Last Friday, I had the pleasure to present to parents at Middlebridge School in Rhode Island during their first parent weekend (Go Owls!). My talk focused on navigating students' visits home from boarding school.

On the drive home, I found myself thinking about an analogy: Parenting teenagers today is like being handed a helmet and uniform, pushed onto a football field, and told to play—without knowing the positions, the rules, or any of the plays.

Had I given those parents the plays? The actual strategies they need to effectively parent their kids?

I feel I fell short of this, hence the inspiration to write this blog.

Know that I came at this wisdom the hard way. I too was a parent of a "hard to parent" teen, and I made many, many mistakes. I wish I had this knowledge when I was in the thick of it. Now, I hope to share my hard-earned lessons with those parents needing the plays.

The bottom line: Structure, boundaries, and expectations support growth. When these disappear, regression ensues.

The Plays: Your Strategies for Success

Play #1: Know That You Have the Leverage

Though it might be uncomfortable using it, know that you have the leverage in this relationship with your child. And you'll need it.

You finance every aspect of your child's life, their residence, their clothes, their phone, their car (or access to one), grooming products and services. They want things from you. A lot of things.

Too often, the power dynamic has shifted to the teen having the power, running you ragged, draining your emotional bandwidth. It's time for a reset.

You can't be afraid of your kid. You can't permit them to terrorize you with threats. They don't want to abide by your technology rules? I know this sounds tough, and might even exacerbate your anxiety, but … Take their phone away. They refuse to meet household expectations? The car stays parked. Shopping and grooming appointments gets cancelled.

Here's the key: They have to want it more than you.

When you're more invested in giving them what they want than they are in earning it, you've lost your leverage.

This is what boarding schools do so well. They care for your child, but they're not as emotionally invested as you are. It's easier for them to set the hard "no" because they can take the emotion out of it.

You need to do the same. Know what you provide. Know what matters to them. Take the emotion out of it. Use your leverage wisely, but use it.

Play #2: Align With Your Co-Parent

You and your co-parent must be on the same page. When parents aren't aligned, kids will exploit the gaps and create a wedge.

One of the things I hear most often from the parents I work with is that co-parents aren't aligned in their parenting. They don't agree on the boundaries and rules for their child. And this is a big weakness. I urge any parent struggling with this to work with a parent coach to more effectively align. This is mission critical in terms of parenting your teen.

Usually one parent is a softie, the other taking a harder line. Kids learn to exploit this, triangulate the relationship, creating more and more co-parenting friction. When co-parents are aligned, they are a united front, and kids feel safety and security in this. This is true for unmarried, divorced, or married co-parents.

Sit down together and agree on a hierarchy: Safety comes first. Education comes second. Social life comes third.

When your child wants to skip homework to hang out with friends, you both know the answer because you've agreed on the priorities.

Determine which boundaries are most important for you to keep and which ones are non-negotiable. The non-negotiables are likely the ones related to safety—seatbelts, substances, knowing where they are, who they're with.

Everything else? You need to pick your battles. Not every boundary deserves the same level of energy. But the ones you choose to hold—especially the safety ones—you hold together, consistently.

Write down your agreements. You don't want to be negotiating with each other in front of them.

Play #3: You Can't Control Your Children—Only Your Response

You can't control your children. You can only control how you handle their actions.

This is the most important shift you can make as a parent of teenagers. Your child will make choices you don't like. They will push boundaries. They will test you. Your job is not to control them. It's impossible anyway. Your job is to stay in control of yourself.

You are the more mature person in the room. Act like it. Don't get pulled into arguments with your children. Don't match their emotional intensity. Don't let their dysregulation cause you to become dysregulated.

When your teenager is yelling, your calm is the anchor. When they're melting down, your steadiness is what they need—even if they can't see it in the moment.

Try not to let them see you sweat. Once you've lost your composure, you can't dial it back up. Your teenager will remember that you came unglued, not the point you were trying to make.

**Stay calm. Stay consistent. Control what you can control: yourself.**

Play #4: Once Negotiation Starts, You've Lost

This is about the words you use after you've stayed calm. Once you start negotiating about a boundary you've set, you've already lost the battle.

Teenagers are master negotiators. They will wear you down. They will argue. They will find loopholes. They will say "But why?" seventeen times in a row.

Here's what happens when you negotiate: You explain your reasoning. They counter with their reasoning. You explain again, differently. They poke holes in your logic. Before you know it, you're in a 45-minute debate about curfew at 10:30 pm on a school night, and everyone is exhausted.

Don't do this!

State the boundary clearly once. When they push back—and they will—don't re-explain. Don't justify. Don't get pulled into the debate.

Simply: "I understand you're frustrated. The boundary stands." Then walk away.

Your teenager doesn't need you to defend your decision. They need you to hold it. The boundary itself is the answer.

Play #5: The Technology Battle—Have a Real Plan

Technology will be the biggest battleground. Don't wing this.

Here's what actually works: When it's time for screens to be off and they won't comply, remove the devices. And protect your devices—once they don't have theirs, they will try to access yours. Get a safe.

I know what you're thinking: But I need the internet for work. I have a deadline. Yes, removing the router or turning off the internet impacts you too. So be strategic about timing when you can, but don't let that stop you from holding the boundary when it matters.

And I'm not implying you should set off World War III. The key is calm, consistent follow-through. State the boundary. When they don't comply, remove the devices without drama. Lock them up if you need to.

Yes, they'll be angry. But you know what's more uncomfortable? Endless battles every single night and a child who learns that if they wear you down enough, you'll give in.

Decide the technology rules with your co-parent ahead of time. Write them down.

Play #6: Let Them Scrape Their Knees

Natural consequences are your friend. When you rescue your child from every consequence, you rob them of the chance to learn.

In *The Anxious Generation*, Jonathan Haidt writes about how kids today are too sheltered and hovered over by "helicopter"—now bulldozer—parents. We've become so afraid of our children experiencing discomfort or failure that we pave the way for them, removing every obstacle before they even encounter it.

You can purchase this book here, and a portion of the proceeds supports Sky’s The Limit Fund.

But here's what happens when kids don't learn from mistakes, when parents don't hold them accountable: You're giving them an indirect message that says, "We don't think you can handle this yourself, so we're doing it for you." And kids are not building grit or resilience when you do this for them.

That's not a message you want to convey to your child. You want to empower them. You want to convey that you have faith that they can figure it out on their own.

The law of natural consequences is one of the most powerful teaching tools you have. Forgot their homework? That's between them and their teacher. Stayed up too late and feel exhausted? That discomfort is teaching them something. Spent all their money and now can't afford what they want? They'll remember that lesson far better than any lecture.

Your job isn't to prevent all discomfort. It's to be there when they need you while allowing them to learn from their choices. Let them scrape their knees. Let them feel the natural consequences of their decisions. That's how they develop resilience, competence, and confidence.

Play #7: Strong Boundaries Doesn’t Equal A Lack of Empathy

Maintaining strong boundaries doesn't mean you have to be cold, lacking in compassion and empathy.

The hardest moments are often invitations to deeper connection, if you know how to read them. You can hold firm on consequences while still being warm, present, and understanding.

When your child is struggling, don't fix everything. Just be present. Validate their feelings. Acknowledge their strength. Refrain from fixing it for them.

Sometimes the most powerful thing you can do is hold the boundary and say: "I see you're struggling. I'm here. What do you need?"

You can say no to their request and yes to their feelings. You can be firm and kind at the same time. Strong boundaries and deep connection aren't opposites, they work together.