Organizational scholars have long been interested in how jazz musicians manage tensions between structure and freedom, plans and action, and familiarity and novelty. Although improvisation has been conceptualized as a way of managing such paradoxes, the process of improvisation itself contains paradoxes. In this essay, we return to jazz improvisation to identify a new paradox of interest to organizational scholars: the paradox of intentionality. To improvise creatively, jazz musicians report that they must "try not to try", or risk undermining the very spontaneity that is prized in jazz. Jazz improvisers must therefore control their ability to relinquish deliberate control of their actions. To accomplish this, they engage in three interdependent practices. Jazz musicians intentionally surrender their sense of active control ("letting go") while creating a passive externalized role for this sense of active control (using a "third ear"). Letting go allows new and unexpected ideas to emerge, while the metaphorical third ear can identify promising ideas or problematic execution and, in doing so, re-engage active agency ("grabbing hold"). Examining the practices within creative improvisation reveals the complexity of the lived experience of the paradox, which we argue suggests further integration among organizational research on improvisation, creativity, and paradox.