This paper explores liberal democratisation and the question of sovereign self-determination in Taiwan as an articulation of coloniality. It contends that liberal democratisation is imbuing divisiveness and occasioning a politics of inertia between the dominant actors that has left Taiwan’s sovereignty question largely opaque. While some scholars have cited the symmetry of ‘two destinies’ in one, others have debated the influence of the United State of America (US) on maintaining the ‘balance’ between the People’s Republic of China (PRC) and the Republic of China (ROC), Taiwan. Little attention has been paid to the role of democratisation in sustaining the ‘impasse’. One may, for example, note that discussions on Taiwan’s identity are alive and well both at micro and macro levels, yet the same is not clearly identifiable at the national level of political discourse in contemporary times. How does democratisation affect the Taiwan Question as a Nation-state? This paper contends that both the tactical pro-China stance of the hitherto dominant Kuomintang (KMT) and the methodical ambivalence of the ruling Democratic Progressive Party (DPP) compound than address the identity of Taiwan. This paper is grounded in decoloniality as an epistemic lens, and employs Pierre Bourdieu’s field theory as an analytical tool to unearth how the origins of democracy in Taiwan continues to shape its quest for identity. Specifically, the paper demonstrates how, through the disciplinary “field of power” enunciated via liberal democratisation, discourses on Taiwanese identity is impelled by the imperative for ‘regional security and stability’ however leaving the concerns of whose strategic interest unexplored.