Recently, a colleague in a joint writing project inserted a phrase that I called into question. “Don’t you agree with Winnicott?” he asked. “Which Winnicott?” I responded. The combination of ingenious conceptualisations, occasional formulaic theory, and a superficial lack of coherence in Winnicott’s writing makes reading Winnicott exhilarating, confusing, and finally, liberating. In this chapter, I will describe how my reading of Winnicott has guided me in some clinical discoveries that I might not have found without his intellectual mentorship. I organise the chapter around the concept of “gaps” in clinical experience, which, as I discuss below, can represent initial disconnections or mismatches that are ultimately productive in furthering growth.