Dear Jackson and Oliver,

Tonight the house feels a little different. Your new backpacks are lined up by the door, pencils are sharpened, and I keep having to remind mom that bedtimes actually matter tonight. Tomorrow you both walk into a brand-new school year… Jackson into sixth grade, Oliver into third… and I couldn’t let this moment pass without reminding you of a few things.

First, I love you. More than you’ll ever know, more than any words can capture. I am proud of the young boys you’re becoming… not just because of grades, or sports, or accomplishments, but because of the kind hearts you both carry.

School isn’t just about math problems or reading levels. It’s about learning how to be the kind of people the world needs: leaders who listen, friends who show up, people who stand tall when it isn’t easy. That’s what leadership really is… it’s courage. It’s raising your hand not just to answer a question, but to include the kid sitting alone. It’s choosing gratitude when things don’t go perfectly. It’s forgiving quickly so you don’t carry heavy stuff in your heart. And it’s showing compassion not just with words, but with action.

Jackson… you’re stepping into the big kid role at your school now. Remember: being a leader doesn’t always mean being the loudest voice in the room. Sometimes it means being the one who listens the most. Trust yourself. You’re ready.

Oliver… you’ve still got that spark that makes every room brighter the second you walk in. Third grade is a chance to learn, to play, to keep asking big questions. Don’t ever lose that joy. People will follow your lead because you remind them how fun life can be.

And both of you… never forget one of the best pieces of advice I’ve ever learned… “have a lot of fun” in everything you do. Yes, work hard, pay attention, and respect your teachers, but don’t forget to laugh, to play, to find the joy in every single day.

So tomorrow, when you walk into those classrooms, walk in with love, with courage, with gratitude. Be leaders. Be listeners. And above all, be kind.

Mom and I couldn’t be prouder to be yours.

I love you forever,
Dad