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Self-funded leave is an employee benefit that provides a time resource to those who wish to develop interests and other life roles. Semistructured interviews were used for this qualitative study to explore the motivations for enrolling in the self-funded leave program, how the leave contributed to work-life balance through development of other life roles, and the difficulties that arose during the program. Adult transition theory is used to conceptualize the process of participating in self-funded leave programs and to suggest how employees who undertake self-funded leave can be best supported by career counselors.