Parenting a Highly Sensitive & Introverted Boy: Our Journey Toward Healthy Confidence

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From the moment my son was born, I knew there was something unique about him.

First of all, he cried… a lot. Part of it was due to some health issues, but I intuitively knew there was more to it.

He acted like a grumpy old man in a baby's body. I used to half-joke that he was like someone struggling to accept that he had been born again and now had to do life all over. And once or twice, I actually did whisper to him to just let go and enjoy being a baby again😅.

At three months old, he cried in frustration because he tried and tried but couldn’t yet sit upright. Later, when he began crawling, he got angry that he couldn’t yet walk. He started talking late, but he skipped all baby talk and went straight to serious topics: "why is my milk white?"👀.

I’ll never forget the day, just before his third birthday, when he stood in front of the mirror in my bedroom, looking sad and perplexed at himself, and told me he wasn’t supposed to look like that. That something went wrong and that he was ugly…😞

My mama heart shattered💔.

For years I had dreamt of a son just like him, and he looked exactly the way I imagined he would—a perfect copy of his dad: the bluest eyes, golden skin, and blond curly hair. To me, he’s the most beautiful boy I’ve ever seen.

How could he see himself any other way at such a young age? Why was he being so hard on himself and showing signs of low self-esteem at 2 years old?! (Nope, he didn’t experience any traumatic event, bullying, abuse, or whatsoever...)

I could see how deeply he struggled. But reaching him was even harder.

Now he’s 11 years old. He’s still that highly sensitive, introverted, smart boy, but I can’t tell you how proud (and relieved) I am of the progress he’s made.

I’ve tried many traditional strategies to help boost his self-esteem. Most didn’t help. But here are 5 things that actually did. Who knows—maybe they’ll help your kid(s) too.

1. Give compliments indirectly

He used to get very uncomfortable when he received a compliment. He would brush it off, run away, or get downright angry and scream, “NO!”. 👀

I thought that to be so strange—because who doesn’t like getting compliments? Not even from their mom? But I later learned that kids who are extremely perfectionistic can feel pressure, as if the compliment sets a new standard they must now always live up to. They may also perceive it as inauthentic if it clashes with their own inner judgment of themselves.

One time, when he was five years old, I was putting his school picture up on the fridge. As I did, I spoke to the photo, telling it how beautiful he was, knowing he was in the living room and could hear me. He didn’t respond, and I thought, Wow, that’s progress.

So I started doing it more regularly—giving him positive feedback indirectly by talking to his picture within earshot. One day, I caught a little smile in the corner of my eye🥰. And that’s how I knew it was working! I also made sure not to compliment achievements too much (which can make perfectionism worse), but to focus on character qualities and efforts made.

And so, over the years, I switched from the picture back to him directly. Now he receives compliments with a smile (even though he’s still not always comfortable with it).

There's always room for a picture though ☺️

2. Offer advice indirectly

Giving compliments isn’t enough to build up positive self-esteem. I wanted to talk to him about his struggles, his experiences, offer advice—but he often took it very personally, and it ends up having the opposite effect.

I didn't completely erase these talks, but I started using a different method, additionally.

He has a whiteboard in his room, and about once a month—after giving his room a deep clean—I write a few relevant affirmations or quotes on his board that promote healthy confidence.

Every time I clean his room, the first thing he does is go to the board to read that month’s advice. It’s become a quiet, meaningful ritual between us.

3. Help them find a healthy emotional outlet

He doesn’t like to talk about...anything! But especially not about his feelings. I tried everything to get him to open up when something was bothering him. I suggested writing it out—he wouldn’t. I suggested painting—he wouldn’t. He would just sit and fester. Not knowing what was going on inside him, I would get frustrated, which only created more tension between us...

But I knew he had to learn to let it out somehow, because I could see the water boiling beneath the kettle. I wanted to prevent what I felt was coming 💣💥.

We eventually discovered something that does help: his passion—soccer. He’s been playing three times a week since he was five. Now, whenever he’s happy, angry, frustrated or sad, he goes outside and plays with the ball—on the trampoline or against the wall—until he feels better.

It’s still a work in progress though. But, the advice and note to self here is: don’t push or impose your way onto your child. Instead, observe. Notice the healthy outlets they naturally gravitate toward—and help them hone those. And most of all, give them the time and space they need to process in their own way.

4. Gently Push Them Out of Their Comfort Zone

When he was younger, we used to play checkers. And even though he was often genuinely better than me, I would still let him lose sometimes. Losing really triggered him. He would get angry, refuse to play anymore, and lock himself in his room.

It was tempting to just let him win every time—or only play cooperative games to avoid the emotional fallout. But then he’d never learn to manage or regulate those difficult emotions.

So instead, we take the long road: gentle exposure.

He loves routines, familiarity, and his interests are very limited and specific. But once again—thank God for soccer⚽! Sports naturally bring a wide range of experiences that teach kids to deal with both success and failure.

Still, I try to regularly coax him into stretching his comfort zone. Sometimes it’s as simple as this week’s challenge: “You’re going to get out of the car and help me pick up your sister—say hi to the teachers.” He had to do it, even though he offered to pay me his allowance just to avoid doing that, haha.

Why? Because I know him. If I don’t help him stretch his comfort zone, he’d stay in it forever. And he’d miss out on the sense of success—and the confidence boost—that comes from seeing he can handle discomfort, and even feel proud when things go well.

5. Learn Their Love Language

Every child needs to feel loved—but the way they receive that love can look very different from how we might naturally express it. Learning my son’s love language has been one of the most meaningful ways to boost his self-confidence.

He’s not one to want hugs or deep talks (sadly, because that's me, haha), but he absolutely lights up when I surprise him with food he loves—a favorite meal, a special drink, or a fun snack I picked up just for him. He also loves it when I go outside and kick the ball with him.

What is your child's love language? Is it quality time, words of affirmation, gifts, acts of service, or physical touch? Once you discover it—or them—speak it fluently. It’s one of the most direct ways to fill their inner tank.

In short

It hasn’t always been easy. In fact, some seasons have felt downright nerve-wracking. But little by little—with a lot of trial and error, patience, prayer, and love—we’ve seen incredible growth.

If you’re a parent in the thick of it right now, I want you to know you’re not alone. And don’t hesitate to reach out for support when you need it. The thing about reaching out is that not everyone will understand you, your child, or your situation. Sometimes it’s tempting to keep these difficulties to yourself. But reach out anyway—and take everything you hear with a grain of salt.

I leaned on a combination of literature, reflections from my life and work experience, and advice from a child psychologist to help me find the parenting path that fits my son. But most importantly, I am learning to trust my intuition to lead the way.

Trust that with time, compassion, and the right help, things can get better.

Your sensitive, beautiful child is not broken. He’s just becoming. And by this, I mean learning to become that version of himself who can honor who he really is, while also developing the resilience and confidence needed to live in this society.

This magical piece is called Give Your Soul by the wonderful artist Lara Bonomo. Click here to listen to the beautiful poem she shared with this painting, and be sure to show her page some love!