My family and I came to Caldwell Academy in 2016 and have seen some big changes over the past six years. For instance, Caldwell Hall didn’t exist. It was just a drawing. The Forum was the cafeteria, and Horse Pen Creek Road was a two-lane road with ever-present traffic barrels. 

But there have also been changes others may have missed. A little third-grade boy with such bad stage fright that he hid behind the church choir is now writing a mini-thesis with zero fear of public speaking. A young second-grade boy who wondered if he could handle “Caldwell work” was inducted into the Beta Club. Caldwell’s environment pushed my boys way beyond their comfort zones and they not only survived, but they have thrived. 

Every year and each grade level bring new challenges. We go through a growing season every year and every year we conquer the mountain. It doesn’t happen overnight and it doesn’t happen in a bubble. Our students, families, and communities, make it through these tough seasons together and come out better.

As my boys were leaving the Grammar School and headed to Dialectic School, I noticed that life suddenly hit the fast-forward button. My chubby-cheeked little boys became young men, with deep voices and legs that seemed to grow overnight. I saw glimpses of the future. It started small - pulling away to stand on their own, spending more time with friends versus home, seeing their circle of influencers include folks other than their dad and me. It’s normal and natural. It’s everything that should happen. And quite frankly, I didn’t like it one bit!

However, instead of dragging my feet, I jumped in… all in!

In poker, there’s always the elusive can’t-lose hand where the player goes “all in.” They bet all they have on one outcome. It’s risky and it’s bold. It takes guts. But the payout can be huge—life-changing. That’s where I’m living right now because if I want the outcome to be two God-loving men of character, then “all in” is the only way. 

After all, we only have 938.57 weeks!

I did the math and determined we have 938.57 weeks with our babies from birth to 18. YIKES! That’s the reason, I can honestly say I am all in. I am all in for the games, the matches, and the meets. I am all in for the homework, studying, and homemade practice tests at the kitchen table. I am all in for the plays, the clubs, the concessions stand, and the Bible studies. I am all in for the friends eating everything in the pantry, drinking every Gatorade, the texts, and the gaming. I am all in with the Parent Volunteer Association (PVA), the committees, and the Board of Directors. I am in for all of it, every single moment of every week of every single one of their 938.57 weeks.

Why? Because 938.57 weeks isn’t enough time to teach them everything I want them to know and the reason why I am so thankful for Caldwell Academy. The Caldwell community is there for my boys every moment I can’t be. It steps in when the season is tough, when we need one more prayer partner, and when we need just a little bit more.

I know the day is coming when my boys won’t need me to take them to practice. One day, I won’t have to drive 100 miles a day during the week for school. No one will want me to quiz them on Latin, humanities, science, and math one day. But I know my community will still be there watching out for my boys as I watch out for their children. That’s what community is.

So here I am. Sitting in Caldwell’s parking lot… again. This is a busy place after 3:00 p.m. Student-athletes are coming in and going out. People are dressed up to see the Our Town or Winnie the Pooh productions. Parents are dropping off and picking up students at every building. Students who can drive themselves coming and going. Sometimes, it seems like I am here more than my home!

But I love to find a peaceful moment to sit and watch this community for which I am so thankful to be a member.