When tragedy struck - first a stillbirth, then her father's death - Anne Lerner's Jewish spiritual practice deepened in unexpected ways, catalyzing a journey from Conservative Judaism's traditional gender roles toward embracing historically male ritual obligations. Through autobiographical reflection and theological analysis, Lerner examines her path to adopting daily prayer, tallit, and tefillin while navigating the complex terrain between preservation and innovation in Jewish women's spirituality. Her narrative, framed through the traditional lens of Torah study, avodah (divine service), and gemilut hasadim (acts of loving-kindness), reveals both gains and losses in this spiritual evolution. As women access previously male-dominated ritual domains, uniquely feminine Jewish traditions risk being overshadowed. Lerner's experience illuminates how contemporary Jewish women stand at a transformative crossroads, positioned to redefine traditional gender boundaries in Jewish spiritual life. Yet this generational work of integrating women into traditionally male Jewish practices remains incomplete - creating new possibilities for spiritual expression while raising fundamental questions about gender-specific religious domains.