Inspired by a Tolkien quote, "Not All Who Wander Are Lost," the authors introduce the concept of "career wandering" in the context of undergraduate student development. Proposing an alternative to traditional linear career trajectories, we conceptualize a dynamic approach that embraces nonlinear paths, indecision, and adaptability in a rapidly changing labor market. Drawing from our experience as educators, we define career wandering by integrating principles of lifelong learning, flexibility, chance events, and openness to diverse experiences. We explore the implications of career wandering for student affairs professionals, emphasizing the need for supportive, inclusive environments that encourage exploration and holistic student development. Addressing potential critiques, we acknowledge the challenges of equity and accessibility, and the need for intentional institutional support. Ultimately, the career wandering approach aligns with the evolving nature of work and promotes a more inclusive and adaptable model of career development in higher education.