This paper illustrates the importance of self-knowledge and the process by which two people attained such illumination. Does a person need to have an accurate self-awareness to enable them to choose long-term goals? And if so, how might one achieve such self-discovery given that many of us choose a profession at an early age? The individual journeys of two very different women are presented in this paper. Both women undertook journeys through India; one through the Himalayas and the other crossed India on the back of an elephant. Surviving their individual challenges led both to completely new careers in the non-profit sector. Linked by an original bond of lecturer-student both women developed a deeper relationship of mutual respect and shared understanding. How they travelled may have differed but their final destination was the same – a new knowledge of themselves that altered their future direction in life. Thus, does the journey lead to a more fulfilling career? The understanding of inner self providing direction in careers that, overall, are more satisfying than those that act contrary to our inner selves. What are the lessons we can all learn from the separate journeys of these two remarkable women?