An emerging and growing body of research has clearly established the importance of youth building sociopolitical consciousness in order to be more democratically engaged citizens. An overwhelming amount of sociopolitical youth development work occurs outside of school. Much of the research on this work has focused on youth outcomes, and we know little about sociopolitical youth workers, the types of experiences and influences from which they draw, and how those experiences and influences emerge in their work. To attempt to fill this void, the author uses life history methodology to showcase two sociopolitical youth workers ("activist mentors"). Using Watts, Williams, and Jager's eco-transactional model of sociopolitical development as an analytic tool, the author explains and uncovers ways in which an amalgamation of past events, relationships, and environmental influences inform and emerge in activist mentors' work with youth activists. Findings indicate that activist mentors' ecological and transactional influences shape the ways in which they discuss their development of collective identities with their mentees, developmental spaces, and healing approaches to their work. This study points to a need for further research to understand what informs the work of sociopolitical youth workers, how their work is influenced, and the role of critical self-reflection in sociopolitical youth development work.