The purpose of this study was to learn from the experience of adopting a deliberately developmental approach to delivering the co-curriculum to first- and second-year undergraduate students on a residential college campus to better equip them to navigate the increasingly complex future that awaits them. The project's goal was to create conditions that would support greater coherence across the student experience and foster meaning making in the system. As an action research study, the study was concerned with generating actionable knowledge and change. Facilitating movement and change through action research required participants to be able to imagine a new future; act on that vision with intention; be guided by commitments to democracy, collaboration, equity, accessibility, and individual and collective agency; and be willing to engage in reflective learning. As a methodology and in the context of this particular study, action research supported a range of motivations, including a deeper understanding of both the student experience and the educator experience, leveraging the collectively held research experience as a form of staff learning and development, and responding to a moment when a liberal arts education is being examined and critiqued for its relevance. An action research team comprised of educators working in student affairs and academic affairs adopted five practices associated with deliberately developmental organizations as guidelines for designing and delivering cocurricular content. Because the COVID-19 global pandemic informed the entire arc of this study, the action research team was challenged to be responsive and innovative at a moment in time when they often doubted their ability to do so. The volatile, uncertain, complex, and ambiguous (VUCA) conditions of the surrounding environment as defined by changing student needs, the macro landscape of a changing workplace, and the constant organizational changes of the campus comprised the backdrop for this work. Harnessing VUCA conditions as an opportunity, this process served to not only teach us educators about our student community, but also taught us lessons about ourselves as individuals, about how we work together as educators committed to our community of learning, and about the strengths and limitations of the system in which we operate. [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.]