Developing wellbeing at work is one of the most challenging tasks in contemporary society. As no single definition of wellbeing at work is commonly accepted as the most comprehensive and relevant, we introduce a discursive definition. We argue that wellbeing at work is associated with many contradicting dilemmas concerning both the development process and wellbeing at work itself. In the development processes of four organizations, analysed using data gathered in interviews with the key actors in the processes, seven such dilemmas of major importance for development are identified. The dilemma theory is helpful in charting the emerging dilemmas in developing work wellbeing and the theory contributes to the construction of better development processes.