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The quote from the stone at Bollingen begins, “Time is a child playing like a child playing a board game; the kingdom of the child.” It holds much value for those of us working with children: we are entering their world, their “kingdom” to understand and to help them develop so they will thrive in this world. The case of an immigrant family from a South Asian background who were trying to assimilate into the American culture, and yet hold on to their valued traditions, placed much pressure on their eldest male child to succeed. Like the orphanus sum quote on another side of the stone at Bollingen, he felt orphaned, and alone to face the disappointments he experienced from his parents. The eight-year analysis presented in this paper follows his journey from orphan to warrior. To enter relationship and to know oneself is key to all healing: Jung said “… the process of coming to terms with the Other in us … [helps us] to know aspects of our nature” (1955–1956, para. 706), and this is particularly true in our work with the child, as we enter the relationship going from non-understandable to understandable— a courageous journey.