The rapid re-expansion of agriculture following a decade of drought highlighted long-standing unresolved issues in the Australian agriculture workforce. This paper investigates the career paths of existing farmhands, through a theoretical lens to increase our understanding of career pathways on agriculture. Semi-structured interviews were conducted with five farmhands and eight farmers on cotton-producing agricultural farms in New South Wales, Australia. These results show there is a discernible farmhand career with attributes of the primary labour market. This career is the embodiment of the boundaryless career, with farmhands choosing agriculture and their current employer. However, the importance of the person-environment fit is an element consistent with traditional career theory. The psychological contract remains important, with elements consistent with pre- and post-globalisation. This modest first attempt at theorising the farmhand career to understand career pathways in agriculture shows promise.