The tendency of teacher to sign out from teaching profession has been recognized as a significant issue in the education lately. This study aims to investigate how teachers’ occupational wellbeing predict stress and burnout, and intention to leave teaching. The study administered teachers’ occupational wellbeing questionnaire to 318 high school teachers in Samarinda. A confirmatory factor analysis and structural equation modelling are performed to examine the path coefficient of the measured variables. The result demonstrates that teachers’ occupational wellbeing has a significant effect on predicting stress and burnout that leads to the increase of teachers’ intention to leave their teaching career. As to teachers-socio demographic characteristics, the female English teachers appear to have higher occupational wellbeing compared to the male English and Non-English teachers. It was found that the tendency of younger English and Non-English teachers to leave teaching are higher than older English teachers. Additionally, in mediating intention to leave teaching teachers experiencing stress and burnout tend to have more reasons to leave teaching and positively increase their intention.