Research concerning the social-political culture of twentieth-century dictatorships has been dominated by two diverging views committing the same reductionist flaw: the long-entrenched one (Arendt, 1951; Lewin, 1985) posits a structural-determinist conviction that totalitarian regimes thrived on the subjugation of individual autonomy; the new discourse (Aharony, 2015; Dikötter, 2015), adopting the methodology of history from below, upholds the notion of grassroots resistance to foreground the primacy of the individual as a subversive force that challenged the ruling political order. Reducing power to macro and micro ends of the scale respectively, the two approaches underpin however the same notion of state-society opposition. The present paper, departing from such Manichean dualist views of structure and agency, advocates an alternative perspective to understand the impact of ideology on everyday actors under totalitarian rule. The case under examination is ordinary people’s diaries produced in Mao-era China. Through detailed textual analysis of the personal documents, supplemented by interview data collected from former diarists, this paper reveals a vigorous yet tumultuous process of individual self-fashioning marked by both conformity and deviations from the larger ideological matrix, thereby highlighting the complex dialogical nexus between ideological frameworks and individual capacities in generating unintended possibilities at the grassroots.