This narrative chronicles the journey of a 15-year veteran English teacher who spent most of his career in suburban schools before deciding to transfer to a small island, Ieshima. He moved there after going through a lot of hardship and learning a great deal. Ieshima means ‘a home island’. His teaching life on that island was completely different from his earlier teaching career in the suburbs of a medium-sized city. In teaching English at a junior high school on the small island, he realised that his mission was to foster deep and meaningful relationships with individual students, teaching not just the English language but also offering broader perspectives on life and improving students’ expressive abilities to be useful in society and an attitude of independence. Through his work, he sought to connect the school and community, creating an inclusive atmosphere where everyone could engage with English education. Initially, he struggled to adapt to the unique culture and interpersonal dynamics of the island. Over time, his interactions with the students and their unspoiled perspectives helped him adjust, ultimately enabling him to try innovative approaches to teaching. His written narrative illustrates how his teacher’s beliefs started to take root in Ieshima.