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23. Pushing Your Child vs. Waiting Until They’re Ready (challenges of the shy kid)

If you have a little one who is super timid, then this will be a great episode for you. I have a little guy who gets quite nervous in new situations, AND…. I was a shy kid growing up.

I was afraid of my own shadow… OK, maybe not actually :) But I would never raise my hand in class and I definitely wouldn’t order for myself at a restaurant. I’d rather starve than speak to a waitress!!  So I can definitely shed some light on shyness and overcoming that label and those feelings as I progressed into adulthood.

I want to tell you this story of when my son started junior kindergarten a couple of years ago.

He was the kid SCREAMING bloody murder at drop-off each morning. The kid that had to be pried away from his mom's arms.  And I was the parent hiding in the bush nearby so he couldn’t see me, crying and praying he would calm down. It was heartbreaking. 💔

No parent wants to see their kid struggle this much. And when your child is screaming like that, it kind of rips your heart apart. It’s almost physically painful.  

Now, I hadn’t been expecting that kind of reaction. Yes, he was timid and often clung to me in new situations. BUT I had been dropping him off at daycare each and every day for years with very little issue. And on the days he did cry and cling, he stopped as soon as I left. And I could see this through the one-way glass into his preschool classroom. 

Now, in hindsight, there are a variety of reasons why the school drop-off was so traumatic for him and I’m so grateful for the ECE he had who would stay outside and talk with him until he calmed down and was ready to go into the school on his own. 

But that first week and a half was HARD. He did much better when my husband dropped him off…. He was always better at being dropped off when Dad was doing it. Many kids are. They don’t cling to their dads the same way. 

My son did better as the weeks went on. He was capable of going on his own and he eventually figured out that it was OK for him to go.

Now, there is a FINE LINE between pushing our kids and respecting their need to go a bit slower. 

Did I do the right thing by letting him go screaming every day? It’s a couple of years later and I still can’t answer that question. 

This is the gray area of parenting. These are the times when our goals or values may conflict with one another, so what do we do?

We want to support our child's emotions, respect their need to take things slower, and trust that they’ll eventually get there at their own pace. We want them to know that we’ve always got their back and will be there for them when they struggle.

There is a real and valid argument for turning around on those first few days of school and saying “we’re just not ready.”

But sometimes this just isn't possible if you have to get to work. You won't have a choice. So sometimes, we’ve just got to rip the bandaid off and trust that they'll get over it. And they will eventually.

Sometimes there is a consequence to being over-supportive though. Sometimes the real need that they had initially turns into an attention-seeking behavior or an attempt to control you.

When we can step into our child's shoes, this makes sense. Kids do what works.  It feels good to be with mom. It feels comfortable and safe and I can get her all to myself if I scream and fight at school drop-off or tell her I’m scared.

And this might be especially applicable if there are siblings…. 

The older siblings go to school and I’ve got mom all to myself. Or I don’t want mom staying home with the younger siblings. I want to stay home too. 

So what was initially a legitimate fear is now a recurring behavior. 

And it still might be true that they’re not ready for the school environment. 

 However, there will come a time when your child will have to push past their fear and walk into an uncomfortable situation. They also need to know they are capable of dealing with discomfort.

So the alternative argument or flip-side of this discussion is to push your child (as I did in the particular example I gave with my son starting school) because you trust and KNOW deep down that your child is capable. 

There’s something to be said for pushing your child out of their comfort zone. Half of your life (if you’re really living it) will be spent outside of your comfort zone. If you ever want to travel, learn a new thing, meet new people, get a job…. So much is new. So much is uncomfortable.

Our kids need to learn that they are capable of pushing themselves. That they’re capable of doing new things. They’re not going to die. They will survive.

Pushing your child is also a valid option too.

So how do you pick? Which one wins out?

This is where it gets really tricky because there’s no right answer. There’s no secret formula.

It’s always a good idea to support your child and trust that they know themselves best. AND it’s always a good idea to believe and trust they’re capable of doing something hard even when they don’t yet see it themselves. 

This is one of those situations where we really need to trust our instincts while recognizing that no decision is ever permanent. We’re not going to harm our child if we get it wrong. We always have the ability to change our minds or alter our decisions. 

We are learning with our child and each step forward brings us new information to help us inform our decision. And this new information might validate the path that we’re on, or it might indicate that we need to switch things up. 

We can’t be afraid to take a step forward.
There’s no getting it wrong.
The only thing we get is more information or a slightly new perspective to then help us figure out the next step.
That’s it.

It’s really not more complicated than that.

And if you’re worried you’re going to screw up your child then I’ve got news for you: You can’t.

They are meant to live the life they’re living. They’re meant to live their life with you as their parent. They chose you to do life with and it’s not going to be perfect. They’re not meant to live in these perfect little bubbles.

If they’re shy and timid, that’s OK. We can accept that that’s the way they are. AND we can help them change over time if they want to. We can believe in them when they don’t believe in themselves. We can see them as capable even when they’re afraid.

And we can still support their feelings as they walk into uncertainty with us alongside them, even if that’s not always in a physical way. Even if it’s only in the emotional or spiritual way. Because those ways matter.

Parenting is never black and white. It’s always this murky gray area that we have to muddle through and sometimes there will be straightforward answers and other times you’ll have no idea and you’ll second guess yourself every step of the way. 

We too have to get comfortable navigating this uncertainty. 

And if you want help with that, I encourage you to join my parenting mastery program. You can learn more about it by checking out my free training on getting your kids to listen at or send me a DM on Instagram and we can chat about your specific situation to see what makes sense for you.

And until next time…. Happy parenting!

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