It is often assumed that for middle class and academically able children, schooling is a straightforward process that leads to academic success, higher education and entry into middle class occupations. However this publication shows these relationships to be complex and often uncertain. Based on the biographies of 350 young men and women who might have been considered "destined for success" at the start of their secondary schooling, the book maps out the educational pathways they took. It analyses their subsequent achievements and entry into employment and compares them with their parents, with one another, and with their generation. Identifying patterns in the data, it also explores examples of extraordinary success and failure, and various forms of interrupted and disrupted careers. As well as documenting a compelling human story, the findings have important implications for current policy debates about academic selection, access to elite universities, and the limits of meritocracy.