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After the fall of the Berlin wall in 1989, systematic political changes were happening in all communist societies. This moment, triggered new political developments, challenges, as well as democratic approaches through negotiations and new democratic political party organizations, in all Eastern European countries. The beginning of this post- communist political period (the transition period) it was introduced through ideas of democratization, rule of law, freedom of speech and economic developments for all societies that were captured previously by the concept of socialism and planned economy. The concept of transition from communism and planned economy towards democracy and free market economy was expected to bring fast and visible changes through economic progress and freedoms but we have to admit that individual and political freedoms were not achieved with an immediate economic progress, as somebody would have assumed. Economic progress will be visible quite later due to the economic and political culture, human resources capacities related with low educational frames, corruption and state and institutional building capacities. In this essay, I will try to elaborate the initial processes of democratization and political changes after the fall of communism in both countries of Poland and Bulgaria, while investigating the process of preparation via different civic activities, new political parties, negotiations for their future democratic institutions, elections and their political culture. This, will help us to show and reveal not only the democratic initiations in the both countries, but will capture the democratic initiatives triggered in all communist societies, of course through different actors and contexts.