The complexity of modern careers requires personal agency in managing career development and employability capital as personal resources for career success. Individuals’ employability capital also serves as a valuable resource for the sustainable performance of organizations. Individuals’ ability to proactively engage in career self-management behaviors through the use of a comprehensive range of self-regulatory capabilities, known as career metacapacities, contributes to their employability capital. Organizational career development supports initiatives that consider individuals’ proactivity in light of conditions that influence their motivational states, and availability of personal resources helps organizations benefit from individuals who bring information, knowledge, capacities, and relationship networks (i.e., employability capital) into their work that ultimately contribute to the organization’s capability to sustain performance in uncertain, highly competitive business markets. Career development support practices should embrace the individualization of modern-day careers, the need for whole-life management, and the multiple meanings that career success has for individuals.