In this final episode of the season, Ken and Jim look back at the moments in this season of Gen X at 60 that shaped them — the conversations that opened them, surprised them, or shifted something deep inside as they navigated the transition to 60.

Together, they explore why endings matter, what they reveal, and how they quietly change us long before we realize it.

A thoughtful, honest conversation about the part of growth we so often avoid: the endings that make space for something new.

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Forgiveness sounds so simple: Just let go of the resentment you feel about someone’s offense, flaw, or mistake. But for Gen X — the generation raised to “suck it up,” and keep moving — forgiveness is a bit more complicated.

In this episode, Ken and Jim dive into the real work of forgiving others and ourselves without pretending the past magically disappears. They explore the difference between guilt and shame — how one opens the door to learning and growth while the other holds us down — and why the old commandment to “forgive and forget” never matched the way memory, hurt, and hope actually behave in the human heart.

With humor, honesty, and the perspective that comes with turning 60, they look at what it means to lighten the emotional loads we’ve carried for decades. What grudges have shaped us? Which ones still grip us? And what might shift if we learn to release the parts of the past that are still weighing us down?

This is Forgiveness, Gen X style: thoughtful, imperfect, and rooted in the desire to move into what’s next with a little more freedom.

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Stanford researchers say we hit biological pivot points at 44 and again at 60 — moments where our bodies shift and our choices matter a little more.

In this episode, Ken and Jim explore what those pivots actually mean for Gen X, why they’re not warnings, and how small, intentional changes can shape a healthier path forward. They unpack the science, share personal stories, and talk honestly about hope, forgiveness, and the freedom that comes from knowing it’s never too late to turn in a better direction.

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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 surprisingly empathetic conversation that reveals both the envy and the understanding that surface when generations talk honestly about purpose, identity, and the lifelong pursuit of feeling fulfilled.

To learn more about Madison…

Socials - IG @we_used_to_work

Website - MadisonAsherCoaching.com

Podcast-We(UsedTo)Work Podcast

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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 make us sound like museum pieces.

With humor, honesty, and a touch of nostalgia, they explore what it really means to be the generation still figuring it out as we go.

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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. It’s the magical stretch of life when music, first loves, first jobs, and first risks all fuse together, and the songs we heard then become time machines we can ride for the rest of our lives.

So, put another dime in the jukebox, baby — and see which songs carry you straight back. Oh, and before or after, why not explore some of the music mentioned in this episode? Let the music play!

Hot Dogs and Hamburgers by John Cougar Mellancamp https://music.apple.com/us/song/hot-dogs-and-hamburgers/1823072786

El Paso by Marty Robbins https://music.apple.com/us/song/el-paso/158518000

Neon Moon by Brooks and Dunn https://music.apple.com/us/song/neon-moon/258643362

The Glamorous Life by Sheila E. https://music.apple.com/us/song/the-glamorous-life/124887851

Funeral for a Friend/Love Lies Bleeding by Elton John https://music.apple.com/us/song/funeral-for-a-friend-love-lies-bleeding-2014-remaster/1440863114

Addicted to Love by Robert Palmer https://www.youtube.com/watch?v=XcATvu5f9vE

Purple Rain by Prince ‎Purple Rain (Deluxe Expanded Edition) [2015 Paisley Park Remaster] - Album by Prince & The Revolution - Apple Music

Sara Smile by Daryl Hall & John Oates https://www.youtube.com/watch?v=dYEpFJhuu1E

Stop Making Sense The Movie https://www.youtube.com/watch?v=9WMG2h8XLuI

Tezeta by Mulatu Astatke (Ethiopian Jazz) https://www.youtube.com/watch?v=8ygSCd6TaTg&list=RD8ygSCd6TaTg&start_radio=1

Claire de Lune by Claude Debussy https://www.youtube.com/watch?v=WNcsUNKlAKw&list=RDWNcsUNKlAKw&start_radio=1

MTVs First Day - August 1, 1981 Playlist https://open.spotify.com/playlist/1lQKTYlkt7cI0MVLp3NmbH

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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 realities of aging, that awareness matters perhaps more than ever. Resilience isn’t always loud or heroic. Sometimes it’s as simple as showing up, bending but not breaking, and trusting that the tough stuff you’ve survived before can guide you through what comes next.

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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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