This work aims to explore how authenticity of a newly independent country is being restored in the face of legacy left by invaders. To surface crucial elements of geopolitical authenticity, I turn to Estonia as a country representative of many nations that went through the tumultuous changes of the last century. The end of the twentieth century left a powerful mark on the geopolitical scenery of the planet. Countries’ borders were changed or restored, and new formal maps were redrawn. Only the break up of the former Soviet Union has resulted in 15 independent countries, with Estonia being one of them. The joy of freedom came up with economic, political, and cultural challenges including the challenge of restoring authenticity of a country.