Both Sides of the Family, How Friendship Becomes More: Lessons From Jenn & Ken

Friendship like this doesn’t just happen. It isn’t built by accident or by keeping walls up. It takes vulnerability, intention, and years of showing up.

That’s what makes our friendship with Jenn and Ken so special. For nearly twenty years, we’ve lived life together in ways big and small, raising kids, cheering at events, navigating loss, celebrating milestones, planning trips, and creating traditions that stick. We’ve learned that deep friendship requires being willing to let people see the messy, not just the polished.

And while Jenn might prefer to deny that emotions exist, the truth is she is one of the deepest feelers and thinkers we know (don’t tell her we said that). She and Ken have taught us so much about how to think, how to listen, and how to love people with both head and heart.

We’ve worked at this friendship. We’ve found ways to connect on projects, in classrooms, and at conferences. We’ve carved out time for vacations and adventures, even if it meant hauling kids and luggage halfway across the country. We’ve shared dreams on long bike rides, laughs over cocktails (yes, even the infamous Malört experiment - see below), and encouragement in our both sides of the family text threads that have become our own lifelines and connection points.

We’ve been there for the small, tender moments too: celebrating first teeth lost, swapping recipes that became staples in each other’s homes, creating holiday traditions that made our kids feel like cousins (because they are). These little rituals, the meals, the milestones, the memories, are what knit us together as much as the big trips and projects.

We love them dearly, and we know it goes both ways. This isn’t one-sided, it’s mutual, intentional, chosen again and again. And that’s what makes it rare.

What We’ve Learned Along the Way

✔️ Proximity isn’t the secret—intention is. We live two states apart, but our traditions, texts, and trips make the distance disappear.

✔️ Kids thrive when they’re surrounded. Studies show children with multiple trusted adults outside their immediate family grow up more resilient, confident, and emotionally healthy. Our kids see Jenn and Ken as aunt and uncle. Their Lulu sees us as family. That belonging matters.

✔️ Shared projects deepen trust. Whether it’s a book, a bike ride, or planning a trip, working toward something together builds closeness in ways that small talk can’t.

✔️ Differences don’t have to divide. We don’t see eye-to-eye on everything, faith, politics, even baseball teams, but respect and curiosity keep us connected. Love is bigger than the divides.

✔️ Community makes life healthier. Harvard’s 85-year study on adult development found that close relationships are the single strongest predictor of long-term happiness and health. People with deep connections live longer, get sick less often, and recover faster.

Why This Matters

Too often, we assume friendship will take care of itself. But deep, sustaining friendships, the kind that last decades, don’t happen without effort. They require planning, vulnerability, shared traditions, and the courage to let people see your whole self.

They also require forgiveness and flexibility. Not every season will be equal. Sometimes you’ll be the one showing up more; other times you’ll be the one receiving. But the give-and-take is what makes it real.

An Encouragement

If you have friends who feel like family, don’t take it for granted. Nurture it. Send the text. Make the trip. Start a tradition that will outlive a busy season. If you don’t yet, be open. Vulnerability is the soil where deep friendship grows.

We’re grateful beyond words for Jenn and Ken. This episode of Running Ahrens is a wonderful sharing to the kind of friendships that carry us through.

👉 Episode 13: Designing Friendship with Jenn & Ken Visocky-O’Grady

Because in the end, it’s not about finding people who agree with you on everything. It’s about finding the ones who keep showing up, no matter what.

—Justin & Sarah

PS: Try the Two Step Dads if you dare:

The Two Step Dads Recipe:

4oz Rye
1oz Sweet Vermouth
.5oz Reposado Tequila
.5oz Jeppson’s Malort
Dash of Turkish Tobacco Bitters
Mezcal Rinse

Stir and serve up or over big rock ice