Issues of sociopolitical systems’ stability and risks of their destabilization in process of political transformations belong to the most important ones as regards the social development perspectives, as has been shown again by the recent events in Ukraine. In this respect it appears necessary to note that the transition to democracy may pose a serious threat to the stability of respective sociopolitical systems. This article studies the issue of democratization of countries within globalization context, it points to the unreasonably high economic and social costs of a rapid transition to democracy as a result of revolutions or of similar large-scale events for the countries unprepared for it. The authors believe that in a number of cases the authoritarian regimes turn out to be more effective in economic and social terms in comparison with emerging democracies especially of the revolutionary type, which are often incapable to insure social order and may have a swing to authoritarianism. Effective authoritarian regimes can also be a suitable form of a transition to efficient and stable democracy. The article investigates various correlations between revolutionary events and possibilities of establishing democracy in a society on the basis of the historical and contemporary examples as well as the recent events in Egypt. The authors demonstrate that one should take into account a country’s degree of sociopolitical and cultural preparedness for democratic institutions. In case of favorable background, revolutions can proceed smoothly (“velvet revolutions”) with efficient outcomes. On the contrary, democracy is established with much difficulty, throwbacks, return to totalitarianism, and with outbreaks of violence and military takeovers in the countries with high illiteracy rate and rural population share, with low female status, with widespread religious fundamental ideology, where a substantial part of the population hardly ever hears of democracy while the liberal intellectuals idealize this form, where the opposing parties are not willing to respect the rules of democratic game when defeated at elections.