There is a large gap between the formerly socialist countries from Eastern Europe and the countries that we most commonly refer to as the Western Economies. Even though the historic circumstances can account for the development discrepancies between Eastern and Western Europe, they do not explain why there are such large and increasing discrepancies between the former socialist countries from Central Europe and those from Eastern Europe. Data from the World Bank shows that in the past 20 years countries from Central Europe (Czech Republic, Slovakia, Poland, Hungary, and the Baltic States) have shown significantly better results in transitioning from centrally planned economies towards market economies compared to the former socialist countries from Eastern Europe (Belarus, Ukraine, Romania, Moldova, Russia, etc.). By analyzing the development path of the countries from Central Europe, it is easy to identify consistent linearity in the process of establishing western-type societies through reform programs. In contrast, the Eastern European countries do not exhibit such linearity even though the implemented reform programs are similar and arguably can be described as one-size-fits-all reform packages, shaped mostly by the technocratic approach taken by the donor governments. In this article, we focus on understanding why these discrepancies exist and what are the factors that resulted in the lag in economic development for Eastern European countries, despite the efforts of achieving economic convergence on the European Continent.