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Within the diverse population of working women, those who experience pregnancy for the first time may face some particular challenges when it comes to their career development needs and issues. These include discrimination in the workplace, responding to social expectations and pressures, negotiating life roles, and evolving personal identities. This article discusses the major career problems encountered by this target group, both structurally and socially, with a focus on individual strategies to access personal agentic functioning and empower women facing these challenges. These workers are often overlooked in the career literature; yet, there is a range of career theories to draw upon to assist them in their needs. The application of the life-span, life-space career theory, and the narrative therapy approaches are explored in relation to the helping process. These two theoretical orientations were chosen as they address the particular challenges faced by pregnant women in the workplace, especially around negotiating life roles and an evolving personal identity. There is a need for a stronger understanding of these challenges and opportunities to support pregnant women as they seek vocational wellbeing, and how to tailor suitable, well-established career counselling strategies to meet their unique needs.