The Midlife Chrysalis20 Aug 2025

Aging Boldly and Living on Your Own Terms with Karen Walrond

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/

#AgingBoldly #MidlifeReinvention #RadiantRebellion #LifeOnYourOwnTerms #NeverTooLate #MidlifeTransformation #CuriosityAndPlay #JoyfulAging #BreakingFree #LiveFully #MidlifeMotivation #RedefiningSuccess #KeepYourSparkAlive #IntentionalLiving #TrySomethingNew

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