The recent convergence of Asian and Western culture has generated interest in meditation as a practice and clinical intervention. The Burmese Mahasi style of vipassana meditation, in particular, has been a wellspring from which mindfulness-based treatment protocols have been derived. And while these clinical interventions have proven efficacious in treating a wide range of psychological disorders, clinically oriented mindfulness training is generally geared towards beginners. Further, current approaches investigating the science of meditation have almost exclusively focused on objective measures to assess the neurological effects of mindfulness leaving a rather incomplete perspective of the contemplative experience. Using qualitative narrative techniques of enquiry and analysis, this study investigated the lived experiences and ensuing subjective changes in 11 individuals advanced in the Mahasi meditative practice. The model that emerged included 7 primary themes experienced as processes and insights in the participants’ meditative practices: (a) meditative experience, (b) transformation, (c) mental/cognitive processes, (d) disturbing emotions, (e) relationships, (f) morality, and (g) living life. Several important sub-themes also became apparent such as: universal agreement on the profoundly transformative nature of intense practice; challenging stages (Dukkha-nanas, Dark Night stages) manageably navigated with (a) acceptance, (b) observation, (c) contextualizing by qualified teacher, and (d) precise guidance by teacher; moral thought and conduct based on the understanding that actions beget consequences. The study’s importance lies in broadening the awareness of advanced mindfulness meditation as a therapeutic, emotional, contemplative, and cultural enhancement to personal development, as well as providing qualitative information relevant to present and future bio-behavioral investigations.