What’s your parenting hill to die on—and what are you willing to let go?

Dr. Siggie Cohen is back for a game of “Parenting Hill to Die On,” where Roxy throws her a series of everyday parenting dilemmas and Dr. Siggie has to decide: is this a battle worth fighting, or one parents should simply let go?

From kids refusing to wear a coat and quitting activities to bad grades, swear words, smartphones, and saying no to Grandma’s hug, Dr. Siggie weighs in on when parents should hold the line—and when giving kids autonomy matters more.

Along the way, she explains why not every uncomfortable parenting moment requires intervention, why some boundaries are non-negotiable, and how knowing which battles matter can help us raise more independent, resilient kids.

And yes, there are a few answers that might surprise you.

🎧 Missed our full conversation? Listen to Dr. Siggie Cohen: Has Gentle Parenting Gone Too Far? on The Iconic Midlife.

➕ Follow The Iconic Midlife and follow Roxy Manning on social media (@theiconicmidlife and @redcarpetroxy) for more conversations about parenting, relationships, health, identity and navigating midlife.

What’s YOUR parenting hill to die on? Tell us.

The name of this game is parenting hill to die on.

I will give you a scenario or a trend and hill to die on is no, I'm going to hold this boundary.

But let it go is it's not worth the battle.

Your kid refuses to wear a coat when it's freezing outside.

Hill to die on or let it.

Go, depending on your child's age.

But here's what you want to actually do.

It's not a hill to die on.

Your child tells you, I hate you because you said no Hill to die on.

Let it go.

Definitely heel to die on.

Yeah.

No, you can say I'm very angry.

Yeah, no, you don't hate me.

But I understand right now you're so angry that it feels like, hey, no, I really hate you.

You hate what just happened.

It's not about fighting.

You are the guide, the mentor.

You are the leader.

You're the wise one.

You're here to guide them through even those ugly tough moments at the end of every episode.

We love to play a game with our guests, if you would be up for it.

Ok.

I don't know.

I'm scared now.

You got this.

I know you've got this.

So the name of this game is parenting Hill to die on.

So I will give you a scenario or a trend and hill to die on is no, I'm going to hold this boundary.

But let it go is it's not worth the battle.

Your kid refuses to wear a coat when it's freezing outside.

It's heel to die on or let it go.

Such a good one.

Definitely depending on your child's age.

But here's what you want to actually do.

It's not a heel to die on, but it is for you to foresee that they may actually need that coat.

And you work with no, you have to put it on now.

It's cold.

It's like you can do a few things in between that friction and conflict and, you know, do or die kind of a thing.

So teach them about the weather, go outside and you see for yourself rather than we are now.

Oh, it's so warm and cozy in the house.

I don't need it.

Just step outside, sweetie.

Stand there for two minutes and see what it feels like.

And then you decide you want to give some autonomy.

You create a parameter that is safe for them to fail on and then you fill in some of the blanks when you actually know the big picture.

Good point.

We've had a few of those conversations.

My 10 year old wants to quit the sport.

They begged you to sign them up for halfway through the season, hill to die on or let it go.

It's not a hill to die on, but it is a teachable moment and a teachable lesson.

So.

So absolutely they don't have to do everything.

And really they're not even good at it or they're not enjoying or something.

You know, kind of like look at the whole thing.

But don't just let them quit because today they're not feeling like going out there into the field and I hate it.

I don't want to do it.

You have to be the wise one and know and see the big picture.

And sometimes remembering, not necessarily reminding them, but sometimes it is remembering what it is like for them when they're out there.

Are they actually somewhat maybe good at it is one thing.

Enjoying it when once they're already there, you can actually say that, you know what, we're not quitting mid season and don't go into lecture your teams and we made a commitment and the money, all these adult stuff.

Keep away from them because they're irrelevant.

But what is relevant is we're sticking with this.

We can revisit it at the end of the season 100%.

But here's what I want to tell you.

I know right now in this moment, you're like, oh, I don't want to go out there into the cold or the heat, whatever it is.

Right.

I get it.

We're still going to do it.

Because I remember that once we're there, once we get over the hump of this transition, you actually are enjoying it.

You love seeing your friends, you like, your coach, you.

You're actually even good at it.

And that's why we're sticking with it.

Your teenager wants to wear something you think is completely inappropriate hill to die on or let it go.

Up to a certain degree.

Obviously, I would say it's almost like food.

