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This paper examines the problematic question of caregiving from a Freudian and Lacanian perspective. We analyse how both general and professional caring attempts to negate or reduce the sexual and destructive tendencies of the subject. Yet, as Freud indicates, the act of caregiving itself evokes these tendencies, thereby causing certain subjective difficulties. We show how, from a Lacanian perspective, the problem revolves additionally around the carer's own polymorph perverse enjoyment (‘jouissance’). Caring paradoxically evokes one's own tendency to enjoy at the expense of the other, especially in cases when the other is experienced as radically different from the self. Such jouissance is not only morally unacceptable but, from a Lacanian standpoint, it fundamentally destroys the narcissistic basis of the caregiver's identity. In such cases, doing good might itself be considered an attempt by the subject to defend against this problematic enjoyment. Finally we suggest that professional burnout can be understood as an effect of the subjective paradox caused by caregiving. Through illustrations provided by clinical vignettes, we show how the core burnout symptoms of emotional exhaustion, depersonalisation and reduced personal accomplishment are the result of a withdrawal from one's own cruelty.