Why You Keep Waiting to Enjoy Your Teenage Son (And How to Stop)
Jun 22, 2026
Have you ever caught yourself thinking, "I'll really enjoy this kid once we get through this phase"?
I have said some version of that more times than I can count. And here is what no one tells you when you are in the thick of raising a teenage boy: there will always be another phase. While you are waiting for the right moment to actually enjoy your son, the moments are ticking by.
I want to give you a simple explanation for why this happens, and some tools that will help you have fun now. Not later. Not once he stops doing that thing that drives you crazy. Now, in the phase you are actually in.
You Want to Enjoy This Boy.
I think often about what moms of teenage boys want most. And at the end of the day, you just want to enjoy this boy. There is so much getting in the way of that, and trust me, I get it. Much of what gets in the way is justified. We want to raise a good man. We know what goes into that. So sometimes we get caught up in the weeds of grades, behavior, screen time, and curfews, and we forget the bigger goal: enjoying this boy while we have him in our home.
I have lived this as a mom of five boys. I know what it feels like to be so busy surviving that you forget to actually enjoy the ride. I also know how easy it is to tell yourself that enjoyment is coming. It is just one phase away.
Here is why today matters. The window is closing. We do not have a lot more years with our sons under our roof. I do not say that to scare you or make you panic. I just want to be real. These years are short. The days are long, but the years are short. These boys are counting on us to be present with them, not just present in the room.
What a Last Lacrosse Game Taught Me About Joy
Our youngest son just graduated from high school. Sports were a big part of our life for years. The boys played, and we sat in the stands more times than we could ever count.
A few weeks ago, Dawson played his last home lacrosse game. We drove home from that stadium where we had sat for literally years, and I could not stop crying. I knew it was going to be emotional. I did not expect to be surprised by why I was crying.
It was not sad that it was over. It was okay. We will not be doing more sports seasons with our kids the same way again, but it was okay. I was overwhelmed with gratitude for the ride.
The best way I can explain it is like a rollercoaster. While you are on the ride, going up and down and through the loops, you are not always sure if you like it. But when the ride slows down and you know it is over, you often think, "Wow, what a ride. That was so fun." That is exactly how I felt driving home from that game. Not every game was fun. Not every practice was easy. But the ride, as a whole, was so fun.
Maybe sports is not your thing. Maybe it is orchestra, theater, mechanics, or computer science. Whatever it is for your family, at the end of it, you are going to be so glad for that ride. You do not want to look back and wish you had enjoyed it more. You want to enjoy it while you are in it.
The Phrase Every Mom of a Teenage Boy Has Said
How many times have you said some version of this?
"I'm really going to enjoy him once he stops having meltdowns." "I'll enjoy him once he gets out of this 14-year-old phase." "I'll enjoy this season once he can drive himself." "I'll enjoy him once summer ends and he goes back to school."
Do you see the pattern? I'm going to enjoy this when. I can't wait until this is over. It is okay to look forward to the next phase. But we cannot lose sight of enjoying the one we are actually in.
Brene Brown has said that the hardest emotion for human beings to feel is joy. That surprised me the first time I heard it. We have a hard time feeling joy because we are always waiting for the next thing. We hold back because we are scared of what happens after the joy. That is exactly the emotion we want to start feeling on purpose as we raise these teenagers.
There Is Always Another Phase
Here is the hard truth. The phases do not stop. They just change. If you keep waiting for the perfect conditions to enjoy your son, you will wait forever.
I call this the swimsuit metaphor. You know the one. "I'll put the swimsuit on and get in the pool once I lose ten pounds." Meanwhile, summer is passing. Your kids are splashing around having a great time, and you are sitting on the edge, watching, waiting, and missing it.
We do not want to be that person with our teenage sons either. We do not want to sit on the edge waiting for conditions to be just right while the fun is happening right in front of us. The phase you are in right now might be a hard one. But there are redeeming moments inside of it. I promise. The memory your son will carry is whether you were in that phase with him, or watching from the sidelines.
I Know Some Phases Are Genuinely Hard
I want to pause here, because some of you are thinking, "I hear you, Heidi, but you don't understand the phase we're in right now." I do understand. We have walked through some very hard phases in our own family.
