Organizations face several managerial challenges during their growth period. Growth spurts are realized when organizations overcome these challenges. Though the literature is full of studies on the enterprise growth, the knowledge about how these challenges facilitate or hinder growth is limited. We conceptualize and explain five challenges faced by an enterprise along its growth trajectory. For evidence, we then look at history of three organizations from different sectors and trace their strategies to overcome the challenges faced by them. The firm and the environment interact and make certain strategic choices, which in turn results in growth spurts in the organization. We draw insights from their growth stories and discuss the different strategies and interactions between the firm and the environment.