Transplants - Conversations With Women Thriving Abroad #13 When Paradise Stops Being Paradise | Kaila Krayewski | Canada → Thailand
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Dec 2, 2025 Kaila Krayewski, a Canadian-born writer, has spent years embracing life abroad, from teaching English in Japan to finding paradise on Thailand's Koh Phangan. She candidly shares her journey of building a life while grappling with loss, entrepreneurial challenges, and relationship strains. Kaila discusses the harsh realities that come with island life and reflects on her decision to leave Thailand for a fresh start in Valencia. She also offers heartfelt insights on coping with grief and maintaining connections while living away from home.
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Challenging Start In Japan
- Kaila moved to Japan at 21 to teach English and quickly felt out of place in a homogenous, watchful culture.
- She lived alone in a remote farming village, experienced her breakup there, and remembers wishing she could comfort her younger self.
Falling For Koh Phangan
- On a holiday from Japan Kaila fell in love with Koh Phangan's beaches and relaxed pace, which contrasted sharply with her Japan experience.
- She admits the attraction was as much about escaping structure as about Thailand itself.
From Blog To Business Pivot
- Kaila launched a travel site called Blonde Traveler to support women backpacking Southeast Asia after finding few female-focused resources.
- The project taught her product and market limits and ultimately failed, but led her to settle in Bangkok and later the island.