Academic work demands behavioural ambidexterity: the ability to simultaneously demonstrate exploration (creativity in research and/or in innovative teaching and learning practice) and exploitation (compliance with quality assurance). However, little is known about the effects of behavioural ambidexterity on the well-being of individual employees. We explore the experiences of men working in academic roles at universities in Sweden and the UK. More specifically, we examine the relations between behavioural ambidexterity and perceptions of well-being using an interpretative approach based on narrative analysis. Despite societal differences between Sweden and the UK, academics in both countries felt ill equipped to fulfil the demands for ambidexterity. This resulted in mixed performance outcomes with serious implications for well-being. We identify and discuss the influence of personal circumstances and the role of agency in work design as two key antecedents of positive well-being outcomes.