The whole world endorses women’s equal rights in workplace, family, and society (Pew Global 2020). Researchers find gender inclusion benefits workers and companies through enhanced worker and customer satisfaction, increased profits, and worker well-being. Why does gender workplace equity remain a “stalled revolution”? We suggest work/family dynamics supporting challenges of care for the most vulnerable—children, elders, the disabled, adults experiencing ill health—need to be “re-visioned” as “wicked problems” within applied complexity/developmental systems sciences. Complexity sciences argue gendered inequalities maintain stability through entangled forces at multiple levels yet can be transformed through problem-and-setting specific ecological analysis, identifying leverage points for maximum impact toward achieving valued outcomes. We apply transdisciplinary cultural/developmental systems perspectives on the gendered, interdependent life course, highlighting shared individual, family/kin, business, and public responsibilities toward supporting work and caretaking (Brandth, Halrynjo, & Kvande, 2017). These approaches help map multi-systemic factors offering impactful leverage points catalyzing measurable change. Global comparative literatures identify three transformative leverage points: (1) Gender-neutral paid family/kinship care leave when meeting life course challenges of childbearing/adoption and infant care; (2) Public/private partnerships providing flexible, predictable employment and institutional supports for early childhood care, schooling, and dependent caretaking needs for workers at all income levels (Thébaud & Halcomb, 2018); (3) Systems-minded organizational interventions addressing gender stereotyping of work/family decisions in Human Resources administration and in leadership training for both managers and workers.