This article focuses on Aliza Levenberg, an educator who taught at a Kiryat Shmona high school at the beginning of the 1960s. For three years Levenberg, a middle class Western European, travelled every week from her home in Tel Aviv to the poor town in the northern periphery of Israel, the inhabitants of which were mainly immigrants from Islamic countries. Levenberg was a productive writer. Her most famous book, "Kiryat Shmona Chapters," tells of her complex encounter with a culture and way of life so different from her own. Analysing this text, our article addresses the cultural clash she experienced, illuminating its impact on her educational, social, and political perspectives. As we show, Levenberg, who at first was a "dedicated soldier" of the melting pot vision, aiming to bring enlightenment to the poor, eventually refused to take part in this forced conversion. She focused instead on listening to her students, and creating a space that would enable them to form their opinions, and express their fears and hopes. As a result, she developed a more flexible and sensitive educational vision. Reading her book as literary autoethnography enable us to expose the hidden layers of the emotional, social, and political process she underwent during this period. We argue that this process exposes the dualistic attitudes of educators who have worked on the deprived social margins. On the one hand, feelings of compassion and empathy impelled many of them to activism, yet on the other, cultural and social differences often elicited paternalistic and orientalist sentiments, which obstructed their educational efforts.