Our Family's Journey to Caldwell Academy

Posted by Amanda Bailess P '32, '35
Is it time to switch schools?

This was the question that weighed heavily on the hearts of the Bailess family for quite some time. Read how the Lord guided us throughout our journey to Caldwell Academy.
Deciding on your child's education is never a small decision. It’s something that should be deeply prayed over, approached with humility, and rooted in obedience. For us, public school had always been the plan. We even made the decision to sell our home and move into a preferred school district. But, over time, God began to stir our hearts and show us that something wasn’t quite right.

When my husband and I decided to move away from public school, we outlined our ideal school environment. We hoped for small class sizes, active parent involvement, hands-on learning, ample outdoor time (especially for our five-year-old), fine arts, and competitive sports. While we initially focused on the immediate needs for our younger children (TK and 2nd grade), we also kept the long-term vision of high school in mind. But there was one non-negotiable for us—whatever school we chose, it must be built upon Christian principles. This narrowed our choices down to either private school or homeschooling.

By February, we became serious about making a change. Many private schools now offer virtual tours and videos that make initial research easy from the comfort of home. I highly recommend visiting Caldwell’s "Welcome to Caldwell Academy" page.

While the online resources were helpful, we wanted real-life feedback, so we reached out to friends who had connections with Caldwell. The responses we received were overwhelmingly positive—Caldwell was Christ-centered, felt like family, loved and cared for the kids, and offered a strong education. It seemed like a perfect fit for what we were seeking in our next school.

After our initial research, we were eager to take the next step and reached out to the Enrollment Director. She was incredibly patient and thorough in answering all of my questions. And trust me, I had many! What does a typical day look like? What curriculum do they use? What’s the class size? What are the expectations of parents? How is Christ integrated into the curriculum? What’s the carpool situation like? What health and safety protocols are in place? For every question, April provided thoughtful, detailed answers.

By the first week of March, we were ready to see Caldwell in person. April kindly gave our family a tour of the campus. We explored the Grammar School classrooms, art and music areas, and the library—each space was vibrant and inviting. We had the opportunity to observe teachers in action, interacting with students who were engaged in learning and creativity. The tour took a slower pace once we reached the outdoor spaces. We had to stop and admire the flowers and vegetables growing in the garden. Our kids gave the playgrounds an enthusiastic thumbs up! April shared details about the outdoor covered pavilion and the numerous outdoor classrooms, which impressed us even more. By the end of the tour, our kids were tugging at our arms, giving us those "please-can-we-stay" looks.

As we left, we took a moment to pray and hold a quick family meeting. It was clear—we had found our top choice in Caldwell Academy.

While the decision felt right, it was still challenging. It meant stepping away from what was familiar—school friends, bus transportation, public school events, and the financial commitment. We spent much more time in prayer, asking God for discernment and, ultimately, for the courage to move forward in faith.

It took two weeks of prayer before we were certain that God was calling us to move forward with Caldwell. Once we made that decision, the application process began. April continued to support us through every step. The application was thorough (set aside an hour to complete it!), but once Caldwell received the records and reviewed our application, we scheduled assessments for both of our kids. They were understandably a little nervous at first, but that quickly faded. When they came out of the assessment rooms, they were all smiles! The experience was positive and boosted their confidence.
In May, we received the exciting news that our kids were officially accepted for enrollment! It was time to shift gears and prepare for the upcoming school year. Caldwell’s communication was incredibly helpful. I received details about uniforms, the school calendar, the supplies list, and introductions to other current Caldwell families.

The hardest part of the whole process was waiting for school to begin! Thankfully, Caldwell hosted “Popsicles on the Playground” during the summer, where new families could meet and connect. This event was such a blessing—it gave our kids a chance to make new friends and have familiar faces when they walked into their new school. As a parent, it was incredibly reassuring.

Fast forward to October, and we are now almost done with the first quarter. My children have fully settled in and are enjoying every aspect of their Caldwell experience. You’ll soon become familiar with terms like Grammar, Dialectic, and Rhetoric, and the uniforms will simplify life. And, if you’re like me, you’ll find that the carpool line is a perfect moment for a deep breath and a moment of peace.

Our family’s journey to Caldwell Academy has been nothing short of a blessing. The transition was not without its challenges, but looking back, we see God’s hand in every step of the way. We are excited for what lies ahead!
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    • Two Transitional Kindergarten students walking hand-in-hand in the McDonald Pavilion.

    • A young Caldwell Academy student reads a report from the front of the class.