This paper proposes a new tool of measurement for Self-Knowledge and monitoring of health. The presented concept leverages on people's self-reflection, empathetic interactions with smart objects, and HCI applications to reach transformative insight and Self-Knowledge. The particular emphasis is on evaluating needed variables within the processes of Personal-Informatics, Self-Reflection, and Realizing Empathy found as gaps in fields contributing to Self-Tracking and analysis. After those variables were translated into designed, interactive, smart behaviors, tests were done to verify their initial effectiveness a new method for visualizing and understanding one's own data measurement, encouraging the person to Self-Reflect. The concept is contextualized within a dieting or body regime experience.