Continuing education (CE) professionals are experiencing continuous changes in their practice, including situations where they see a need for change but feel overwhelmed with change implementation. This article is a reflection on our experience of (1) transitioning from independently operating health professions CE units in medicine, nursing, and pharmacy to becoming a Joint Accreditation provider of interprofessional CE and (2) developing and using a Diversity, Equity, and Inclusion Toolkit for Accredited Continuing Education. We examined these instances of substantial change to identify what made them achievable and supported our well-being throughout the process. We also considered a social cognitive theory, a schema theory, and a normalization process theory. As a result, we identified five steps of the CE planning and implementation process to be our trusted mental model and the key factor in making the changes doable for our team and supporting our resilience and a sense of well-being. Interviews with three clinician-learners, which were conducted in search of additional insights, reminded us that positive reinforcement occurs when we see the desired result. Thus, measuring the CE change and its impact on learners and their patients is also a tool to sustain emotional comfort during the turbulence of a change cascade, given the measures show progress in a desired direction. We hope this article will stimulate peer discussions, reflections, and sharing of lessons learned from similar journeys.