Before You Move the Sofa: Choosing Where to Move Abroad
About our Guest Simon D. spent fifteen years running his own renovation business in Hamilton, Ontario, before he and his wife swapped Canadian life for Belize in 2022, a country they first fell for on their babymoon. Leaving his trade behind, he turned to content writing just as large language models arrived, and rather than retreat, he went all in. Today he helps founders and small businesses build AI integrations and automations, hosts the podcast Foreign Radio, and writes about life ...
Key Takeaways
- Simon D. shares his journey of moving from Hamilton, Ontario, to Belize in 2022 after spending fifteen years running a renovation business.
- Many expats fall into the trap of moving abroad based on a holiday version of a destination, leading to high turnover rates within the first year.
- It took Simon's family two and a half years to truly feel at home in Belize, highlighting that settling in is a gradual metamorphosis rather than an instant fix.
- Understanding cultural nuances, such as navigating high- and low-context communication at local immigration offices, is crucial for a successful transition.
- Simon combined his experience as an AI writer and creator of MoveSmart to build tools that help people realistically evaluate where they might thrive abroad.
About our Guest
Simon D. spent fifteen years running his own renovation business in Hamilton, Ontario, before he and his wife swapped Canadian life for Belize in 2022, a country they first fell for on their babymoon.
Leaving his trade behind, he turned to content writing just as large language models arrived, and rather than retreat, he went all in. Today he helps founders and small businesses build AI integrations and automations, hosts the podcast Foreign Radio, and writes about life abroad on Substack. His newest project, MoveSmart, brings those two worlds together: an AI tool built to help people decide where in the world they might thrive.
What You’ll Walk Away With
Doreen and Simon explore self-initiated expatriation and the gap between the holiday version of a place and the lived one. Simon describes a pattern he sees again and again in Belize: people sell everything, ship their belongings, build a house, and are gone within eight to twelve months.
His own family took two and a half years to feel truly at home. He talks about smashing the rose-coloured glasses, from months of sargassum on the beach to the quaint old town where you can never find parking, and shares a wonderfully telling story about high- and low-context communication at the immigration office, where the right question unlocked a stack of paperwork the wrong one never would have.
An honest conversation about building and using your own judgement when moving overseas.
Connect with Simon
Email Simon at simon@movesmart.world
You can find him on Substack at Simo’s Substack, read his AI writing at BotBot, and connect with him on LinkedIn as Simon D.
Share this episode with someone who’s standing at one of those thresholds — a new country, a return home, or simply a life that’s asking them to become someone they haven’t quite met yet.
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You can map the move. You cannot map the metamorphosis. Nomadic Diaries explores the interior journey of expat life — the belonging, the identity shifts, the repatriation, and everything that travels with you that can't be packed in a suitcase.
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Frequently Asked Questions
Who is Simon D. on Nomadic Diaries?
Simon D. is an expat, AI writer, and creator of MoveSmart who moved from Canada to Belize in 2022 and discusses the realities of self-initiated expatriation.
Why do many expats leave Belize within their first year?
Many expats leave within eight to twelve months because they move based on a romanticized holiday version of the country without preparing for the realities of daily life.
What is MoveSmart?
MoveSmart is an AI-powered tool created by Simon D. designed to help people evaluate and choose where in the world they might truly thrive.
How long does it realistically take to feel at home after moving abroad?
While many expect an immediate transition, Simon's family experience shows it can take two and a half years or longer to feel truly at home in a new culture.