In this article, I suggest recent sources of influence on psychoanalysis and describe a contemporary relational self psychology that is my personal attempt at integration. Even with this integration, I struggle to find the right “therapeutic” balance between my essential but imperfect instrument for empathic listening, on the one hand, and the risks of authentic engagement, on the other. These dialectical tensions in me mirror those in the psychoanalytic community as a whole, poised between a scientifically based practice and a healing “art”—or between a complex but teachable methodology or discipline—and an ordinary (yet extraordinary) human relationship in which spontaneity and even improvisation play a role. Complicating this balancing act, there is new evidence from neuroscientists, attachment theorists, and infant–caregiver researchers that, from birth onward, bidirectional influences on brain and psychic development create contingent and unpredictable outcomes in every intimately related dyad. Thus, the contemporary analyst must expect to be changed by the work and—while taking full responsibility for his or her own contribution—must recognize patient and analyst as co-creators of the psychoanalytic project. At the same time that we now recognize contingency, complexity, and chaos at the heart of human minds and relationships, we also acknowledge the central importance of a sense of continuity and coherence as the individual undertakes the pursuit of goals and relationships in life. What kind of relationship can facilitate these qualities in the sense of self? That is the question that this article undertakes to answer.