In reminiscence and appreciation of two decades of friendship and collaboration with Fred W. Vondracek the present chapter sketches the debate about the impact of contextual constraints vs. personal agency on individuals’ career development. It is suggested that scholars’ theoretical positions with regard to these two poles are influenced by their socio-historical context as well as their own biographical experiences. In a historical flashback, the major impact of Donald E. Super’s work in the 1960s and the 1970s is highlighted. He had coined the prevailing Zeitgeist in vocational psychology when Fred began his career in this academic domain. However, Super’s theorizing and work did not remain unchallenged. His strong emphasis on the self and personality was questioned by Walter S. Neff, a very creative spirit who has become almost forgotten in the field. In his 1968 book, one may find precise anticipations of social change phenomena as well as precursors of modern dynamic systems notions applied to career development. The chapter finishes with a critical reflection on new concepts such as protean and boundaryless careers.