Before a place becomes a home, it’s often a headline. Alan J Roberts—musician, entertainer, and creative strategist—heard “don’t go,” went anyway, and found something different: a welcoming community and a career that finally fit.
In this episode, we discuss embracing curiosity over fear, turning risk into opportunity when life at home doesn’t feel right, and how living abroad can challenge long-held beliefs about the world and about home.
What you’ll hear
* Warnings vs. welcome: testing headlines against lived reality
* Risk as a tool: how to turn uncertainty into an actual plan
* Building a portfolio career abroad (work, community, creative practice)
* Personal adjustments that make integration easier
* Seeing your home country differently after time away
Show Notes
* Warnings vs. welcome: Alan’s first-hand take on the Middle East and why he stopped outsourcing his view to headlines
* The leap: how a quick decision (“I’m gonna take the risk and see what happens”) became the best risk he ever took
* When home stops fitting: coming back to Canada, feeling the mismatch, and deciding to leave again
* Turning risk into a plan: simple ways to choose curiosity over fear and make uncertainty practical
* Building a life abroad: work lanes (full-time + freelance + business license) and why a portfolio approach works
* Cultural fit & acceptance: everyday reality in the UAE; locals, expats, and a city built by international talent
* Personal adjustments that help integration: the habit shift that made social life clearer and more respectful
* Career & creativity: from Toronto MC roots to Dubai residency to creative strategy across entertainment and emerging tech
* Seeing home differently: how time abroad reframed beliefs about Canada and the West
* Advice for the stuck: “Don’t hold yourself back”—looking for options when opportunity feels limited
* Emotional undercurrent: balancing distance, family, and the occasional guilt of being away—without wasting the chance to build
* Cliffhanger prompt: “College or a one-way ticket?”—a decision lens for anyone debating the next move
* Takeaway: living abroad as a path to acceptance, a wider perspective, and self-designed work and community
Recorded on September 12, 2025
More About Alan
Alan J Roberts is a Canadian-born musician, songwriter, and creative strategist whose work connects music, culture, and digital storytelling. Early in his career, he served as Vice President of the Canadian Caribbean Association of Halton, helping advance race relations, produce cultural showcases, and create employment pathways for Black youth in partnership with the Canadian government.
He emerged in Toronto’s live scene as an MC before evolving into a genre-blending artist, drawing on influences from R&B, Afrobeat, Latin music, techno, and dance; driven by emotion, rhythm, and narrative.
After moving to Dubai, Alan grew artistically through a residency at Lucky Voice and built a portfolio career leading content and brand experiences across gaming, entertainment, and emerging tech. Whether performing or building creative strategy, he lives with intention, bringing creativity, culture, and connection into the same conversation.
If you want to know more about the life Alan is building in Dubai, you can connect with him through the following channels:
* YouTube @alanjamzing
* Instagram @alanj_amazing
* LinkTree
* Spotify
* TikTok- @alanjamazing
Simo’s Substack runs on curiosity, reflection, and subscriber support. If you find value in these conversations, consider becoming a subscriber, especially a paid one. It’s the best way to keep this work going and show that this content matters.
If you enjoy this podcast, you might also like the A Foreign Perspective, Foreigner501, Foreign Tales, the Lili Art Blog, or my award-winning book Home in Good Hands. If you’d like to support this Substack and help me keep creating stories and essays about life abroad, consider subscribing, sharing, or buying me a coffee. And to those who already have—thank you. Your support means the world.
