Understanding transitions in the Russian economy was examined from two different perspectives: 1. the perceptions and attitudes of the people towards that transition and 2. the nature of the values and self perceptions of those people that allow one to understand what to expect from those people. This dual process is proposed as a way to more fully understand the issues, this study is presented as a model for further investigation of societies in transition. The Russian people are far more concerned about their material well being than with political issues. Their primary concerns were with policies that create severe inflation which prices goods out of the reach of the majority of people. Many people need, first, the basic necessities of food, housing, clothing, health care and furniture. They reported that they could not afford the basic goods and services. Still, among these concerns about inflation and meeting their basic needs, there was an overwhelming support for the privatisation of land ownership and the encouragement of small businesses, foreign investment, and the development of cooperatives. When the values and self perceptions of these people were examined in relationship to these fears, concerns and the support for emergence of an enterprise system with privatisation and business development, consistent profiles describe how the fears and hopes exist side by side. The emergence of a free enterprise system touches a core aspect of the Russian people: freedom. There is a freedom from fear and a freedom to improve that lies at the core of the Russian aspirations. Privatisation holds hope. Support of small businesses, investments and cooperatives provides opportunity. Against fears and the threat to the security of the Russian people stands a parallel hope and expectation of freedom from fear and real opportunity. The current problems must be overcome and fear may drive a societies response to our questions; but, if there are those with some hope and a desire for freedom, the transition may have the support that is needed to withstand the immediate fears and concerns.