This article explores the experiences of four early career academics as they begin to undertake doctoral supervision. Each supervisor focused on one of their supervisees and drew and described a Journey Plot depicting the high and low points of their supervisory experience with their student. Two questions were addressed by the research: (1) How do early career academics experience doctoral supervision? (2) What challenges do early career academics face as they learn to supervise? Analysis of the data confirmed new supervisory experiences as variable, personalised, and emotional and further identified them as marked by agency and resilience, with time an important factor in supervisor development. Three common areas of challenge were noted: unrealised supervisory expectations, student-supervisor relationships, and commitment. Navigating these challenges was key to these individuals developing their expertise as doctoral supervisors.