This paper traces the remarkable, non-linear career of Chris Brewster, who began as a steeplejack and ultimately became a leading scholar in International Human Resource Management. Brewster’s professional journey, marked by serendipity rather than strategic planning, spans physically demanding labour, public service, trade union advocacy, journalism, consultancy, and academia. Applying the Social Chronology Framework, the analysis shows how Brewster navigated shifting social spaces, developed a resilient and value-driven professional identity, and transformed accumulated experience into scholarly influence. His story demonstrates how openness to chance, reflective decision-making, and continuous learning can shape a fulfilling and impactful career. Even in later life, Brewster remains an active “working academic,” dedicated to research, mentorship, and challenging conventional perspectives within HRM. His trajectory exemplifies how unplanned transitions can foster innovation and meaning across an entire working life.