This practitioner reflection focuses on the challenges and possibilities of encounter dialogue-music education organizations in Israel/Palestine using musicking (Small, 1995) and dialogical programming to examine, question, and reflect upon the purpose and role of Israeli and Palestinian national days, markers which build individual and collective identity in irreconcilable dissonance with each other. By entering this vulnerable space, we as educators are not exempt from the internal and critical search for understanding of self and community while educational planning and teaching. By exploring “the heart of the educational mission” (Palmer, 2010, p.50) at its foundations of “how do we know what we know” and “by what warrant can we call our knowledge true,” we can collectively uncover through musicking past realities, while also co-creating new locations of possibility (hooks, 1994) in the pursuit of (e)quality of education.