Drawing upon the mutually constitutive notions of possible selves and agency, this study illuminates how maintaining a future orientation in doctoral education acts to supply candidates with a pivotal sense of direction and drive their experimentation with disparate pathways to realise their academic career aspirations. In-depth analysis of two longitudinal cases reveals that participants' trajectorial differences were closely linked to their exercise of agency towards different ends and to different extents under the biographical, institutional, local/national, and global conditions and contingencies they engaged with. However, neither was immune to the risk of suffering an unpredictable employment outcome following candidature. While this plight has much to do with the fierce competition inherent to the neoliberal academic job market, findings also underlined its association with the prominent absence of supervisory and programme support along their doctorate. The study concludes with proffering practical implications beneficial to nurturing and supporting candidates' (diverse) career-possible selves.