New Monasticism is a concept that describes the phenomenon of agents and teachers emerging from religious institutions (e.g., monks and clergy) to teach a largely liberal and perennial spirituality to a diverse and globalized audience. Examples of these new monastic teachers include Richard Rohr (a Franciscan friar who founded the Center for Action and Contemplation to promote his brand of new monasticism), Cynthia Bourgeault (an Episcopal priest who teaches a perennialist sense of wisdom spirituality), and James Finley (a retired clinical psychologist who studied with Thomas Merton and teaches from Merton’s interreligious contemplation). All three attempt to contextualize their perennialist writings through discursive techniques common among past esoteric texts and teachers. However, these same new monastic authors have distanced themselves from the “esoteric” as a description of their teachings, arguing that their spiritualties are anything but “secretive, elitist, or obscured.” Can religious authors structure their teachings with elements common in esoteric literature while simultaneously rejecting the general nomenclature or concept of esotericism? I argue that Rohr, Bourgeault, and Finley engage with a dynamic tension between employing esoteric techniques while denying a general understanding of the “esoteric” within their works. I will examine Bourgeault’s The Wisdom Way of Knowing (2003), Rohr’s The Enneagram: A Christian Perspective (2001), and Finley’s Merton’s Palace of Nowhere (1978) to demonstrate how this tension is reflected in each author’s early work. I will use the typology of esotericism created by Antoine Faivre (Access to Western Esotericism) and Kocku von Stuckrad (Western Esotericism and Locations of Knowledge in Medieval and Early Modern Europe) to identify the esoteric elements present with each of the three works above and their respective author’s teachings. My conclusion is that it is not only possible to participate with this tension on esotericism but that it is likely inherent within new monasticism in general, specifically with their shared goal for their teachings to improve the lives of individuals and the entire world.