<p>Managing the simultaneous demands of career and parenthood often generates tensions—particularly for women, who have historically been expected to take primary responsibility for caregiving. These gendered expectations persist, even as men increasingly express a desire to engage more actively in caregiving while maintaining their professional roles. Drawing on paradox mindset theory and work-family enrichment literature, this research investigated whether a paradox mindset—a cognitive tendency to embrace and value tensions—is positively associated with an aspiration for enrichment between work and parenting roles. In turn, this aspiration is hypothesized to predict intentions and outcomes related to dual-role pursuit. Three cross-sectional survey studies were conducted in Singapore among married, full-time working adults. Mediation analyses supported the hypothesized positive indirect relationship between paradox mindset and dual-role pursuit intentions among working women without children (Study 1, <i>N</i> = 186), as well as between paradox mindset and experienced dual-role success and satisfaction among working mothers (Study 2, <i>N</i> = 312) and working fathers (Study 3, <i>N</i> = 333), with aspiration for dual-role enrichment serving as the mediator. These findings highlight paradox mindset as a potentially beneficial psychological resource in navigating the complexities of the work-family interface and identify aspiration for dual-role enrichment as a key mechanism linking paradox mindset to dual career-parenthood pursuits. Practically, these findings suggest that organizations should encourage both a paradox mindset and an aspiration for enrichment to better support employees in balancing work and family demands.</p>