Sustaining our health and wellbeing requires lifelong efforts for prevention and healthy living. Continuously observing ourselves is one of the fundamental measures to be taken. While many devices support monitoring and quantifying our health behavior and health state, they all are facing the same trade-off: the higher the data quality is the higher are the efforts of data acquisition. However, for lifelong use, minimizing efforts for the user is crucial. Nowadays, few devices find a good balance between cost and value. In this interdisciplinary workshop we discuss how this trade-off can be approached by addressing three topics: understanding the user’s information needs, exploring options for data acquisition, and discussing potential designs for life-long use.