Based on a qualitative case study, this paper presents the initiative, motivation, and challenges faced by Filipina foreign domestic workers (FDWs) who volunteer to teach their peers care-giving. This case is embedded in the context of a nonformal education program provided by the Humanitarian Organization for Migration Economics (HOME), a nongovernmental organization (NGO) located in Singapore. Data were collected during 2017, including individual interviews and focus groups, and analyzed using a three-step ethnographic process of direct observations to emphasise local knowledge and context and direct personal engagement of the researcher with the community of FDWs. This paper links the FDW's complex personal, societal, and cultural factors to the leadership style of the Filipina volunteer trainers, suggesting that the heritage of colonialism influences the values and identity of the Filipina FDWs while they try to lead for social mobility and identity transformation through continuing education.