In the research project which formed part of my PhD study, I dealt with the topic of inequity in education. My main interest was to find out how (formal) educational careers can be fostered even if the starting position within the system is one which makes a successful educational career very difficult. Despite the fact that in the Austrian education system intergenerational social mobility is very low, there are some pupils who manage to achieve very successful careers despite coming from so-called high-risk backgrounds. On the other hand, many young people leave school early—also pupils from supportive backgrounds. This led me to the question how success and failure in educational careers can be explained and—on the basis of this knowledge—what we can do to support young people from all backgrounds in achieving successful careers. This case study gives an insight into the progress of my research project from a general interest in the topic to a specific research question, the development of the research design, and the phase of data collection, analysis, and interpretation to structuring the findings for the conclusion of my work. It shows the different stages of the project and their respective challenges, especially questions concerning the choice of the best suitable research methods (narrative interviews for data collection and the documentary method for data analysis and interpretation) as well as their application.