Author, speaker, and “Radiant Rebel” Karen Walrond joins Chip Conley for a warm, inspiring conversation on how to age with joy, live on your own terms, and keep your spark alive.
From growing up between Trinidad and the U.S., to leaving engineering and law for a creative life, Karen’s story is full of bold choices and unexpected turns. She shares cultural insights on aging, how to break free from the “success script,” and the seven playful experiments from her new book In Defense of Dabbling that prove it’s never too late to try something new.
Packed with heart, humor, and practical wisdom, this episode will leave you smiling and inspired to chase your own adventures.
Timestamps:
00:00 Intro
00:45 Introduction to Karen Walrond
01:58 Growing up & career journey
06:50 Midlife shift toward writing and creative work
11:38 Cultural perspectives on aging in Trinidad vs. the U.S.
16:55 Defining the “Radiant Rebellion”
19:14 Resisting societal scripts
23:06 Aging in non-white cultures
31:43 Collaboration with Brené Brown
36:12 Introducing In Defense of Dabbling
40:03 The 7 attributes of dabbling
44:08 Why trying new things matters as we age
50:42 Karen’s experience teaching at MEA workshops
53:11 Karen’s wisdom bumper sticker
57:10 Chips’s closing reflections on joy, culture, and lifelong learning
Learn more about MEA at https://www.meawisdom.com/
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