The aim of this study is to address a gap in research on educational careers: the missing consistent explanations for reasons behind educational failure or success. The project focuses on two types of educational careers: formally unsuccessful (early school leaving) and very successful ones (educational upward mobility). Biographically oriented narrative interviews were conducted with Austrian representatives of these two groups. On the basis of theoretical models explaining social inequality and findings regarding common risk factors, the research project emphasizes the interplay and actual relevance of factors influencing individual students. The main finding of the qualitative study is the reconstruction of patterns of orientation in formal educational careers. The typolog y presented can account not only for the contrasting degrees of success in the educational careers examined but also for the varying relevance of common factors of influence.