This book is a compilation of essays on several themes intended to provoke thought on and promote understanding about everyday political and social life on an island facing constant geopolitical and domestic political challenges. The themes of this books are: 4/21 Terror Attack and National Security; China, Belt and Road Initiative and Sri Lankan Foreign Policy; Geopolitics; Sustaining Democracy and Facing a Pandemic; and Domestic Political Stability, Leadership and Economic Crime. Most essays have captured the domestic viewpoint from which to begin drawing a wider picture of the global geopolitical tapestry. The chapters enframe a variety of domestic political incidents, conflicts of various actors, and the conundrum of an island in the Indian Ocean, stuck in the triangular maritime power dynamics among the United States, China, and India. They also examine the influences from foreign nations towards Sri Lanka's foreign policy and the dynamics of security challenges in the larger geosphere and marine sphere of South Asia and the Indian Ocean respectively. The chapters offer the reader an Olympian viewpoint of the challenges Sri Lanka faces, attempting to find connections and patterns towards greater external geopolitical influence and how it impacts domestic politics.