It Started With a Question

Three Stories, One Hope, and the Road Ahead

A few years ago, a friend asked how I thought Sarah and I were doing as parents. I remember answering, "I think we're doing okay… but check back in about fifteen years for a more definitive answer." 

It seems like yesterday. They were so little. But even at a young age, we stretched to give them freedom to explore.

That conversation has stuck with me. It's become a quiet prompt, reminding me to step back now and then and ask, How are we doing?

Like most things in life, some moments feel solid, like we've hit the right notes. And others where I know we've missed.

A couple of weeks ago, I asked the boys to shoot straight with me. What are a few things they think we got right? And where have we missed the mark? 

Both of them said they've always appreciated that Sarah and I have honest conversations with them. That meant a lot to hear.

They also reminded me of a few times when we, okay, mostly me, crashed out on them, lost my cool, raised my voice, got frustrated.

We spend a lot of time in Sunriver, OR. Watching them become best friends has been one of our greatest joys in life.

The crazy thing is, I remember those same moments. Not because I said something I regret, but because I didn't show up the way I wanted to. I let stress or fatigue get the better of me.

Those moments stick with me, not so much as failures, but as reminders. Reminders to stay grounded. To parent with poise when things get hard. And to give myself a little compassion, too. Because sometimes, even when you're doing your best, you lose it.

One thing I've come to realize is this: parenting isn't about perfection, it's about presence, consistency, and showing up in a way your kids can trust.

As I reflect on the moments that matter most, the ones that feel like they've stuck, I've noticed a few things rise to the surface, seemingly small lessons, but ones that have had a lasting impact on how we parent.

Here are three of them.

1. Owning the Hard Moments

We are a skiing family. But not the type who had our kids on skis before they could walk. We waited until they were 9 and 7, old enough to carry their gear from the car. That alone may

We waited to hit the slopes until they could carry their gear.

have been one of our best parenting decisions to date, as it saved many tears from both me and the boys.

From the beginning, we wanted skiing to be something they owned (which we try to do with all their activities). As soon as we bought them their skis and boots, I gave everyone, including Sarah, their own gear bag. On each of the boys' bags, I put a laminated tag that's still there today. It reads: "If you forget any of these, you won't be playing on your skis," followed by a list of 12 essential items, such as long underwear, gloves, sunscreen, and so on. 

Ever since, Sarah and I haven't reminded them what to bring. If they want to ski, they pack their bag. Simple as that.

Possibly one of the best purchases we've made. Our skiing "go-bags" are always ready at a moment's notice. We can be in the car and on our way to the snow in no time at all.

It wasn't just about convenience; it was about teaching them to take responsibility. To follow through. To prepare. And over the years, those little laminated cards have paid off.

But let's be honest, accountability isn't just something I've expected from them. It's something I've had to learn and live out,

too, especially in the moments when I miss the mark.

There was this one day on the mountain when Rocco wiped out and couldn't get his ski back on. It was windy, cold, and I was tired. And what should have been a two-minute fix turned into a twenty-minute struggle, complete with frozen fingers, mounting frustration, and, eventually, me completely losing my patience.

With just a little prompting, they can own their activities and have what they need.

I snapped. Got short. Yelled at him. And in doing so, I made a hard moment even harder.

Thankfully, these "crashouts" have been rare, but they were real. Every parent has them, and they offer us and our children opportunities to grow.

I know I didn't show up for Rocco the way I wanted to that day. Or the way I would've wanted my father to show up for me. It hit me hard. So I pulled Rocco aside, looked

him in the eye, and apologized.

When we give them proper guidance, they're able to take flight while we sit back and watch (or take photos).

Not one of those "sorry, but" apologies. A real one. I told him I lost my cool, that I let stress get the better of me, and that I was sorry.

That moment still comes up from time to time in conversation. And I apologize each time. Not because I want to dwell on it, but because I've learned and want to pass on to them that true accountability doesn't expire.

It's easy to tell our kids they need to be responsible. But we have to model it, too. Sometimes that's hard to swallow as a dad. But I've learned that when I outwardly own my mistakes, it doesn't make me weak; it makes me real. 

