The following study is based on the comparison of the actual transition processes in Estonia and Slovenia in 1991-2000 with the aim of testing two conceptual models (shock therapy versus gradualism) of transition theory in practice. This article has two main goals, closely interlinked with each other. The first task is to analyse whether the reform paths undertaken by Estonia and Slovenia followed the theoretical concepts of 'shock therapy' and 'gradualism', the models the states are often symbolising in theoretical debates. The second task is to evaluate the ability of the theoretical models to correctly allocate the classical country examples to the shock therapy and gradualist models. This research study is also interested in what are the advantages and disadvantages of a polarised approach to transition theory models and how these models can be improved.