Self-management technologies are promising in healthcare. In the name of patient empowerment, they can address an important challenge: how to meet an increasing demand for care without additional resources. We designed and evaluated the PICASSO-Tx system: a technology solution to support transplant patients and their self-management of diet, physical activity and medication adherences. In a Sield study, 19 patients used the system for two weeks at home. We discovered that although we intended patients to become actors in the management of their own health, they saw themselves rather as a subject, leaving the active role for caregivers. In this paper, we describe how patients expected their data to be shared with others, how they perceived the system as a tool for monitoring by caregivers, and what expectations towards these caregivers this perception brings. Furthermore, we discuss the barriers we encountered caused by the 'self' and conclude with design recommendations for self- management technologies in healthcare related to these expectations, perceptions, and barriers.