I want my boys to know they don't have to be perfect. Mistakes happen. What matters is how they recover, reflect, and move forward.

2. Giving Them a Voice

Some of our most meaningful family decisions have come through everyday conversations, about trips, screen time, or how we handle conflict. From the start, Sarah and I have tried to make space for the boys’ voices, even when we don’t all agree, because we’ve always believed they deserve to be part of the conversation.

Heading out into the forest to harvest our own Christmas tree has become a family tradition. Everyone gets a vote.

We’ve always been intentional about treating our boys like the whole humans they are, not just kids to manage or control. They have thoughts, opinions, questions, and emotions that deserve to be heard and respected.

Don't get me wrong, there's still a pecking order in the house. Sarah and I are the parents. But it's not just about authority. It's about creating mutual respect and making sure everyone is seen, heard, and valued.

In our experience, our boys are far more likely to engage when they feel heard. When they know their input counts, they invest more in the outcome, even when the final decision doesn't go their way.

And we've realized the opposite, as well. When we shut them down or dismiss their perspective, it doesn't just end that conversation; it sends a message: we don't trust them enough to have a voice. 

Sometimes we have a tie. So we get two trees!

They know they won't always get their way, but their input is welcome. They've learned to advocate for themselves, to ask thoughtful questions, to challenge ideas respectfully, and to share their own, enthusiastically.

It's not always easy, for them or us. There are days when we're distracted or don't have the bandwidth for one more conversation. But over time, giving them a voice has helped them feel like they belong, not just as kids, but as contributors to our family, an essential part of our tribe.

And here's the part I'm most grateful for: in a world that's constantly telling them what to think, what to wear, what to eat, and who to be, our boys still march to the beat of their drum. It's not always perfect. It's not always easy. But it's certainly validating.

3. ROOTED IN RESILIANCE

From the time they could walk, they were fixated on climbing. I know that will allow them to see the world from a perspective I never could.

I'm terrified of heights. Always have been. Climbing trees was a challenge when I was a kid. Even getting on and off the roof of our one-story house is enough to make me freeze up.

And yet, I've always made a conscious effort not to pass that fear on to my kids.

When they were young, I'd watch them scale playground equipment or climb trees with ease, reaching heights that would've sent me into a full-blown panic. But instead of yelling "be careful," or pulling them down, I held back. I encouraged them. I let them explore. Because deep down, I knew that just because something scares me doesn't mean it has to scare them.

Looking back, that choice, to step back and let them take the risks I wouldn't, has been foundational in shaping who they're becoming. Confident. Capable. Resilient. And yeah, really good at climbing things too.

Of course, there's a line. As parents, it's our job to assess risk, to help them understand what's at stake, and to step in when something truly crosses that threshold.

If there aren't any trees, they'll find something to climb. In this case, it was a wall of rocks at the coast.

But I've seen how easy it is to step in too soon. To micromanage every movement, trying to prevent every scrape, bruise, or broken bone. We think we're protecting them, but sometimes, all we're doing is robbing them of the chance to learn through experience.

We try to eliminate risk, but too often we end up removing growth opportunities.

By letting them climb, literally and figuratively, they've learned to trust themselves, take healthy risks, and grow through experience because we don't build resilience by staying in our comfort zones, but rather by falling, scraping knees, and then learning from those mistakes.

The Road Ahead

From climbing trees and rocks to hitting the slopes, we've encouraged them to step out of their comfort zones so they can learn and grow.

The crazy thing is that the fifteen-year threshold is now right in front of us. Rocco is 17, and in four or five years, he'll be out on his own, with Gio, at 15, not far behind.

I have no idea what their paths will look like. But I hope they remember that they were seen, heard, and trusted. That they had space to stumble and speak up, and that we embraced who they were in each season, not just who they might become.

My hope is simple: that they carry with them the kind of confidence, trust, and resilience we tried to build, one imperfect moment at a time. 

If they carry that forward, I’ll know we did something right.