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This case study of Dr. Esther Perel's How's Work? podcast focuses on couples who work together. Two primary types of relationships shape the study: those in business together who are blood related and those who are married or partnered. In this work, taboo is constituted as uncomfortable topics that remain undiscussed. Prior to therapy, Perel's dyads did not openly speak about their issues with one another. What they did do, however, was mentally roll over the issues on their own. Even though both parties deeply considered the taboo issue(s), they did not directly address taboo topic(s) with their partner until they had the opportunity to do so with Perel. To that end, this work is an extension of Roloff and Johnson's research on taboo topics that are left undiscussed until they are carefully addressed in a planned interaction. This chapter contributes to knowledge around taboo topics relevant to family business and how different types of families have differing taboos.