This chapter focuses on four areas which the country failed to take advantage over the past four decades. The net effect has seen the economy failing to realise its full potential in terms of growth and sustainable development. Specifically, the chapter dissects demise of growth points, failure to embrace industrial clusters, weak social security nets and dependence on aid in development as the Achilles heel to the real transformation of the economy, issues which are often overlooked in Zimbabwe’s economic history. The growth point strategy of the colonial past and the first economy are compared drawing lessons on how growth point strategy could have been leveraged to also develop the rural economies. Similarly, lost opportunities through lack of robust cluster strategies are explained as well as strategies for efficacy of the strategy. In the chapter, two types of Aid are explored and how they have not helped much for the development of the country. The chapter also elucidates how weak social security has also contributed to the development currently obtaining for the country. While acknowledging several attempts to put in place social security systems to cater for mostly the vulnerable people, the chapter looks deeper into the resulting challenges at the backdrop of absence of robust systems. Drawing from lessons in peers in the continent and beyond, the chapter shows how weak social security nets is among the blunders committed. The chapter concludes by locating a nexus in the four blunders and development trajectory of Zimbabwe post-independence.