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.

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In This Episode

Peyten and Chris discuss:

• Why parenting is one of the hardest things we will ever do
• The myth that parents have total control over how their children turn out
• Why children need opportunities to make decisions and experience consequences
• How to move from rule-based parenting to decision-making parenting
• Why parents should “never waste a mistake”
• The difference between being disappointed in a decision and disappointed in a child
• How to use the “microscope vs. telescope” lens in parenting
• Why parents often unintentionally communicate that achievement matters more than character
• The “Graduation Game” and how it can help parents clarify their long-term vision
• Why raising a great human being matters more than building a great résumé

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Guest Bio

Chris Cleveland has served as Wesleyan School’s head of school since 2014. He originally came to Wesleyan in 2002 to serve as middle school principal, became principal of the high school in 2004, and assumed the role of assistant headmaster for advancement in 2010. Originally from Atlanta, Georgia, he earned a bachelor’s degree in history from Auburn University and a master’s in administration and supervision from the University of Tennessee-Chattanooga. A member of the Rotary Club of Atlanta, Chris serves on the boards of the Georgia Community Foundation, the Georgia GOAL Scholarship Program, the Cleveland Group, and the Executive Committee of the Council on Educational Standards and Accountability (CESA). Chris and Julie have been married since 1991, and they are proud parents of Kyle and Sam.

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Key Takeaways

1. Parenting is hard—and that does not mean you are doing it wrong.

Chris begins by naming what every parent knows but often needs permission to say: parenting is hard. Children do not come with instruction manuals, no two children are exactly alike, and what works for one child may not work for another.

Parents can play an important role in setting boundaries, teaching values, and offering guidance, but they cannot fully control the outcome. That truth can feel scary, but it can also be freeing.

2. Parents are guides, not outcome-creators.

One of the central themes of the conversation is that parents are called to guide and shepherd their children, not control every decision or guarantee every result. As children grow, especially into the middle and high school years, parents need to shift from simply enforcing rules to helping children become wise decision-makers.

3. Children need practice making decisions.

Chris encourages parents to start small. A spelling quiz, a homework assignment, or a minor responsibility can become a safe opportunity for a child to make a decision, experience the result, and reflect on what they might do differently next time.

The goal is not to let kids fail and leave them there. The goal is to let them learn, repair, and grow.

4. Never waste a mistake.

Mistakes are some of the most powerful teaching moments in a child’s life. Parents can allow children to feel the weight of a poor decision while still communicating love, belief, and support.

A child needs to know:
“I love you completely, and I am disappointed in that decision.”

Those two truths can exist together.

5. Use the telescope more than the microscope.

Chris shares a powerful metaphor for parenting: the microscope and the telescope.

When parents look through the microscope, they magnify one moment—a bad grade, a poor choice, a disappointing performance—until it feels much larger than it really is.

When parents look through the telescope, they see the bigger picture. They remember the child’s whole life, development, relationships, character, and future.

Parents need both lenses, but many of us default too quickly to the microscope.

6. Character matters more than the résumé.

One of the most powerful parts of the episode is Chris’s “Graduation Game.” He invites parents to imagine their child’s high school graduation day and ask:

What five words would I want to use to describe my child?

Most parents do not choose words like “high GPA,” “varsity athlete,” or “AP scholar.” They choose words like resilient, kind, independent, faithful, responsible, loyal, honest, or prepared.

The follow-up question is the one that matters most:

What am I doing today to help my child become that kind of person?

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