Contemporary risk management is based on statistical analysis. Such an approach has a few crucial disadvantages. First of all, it has limited applicability to new technological solutions. In this paper, a new idea for risk evaluation and management is put forward. The proposed approach is based on the autonomous systems theory. The theoretical foundation of the proposed idea is described and its prospective applications are discussed. The proposed measures of risk are based on the idea of the controllability of the system—the greater the level of controllability, the lower the risk. Various aspects of controllability are analyzed—economic, technological, and industrial. For each aspect of controllability, the problem of defining adequate measures for the level of risk is discussed. The proposed approach allows the risk assessor to analyze the system deeply. As a consequence, the analyst can assess the risk based not only on a posteriori statistics but also on an analysis of the crucial properties of the system. This allows the investigator to predict a priori possibilities of critical events. The proposed methodology is applied to the power industry.