This collaborative lecture – between an esteemed Swahili poet and a German anthropologist/philosopher – shall introduce the audience to the ways in which philosophical reflections have long been part of the vivid dynamic lifeworlds on the Swahili coast (and more widely inland, upcountry). With philosophical reflections, we mean deep insights into the meanings and struggles of human existence, social critique, or performances of fundamental (self)questioning. The Swahili language has been used by male and female thinkers and authors to express and question fundamental insights or assumptions about human existence, a good life, and related matters.