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Generational Conversations

Ep 16 – A 78-Year-Old & a 22-Year-Old on What They Had to Unlearn

Growth isn’t just what we learn — it’s what we’re brave enough to let go of.   This episode brings together two voices nearly 56 years apart: Tommy, 78, a retired junior college English professor who spent over a decade as an anti-war activist in the 1960s and ’70s before reinventing himself as a mailman, cab driver, and eventually a journalist and writer — and Sasha, 22, a newly minted insurance broker two and a half months into living on her own for the first time.   The conversation moves from the personal to the historical and back again: Sasha unpacks what it’s meant to unlearn the idea that asking for help is weakness, and that being hard on herself is a form of motivation. Tommy takes listeners back to the anti-war movement, the draft, and the moment he realized the privilege he’d never had to notice — plus the day he walked away from activism entirely, quit his cab-driving job on the spot, and started over as a writer. Both guests close with the one truth they’ve each come to trust about themselves.   Guests Tommy — 78, retired junior college English professor. Spent 12 years as an anti-war activist in the 1960s–70s, including time organizing with a movement influenced by the Black Panther Party, before leaving activism in 1980 to pursue music, journalism, and writing. These days he’s occupied with piano practice and three very energetic dogs (Kima, Easy, and Gizmo).   Sasha — 22, newly working as an insurance broker and about two and a half months into her first solo apartment. A painting major navigating what independence, self-trust, and “adulting” actually feel like in real time.

Solo Reflections

Ep 15 – Feeling Lost? Here’s How to Find Yourself Again

Maybe becoming isn’t about becoming someone else—maybe it’s about returning to who you were before the world told you who to be.   In this solo reflection, Kirby sits with the lessons from his conversation with Chris (64) and Kaitlyn (26)—one of the most healing conversations of the season—and opens up about his own becoming: building Kirby Studios in Bangkok at 26 with no idea what he was doing, the 2020 health crisis in New York that changed everything, and the slow shift from chasing success to living from the heart.   He gets honest about the parts of himself he’s learned to hold with compassion, why he still gets triggered even with all the awareness, and the reminder from Chris that stayed with him most: the process of becoming matters just as much as getting “there.”

Generational Conversations

Ep 14 – The Truth About Finding Purpose in Your 20s & 60s

What if becoming the person you’re meant to be isn’t about achieving more—but about growing through every stage of life?   We’re all in the middle of becoming—whether we realize it or not. So who are you becoming?   Kirby sits down with Chris (64)—a former aerospace engineer turned educator who now brings art programming and mindfulness to senior communities—and Kaitlyn (26)—a writer navigating survival jobs and the long road to a creative career—for an honest conversation about identity, purpose, turning points, and the versions of ourselves we’re still growing into.   Meeting for the very first time on camera, they explore what happens when the plan doesn’t go the way you thought, why chasing what’s easy can quietly limit who you become, and how the pressure to “arrive” keeps us from living the life that’s happening right now.

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