In 2024, women continue to be inadequately represented in senior positions within Dutch academia. The slow progress towards gender equality in these positions is often attributed to individual factors such as (a lack of) ambition, motivation, and skills. However, this thesis starts from the viewpoint that career advancement is inherently contextual and not exclusively a personal asset. Few scholars have attempted to explore career dynamism experiences through qualitative (longitudinal) research. This thesis addresses this lacuna by examining how both individual agency and the contextual structures interact throughout the process of career advancement. It does so with a specific focus on mid-career academics’ experiences in terms of shaping their careers according to personal preferences and needs. The conclusions highlight that the dynamics in career authenticity are established through an interplay of three elements: envisioning, enacting, and enabling. This thesis challenges the conventional claims about the existence of the ideal linear and self-directed academic career path and shows the far-reaching career authenticity consequences of this myth.