Deficits in school leadership and student achievement have occurred when principals were not adequately prepared. Similarly, assigning educators to administrative roles in low-performing schools without first training and preparing them have seemingly created situations that first-year principals described as particularly stressful. This narrative qualitative research study has been designed to capture the experiences of first-year principals in low-performing public primary schools in Barbados. Its purpose has been to better understand the journeys and the needs of the first-year principals assigned to low-performing schools. Their stories revealed that the participants’ leadership became more challenging when they assumed the principalship from those career paths that did not emphasize the need to constantly reinforce educational leadership skills. In addition, this qualitative data collected was consistent with existing literature, showing that in order to raise the quality of education in low-performing schools there was a need for effective principals to be equipped with skill sets that enabled them to meet those challenges that were unique to low-performing schools. The focus groups and interview schedules data revealed perceptions of the participants’ first year journeys. The emergent themes generated a better understanding of these perceptions and the need for mentoring. The interview findings pointed to the need for modifications in how our current principals were prepared, pathways to assuming the principalship, and implications for support. Specifically, this narrative inquiry provided new insights into the preparation and experiences of those first-year principals assigned to low-performing public schools in Barbados. It also offered suggestions for future research and could be used to inform policy and decision making.