This study deals with teachers of Ethiopian origin, i.e. second-generation immigrants from Ethiopia or those who were brought to Israel by their parents as young children. The goals of the study are twofold: first, to trace the obstacles they face against the background of racial discrimination and affirmative action, and second, to describe three prominent journeys that characterize the transition from studying in academic colleges of education to entry into teaching in schools, and how various incentives and support programs shape these transitions. The data was collected through life-story interviews with 10 teachers and semi-structured interviews with 10 dedicated support programs' coordinators from academic colleges of education. The findings revealed a complex relationship between racial discrimination that these teachers face when entering teaching, and affirmative action policies that sometimes work against EDOT. The discussion interprets these consequences by using both Critical Race Theory and Optimal Distinctiveness Theory.