Sensors in offices mainly measure environmental data, missing qualitative insights into office workers’ perceptions. This opens the opportunity for active individual participation in data collection. To promote reflection on office well-being while overcoming experience sampling challenges in terms of privacy, notification, and display overload, and in-the-moment data collection, we developed Click-IO. Click-IO is a tangible, privacy-sensitive, mobile experience sampling tool that collects contextual information. We evaluated Click-IO for 20-days. The system enabled real-time reflections for office workers, promoting self-awareness of their environment and well-being. Its non-digital design ensured privacy-sensitive feedback collection, while its mobility facilitated in-the-moment feedback. Based on our findings, we identify design recommendations for the evelopment of mobile experience sampling tools. Moreover, the integration of contextual data with environmental sensor data presented a more comprehensive understanding of individuals’ experiences. This research contributes to the development of experience sampling tools and sensor integration for understanding office well-being.