In this chapter we aim to open the reader up to alternate ways of seeing and doing reflective practice. Our contention is that reflective practices are often too heavily influenced by techno-rational thinking in which a practitioner is always seeking to break an experience in to its constituent parts in a search for a solution to the challenges of their practice. This limits the capacity for the practitioner to explore the deeper meaning of their experiences. Drawing on three philosophical concepts from Heidigger and Wittgenstein, a technological attitude, dualism, and the concept of being, we argue that there are alternate ways to engage in reflective practices that allow the practitioner to explore deeper questions about how they might live a worthwhile life. The chapter takes the form of a conversation between Emily and Andy in which Emily introduces underpinning philosophical ideas and Andy then discusses how he sees them in relation to drawing greater meaning from his reflective practices.