This chapter examines entrepreneurial expectations in colonial and postcolonial Africa, focusing on railway construction in German colonies and aviation in post-independence West Africa. It shows how predictions about future business opportunities were shaped by the economic, political, and technological contingencies of these eras. Under colonialism, expectations aligned with imperial resource extraction, but reliance on private firms created tensions with state development goals. After independence, aspirations for rapid modernization through state-led industrialization guided entrepreneurs and managers, but unrealistic hopes often went unfulfilled. Through case studies of infrastructure projects, the analysis reveals how uncertainty and instability necessitated close ties between the state and businesses. However, this interdependence bred inflated expectations and long-term dilemmas. The chapter underscores the complex dynamics of expectation formation at the nexus of economic, technological, and political factors. It highlights the need for nuanced understandings of diverse organizational behaviors adapted to colonial/postcolonial settings beyond dominant narratives.