Amid the disempowerment and marginalization faced by young girls, character development programs are being implemented to change the course for girls by fostering strong and empowered feminine identities. I explore the challenges of implementing one such program through my ethnographic and community engaged research with a character development program designed to equip 3rd through 5th grade girls with the skills and confidence they need to grow into empowered women. Through a qualitative analysis, I empirically demonstrate the importance of community engaged scholarship for uniting theory with practice. My analysis extends research exploring community engaged, empowerment programs by highlighting the ways empowerment is experienced differently by every girl. I point to the tension between empowerment in theory and in practice, specifically addressing the assumptions: 1) of girls’ uniform experience base, 2) about the influence of the GRL message among competing others, and 3) regarding the utility of certain strategies in diverse situations, all of which undermine the process of empowerment. I describe my experience working with the founder of the organization to revise the curriculum and offer a set of practical implications for this and similar organizations to productively respond to the tensions between the theory and practice of empowerment. Finally, I argue for a conceptual shift in the way we theorize empowerment as an ongoing and constantly negotiated state of engagement, rather than an endpoint or stable state of being.