Technology designed to sense behavior, often neglects to directly incorporate subjective input from (elderly) users. This paper presents experiences in deploying technology that considers the elderly user and their subjective input as a way to enrich sensor data systems and empower the user. For this purpose, the paper draws on: (1) Observations of shortcomings in terms of capturing objective data from sensors as experienced in long-term deploymentt in the homes of older adults; (2) The design and evaluation of a wide range of applications especially designed to enable older adults to give subjective input on how they are doing, including an interactive television quiz, a talking picture frame and a tangible mood board, and (3) The development and field study of one application, the ‘Mood button’ in particular, that was tested in real-world sensing settings to work with a commercial sensing system. In doing this, this work aims to contribute towards successful sensing deployments and tools that give more control to the (elderly) end-user.