This chapter uses Fred Vondracek’s Living systems theory of vocational behavior and development to analyze how his personal lifespan development helped shape his approach to education and work. Based on more than 50 years of common history at the Pennsylvania State University and Fred’s accounts of his early family history during World War II and his immigration to the United States, Fred’s career development from tile setter’s apprentice to internationally recognized scholar and academic leader is examined. Evidence is presented to demonstrate how vocational development pathways emerge from creating, performing, and evaluating goal directed behaviors in varied contexts.