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 left the economy narrow and undiversified. Botswana now has to contend with critical economic and social challenges emanating from these weaknesses among them, high youth unemployment rate, income inequality, extreme poverty and economic diversification. This paper, will address these challenges discretely as a starting point for deciphering the narrow 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.