This article discusses the clinical and theoretical work of Phyllis DiAmbrosio in relation to her patient, Jackie, and proposes a contextualist perspective informed by complexity theory. The notion of individual resilience is understood as a product and property of the larger, complex relational system in which both patient and analyst live. The crucial distinction is made between thinking and speaking phenomenologically as opposed to explanatorily. The concepts of attachment and accommodation are considered vis-à-vis how therapeutic action is understood in this particular clinical context.