This chapter addresses the critical question of how the Cooperative Extension System prepares the next generation of Extension professionals who will support the well-being of tomorrow’s children, youth, and families. This chapter details the career landscape of Extension in five parts. Part 1 presents a synopsis of career development research highlighting how a person identifies and advances in a career as well as different Extension careers to demonstrate the multiple career pathways and roles in Extension organizations. Part 2 provides a discussion of competencies and skills needed for successful Extension professionals. Parts 3, 4, and 5 explore each of the primary mechanisms for preparing the next generation of Extension professionals, including formal instruction through college programs, career development activities (e.g., internships); and education that occurs on or after hiring (e.g., onboarding, continuing professional development). Information from this chapter can help guide those interested in pursuing Extension careers, as well as those in leadership positions who oversee hiring and retaining talent for Extension.