Small states all over the globe have peculiar challenges foisted on them by their meagre population which may make some unviable and inconsequential in the comity of nations. While this can be said to be normatively politically correct, the realities have proven otherwise. Countries like Singapore, Qatar, Oman, Switzerland, etc., have crafted enviable statecraft that positioned them in strategic socio-economic and political vantage positions. For the Caribbean country of the Cooperative Republic of Guyana, the quest to succeed as a strong and virile small state has remained daunting due to a lot of intervening internal and external dynamics. This study is therefore poised to evaluate the Guyanese national trajectory towards a sustainable and stable Caribbean nation in the face of precarious post-colonial history, political alliance and nuances of intra and inter-regional influences on a country with great economic and geo-strategic potentials and the contradictions of a small population. In achieving this, the study relied on historical research design which is qualitative and explorative in nature. Study therefore relied extensively on secondary source of data via literature survey of books, reports from dailies and periodicals, government official publications, conference papers, journal publications and internet sources. Study also proffers policy options that can ameliorate the Guyanese post-colonial political challenges occasioned by the precarious colonial experiences, internal and external security challenges.