This chapter examines the changing perceptions of parenting wealth, particularly in first-generation families, where the focus has shifted towards creating comfortable lives for children rather than resilience and hard work. It discusses the pressures of competitive youth sports on families, the need for developing life skills alongside athletic prowess, and the importance of instilling a strong sense of personal confidence. Additionally, it reflects on relationships, integrity, and the significance of setting boundaries to foster healthy connections in an increasingly complex social landscape.