The Gift of Older Friends

While mentors offer guidance through their credentials, it is the friends with wisdom from lived experiences who profoundly shape our lives. These friends may be in different phases of life, have lived through different eras, made different mistakes, and recognize your struggles as ones they once carried.

For me, friendships with people older than me have been among the most grounding. They provide a lens to view the future with less fear, offering insights that go beyond mere advice. Intergenerational friendships offer more than nostalgia; they provide wisdom, resilience, and a shared rhythm that enriches our lives.

Take my friends Tim and Mary.

They’ve known grief, disappointment, joy, illness, and renewal. They show up for me, not with instruction, but with steadiness and acceptance. Their boys are grown, and their child-rearing days are over. So, when I was fumbling through my kids’ transitions from adolescence to teen years, they reminded me: This is hard, and it passes. When I sent a child off to college, they showed me what letting go with dignity looks like.

Over the years, I’ve watched their evolutions. They’ve made time for pursuits they once set aside: music, voice, and giving back to their community. They’ve used retirement as a runway, not rest. Now in their 70s, they join me weekly as my workout partners. Their presence reminds me that fitness isn’t about appearance. It’s a form of therapy. It’s about staying strong enough,  mentally and physically, to keep showing up for ourselves and each other.

Then there’s Bart.

Bart, my father's lifelong friend, has seamlessly transitioned into a cherished friend of mine. Bart speaks with my father’s Massachusetts accent, the same cadence and directness. When we talk, I don’t just hear my dad’s tone; I hear his memory. Bart tells stories I never knew about their childhood. He shares glimpses of my grandmother before illness shaped her final years. He tells me what my dad would’ve thought about things I’m doing now, like buying a house sight unseen or raising kids, God forbid, who choose to attend colleges outside of the East Coast. And I believe him. 

There’s a shorthand we share, having grown up in the same small New England town. We agree that an old Mercedes beats a new Tesla. That the legal profession is an honorable one. That the Red Sox are the best MLB team ever—hard stop. That you show up to your kids’ and grandkids’ games. That Dunkin’ is superior to Starbucks. 

I value Bart’s wisdom; he carries the map my Dad would’ve drawn for me had he not passed decades ago. Bart’s perspective is rooted in the same ground as Dad’s, yet it’s had time to ripen.

And then there's Bill.

Some friends speak through words and memories, while others, like Bill, speak by example. Arthur Brooks would say Bill, now 87, possesses "crystallized knowledge,” the kind of wisdom you earn through decades of decision-making and failure. I fear mistakes; he expects them. I demand perfection; he embraces good and bad in equal measure. 

I admire how he lives. He actively pursues happiness. He studies and reads about it. It’s a lifelong, daily pursuit of his, rather than a singular destination. He nurtures friendships, plays bridge, works out, and asks hard questions of himself.  He admits what he doesn’t know. And he listens without trying to impress with sage sound bites. He reminds me that to be truly heard by another person, without judgment, is such a rare and generous gift. 

He founded a group called The Henpeckers, a circle of retired leaders from the Denver-Boulder area who meet monthly to exchange ideas. I’ve sat in on a few of their meetings. The intellect and humility in that room are real. It’s what happens when identity isn’t tied to title. How powerful would it be to connect each of them with a younger friend in search of the type of wisdom they are uniquely qualified to offer?

Emotional Clarity: The Unifying Thread.

For me, what unites all of these people—Tim, Mary, Bart, Bill—is not their age, but their emotional clarity, exemplified by their openness in expressing emotions and their genuine interactions. When they’re sad, they say so; when they’re angry, I know it; when they’re happy, it’s obvious. No guessing. No pretense. Being around them has forced an emotional inventory and newfound honesty in me. 

We’re in different lanes. We’re collaborating. And therein lies the beauty: there’s no posturing, just authenticity. They provide the friendships I didn’t realize I needed, but now I couldn’t imagine being without.

Being around them has changed how I view the decades that lie ahead. I used to brace myself for this next chapter: empty nesting, aging, shifting roles. Now I don’t. It's not because it’s easy. It’s not. It’s because, through them, I’ve seen life on the other side. The little reminders they share—such as exercising, maintaining friendships, traveling, reading, and learning—will shape the decades to come. 

So let’s call on ourselves to extend our hands in both directions. With one, embrace an older friend. Ask them questions. Take a walk with them and listen. Make the call. With the other, connect with a younger friend. Offer steadiness and reassurance. Share what you’ve learned. Be honest about your mistakes and regrets.  Tell them what they need to hear: If you find yourself alone in the darkness, keep walking. I’ve been there and left a light on for you.