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I want to share a short story with you, but please don’t judge too harshly. Last year, we had our three kids in a bar on Saint Patrick’s Day 🫣. I promise it’s not what you’re thinking.

We were up in New York, on the Saint Lawrence River. After wrapping up brunch with a very “tired” Easter Bunny (yes, you read that right), we found ourselves looking for something to do. There isn’t much open in that area during March, so we ended up at a local restaurant that also happens to have a bar. But this place wasn’t just about drinks, it had a giant Connect Four game, oversized Jenga, a dartboard, and some seriously delicious desserts. The kids love it there, and on most days, it’s more family restaurant than bar. But it was St. Patrick’s Day, so the bar vibe was a bit stronger than usual.

We were seated at a table but needed to order from the bar. My kids wanted water, so we told them to go up to Ms. Chris, the bartender, and ask for some. Lyla, our youngest, hopped right off her chair, got the water, and returned without hesitation. Nolan and Audrey, however, just stared at us, wide-eyed, as if we’d asked them to climb Mount Everest.

I couldn’t understand their hesitation. All they needed to do was walk across a mildly crowded restaurant, stand at the bar, get a stranger’s attention, and ask for water. Simple, right? Well, not to them. They were flabbergasted that we expected them to do this on their own.

This experience left me reeling. Why was this so hard for them? Why wasn’t it hard for Lyla, who was only five at the time? What were we doing wrong as parents?

After doing some research, I stumbled across an online organization called Let It Grow and the horribly (yes! horribly) informative book titled The Anxious Generation. Both highlighted some key issues that fit my family. They pointed to the impact of mindless screen time (think video games and social media, not coding and creative generation), which often dominates our kids’ attention, and the shrinking opportunities for kids to roam freely and take safe risks. The “shrinking space” isn’t just about our physical surroundings but also about our parenting habits. Helicopter parenting, our tendency to hover and keep our kids within “where I can see you” range, has left children with fewer chances to explore, make mistakes, and build independence.

While our intentions are good, keeping our kids safe and grounded, we may be clipping their wings, making them more anxious and dependent. And the irony? It’s backfiring.

So what can we do to help our kids grow into confident, capable individuals? That’s where Let It Grow comes in. They offer parents a guidebook filled with small, achievable Independence Challenges to help kids develop responsibility and confidence. The challenges include ideas like walking the dog (and cleaning up afterward!), gathering neighborhood friends for outdoor play, riding a bike, crossing the street, getting ready for school independently, and packing their own lunches.

The suggestions span categories like staying outside for long stretches, helping others, having fun with friends, building and creating, increasing responsibility, and taking on personal challenges. There’s even a playful “Kid License” that reads, “I am not lost or neglected,” for kids to carry when they venture out into the world.

The ultimate goal? To raise children who can take care of themselves, interact with the world, collaborate with others, and navigate their surroundings. Let It Grow recommends a simple process:

1. Make a plan.
2. Try it out.
3. GROW!
4. Document, reflect, and celebrate.
5. Explore new options.

This winter break, I challenge you to challenge your kids. Give them a few Independence Challenges and see how they do. Let them stretch their wings, they may just surprise you.

And for those wondering, yes, eventually Audrey and Nolan got VERY thirsty. With a little teamwork, they finally walked up to Mr. Chris and asked for water. Lyla, of course, was already on her second dessert and third cup of cherries, chatting up Mr. Chris like an old friend. When her siblings returned, she high-fived them and praised their bravery.