Increasing numbers of young Israelis annually leave the enclave of the ultra-Orthodox Jewish community. Relying on 16 in-depth interviews, we examine the effects of this disaffiliation on life trajectories and identity reconstruction of individuals who left their society of origin two decades ago. This unveiled a multistep longitudinal process, characterized by moving in and out of various structural stages, coupled with disaffiliates’ agency to highlight specific sociocultural characteristics or the more universal nature of the human condition. The life course of disaffiliates begins with a phase of early struggle with the immediate tolls of disaffiliation, followed by a formative period marked by two steps: military service and acquisition of higher education. Here disaffiliates practice adoption of increasingly inclusive identities, in which the past and present are enmeshed. The formative period is followed by three alternative trajectories: (a) adherence to restrictive Israeli conformity, (b) ongoing search for singularity, and (c) integration of ultra-Orthodox heritage with contemporary Israeli realities. The disaffiliation trajectory from the ultra-Orthodox society is embedded in particular sociocultural, political, and historical contexts. However, narratives of disaffiliates adhere to frameworks of cultural Jewish-Israeli particularism, as much as to those of human universalism, plugging in to certain universal themes of the human condition, namely rigidity, fluidity, alterity, and inclusion.