Yes, And... Grandparenting: Using Improv to Build Connection in Retirement with Chip Brewer

Ep 117: In this episode of The Retirement Success in Maine Podcast, Ben and Curtis explore how the principles of improv can help retirees strengthen relationships and find new ways to connect. Their guest, Chip Brewer, has performed and taught improv for more than 20 years, working with Fortune 100 executives, educators, and students, as well as authoring his debut thriller novel.

Chip shares how core improv lessons like “yes, and,” active listening, and making others look good can bridge generational gaps, spark joy in everyday family interactions, and turn awkward moments into opportunities for deeper trust. From navigating conversations with teenagers, to building shared stories with grandkids, to keeping family gatherings fun and inclusive, this episode offers retirees a playful yet practical toolkit for enhancing connection and meaning in retirement.

Chapters:

Meet Chip Brewer, improv performer, teacher, and author. [00:01–02:44]

From Amsterdam stages to teaching Fortune 100 companies. [03:06–07:19]

“Yes, and,” active listening, and making others look good. [07:47–13:12]

Using improv to bridge gaps with kids and grandkids. [13:12–27:25]

Why embracing flaws leads to deeper trust. [36:05–39:48]

Simple improv games retirees can try at home. [44:23–48:25]

Chip’s personal vision for a fulfilling retirement. [49:12–50:43]