Parenting with the End in Mind: Raising Children of Character with Chris Cleveland

About this episode

Peyten Williams and Chris Cleveland discuss parenting with a focus on raising children of character and the importance of long-term guidance over immediate control.

In this episode of What Great Teachers Know That All Parents Can Use , Peyten Williams sits down with Chris Cleveland, President of Wesleyan School in Atlanta, to talk about what he has learned from more than three decades of working with students, parents, and families. Chris offers honest, practical wisdom for parents who want to raise children of character without falling into the trap of over-control, anxiety, or constant rescue. He reminds us that parenting is hard, children are resilient, and our job is not to manufacture perfect outcomes—but to guide, shepherd, and prepare our children to make wise decisions. Together, Peyten and Chris explore the difference between raising rule-followers and raising good decision-makers, why mistakes are valuable opportunities for growth, and how parents can shift from a “microscope” view of daily struggles to a “telescope” view of long-term character formation. This conversation is full of encouragement for parents who want to play the long game: investing deeply in who their children are becoming, not just what they are accomplishing. Guest Bio Chris Cleveland has served as Wesleyan School’s head of school since 2014. He originally came…

People in this episode

Host: Peyten Williams

Guest: Chris Cleveland

Topics covered

• parenting
• character development
• decision-making
• resilience
• long-term goals

Keywords

• parenting
• character
• decision-making
• resilience
• growth opportunities

Mentioned in this episode

Organizations: Wesleyan School, Auburn University

Places: Atlanta, Georgia

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