Professor Gerald Schamess was a brilliant scholar, educator and clinical social work practitioner. He was an ardent believer in the value of “not knowing” in clinical practice and in the pursuit of knowledge. He embodied the spirit of inquiry and learning. While learning is a developmental and lifelong process, it often forces people to grapple with fear and anxiety as they leave their comfort zones to embrace the unknown in the process of acquiring new knowledge and skill. Inspired by Schamess, I wrote this essay as a reflection on developmental growth and learning through Winnicottian object relations lens. Winnicott has suggested that human development and growth are facilitated by and contigent upon the relationship with the good enough mother/caregiver and the holding environment. In this essay, I demonstrate the application of Winnicott object relations concepts that highlight necessary conditions that facilitated my ability to learn to swim to the deep end, in and out of the pool.