This biographical account situates the unfolding of the life of an educator in varied socio-economic contexts. It is not just a narrative of how an individual evolves but also analyses how a particular mindset develops by being dialectically entwined with the milieu in which one passes different stages of their life. At one level, it is a historical narrative since it deals with a particular period of human history critical to the growth of a specific individual. At another, it provides ethnographic inputs to those who want to understand the peculiarities of the twentieth century. It offers first-hand accounts of the nature of transformative politics which evolved at the behest of Naxalites in India; it also has obvious twists and turns as the individual is exposed to a world beyond India. So, the narrative is individualistic, and it has elements of influences acquired through exposure to an alien socio-cultural milieu. Apart from its analytical importance, this memoir provides a very realistic assessment of India’s education system through the lens of an educator and an academician.