According to the French historian and philosopher Pierre Hadot, ancient philosophy was a living practice based on spiritual exercises and a corresponding discourse. This dissertation investigates one such exercise – the exercise of listening, which formed part of an ancient and rich cultural-philosophical and pedagogical effort of self-(trans)formation, commonly referred to as paideia. Despite the importance attributed to it by the ancients, listening as an acknowledged practice in ancient philosophy today has not received the attention it deserves. This is the first problem I focus on in this project. In addressing this problem, I seek to contribute to the creation of an overview of the history of philosophy on listening in Western thought, which to this day does not exist. My approach concentrates on discerning what we may refer to as the earliest philosophies of listening in the ancient world (more specifically: Archaic and Classical Greece, and Republican and early Imperial Rome), and identifying any continuities that may exist among them. The second issue that I am interested in studying follows from the first but is orientated toward the present. My aim here is to revitalise some of the existential dimensions of spiritual listening for us today and provide some – not exhaustive – orientation for present-day Philosophy as a Way of Life (PWL) practices oriented towards listening. Based on three contemporary instances of philosophical, and thus, paideutic activities – listening to (1) texts, (2) interlocutors, and (3) nature – I argue that listening as a spiritual activity in certain contexts can (and perhaps should) be revitalised today.