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.