Jewish families forge paths between tradition and modernity through a "tradition of invention" - adaptive strategies that maintain religious continuity while embracing contemporary life. Drawing on three generations of educational experiences across the United States and Israel, this ethnographic study reveals how families navigate the frequent tensions between institutional Jewish education and home religious values. Through participant observation and family history analysis, the research traces patterns of educational choice and cultural transmission, documenting parents' persistent search for schools that approximate their religious orientations. Yet these institutions rarely achieve perfect alignment with family values, creating cycles of educational fragmentation where dissatisfied parents establish new schools that eventually confront similar ideological heterogeneity. Middle-ground Jewish families emerge as cultural mediators, exposing children to diverse religious frameworks while moderating institutional influences through family practices. The findings demonstrate that contemporary Jewish continuity relies more on family resources and selective adaptation than on institutional consistency. This dynamic creates individuals with cross-ideological experience who continue seeking optimal balance between Jewish heritage and modern life, suggesting that family units, rather than educational institutions, serve as the primary mechanism for cultural transmission in contemporary Jewish communities.