This paper considers the career paths of four academics at different stages in their career, examining key aspects in the trajectory of their journey to where they are now. The paper considers a range of key issues, pitfalls and barriers, and challenges they have faced in order to provide an insight into the differing journeys that academics may take. The research uses a combined auto-ethnographic and reflective approach to gather and interpret the experiences of the four individuals, in essence developing a reflective account on their personal journeys. The four academics were specifically chosen based on their different career paths, providing important opportunities to develop more in-depth reflective accounts of their stories. While they have all taken different trajectories, findings suggest significant overlap exists around issues such as imposter syndrome, psychological contract and identity. These issues, it would appear, have an interrelated impact upon the individual and, as such, cannot be separated effectively. The paper contributes to understandings of how academic careers progress, and may provide invaluable guidance to new entrants, or those considering entry into the world of academia.