Raising Kind in a World That Feeds on Cool: A Love Letter to My Empathetic Son

By Wanda Thomas | Parenting in Progress

Cristian is the kind of kid who’ll hand you the last slice of pizza even if he hasn’t eaten all day. The type of boy who stops mid-step to hold the door open, who notices when you’re upset even if you haven’t said a word. His kindness isn’t performative—it’s instinctual. It lives in his bones.

And maybe it’s because he’s the youngest… or maybe it’s just how he’s wired. But there’s a tenderness to him that’s different. It’s unfiltered. Unbothered by ego. But it’s also… vulnerable.

He’s 14 now. Teetering on the edge of high school, caught in that strange middle place between little boy and almost-man. You can feel it in his energy—equal parts bold and unsure. He’s still my baby, but his shoulders are getting broader. His voice is deepening. And more and more, I’m watching him try to navigate a world that doesn’t always reward boys like him.

Because the truth is: this world is loud. Fast. Competitive. It wants boys to be funny and aloof, confident without being “too emotional.” It teaches them to trade kindness for coolness, to hide their gentleness behind sarcasm and swagger. And that breaks my heart.

Because Cristian is not built like that. And honestly? I don’t want him to be.

I want him to stay soft in the right places. To keep seeing the good in people. To keep asking questions, leading with curiosity, checking in on his friends when they seem “off.” I want him to stay empathetic, even when the world tells him that’s not the “cool” thing to be.

But I also know what’s coming. I know how middle school can strip kids down. How high school culture starts whispering that being tender is weak. That ADHD makes you “too much” or “too different.” And I know there will be moments when Cristian starts believing those lies.

He already does sometimes.

I see it in the way he hesitates before raising his hand in class.
In the way he shuts down after a rough social interaction.
In the way he apologizes too often—even when he hasn’t done anything wrong.

Sometimes, I see him shrink himself to fit in. And I want to scream, “Baby, you were never meant to fit. You were meant to shine.”

But that’s not my line to deliver—it’s his to discover.

What I can do is this:
I can remind him—over and over—that being kind is powerful.
I can help him understand his ADHD not as a flaw, but as a lens that helps him see things others miss.
I can celebrate his emotional intelligence as much as his grades.
I can keep reflecting back to him what I see: a resilient, thoughtful, hilarious, big-hearted boy who is still becoming.

And I can do the harder work too:
Like stepping back when he needs to learn by trial.
Letting him stumble through awkward moments without rescuing him.
Not projecting my old wounds onto his new story.

That’s the hardest part, really—learning to parent the kid I have, not the kid I used to be. To not panic when I see in him parts of myself I used to hide.

But Cristian isn’t me. He’s his own story. He’s his own kind of magic.

And no matter what this world throws at him, I hope he always knows this:
His softness is not a liability.
His empathy is not a weakness.
And his mama will always—always—be in his corner, cheering for him to stay exactly who he is.

Even if that means standing out in all the best ways.