An individual's career trajectory evolves with each job and role transition. Over time, job/role experiences trigger choices as to whether to stay in a particular job setting or role. Reflective questions guide the process of deciding whether and when it is time to transition. Considerations include role fit with lifestyle expectations, need for advanced knowledge and formal education, and readiness for upward or lateral movement. Using a framework modeled after the work of Bolman and Deal, this article presents 4 lenses to guide a careerist's readiness and need for change: human resource, structural, political, and symbolic factors. Each lens is introduced to reinforce a holistic approach to key triggers and considerations in career change. The summary culminates with how to foster a joy-filled career.