Shaina Feinberg experienced the struggle that so many women face: being a mom of two kids and having a career as a filmmaker. In recent years, she felt she was failing at both and wondered if she gave one up, would she be more successful at the other?

But, when it came to her career, she had a monkey on her shoulder: Shaina's mother had given up her career aspirations to be a full-time mom and she'd always expressed regret about it.

Then—while working on a freelance job—Shaina met Joan Darling, a 90-year-old, retired TV director. Joan was an Emmy-winning pioneer with successes like The Mary Tyler Moore Show, MASH and Magnum PI to her credit.

While Zooming with Joan, Shaina felt an inexplicable connection, and she was driven to meet the TV veteran in person. Shaina took her camera and flew from New York to Joan's home in Maine. In this episode, Shaina shares the beautiful story of how the two connected over the 3-day visit—and how Joan helped Shaina think thru her struggles while boosting her self-esteem. Tapping on everything from grappling with parents' regrets to holding on to a dream that, at times, feels futile, this episode both thought provoking and touching.