This study explores how Cubans organize their everyday livelihood strategies between the tacit principles of capitalism and socialism. Having conducted four months of ethnographic fieldwork in Cuba, I examine how individuals negotiate the contradictions which unfold within the island's economic system, where competing ideals of free market liberalization and social redistribution collide in discourse and practice. This collision is highlighted through ethnographic vignettes which showcase how Cubans who have grasped the legalized opportunity for self-employment have simultaneously been required to navigate difficult political economic circumstances, as committing oneself to these forms of independent labor also compels them to encounter their own in-formal ways to make up for systemic deficiencies. Blending semiotics and performativity with a political economic approach, I draw out how Cubans improvise beyond these structural limitations, showing how their performances of 'making do' often involve intermeshing seemingly contradictory socioeconomic dynamics.