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 Intro00:45 Introduction to Karen Walrond01:58 Growing up & career journey06:50 Midlife shift toward writing and creative work11:38 Cultural perspectives on aging in Trinidad vs. the U.S.16:55 Defining the “Radiant Rebellion”19:14 Resisting societal scripts23:06 Aging in non-white cultures31:43 Collaboration with Brené Brown36:12 Introducing In Defense of Dabbling40:03 The 7 attributes of dabbling44:08 Why trying new things matters as we age50:42 Karen’s experience teaching at MEA workshops53:11 Karen’s wisdom bumper sticker57:10 Chips’s closing reflections on joy, culture, and lifelong learningLearn more about MEA at ⁠https://www.meawisdom.com/#AgingBoldly #MidlifeReinvention #RadiantRebellion #LifeOnYourOwnTerms #NeverTooLate #MidlifeTransformation #CuriosityAndPlay #JoyfulAging #BreakingFree #LiveFully #MidlifeMotivation #RedefiningSuccess #KeepYourSparkAlive #IntentionalLiving #TrySomethingNew