Inspired by the work of Louis Sander (2008), this article explores the paradox of the developing individual who is at once singular and self-regulating, as well as systems-embedded and systems-property organized. Relying on a background of intersubjective systems theory, relational theory, and psychoanalytic complexity theory, examining this paradox reveals a deeper understanding of the evolving person and, indeed, what it means to be an individual. It also posits that a substantial developmental step includes one's capacity to tolerate two affectively discrepant dimensions of experience-that of being personal, singular, isolated, and agentic, and that of being intensely contextualized and relentlessly embedded in larger complex systems that determine much of one's life situatedness.