This chapter tackles three thematic areas. Briefly, it outlines the short-lived bubble of expectation in people ushered by the first economy of Zimbabwe post-independence. It was the dawn of a new era. With the majority rule came the hope of a better country in which everyone has a fair share of the national cake. An inclusive economy in which living standards of people would improve was one of the aspirations of the people post-independence. The inherited jewel economy did not last. Like other post-independent African states, challenges would soon follow. One after the other, the chapter examined the performance of Zimbabwe in selected macroeconomic areas such as corruption, ease of doing business as well as foreign direct investment, debt and currency stability. Most importantly, comparisons are made with selected peers in the continent. The resulting gap between Zimbabwe and the peers reveals an economy which has largely struggled as will be fully explored in later chapters in other parts of the books. In the chapter, the narrative of Zimbabwe’s economic struggles is well documented in the media both local and international. A synopsis of several headlines covering a wide range of economic issues is captured to give a general picture of the unfolding challenges through time. Notably issues such as struggling workers and masses, currency crisis, inflation, land reform, infrastructure and sanctions take centre stage in the timeline of selected headlines. The chapter winds up by exploring the role of music and arts as Zimbabwe’s economic history unfolds. The contribution of this key sector helps to further illuminate the multi-layered nature of Zimbabwe’s economic challenges in the past four decades.