The Kindergarten Talk: Wisdom from a Pro and a Curious Little Heart

Two years ago, when my daughter was almost starting kindergarten, she was curious and nerves. She asked a million questions about what school would be like. But here’s the thing: she didn’t totally believe my answers. Some questions came up again and again. I could tell that she was anxious.

Thankfully, my sister in law is a public school teacher with 27 years of experience teaching kindergarten and first grade. So, I said, “Why not ask Auntie Aaron? She’s the real expert!”

And that conversation? Absolute gold. It gave me a peek into what five-year-olds really wonder before school starts, and reminded me how powerful a caring, wise adult can be.

My daughter asked: “What if I cry? Will people laugh at me?”

Auntie Aaron said: “It’s okay. Everyone cries sometimes. If you’re feeling upset and you cry, that’s totally normal.”

My daughter kept asking: “Do I bring lunch or eat there?”

The answer is “You can bring lunch or eat at school. Most teachers also let you bring a snack. Just don’t bring something super messy. You want time to enjoy it, not spend all of snack time cleaning up.”

My daughter asked more: “What will I do at school?”

Auntie Aaron said “You’ll learn letters, and how to write your name.”

My daughter looked proud, confused, and wondered. She replied: “But I already know that!”

Auntie Aaron gave her a smile and said: “That’s great! You’ll also learn math. But don’t worry, your teacher will help you go step by step.”

Then came the best part.

This wonderful, experienced, and caring teacher leaned in, looked my daughter in the eyes, and said:

“In school, you’ll need to learn how to be a good loser.”

She further explained: “There are lots of kids. You’ll take turns playing games. Sometimes you’ll win, but sometimes you’ll lose. When you lose, it’s important to lose with grace. No yelling or meltdowns. Because if you do, others won’t want to play with you next time. You won’t always be the best at everything, but you’ll have moments when you shine. Just be patient.”

That moment hit me.

As parents, we pour so much into helping our kids succeed. But life isn’t just about winning. It’s about showing up, trying again, and learning how to handle the hard parts. It’s about being kind to yourself, even when you’re not first.

My daughter felt heard, seen, and encouraged. I asked her afterward, “Do you have any more questions?” She smiled and said, “Nope. I know everything now.”

And maybe, in that moment, she kind of did.