Research on creative organizations often questions how artistic practices can be squared within the rational decision-making of economic thinking. This paper examines how the relational language, or conversation, between artistic and economic rationales unfolds for creative entrepreneurs. Through ethnographic work with a designer-entrepreneur, this paper presents a fine-grained analysis of the conversation the designer cultivates between artistic and economic rationales through work practices. We contribute to the literature about artistic and economic rationales at work, and more specifically to the concept of conversation. First, we show that high levels of conversing make way for low levels of conversing and vice versa. In the studio, the designer's engagement with either rationale varies as the creative process progresses. Second, on a more global dynamic, we demonstrate the conversation is continuous. It relies on its variations, which ensure the balance between rationales in the long run. We also contribute to the field of creative entrepreneurship research. We identify here one type of creative entrepreneur, with what we call a 'small is beautiful' attitude. Far from the mythical figure of the entrepreneur, this unconventional entrepreneur aims for sustainable use of creative resources rather than growth at all costs.