Maybe you don't feel like you have the bandwidth right now. Maybe you are scared your son is making mistakes that will affect his future. Maybe you are just so tired. Here is what I know about you. You are not lazy. You are not checked out. You are managing a house, working to help provide for your family, feeding people, monitoring grades, driving to practice, holding boundaries, and teaching values. Somewhere in the middle of all of that, you are trying to stay connected to a teenager who sometimes acts like he doesn't even want to be around you.
You are not withholding joy on purpose. You are tired. And when you are tired, you slip into survival mode. You start managing instead of enjoying. You start reacting instead of connecting. Underneath it all is a fear that if you loosen your grip even a little, everything will fall apart. His grades will slip. His behavior will tank. The structure will crumble.
So you hold on tighter. You do more. You control more. Which means you enjoy less.
Here is what I want you to hear. The structure is not what holds your family together. It is you being you, not you doing everything, that holds this family together. You are allowed to enjoy the people you are working so hard for.
How to Actually Feel More Joy Right Now
I am not suggesting a complete 180, where you stop doing the responsibilities and tasks of motherhood and just enjoy all day long. That is not realistic. But here is a question worth asking yourself often: how could I make this easier and more fun?
Not the next phase. Not the last one you miss. This one, the one you are actually in.
It does not have to be all the time. It can be moments. Like that drive home from the last lacrosse game, where I let myself cry, let myself mourn one phase, and let myself feel grateful for the joy I had during it.
Step One: Define What Enjoying Him Actually Looks Like
This sounds obvious, but most moms have never stopped to define it. You are chasing a feeling you cannot describe, which means you will never know if you found it.
I worked through this with a client recently. She told me, "I just want to get along with this boy." I asked her what that would actually look like. She sat there for a minute and admitted she didn't know. So we worked through it together. By the end, she felt closer to the thing she had been longing for, because she could finally see it.
Ask yourself: what would it look like, specifically, to enjoy your teenage son today, in the phase you are in right now? You don't have to enjoy everything about him. He doesn't have to change for you to find some joy.
Is it laughing together at dinner without phones out? Is it a Sunday breakfast where he actually stays and talks? Is it showing up to his game and being fully present instead of running through your to-do list? Is it asking him what he likes to do, and then doing it with him?
Write it down. Make it specific. Vague goals produce vague results.
Step Two: Compare Your Values to Your Days
Here is a short exercise that changed something for me the first time I tried it, and it has stuck with my clients too.
First, write down the four things you value most in your life right now. Not what you think you should value. What actually matters most to you. It might be connection with your kids, your faith, your health, your marriage, or your purpose.
Second, write down everything you did yesterday, from morning to night.
Now compare the two lists. How much of what you did yesterday actually connects to what you value most?
When I did this exercise, it was eye opening. I realized I was doing a lot of things that had nothing to do with what I actually valued. The things that mattered most got the least amount of my time. That was enough of a shock to make some changes right away.
If one of your values is enjoying your teenage son more, and you have defined what that looks like, you now have your prescription. Do that thing. Every day. You will likely see a shift in his behavior within a week or two.
The Fastest Way to Change His Behavior
I will say this until the day I die: the fastest way to get your son's behavior to improve is to improve how you are showing up in his life. That does not mean controlling him more. It means that when he feels your love, your investment, and that you genuinely want him to succeed (not just behave so you feel better), his behavior improves.
This is not about adding more to your plate. It is about prioritizing what already matters. The more you do that aligns with your values, the more energy you will have. The more energy you have, the more you want to participate in your own life and his.
The Real Goal Was Never Just Getting Him to Adulthood
That part matters, but it is not the whole goal. The real goal is to actually know each other when he gets there. To have a relationship built on moments, inside jokes, hard conversations, and showing up, not just surviving under the same roof.
These teenage years are not something to simply endure. Yes, they are hard. Yes, they are complicated. But they are also really fun. Look for those moments. Define what they would look like for you. Align your days with what you value. You don't need a big overhaul. You just need small decisions to show up a little differently in the moments you already have.
Sit down when you would normally stand and do ten things. Ask him a question, then actually listen to the answer. Stay five more minutes when you would normally leave the room. These little moments compound. They build your relationship, your connection, and your influence, far more than your to-do list ever will.
You're doing better than you think. You really are.
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