Abstract This paper gives an overview of individual’s dream career and their real career, using the teaching profession as a case study. Through the use of Philosophical concepts of phenomenon and noumenon, one can see the difference which may be seen between that which appears to them and the thing in itself. The process of data collection involved qualitative approach whereby evidence from the philosophical anthropology literature, interview guides and review of literature were used as tools for gathering data. The study revealed that in the teaching profession there are mixture of teachers who had different dream carriers. For example some of them were dreaming to become: lawyers, doctors, soldiers, engineers, politicians and businessman. The study also identified factors which influenced them to be teachers these factors included: advice from parents, poor economic background, poor performance in science subjects at ordinary level of secondary education, and safety nature of the teaching professional. A person who appreciates education and enjoys imparting knowledge, for instance, could logically want to become a teacher because they see it as a profession that blends their natural skills with the demands of society. A deeper consideration of one’s purpose and the moral implications of promoting human flourishing are part of this deliberative process, which goes beyond simple utilitarianism (Maslow, 1943). Individuals attempt to strike a balance between self-fulfillment and group duty by using reason to negotiate the conflict between their own aspirations and the needs of reality. Philosophical traditions emphasize that reason helps people choose jobs that advance their own and their community’s well-being. One example of this is Aristotle’s concept of Eudemonia, or flourishing (Aristotle, 2009). Therefore, choosing a job is not a single decision; rather, it is deeply rooted.