This study seeks to understand, through a qualitative phenomenological design, the meaning of happiness at work for clinic managers who work for a mission-driven healthcare organization. There exists many organizational dynamics that can influence happiness at work; nevertheless, for the scope of this investigation, this paper converged on three theoretical premises: (1) Positive Psychology: Happiness at work which is divided into eudemonic and hedonic happiness, (2) Intrinsic Motivation Theory: Self-determination, and (3) Extrinsic Motivation Theory: Self-determination. The evidence discovered in this study demonstrates the importance of understanding the context for what happiness at work means for management-level caregivers/employees. The clinic managers that participated in this study overwhelmingly displayed a strong sense of intrinsic motivation/eudemonic happiness, in part, because they take happiness to work and they display a strong desire to help develop and grow their respective staff. Yet the study also realized that extrinsic factors influenced their happiness at work. For example, a key extrinsic factor on the clinic manager’s happiness was his/her direct supervisor, a prime illustration, if the clinic manager’s direct supervisor fails to recognize the clinic manager’s skills/abilities and if the direct supervisor of the clinic manager was a micromanager. Notwithstanding, when clinic managers utilize their full skills and when they were able to support, encourage, and develop their direct reports, it seems that clinic managers maintained a sense of happiness at work despite any external negative experiences. Several contributions have been realized based on the findings of this study. Most interestingly, the phenomenon of happiness at work has been found to be dynamic and multidimensional.