Remember those collages of photos on your wall—snapshots of laughter, adventures, and milestones with friends? In this episode, Jim creates an audio collage from conversations with five friends who’ve shared decades of life with him.

Jim and Tessy reminisce about meeting in kindergarten. Carl and Rodney, his first friends at his first job, reflect on how workplace bonds can grow far beyond the office. Kathy shares how their friendship blossomed after connecting through mutual friends. And MJ offers lessons on the meaning of friendship as she steps into her third act of life.

It’s a celebration of connection, memory, and the timeless lessons friendship brings—listen in and be inspired to reflect on your own circle of lifelong friends.

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You know that friend from way, way back...the one who knew you before you knew yourself? For Ken, that's Nicky. They were inseparable as kids, then...forty years of radio silence. Until now.

This conversation isn't just a reunion, it's a time capsule cracked open. You'll hear what shaped a childhood friendship, what made it fade away, and what remains of it today, if anything.

Buckle up! We're about to put an old 8-track of Ken's into the dash.

Trigger Warning: Eating Disorders, Body Image 

This episode discusses experiences with disordered eating. We encourage you to prioritize your well-being while listening.

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In this episode, Ken and Jim dive into the complicated, essential world of friendship. Two Gen Xers, raised on self-reliance and independence, who approach connection very differently—one cautious, one trusting—but both fiercely aware that friendships shape how we age.

In discussing their own experiences with friendship, including their own, they unpack some of what makes friendship so important and at times challenging for our generation. 

Is friendship the same for us at 60 as it was at 20? 

Grab a friend, listen together, and maybe start a new conversation about what friendship really means.

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What does it mean to stay relevant as we age — and who gets to decide?

In this conversation with guest Coralie Hooper, we crack open the cultural conditioning that taught us to “look the part” to earn our place, especially at work.

We reflect on the visual and behavioral rules we learned — especially as Gen Xers — and ask: what happens when we stop trying to fit into someone else's version of relevance?

We touch on:

• The lingering pressure to “present” a certain way
• How our generation was trained to perform success before we truly defined it
• The quiet freedom of aging into authenticity — of choosing to whom we’re relevant
• The evolving link between relevance and self-expression

It’s part nostalgia, part reckoning, and all about reclaiming relevance on our own terms.

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This episode, Jim and Ken walk the tightrope of expectations. When Jim’s birthday plans fell through, the disappointment surfaced an old question: Is having expectations a setup for heartbreak — or are they necessary to feel alive and hopeful?

The research backs it up — the happiest people as they age aren’t the ones whose plans always worked. They’re the ones who learned how to hold the plan lightly — and themselves tenderly — when it didn’t.

From broad, open dreams to rigid requirements, let's unpack what it means to trust life enough to loosen your grip — without letting go of what you truly want.

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Psychologist and author Dr. Camille Preston joins Ken and Jim for a deeply personal and timely conversation inspired by her new book, Living Real. Together, they explore what it means to live with emotional depth in a world that pushes us to stay busy, be upbeat, and get distracted.

Camille introduces the concept of shallowing—the habit of avoiding life’s hard feelings in a misguided attempt to stay afloat. But as she explains, when we numb the lows, we also miss the highs.

This episode is about burnout, grief, identity, and the lifelong journey of unlearning the pressure to always do—so we can remember how to truly be. Whether you're navigating a transition, wrestling with questions about what really matters, or simply tired of feeling stretched thin, this is a conversation that invites you to slow down and live real.

For More about Dr. Camille Preston click here.

Get you copy of 'Living Real: Redefining Success, Presence, and Happiness

For more about Living Real, including resources and activities, click here.

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While parents weren't always there to teach Gen Xers life lessons—the movies were, for better or worse. In this episode, Ken and Jim revisit seven films from the 80s and early 90s that shaped how they saw themselves, the world, and who they were supposed to become.

From unexpected alien friendships to having a head for business and a bod for sin, these stories carried lessons about love, loss, identity, and possibility. 

Decades later, they’re asking: What stuck? What fell flat? And what might leave other generations scratching their heads?

Watch or revisit the movies discussed in this episode and see what lessons come to you:

ET

Fright Night

The Last Starfighter

Longtime Companion

Terms of Endearment

Working Girl

City Slickers

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When Jim returns from a month-long facilitation tour of Japan, what starts as a virtual travelogue turns into something deeper. Ken and Jim explore how our appetite for risk, adventure, and newness shifts with age—and why learning still matters, maybe more than ever, after 60.

They talk about homesickness, self-judgment, and the tension between comfort and adventure. Is it possible to keep evolving without blowing up the lives we've worked so hard to build?

Old Dogs...New Trips is a candid conversation about the courage it takes to keep stretching—just enough to stay curious, but not so much we lose our footing.

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What started as a thoughtful nod to Ken turning 60 quickly turned into a surprisingly loaded conversation—because it turns out, “eldership” means very different things to each of us.

For one of us, it's the recognition of our accumulated wisdom, and a sacred passage to becoming a respected guide. And for the other? It feels more like a lifetime achievement award with no cash value and zero sex appeal.

In this episode, we talk candidly about what the word “eldership” evokes for each of us, why we didn’t quite see eye to eye, and how this stage of life asks us to wrestle with identity, agency, and what we’re still becoming.

Click here to learn more about Mike Iamele's work on mapping Sensitivities.

For a free mapping demo with Mike, click here.

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We’re the first generation arriving at 60 without a clear script for retirement. For our parents and grandparents, retirement was the endpoint. A gold watch. A pension. A La-Z-Boy recliner with a view. But for us? The lines are blurrier.

In this episode, we talk with fellow 60-year old Paul Scott, the mind behind LifeDesign, a venture focused on helping people consciously design the next phase of life after full-time work.

Together, we explore what happens when your job stops defining you… and you finally get to decide what comes next.

Whether you’re ready to reinvent, slow down, or just think out loud about what’s next, this conversation is for anyone staring at the second half of life and thinking: there’s got to be more than this.

Learn more about LifeDesign Associates by clicking here.

Learning more about Paul Scott by clicking here.

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