The nature and context of education have changed dramatically in recent decades. The increased prioritisation of standardisation, performance indicators and metrics often means that holistic, afective and wellbeing education are seen as less important in the educational endeavour. The value of education for education's sake is under siege. Previous emphasis on the education of the whole person (i.e., moral and creative aesthetic development) is often replaced by a more functionalist perspective of education as servicing economic need and global capitalist interests. Marketization of education has increased at an exponential rate and has had an adverse impact on the health and well-being of both educators and students. This chapter elucidates how the triad of assessment, student well-being and academic well-being intersects in the ever increasing performative and neo-liberalist cultures of higher education. It demonstrates the reciprocal dynamic of stress that is becoming more and more evident among educators and students. The chapter makes the case for more empowering and human-centred educative contexts in order to facilitate beter educational outcomes for students and healthier outcomes for all involved in the educational endeavour.