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.