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Much has been written about the dialogical nature of group improvisation (Bailey, 1992; Berliner, 1994; Borgo, 2004; Fischlin & Heble, 2004). Dialogue sits nicely in a situation where many people are ‘speaking’ musically to each other around a common ‘topic’ or referent. But what about improvisation when it occurs outside the social setting of group playing? Is the act of solo improvisation a monologue given the absence of fellow ‘speakers’? Building on research in cognitive studies (Sarath, 1996; Pressing, 1987; Gustavsen, 1999) as well as empirical research in the field of pedagogy of improvisation, this paper argues that the act of solo improvisation is inherently dialogical – a dialogue between musician and musical entity as ‘Other’ – and proposes that the existence of that dialogue is predicated on the art of listening. This art of listening will be discussed in light of two opposing directionalities or listenings: (1) inner directionality is expressed in the musician's audiating of her inner musical imaginings and translation of those imaginings into what the fingers play and (2) outer directionality: perception of and response to the emergent qualities of the musical idea (Gustavsen, 1999) as it manifests itself in the “sacred space” of play (Huizinga, 1949) between the musician and the improvisational continuum which constitutes the musical entity. Field research will be discussed which suggests that successful mastery of these two types of listenings in tandem is what allows the improviser to engage in dialogue with the musical entity, and affords the improviser a new ‘way of knowing’ the musical entity. The same research suggests that in the course of mastering these listenings, the improviser calls into play a number of socio-cognitive functions which, in turn, reflect multiple social positionings. These include: decision-making (authorship), divergent thinking and willingness to embrace the unknown (diversity and inclusion), risk-taking and problem-seeking (unsettling certainty), accountability and self-assessment (responsibility, integrity, and challenging assumptions). Herein, the dialogue of improvisation affords the improviser an ‘epistemology of self’. Acknowledging solo improvisation as a way of knowing through dialogue may allow educators to construct models of engagement which can lead students toward personally meaningful dialogue between self and art. Additionally, an understanding of the socio-cognitive functions and social positioning traits inherent in acts of solo improvisation suggests that it could play an important role in education for freedom as envisioned by such thinkers as Maxine Greene and Paulo Freire, a freedom exemplified by conscious imagining of possibilities, creating and sharing meanings, and dialogue between self and other.