Language teachers experience many stressors and challenges due to the physical, emotional, and social demands of their work, negatively impacting their well-being and performance. Existing research on language teacher well-being has primarily examined the factors affecting it. However, limited research has focused on how language teachers’ well-being changes over time and across long periods. To address this gap, this study investigates the well-being of two English language teachers in Turkey across the span of their careers from a Complex Dynamic Systems Theory (CDST) perspective, using a comparative case approach based on the PERMA framework, a model of psychological well-being and happiness including five components: positive emotions, engagement, relationships, meaning, and accomplishment. The data were collected through in-depth interviews with two English language teachers using retrodictive qualitative modeling (RQM) as the methodology. The data were analysed separately for each teacher and then compared. The analysis revealed several factors affecting the well-being of both teachers across their careers. The main theme that emerged was perseverance, which characterized the experience of both participants. Other common themes included professional development, responsibilities, social interaction, and student improvement. The study identified several factors shaping language teachers’ well-being across their carreers. The paper concludes with implications for promoting language teachers’ well-being with suggestions for future research.