This essay explores selected Indian characters depicted in Mulk Raj Anand's Untouchable (1935) and Kiran Desai's The Inheritance of Loss (2006). This study finds that these characters are struggling with an identity dilemma which induces their inner-conflicts: double-consciousness, resistance and othering, due to the dominance of the caste and colonial systems. This study observes that both of these hegemonic influences have created the privileged and less-privileged status of the Indian individuals, which have concealed their true natures. Thus, these Indian individuals are confined and recognised through their essentialised identity, as connoted by the caste and colonial systems. Therefore, the objective of this essay is to de-contextualise the selected characters from their essentialised identity, exposing their true nature without the influence of their privileged and less-privileged status. To achieve the targeted objective, this essay discusses the identity dilemma of the selected characters through a Strategic Essentialist reading, a term coined by Gayatri Chakravorty Spivak (1987). This is to detach the Indian individuals from their identity which is defined and structured by the caste system which segregates them under the formation of social hierarchy, as well as detaching them from their post-colonial condition. In the conclusion, this essay discloses the ability of the term Strategic Essentialism to unveil the disguised nature of the privileged members and the hidden nature of the less-privileged members, conveying their identity dilemma which fails their assimilation in their own homeland and foreign land.