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In “Communicating and Not Communicating Leading to a Study of Certain Opposites,” Winnicott introduces the radical idea that communicating with subjective objects is “cul-de-sac” communication (communication not meant for any external or internal object), but which nonetheless endows every aspect of one’s experience with “all the sense of real.” He conceives of the “main point” of his paper to be the idea that “each individual is an isolate, permanently non-communicating, permanently unknown, in fact unfound.” I suggest that the “main point” is more inclusive and might be stated as: each individual needs equally to be found (recognized, but not exposed) and to be unfound (an incommunicado isolate). Winnicott warns that when an analysis has reached the depths of the patient’s personality, interpreting destructively introduces what is “not-me” too close to the core self, so “the analyst had better wait.” An unstated question arises: what does the analyst do while he waits other than remaining silent? I respond to this question by giving clinical examples from my own clinical work. Winnicott ends the paper with the language of poetry in his effort to communicate something of the mystery of being that is “absolutely personal” to each of us. Winnicott at the end of his paper sheds the language of prose and adopts the language of poetry in what I view as his effort to communicate something of the mystery of being.