This dissertation investigated the learning required for individuals to onboard into self-managing organizations (SMOs). Using a qualitative case study approach, 15 participants from various SMOs were interviewed to gain insight into their experiences. In addition, data were collected from a document review and focus group. The study found that: (a) Formal learning enabled a quick grounding in the basic mechanisms of self-management. (b) All participants faced challenges applying the principles and practices of self-management in practice. (c) All participants had to learn to shift their mindsets in order to successfully participate in self-management. (d) Transitioning into self-management was a nonlinear process that unfolded over time. For many participants, it began years before they joined an SMO and continued even after their formal onboarding period was completed. (e) Formal training supported instrumental learning, while mindset shifts were more supported by informal learning. An analysis of these findings led to four primary conclusions. First, an organizational model cannot transcend the capabilities of its members. Second, a new relationship with self, others, and the organization required new ways of thinking and being. Third, formal and informal learning experiences amidst a supportive social context enabled this holistic transformation. Fourth, self-management is a team sport and is therefore likely only able to be learned with and through a group. The study recommended building a learning environment and supporting new members' learning journeys to facilitate a successful transition into self-management. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]