Ken and Jim have an intergenerational conversation with Madison Asher, host of the podcast 'We (Used to) Work', about redefining success across generations — and why the question “What do you want to be when you grow up?” might have been the wrong one all along. Together, they unpack the meaning and purpose of work, the tug-of-war between who we are and what we do, and the pressures of a marketing-driven world that keeps reshaping how we define ourselves. It’s a candid, curious, and sur...

AARP (the American Association of Retired Persons) continues to shine a spotlight on Generation X, and the results are both validating and unnerving. In this conversation, Ken and Jim dig into what some AARP-referenced studies and research says about how we’re aging—from our complicated relationship with technology to growing concerns about financial readiness and emerging insights about Gen X health. They also tackle the idea of “obsolete skills” — the ones we once relied on that now m...

The music of our teens and twenties wasn’t just background noise — it was identity, rebellion, and the soundtrack to becoming ourselves. In this episode, Jim and Ken wax nostalgic about the music that shaped them, why that music still matters at 60 and beyond, and how just one song can transport you instantly back in time. Psychologists refer to other phenomenon as the reminiscence bump — the idea that the memories from our teens and twenties stick with us more than almost any others. I...

In this episode, we take on a word we’ve all heard, but maybe haven’t fully defined: Resilience. Ken and Jim bring their own stories of disappointment, illness, and everyday struggles — and pair them with what research says about resilience and aging. What comes through is that resilience isn’t just grit or positivity. It’s a kind of consciousness — remembering what you’ve already come through, and believing you have the resources to face what’s ahead. For Gen X, now staring down the realitie...

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 ...

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&...

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 a...

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 wayHow our generation was trai...

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, le...

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 ab...

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...

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 co...

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’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… an...

In the ’80s and ’90s, “Dress for Success” was more than a look—it was a message. Shoulder pads, power ties, pantyhose… we suited up to be taken seriously in a world built on someone else’s rules. But did fitting in come at a cost? In this episode, we sit down with our friend, colleague, and fellow Gen Xer Tara Hanlon to reflect on what success was supposed to look like back then, and how gendered expectations shaped both women and men in ways we’re only now starting to unpack. We talk about w...

We've spent years saving, investing, and planning for the future—but have we been making deposits into the most important account of all? As Gen Xers, we grew up in a world that rarely talked about self-awareness, self-acceptance, or emotional well-being. We were raised to be independent, to figure things out on our own, and to push through without asking for help. Yet the Harvard Study of Adult Development suggests that strong relationships—not just resilience—are what keep us happier and he...

If the Harvard Study of Adult Development is right, and relationships are the single biggest predictor of happiness and health as we age—are we Gen Xers completely screwed? We were raised to be independent, skeptical, and self-reliant. We’re the generation that made ‘whatever’ a lifestyle. But research says deep, lasting relationships—not just self-sufficiency—are what keep us thriving, both emotionally and physically. Have we been doing it all wrong? And if so, what do we do about it?" Learn...

Get into to the right school. Pick the right major. Find the right job in the right company to take you all the way to retirement. Did it work out that way for our generation? Was the typical career path for us linear as for many in previous generations or more like Chutes and Ladders? Join us as we take a look in the rear view mirror at our career paths to uncover the roads that got us from there to here, including a cameo by Judd Nelson. Leave your thoughts via Fan Mail

In this episode, we attempt to unpack our beliefs, generational conditioning, and hopeful appreciation of this thing called Wellness. Join us! Leave your thoughts via Fan Mail

Come explore some of the classic stereotypes about Generation X as Jim and Ken weigh in on which are totally bitchin' and which are grody to the max. Leave your thoughts via Fan Mail