This research aims to study vice-principals' career stages and determine their difficulties and achievements in these stages. The data in the study were obtained with semi-structured interview questions. As a result of our research, twenty school vice-principals were interviewed. As a consequence of the interviews, our data were gathered under three themes in line with qualitative research methods and techniques; sub-themes suitable for the themes were created and interpreted by content analysis. According to the results, the vice principals' main challenges in their career stages are professional competence, lack of sharing information from colleagues, sense of belonging, need for mentors, working conditions, lack of experience, inefficiency, and time management. It was revealed that some vice-principals developed and kept themselves up-to-date with in-service training to overcome the difficulties. At the same time, some received support from experienced and older administrators. Based on the interviews' data, it was resolved that the past encounters and experiences in the challenges faced affected the vice principals. It was assumed that these difficulties were easily overcome by the experienced vice directors, who worked as a principal for a long time.