Letting Go
Their freedom, my fears

“Daddy don’t worry I’m just going to scoot over and play down the street with friends.”

If only it were that easy. When I was younger I joked with my mom because she’d stay up late and tell me that she didn’t sleep until I got home. I gave snarky responses like, “If it makes you feel better, I won’t sleep until I get home either.” She was never amused. I didn’t understand why, until now. I should probably apologize, not for going out, but for not understanding how difficult it was for her to let me explore the world on my own.

At 8 and 5, both boys are starting to do things without us, and it’s taking me some time to get used to this newfound independence. I never wanted to be a helicopter parent and still don’t. But how do we know what age we should let them out of our sight to start playing alone? Is it about age or how prepared we think they are and if we trust what we’ve taught them will keep them safe? How are we supposed to remain calm knowing they’ll be ok? 

A while back, I wrote a column worrying about transitioning Adam out of his crib and into a bed. I wrote about our concerns that he would just get out on his own all the time. Those fears were unfounded, so maybe I should try to learn from that experience. 

Now he wants to go scoot with friends down the street. And because he sees his big brother doing things, he wants to do more. Sure I can watch him when he goes, but how far is too far to let him out of my sight? And how long do I wait for him to come back before checking? When I let him go, he’s so proud of himself that I don’t want to discourage those feelings either.

As for Brandon, he wants to play with friends more often too. One of them lives around the corner. Do I let him walk there on his own or do I walk him over? Do I let him explore farther on his own without being around now that he’s in third grade? Or do I lurk nearby and hang out as he explores more of the world around him?

Of course I want them to learn to be independent and responsible, but how do I know when they’re ready? Or are people only ready when we give them the chance to try? And even if they are ready, we have different definitions of freedom: They want to go on their own where I can’t see them and come back when they want. I might want to drop off and be able to peek in a little. 

I guess I’m just writing through the hard time I’m having with it all. I want them to make friends, go play and have fun. But when they’re not with me, I have no idea what they’re actually doing. The hardest part of giving independence doesn’t seem to be whether they’re ready. It’s whether we all are. I guess that’s the whole point, and I know it’s not going to get easier as they get older. 

So I guess we’re now onto figuring out how to give the independence they want within limits we can live with. Sometimes parenting is just coming up with answers to new questions and finding new things to be concerned about each time I feel like I’ve figured things out. 

Read More “Making Time” by Jason Springer

December 2025
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