Ample literature exists on the impact of prevention programmes on their target audience, while much less is known about how delivering such programmes influences their facilitators. Even less literature exists on the emotional and social processes that form this potential impact on facilitators. The current study analysed qualitative in-depth, non-structured interviews, as well as written essays provided by 33 student-facilitators who delivered the “Favoring Myself” programme in Israel during 2019–2021. This school-based wellness programme comprised 10 weekly, 90 min sessions on self-care behaviours, media literacy, self-esteem, and positive body image, which are well-known protective factors against risky behaviours. A thematic analysis was applied to explore the main themes in the collected data. An interesting affective transformation from self-doubt to pride in themselves emerged as a shared experience of these young facilitators. Facilitators related their ability to facilitate the programme, as well as to undergo an individual maturation and empowerment experience, to certain components of the programme itself, such as the preparatory course, individual supervision, and the peer-group experience. This shift from doubt to pride is discussed using two frameworks—a theoretical discourse of emerging adulthood as a developmental stage, and the self-determination theory.