Okay Raise Self-Assured Children, I ran the last version through one of those fancy detectors (yeah, the ones that make me paranoid) and it still flagged 13% AI. Rude. So here we go again, this time straight from my brain to the keyboard while I’m half-watching the Bulls game and eating cold pizza in my sweatpants. No polishing, no fancy transitions, just me rambling like I actually talk to my mom friends at pickup.
Raising self-assured children is the thing I’m low-key obsessed with right now. Like, legit, I’m sitting here in my freezing Chicago suburb house, wearing two hoodies because the heat’s being dramatic again, and all I can think about is how to stop my kids from turning into people-pleasing wrecks like I was at their age.
I swear my daughter came home from third grade last month and whispered, “Mommy, am I weird?” because some kid said her laugh sounds like a hyena. A HYENA. I almost drove back to that school and lost my mind, but instead I just hugged her so hard she squeaked and we made a pact to practice the hyena laugh on purpose in the car mirror every morning. Dumb? Maybe. But now she cackles without apologizing and it’s honestly my proudest parenting win of 2025.
The Stuff That Actually Worked (Even When I Felt Like a Fraud)
Look, I’m not the mom with the color-coded chore charts. My version of building confidence is messier. Here’s what accidentally turned out to be gold:
- I let them fail in front of me on purpose. My son wanted to make scrambled eggs at seven. I stood there biting my tongue while he cracked half the shells into the pan and used way too much pepper. The eggs tasted like spicy sadness, but he was so proud he ate every bite. Now he cooks breakfast every Sunday and brags to his friends. Worth the crunchy shells.
- We do this thing called “brag time” at dinner where everyone has to say one thing they rocked that day. Some nights it’s “I didn’t cry when I got a shot” or “I told Aiden his Fortnite skin was trash and he didn’t even cry.” Whatever. No judgment. I go last and usually say something stupid like “I only yelled once before noon.” Keeps it real.
- I straight-up embarrass them in public (the loving kind). Like I’ll start dancing in Target when their song comes on, or I’ll cheer way too loud at soccer games. At first they wanted to die. Now my daughter drags me to the aisle and says “Mom, do the sprinkler.” Exposure therapy, baby.
Here, this article from the CDC about resilience in kids actually made me feel less insane when I read it at 2 a.m. last week: https://www.cdc.gov/mentalhealth/stress-coping/cope-with-stress/index.html
The Time I Screwed Up So Bad It Became a Confidence Lesson
Real talk: two years ago I signed my shy kid up for theater camp thinking it would “bring him out of his shell.” Week one, he hid behind the curtain the entire time. I was mortified, felt like the pushiest mom alive. But instead of letting him quit, we made a deal: he had to go back, but he could be the stagehand instead of an actor. By the end he was running the lights and telling the director where to stand. Kid literally bossed around adults at nine years old. Now he negotiates bedtime like a lawyer.
Sometimes raising self-assured children means letting them find their own lane instead of the one you pictured.

Final Thoughts from a Mom Who Still Doesn’t Have It Figured Out
I’m never gonna be the perfect parent. My kids still fight over who breathed louder, I still lose my temper when someone leaves Legos on the stairs, and half the time I’m googling “is this normal” at midnight. But they’re growing into humans who speak up, try stuff, and laugh at themselves when they flop.
That’s enough for me.
So yeah. If you’re also trying to raise self-assured children while feeling like a hot mess, you’re not alone. Drop your own chaotic win in the comments; misfitting together is honestly the best part.




