This article examines parallel challenges and avenues for progress I have observed in my efforts to introduce improvisation in classical music studies, and meditation in music and overall academic settings. Though both processes were once central in their respective knowledge traditions--improvisation in earlier eras of European classical music, meditation and contemplative disciplines in Western philosophy--as well as being globally prominent, they nonetheless occupy marginalised roles in the contemporary academy. Other parallels include the challenges and benefits inherent in the interplay between tradition-specific and trans-traditional engagement, where grounding in a musical lineage such as jazz promotes informed trans-idiomatic musical exploration and synthesis, and grounding in a contemplative lineage provides foundations for navigating the often-turbulent waters of the contemporary spiritual smorgasbord. I argue that a more critical look at integrity of practice, consisting in not only methodologies but also views of consciousness and human development, is key to the future progress of the contemplative studies movement and the contributions it may make to education and society at large. Educational Philosophy