Those are issues that if you do not actually fully focus on, they do go away on their own.

You fight with your child on food.

That becomes.

That becomes the biggest problem.

As opposed to just the food.

Clothes is sometimes that let them wear whatever go through fashion styles and trends and as long as it's truly, you know, weather kind of, you know, sensible and also what is out there.

Does your school allow this?

Right.

You have other systems in place, by the way.

You're not all alone there and your child has to in a way abide by the school system.

Even when they say, well, I don't care.

There are some consequences to that.

So, ah, you know, I don't think this is.

This is the best choice.

But you feel good in it.

You think it's okay.

Your school allows it.

Yeah, I'm okay.

Because you know what?

90% Of especially fashion twins do go on and move out of the way.

Right.

And yeah.

Not a heel to die on.

Yes.

Okay.

Good to know.

Your kid says, but all my friends have one about getting a smartphone hill to die on or let it go.

It's.

First of all, you don't want to die on that hill, but you definitely want to be wise about the things that your children tell you that are complete fabrication.

And I want to say, Eli.

Yes.

So it's not that they're lying.

They're pulling a piece of information, maximizing it to make a point and to convince you.

They're like really good salespeople.

Really good salespeople slash publicists.

Exactly.

They can take any little thing and turn it into ta da.

And then you have to.

Because the pressure.

Yeah.

Always know all my friends.

When it starts with all my friends or sometimes even all my friends.

Parents.

Yeah.

Right there.

You know.

Yeah.

No.

And by the way, if we actually called your friend's parents right now and immediately.

No, no, it's this.

But yeah, don't take that at face value ever.

You don't want to die on that hill, but you can definitely stick to your grounding.

Go.

Yeah, we're not getting a phone.

You.

And I'm sorry that I don't know if all your friends have it.

I bet some do, some don't.

This is what we're doing.

End of conversation.

Okay, good.

I'm like, that's definitely going into my arsenal of tricks.

Your child refuses to hug grandma goodbye.

He'll to die on or let it go.

Definitely let it go.

But everything has.

Right.

Almost nothing is just this black or white.

White extremes.

Right.

So instead of telling your child what to do, ask grandma.

Because you see there is a dynamic there, and they're both part of it.

You're not micromanaging that dynamic.

Say bye, do this.

That's not nice.

You know, and meanwhile, grandma is standing there, you know, uncomfortable.

It's.

And again, I don't know how much you can talk to grandma and tell grandma, but you can try gently, Grandma, if you think that your grandson, your granddaughter need to give you a hug.

I don't know.

No.

But they don't want to work with that.

I don't know what to tell you, but we all need to work our own relationships.

And that's another One of them, yeah.

People cannot fix that for us.

They can give us advice, some guidance, you know, narrate what they see is going on.

But then we still have to do the work.

So grandma, I don't know what to tell you.

It's, you know, mom or dad, it's yeah, but they want and they don't.

I'm like, work it out, find a way.

You, you have lived in this world and had many relationships.

This is just one of them.

You've worked.

Some of them didn't work, others.

That's what it is.

Yeah.

Your kid gets a bad grade because they didn't study and asks you to email the teacher.

He'll to die on or let it go.

Yes, in a way also depending on their age.

But they have to face the teacher.

Yeah, make them face the teacher.

But my teacher didn't tell me and they didn't.

You know, there's a lot of blame.

My teacher doesn't care.

My teacher hates me.

Oh, I hear that all the time.

Especially middle schoolers.

All teachers hate all children for some reason.

It's like, wow, must be a very tough place to be.

But back to, you know, I don't want to do homework, you know what, or study for the test.

And then whatever it is that I got, oh, look what I got.

And she didn't.

And he didn't.

Do you, do you want to talk to your teacher about it?

You have something to say?

You don't think the material is right because why they complain we didn't study.

She gave us something.

I mean there's always all that kind of whatever stories.

Talk to your teacher.

I don't know, I don't know what to tell you.

And by the way, even six year olds can talk to their teacher.

Like six year old, seven year old comes every single day.

I'm not doing homework.

I hate homework.

I hate.

I said, you know what?

Here is a good lesson in activism.

By the way, you absolutely wholeheartedly believe that homework is wrong.

Start a petition, go talk to your teacher.

I mean this is, isn't that a teachable moment?

As opposed to me?

Well, he doesn't want to do homework.

Can you give him less?

Can you do this?

Can you like me again?

