The authors consider various forms of non-normative educational pathways within the cultural contexts of Canada, England, Finland, Sweden, Switzerland, and the United States of America. Rather than conducting cross-cultural comparisons of normative educational pathways, the authors focus on (a) identifying unexpected educational pathways across various ages using various analytic methods and (b) examining a wide range of factors that may promote, inhibit, or result from these diverse forms of educational progress. The results are intended to help researchers and policy-makers understand why some students who appear to be on promising educational pathways fail to succeed and why other students, who appear to be at risk for failure, nevertheless go on to negotiate successful educational pathways.