The global security environment has been in flux for almost two decades now, and Turkey has been at the center of the major global shifts that have taken place since the end of the Cold War. The demise of the Soviet Union, the democratic revolutions in the Eastern European countries, the Gulf War, the invasion of Iraq in 2003, the Arab Spring and the subsequent domestic turmoil in some of its neighboring countries, such as Syria, have influenced Turkey dramatically. Among the recent major challenges, one can count an unprecedented refugee flow, the loss of interest by the U.S. in the Middle East and the ensuing opening of a sphere of influence for authoritarian countries like Russia and Iran to fill the vacuum, the revival of terrorist attacks and the halting of the long-awaited peace process to achieve a long-lasting solution to the Kurdish problem, and the strained relations with the EU. All of these challenges coincide with a period in world history characterized by the decline of the institutions-based order, rising nationalism and authoritarianism in the most advanced democracies and-last but not least-a shift from a unipolar world to a multipolar one. In order to meet these challenges, I recommend that Turkey employ a grand strategy of democratic assertiveness, which consists of (a) persistent democratic reforms in the domestic realm and (b) an assertive defense strategy in the military realm. In the present article, I analyze the existing state of the international environment to identify the risks and opportunities and to assess the overall instruments available to policymakers. I conclude with a presentation of the main pillars of Turkish grand strategy for a concrete recipe for policymakers.