The article reveals the evolution of planning activities in the Soviet Union during the years of Soviet power and in Russia during the transition to market relations. The study used a historical approach, methods of induction and deduction, content analysis, and expert assessments. The distinctive features of the first, second, and third pre-war five-year plans, and the specific features of the mobilization economy during the Great Patriotic War are summarized. The main tasks of the fourth, fifth, sixth post-war five-year plans and the seven-year plan of 1959-1965, as well as the achievements and difficulties of this period of socialist construction, are highlighted. The reasons for abandoning the directive nature of planning and switching to indicative planning in the 1980s, as well as for developing plans for economic and social development of the USSR in the early 1990s are analyzed. The timeliness of the transition from command-administrative to market forms of management is substantiated. The results of application of methods and instruments of directive and indicative planning, mechanisms of administrative-economic and economic regulation at various stages of functioning of the national economy of the country are illustrated. The factors of transformation of the Russian economy in the post-Soviet period are shown. The need for activation of activities on strategic management and planning in the post-Soviet economic space is revealed. The advantages of development of strategic documents at the subnational level are established. Recommendations on dissemination of methodological bases and practice of strategizing in territorial and sectoral sections are formulated.