This qualitative multiple-case study explores elementary schools music teachers’ career choice in Vancouver and Hong Kong. Face-to-face open-ended interviews were used for collecting data. The results of this study demonstrated the long-term processes of social learning of music teachers that contributed to their development of personal musical interests to become a teacher. Teachers of the Vancouver cases and Hong Kong cases made their choices according to job opportunities and training opportunities respectively. The factors that had contributed to these teachers’ musical interests were very similar; but the crucial factors that had determined their choice of occupation differed remarkably. The socio-cultural differences of the two societies had noticeable influences on these elementary music teachers’ choice of occupation.