With more data available than ever before, there is a growing literacy around data as a medium for generating information and key insights. Despite increasing interest in Personal Informatics (PI) tools, what is missing are tools that help us make sense of the data that we collect as a byproduct of our interactions with various systems. This project explores untapped potential of broader and deeper personal sense-making by drawing connections between the full diversity of one’s personal data. Through a co-creation design process, the catalysts for and challenges to engaging in rich dialogues with data have been identified, and prototypes representing participants’ aspirations for creating meaning from data have been developed.