Transformation involves rethinking values and ways of seeing and acting, particularly as time stress compounds legacies of oppression and systematic underdevelopment in many postcolonial countries. These are exacerbated by structural challenges, as many societies are undergoing national, democratic, urban, race, class and gender revolutions simultaneously. All these challenges are aggravated by globalised systems of financial domination and mismanagement. Given these contexts, citizens and intellectuals in developing societies need more effective tools for analysing and deconstructing their challenges, and for the formidable tasks of reconstruction. Overhauling old values and systems to address pivotal challenges such as education and social justice requires metacognitive skills. Developing heuristics to enable integrated thinking, particularly in the arts (in this case English literary studies), helps students use disciplinary building blocks to address contextual challenges. This synthesising strategy is used to overcome histories of systemic violence, disempowerment, neglect, division, marginalisation and silencing in society and education.