Rabbi Simon Jacobson, a prominent voice in bridging secular and spiritual realms, is joined by his mother, Sylvia Jacobson, a matriarch of Chabad roots. Together, they discuss how the Chabad movement has adapted through generations, maintaining core teachings while evolving. They explore the sensitive dynamics of parenting and trauma across ages and reflect on their family's immigration journey from Russia to America. With a focus on instilling confidence in Jewish identity, they illuminate the significance of tradition and emotional openness in fostering spiritual connections.