Medicine and health care attempt to prevent and cure disease, restore lost function, and relieve suffering. These are positive aspirations in the face of disvalued states of being. Part of the approach to countering illness can be to encourage or therapeutically increase such states as optimism, emotional wellbeing, peace and meaning, and to try to decrease mental and existential distress and despair, feelings of vulnerability, feelings of loss and loss of meaning. The column briefly examines examples from three fields – cancer, psychotherapy and end-of-life – and the relationships between therapeutic and social pressures for optimism and hope, on the one hand, and wellbeing, health and freedom, on the other. It suggests that in each field there are risks that arise from premature and/or excessive accentuation of the positive, and neglect of the presence and importance of what is conventionally regarded as the negative.