Research on teacher well-being has been historically conducted through predominantlyquantitative methods of analysis that rely on the application of various psychological and sociological constructs onto teachers’ experiences. Consequently, less is known about how teachers themselves define teacher well-being, how they engage in practices related to teacher well-being, and how teacher well-being is contextually impacted from an emic perspective. This dissertation study thus examines how teachers conceptualize teacher well-being and how their well-being is impacted by the various stakeholder groups and contextual factors commonly found within educational systems. Teacher participants’ emic perspectives are centered through usage of qualitative research methods and epistemic network analysis. An additional focus is to understand how educational leaders understand teacher well-being and their possible impact on teacher well-being as leaders, as this area of teacher well-being research is relatively underdeveloped. This study’s findings present a comprehensive detailing of teachers’ and leaders’ perspectives and experiences that are central to teacher well-being across both public and private educational contexts. Implications thereof are offered for educational researchers, school leaders, and the field at-large.