Botswana has gained worldwide prominence among high performing developing countries since becoming independent from British colonial rule in 1966. It has since managed to transform itself from being among the lowest economies worldwide to gaining middle-class status through a diamond-backed economy under five decades. Its adoption of development strategies set by the National Development Planning rewarded her with an appealing macroeconomic and fiscal stance. However, these macroeconomic indicators seem to have disguised key structural flaws later realized to have produced a narrow and undiversified economy. Botswana now has to put up with with key socio-economic challenges emanating from these weaknesses among them, high youth unemployment rate, income inequality, extreme poverty and economic un-diversification. This paper, will address these challenges individually as a starting point for untangling the constricted economic and social environment in which Botswana finds itself. Through each of these lenses, it will determine the means in which each challenge has contributed to this effect, and which challenge has a greater influence on present-day socio-economic climate. It will assess key macroeconomic and social indicators as they relate to each of these structural flaws by hypothesizing what each might say about the country’s economic, social, and political position.