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Through interviews with 21 career nannies, our findings reveal that they face numerous challenges in balancing the dual nature of care work throughout their career cycle: a transactional nature pursuing monetary compensation through their labor and a relational nature bonding with employer families for quality care. We argue that the transactional and relational nature of nanny work simultaneously or independently influence each stage of the career cycle, giving rise to three key challenges: balancing these dual natures, building fair and compatible relationships with employers, and maintaining career identity for professional development. 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