Positive psychology’s focus on human strengths, personal growth, and well-being is frequently applied to career development and the workplace. Such applications also fall within the purview of vocational psychology, yet despite its clear historic and contemporary emphases that support positive psychology goals, the impact of vocational psychology theory, research, and practice on positive psychology has fallen short of its potential. We encourage greater cross-fertilization by explicating how major theoretical paradigms within vocational psychology (person–environment fit, developmental/relational/constructivist perspectives, and social–cognitive career theory) support positive psychology aims. We also summarize recent work on three vocational psychology constructs (work volition, career adaptability, and a sense of calling) that may help to broaden and advance positive psychology’s applications to career development and work behavior. Finally, we discuss future directions for ongoing research related to the vocational and positive psychology intersection, and we outline several implications for career counseling practice.