Trinidadian Nobel Laureate the late Sir Vidia “VS” Naipaul once wrote, “I cannot really explain the mystery of ... inheritance … sometimes we can be strangers to ourselves”. As artificial intelligence forces us to think about what it means to be human, Naipaul’s words ring truer today than ever. While AI is a storehouse for vast amounts of human information and knowledge, it does not know everything. How can we ensure Caribbean people are seen through the lens of 21st Century technologies and applications not created by us for us? And how can we find ways as Caribbean people to process the sorrow, the joy, and the mystery of belonging.