My, you know, managing, micromanaging, all the systems, let them talk to each other.

And yeah.

And by.

Yeah, but she won't listen.

And again, isn't that life?

Yeah, some doors do close and I don't know what to tell you, sweetie.

Yeah, she may not listen, but at least you went and Told her.

And then you have to decide what it is that you want to do.

Right.

You figured this one out.

You know, your kid drops an F bomb in front of you.

Hilt a die on or let it go.

Definitely not a hill to die on.

And again, they start very young, and they use a lot of these words to shock you, to get a reaction.

You can set boundaries.

So is that a hill to die on?

When you set boundaries, you go, whoa, yeah, no, not okay.

You can't say that word to me.

No, I understand that these words run through your mind.

I understand you learn them.

Don't go, where'd you learn that?

And we don't talk like that.

I mean, don't do anything like that.

That's not teaching.

That's just blaming.

Pointing a finger and actually shutting down a conversation.

So go back to whoa, hey, not okay.

And you don't have to explain.

You can't talk to me this way.

This is disrespectful.

You can't use these words.

We don't talk.

Don't go into a lecture.

No is just no.

Now you have these words in your mind.

I don't know what you want to do with those words.

It's up to you to either dump them or.

Or really know when and where to use them on your own.

In your room.

I don't know.

In the tunnel, when the train is right.

There are ways to let something out of my system.

These are good ways.

Sometimes I do need to let something out of my system, but I also need to know when and where and how to use whatever it is information I have in my head.

And as the parent, you want to just set those boundaries very clearly from the very beginning.

Whoa.

No, you.

We do not.

You do not say that to me.

And then you figure out what to do with these words.

And by the way, when they're young, they do use it to shock us, to get a reaction and to overpower us.

So you have to understand that this is a form of, look at me.

Look what I can do.

Right, with that kind of power.

So I can see that you feel like when you say these words to me or you say, that feels very good inside you, like, wow, yeah.

No, that's not the way to do it.

I want you to feel good inside, even powerful.

Not this way.

So let's think of other ways.

Good point.

Your child tells you, I hate you because you said no.

Heal to die on or let it go.

Definitely heal to die on.

Yeah.

No, you can say, I'm very angry.

Yeah, no, you don't hate me, but I understand right now you're so angry that it feels like, hey, no, I really hate you.

You hate what just happened or what is happening.

You definitely hate the fact that I said, no, you don't get what you want.

I get it.

I get it.

It's frustration, disappointment, anger all becomes, you know, hate.

It's not.

There are different emotions and you can express those.

So definitely set the boundary there.

Again, kindly, respectfully.

But notice what I do.

I don't just tell them, don't do that, and immediately have all the good, sensible reasons.

I truly do give them a way to explain themselves and understand themselves and then communicate much better.

I have a feeling this last one goes along with it.

Your kid tells you you're the meanest.

Mom in the world, then I feel such regret.

Right.

Yeah.

Okay.

So that's along the same lines.

Along the same lines.

No, I'm not, but I understand that right now if, yes, you are.

Yeah, no, I'm not.

I really am not.

But right now I get you're very, very angry.

And by the way, you can say that to me.

I am so angry at you.

I think you're being mean.

That's a bit.

I can.

Yeah.

So again, I'm not being mean, but you're right.

I'm being a little tough, little serious, and definitely not giving you what you want.

And I understand how that feels.

So, yeah, they use the word mean.

My friends are mean to me.

They.

They take a lot of times.

Right.

They use words in a very general way.

And what I'm doing is not just saying yes or no or don't do this.

I am giving them an understanding once again, of where they're coming from.

And that's a life skill.

Once again, when we talk about one day, I'm facing challenges.

I'm disappointed.

You know, I don't care what I want.

I'm immediately.

Or I learn to work with it.

I learn to explain myself how it is that I'm feeling and what I can do about these feelings.

So that's what we're doing with all of these statements that are thrown at you as a parent.

And you're like, broken or, you know, fight back, right?

Yeah.

It's not about fighting.

You are the guide, the mentor.

You are the leader.

You're the wise one.

You're here to guide them through even those ugly, tough moments.

Yes.

And the best way to do that is by reading your book.

You are the parent.

Dr. Sige, your advice is gold for parents.

I mean, everybody, please pick up this book.

It's coming out September 8th.

And I just.

Thank you so much, Dr. Sige, for joining me today.

Thank you, Aksi.

Thank you so much for this, Sam.