Today, digitalization has become one of the key factors in socio-economic development. It covers reproduction, science, public administration and entrepreneurship itself. Considering the conditions for the formation of the economic space of the Lugansk People’s Republic, scientists face difficult tasks of finding solutions to the digital transformation of the socioeconomic system of the Republic for full integration into the economic space of the countries of strategic partners. The presented article attempts to systematically analyze the development of the phenomenon of entrepreneurship in the context of the digitalization of the economies of the world’s leading countries. The study compares the simplicity of entrepreneurial activity between countries of the world, assesses the ability of countries to ensure a high level of wellbeing of their citizens and determines the level of economic freedom and the state of the country’s entrepreneurial ecosystem in a local and international context. Evaluation of digital development processes is carried out using an aggregated index of the network state, which characterizes technology, people, management and the level of network development of the studied group of countries. Based on the conclusions made, the main characteristics of the directions for the development of entrepreneurship in the context of the digital transformation of the Donetsk and Lugansk People’s Republic are proposed and substantiated.