The breakdown of SFR Yugoslavia and the independence of Macedonia brought the state and the Macedonian people to a period of transitional changes. Namely, the Socialist Republic of Macedonia, for the needs of the new time, declared independence at the referendum of September 8, 1991. The Macedonian citizens were asked to answer the question: “Are you for a sovereign and independent state of Macedonia, with a right to enter into any future alliance with the sovereign states of Yugoslavia?”. 75.75% of the citizens with the right to vote went to the polls, and 95.1% of the voters voted “for”. Thus, an independent sovereign Republic of Macedonia was created. From the moment of its independence, the Republic of Macedonia faced numerous temptations, both internally (within the existing until then federal state) and internationally, on the way to achieving its international establishment. For Macedonians, the transition meant the moving from a peaceful and calm everyday life, accompanied by secure jobs and wages, to a temperamental life marked by a daily struggle for survival and earnings. What was and remains the biggest flaw of the transition in Macedonia is that all the processes that started have remained somewhere in the middle. The author of the article analyzed almost three decades of the political existence of the Macedonian state, making a synthetic assessment of international regional policy and its impact on the shaping of Macedonia’s state entity in the international arena.