When Giving Your Kids Opportunities Becomes Giving Yourself Pressure

It was mid-winter break. We were somewhere in the Caribbean. Eighty degrees. Blue water. The whole package. And a few of my four kids did not want to be there.

My wife, Theresa, planned an incredible trip. She always does. And when we got off the boat and asked the kids if they'd ever want to do it again, a few said no. Not maybe. Not someday. Just no.

That stung. I think it stung Theresa more. And I know we're not the only parents who have felt that.

The Instinct to Provide

I was talking to another dad at a basketball game a few weeks ago. Let's call him Dan. We got on the topic of opportunities, the things we do for our kids that we never got growing up. The trips. The sports. The experiences. Dan said something that stuck with me: "I find it unfortunate that they don't appreciate it."

And I get it. I feel that too. We're spending real money, real time, and real energy trying to give our kids something meaningful. And when they shrug, complain, or ask to go home, it feels like a failure.

But here's what I'm starting to realize: the opportunities we give our kids often become the pressure we put on ourselves. We decide what they should want. We build the plan. We fund the plan. And then we wait for gratitude that may never come, at least not in the form we expected.

Dr. Jen Dragonette, a licensed therapist, put it this way in a recent conversation: there's almost a biological imperative, as parents, to give our kids opportunities we never had. That's a wonderful instinct. But she asked a question that stopped me: why do we want this for our kids?

Is it because we think they'll get a scholarship? Because we want them to have the social connections? Because we want beautiful photos for Instagram? Or is it something else entirely, something we haven't named yet?

Connor Hellebuyck and the Road Not Taken

Right behind my house is Walled Lake Northern High School. That's where my kids go to school. It's also where Connor Hellebuyck went to school, the goalie who just helped the U.S. men's hockey team win gold at the Olympics.

What I find interesting about Connor's story is what his parents didn't do. In the world of youth hockey, if your kid is talented, you move. You ship them off to play AAA somewhere else. You travel constantly. You spend enormous amounts of money chasing the dream.

Connor's parents said no. They kept him local. He played club hockey, played for his high school, got a D1 scholarship to UMass, and worked his way into the NHL.

I'm not saying that's the right path for everyone. But it challenges the assumption that more investment equals better outcomes. Sometimes the opportunity is right where you are.

The Pressure We Don't Talk About

There's pressure on kids to enjoy what we've planned for them. Pressure to perform in the activities we've invested in. Pressure to be grateful for experiences they didn't ask for.

And there's pressure on parents. Pressure to maximize the time we have left with our kids at home. Pressure to create memories that will last. Pressure to get the ROI on that expensive trip or tournament.

I showed Theresa a one-page document a few years ago. It's something I give to the families I work with. It shows how many summers you have left with your kids before they leave home. That thing hit her hard. And I think it created its own kind of pressure. This feeling that we have to do everything now, because the clock is running out.

But Dr. Dragonette offered a reframe that I keep coming back to. She said, "We are raising adults."

Think about that for a second. If everything goes well, we'll spend decades with our kids after they leave home. The relationship we have with them as teenagers is a tiny sliver of the total time we'll have together. The goal isn't to squeeze every possible memory out of these last few years. The goal is to raise people who want to come back.

Honest Answers as Acts of Trust

Here's something else Dr. Dragonette said that shifted my thinking. When your teenager tells you they didn't enjoy something, that's not a failure. That's trust.

She asked me, " Would you have dared to say that to your parents?" I wouldn't have. I would have smiled and gone along with it, even if I was miserable. So when Madison tells me she'd rather travel with us when she's older and has her own money, she's not rejecting us. She's telling us who she is.

And that's the thing we actually want, isn't it? Kids who can tell us the truth. Kids who know what they like and what they don't. Kids who can set boundaries and advocate for themselves.

If we punish them for being honest, we teach them to hide. And then we end up with adult children who show up out of obligation, not because they want to be there.

Asking Instead of Guessing

When we're stressed, when we feel the pressure of limited time, we default to guessing. We assume we know what our kids want. We build the plan based on what we think will be meaningful. And then we're disappointed when it doesn't land.

Dr. Dragonette shared with me a story about wanting to take her son to her high school reunion. She had built this whole thing in her head about how meaningful it would be. But when she talked to him, he was stressed about missing school and making up the work. He didn't care about seeing where she went to high school. That wasn't important to him.

So she let it go. She went alone. And they agreed to find another time to do something together that worked for both of them.

That's what asking looks like. Not abdicating your role as a parent. Not letting kids run the show. But creating enough space for honest dialogue so you're not guessing at what they want.

The Financial Drag

I'll be honest about something else. The cost of all this matters. Dan and I talked about it at that basketball game. We're not families that can't afford vacations. We can. But that doesn't mean it doesn't feel like a drag when you spend thousands of dollars, and your kids aren't happy.

When money is tight, there's pressure to make every dollar count. But that pressure can turn a vacation into a forced march. And then nobody wins.

One question Dr. Dragonette Jen asks her clients: if you couldn't post this on social media, what would you actually want to do? That's a good filter. It strips away the external validation and gets at what actually matters to you.

Finding Harmony

None of this means we should let our kids dictate everything. Dr. Dragonette was clear about that. Entirely permissive parenting isn't good for kids either. They need guardrails. They need to see that we have interests and desires too. It's okay to drag them along sometimes.

But there's a difference between guardrails and an agenda. Guardrails say: here are the boundaries, and within them you have freedom. An agenda says: this is who you must be, and this is what you must enjoy.

I think the balance comes from naming what matters to us as parents, being honest about why we want certain things, and creating space for our kids to be honest, too. When we do that, the opportunities we provide feel less like obligations and more like choices.

What I'm Taking Away

I still wanted that cruise. I needed to get out of the Michigan winter. I needed a break before tax season buried me. And I'd do it again.

But next time, I think we'll ask more questions up front. What would feel good to you? What kind of trip would you actually enjoy? Maybe the answer is still a cruise. Maybe it's something smaller. Maybe it's staying home and having breakfast for dinner in our pajamas.

There's a quote I keep coming back to from Paul Orfalea, the founder of Kinko's. He said, "Success is when your children want to be with you when they are adults. The most cool thing I've ever been called in my life is dad."

That's the long game. Not perfect vacations. Not maximized opportunities. Just raising people who want to come back.

One Thing to Try This Week

Ask your kids one question: "What would feel really good to you?"

Not what they should want. Not what you think would be good for them. Just ask. And then listen. You might be surprised by the answer. You might not. But either way, you'll be asking instead of guessing. And that's a better place to start.