In this episode, we explore the long game of parenting—how raising children is less about sprinting through milestones and more about pacing ourselves for the journey ahead. Our guest is Chris Cleveland. Chris is the head of school at Wesleyan School and draws on both his 34-year career in education and his own experience being a dad.From maintaining healthy perspective to managing expectations to building resilience, we’ll talk about how parents can stay grounded, present, and connected through the ups and downs of family life. Whether you're at the start, middle, or end of this journey raising school-aged children, this conversation offers encouragement, practical strategies, and a reminder that you're not running this race alone.