Cultivating non-dual awareness involves transcendent movement through specific stages of psyche development. This transition allows for freedom from the constraints of the ego self or the illusory self and the mind, and a new focus on the collapse of dualism into oneness and acceptance of life as it presents itself. Such non-dual awareness was thought to be a rare occurrence, but new research is pointing to its increasing availability and accessibility. This transcendence, however, is not without its plights, crises, fluctuations, and breakthroughs. Using a transpersonal, existential, and phenomenological approach the authors investigated consciousness as it manifested in the journeys of nine novice’s awakening and transitioning from duality and separation into non-dual being. This article focuses on the themes that manifested in the initial transition from duality to non-duality. Existential issues, as well as resistances to them, played an important role in serving as openings into such non-dual states of being. Themes in duality included: Seeking to the fill the void, frustration, and despair; reinforcement of the ego through the other and assumed roles; a lack of sense of belonging resulting in alienation and loneliness; patterns of childhood trauma and resultant wounding; and experiences of betrayal, fear, and adopted coping mechanisms. Themes during the transition into non-duality included: Disillusionment with seeking, failurehood, and the seeker’s hell; ego deconstruction and questioning of reality; experiences of intuitive knowing and gnosis; direct experiences of non-duality; recollection of childhood experiences of no-self and oneness; reassertion of the mind and ego, as well as fluctuations in and out of non-duality; avoidance of spiritual bypass by working through wounds and personal issues; and fueling of the non-dual journey by reconnecting to one’s authentic energy. These themes are explored in the context of transcendence through the stages of psyche development and the implications of the first part of the novice’s journeys of awakening into non-duality are discussed.