This article addresses the art of living in a technological culture as the active engagement with technomoral change. It argues that this engagement does not just take the form of overt deliberation. It shows in more modest ways as reflection-in-action, an experimental process in which new technology is fitted into existing practices. In this process challenged values are re-articulated in pragmatic solutions to the problem of working with new technology. This art of working with technology is also modest in the sense that it is not oriented to shaping one's own subjectivity in relation to technology. It emanates from human existence as relational and aims at securing good relationships. The argument will be developed in relation to a case study of the ways in which homecare workers engaged with the value of privacy, challenged by tele-monitoring technology that was newly introduced into their work.