Many educators are required to further their knowledge and skills through professional development initiatives. These programs are affected by numerous elements. A crucial but often overlooked factor is the well-being of teachers. This qualitative case study explores how acknowledging the well-being of two participants and addressing their needs influenced their involvement in a professional development initiative. These educators worked on developing their pedagogical knowledge and practices related to reading instruction for students learning English as a foreign language. Recognizing these participants' well-being necessitated being cognizant of whether they were in a healthy place. This awareness emerged from direct observations of lessons, interviews with teachers, and the journey maps they created and narrated. The participants voiced concerns about how to engage with this program independently. They also had to contend with contextual factors that regulated how they responded to and progressed through this program. Appreciating these aspects of their affective states led to a calibrated approach to support and guidance based on the unique needs of each participant. When they received assistance tailored to their needs, these teachers were better positioned to benefit.