The research reported in the paper presents a picture of successful principals in challenging urban contexts. This article draws on findings from a larger international study (the findings are obtained from the Polish part of the 'Leading Schools Successfully in Challenging Urban Context: Strategies for Improvement' project) and the literature to examine successful principals of challenging urban schools. Specifically, this article reports case-study findings for four challenging schools in Poland. There are many gaps in our knowledge about successful educational leadership. For example, what leadership strategies are used by Principal of urban schools that served children in poor communities and why they are used? What we can learn from successful leaders’ professional development by reconstructing their career stories? The analysis of narrative data culminated in the reconstruction of a professional self conceived of as indicator for the researched principals’ professional development. The comparative analysis of the stories revealed some important recurring common themes Characteristics and qualities of the principals identified showed a common and consistent set of personal traits, behaviours, values such as high expectations of all, commitment, passion, resilience, empathy with others, trust, honesty, openness and highly developed communication skills. The article concludes with implications for leadership training and future research.