In this paper, we utilized Gilligan’s listening guide as anchored on Hermans’ Dialogical Self Theory to explore the process of embodying mindfulness. The results of the analysis highlight not only the different narrative paths to mindfulness, but also the dialogical nature and struggles in each path. We present the journeys of seven public school guidance counselors and values education teachers, whose narratives clustered under three types of paths with each arriving at a unique personal meaning of mindfulness: (1) struggling path, (2) mechanical path, and (3) receptive path. Results highlight the relationships between personal voices, professional voices, and the mindfulness voice present in each path. This paper presents the value of understanding the multi-voiced self of the facilitator. Lastly, the paper also poses reflections toward a dialogical approach to assessment and training.