Psychobiography has become valuable within the context of professional psychology training. A recent psychobiography purposively sampled Joe Slovo to uncover, reconstruct and illustrate significant trajectories of his development. Slovo’s (1926–1995) lifelong dedication to the struggle against Apartheid has been widely acknowledged, and he held longstanding leadership positions in various South African liberation movements. Levinson’s theory of lifespan development served as the study’s psychological lens. Alexander’s approaches to data identification and extraction were used, followed by a psycho-historical matrix for data categorisation based on the life cycle theory and significant historical periods throughout Slovo’s life. To fully embrace the Levinsonian understanding that an individual cannot be separated from their social world, consideration was given to significant historical and sociocultural forces and events during the data analysis. Therefore, this study’s findings extend beyond Slovo’s individual development to illuminate the complex ways external forces, such as family dynamics, historical events, political movements, community concerns and cultural and language considerations, influence developmental trajectories, life structures and tasks. The authors reflect on the value of sociocultural and contextual sensitivity in psychobiography to help trainee psychologists venture beyond the subject’s inner psychological life, including understanding their outer worlds.