life begins.
What struck me most is how intentional your choices are now. Not chasing novelty for its own sake, but returning to places that already feel like friends (Oaxaca, CDMX), then staying curious enough to let Georgia re-route you entirely when plans fell apart. That train-and-minivan odyssey felt like the real heart of the year — not the hike you planned, but the one that showed up instead.
And the volunteering section stayed with me. It’s easy to romanticize post-work freedom; much rarer (and more honest) to show how purpose often deepens when time is no longer scarce.
Also: the Canaries arrival after that journey, dogs and all — that exhale at the end felt earned.
Six years in, this doesn’t read like escape. It reads like arrival, again and again, in different forms. Thank you for sharing the texture of it — not just the highlights.
Here’s to 2026 continuing to surprise you in the best ways!
– Kelly
Hi Kelly - Thank you so much for your very thoughtful comment! We have found that the post-work journey continues to be interesting on all fronts. It's been a true privilege to have the time and freedom to explore this chapter of life.
Also, I have been meaning to mention how much I've enjoyed reading your content. I've read many, many travel and early retirement blogs over the past few years and find that you have a very unique, self-reflective take on the retirement/travel journey. I'm looking forward to reading more!
This really did make my day — thank you!
Coming from people who are actually living the post-work chapter (not just writing about it), that means a lot. I’m glad the self-reflective layer is landing, because for me the inner shifts have been as interesting as the geography.
I’ve loved following how you’re exploring this season too. It’s a rare privilege, as you said — and a fascinating one. Looking forward to more overlap as we all keep figuring it out. 💛
Love hearing about your adventures and watching the videos. You inspired us to book a week in Mex City in March. Thank you!!
Wonderful! I really hope you enjoy it as much as we did. In fact, we're already thinking about a possible third trip to Mexico City next year.
What a year of adventure! Thank you for the update about your year!
Thanks! It's always enjoyable to relive the best bits of the year.
Happy New Year! Can't wait to hear what you think of the Canary Islands, it looks like a lovely place for the winter.
Looking forward to sharing the full update next month. So far it's been blissfully sunnier and warmer than Ontario. 😅
What a fun year you and Gillian had! I enjoyed reading the full retrospective, you travelled quite a bit in 2025. Now that you’ve been getting used to a mix of home and travel, what would you say is your ideal ratio of each? Sending you two and the pups greetings from San Diego - happy New Year! - Jessica (and Justin)
Happy new year to you as well! Glad you enjoyed it! The ideal ratio of home to travel is very much under debate in our household. Certainly each winter will have a few months of slow travel (more than a few if I win the debate!) and we’re also planning a couple dog-free getaways each year. It’s a work in progress. 😊
Haha I lived in Montreal for 4 years and I fully understand why you'd want to plan longer winter escapes ;) And for sure, life is flexible and I'm sure you'll have fun adapting the balance of home base and travels. We're aiming to be fully nomadic for a few years at least, then buy a home base and find more balance. If only our friends and family didn't live in expensive southern California! Looking forward to your next newsletter with updates on the Canary Islands.