What happens when a self-made billionaire steps away from the company she built and faces the big question: What’s next?

In this inspiring episode, the founder of Spanx opens up about her journey from door-to-door sales to creating a global brand, the emotional challenges of selling her company, and how she’s redefining success, purpose, and identity in midlife. It’s a raw and uplifting conversation about reinvention, intuition, and finding meaning beyond business.

Timestamps:

00:00 Intro

01:56 Family background and kids

03:47 Childhood struggles and early mindset shift

06:32 Discovering Wayne Dyer and self-growth

09:00 Letting go of law school plans

09:46 Intuition and coping mechanisms

13:25 Selling fax machines and rethinking her path

14:17 The idea for Spanx is born

18:40 Building Spanx and landing Neiman Marcus

22:37 Growing Spanx without advertising

25:30 Selling Spanx and facing an identity shift

31:51 Midlife change and grief

34:44 Creating Sneaks brand

43:54 Psychology behind the second venture

47:32 Perimenopause, health issues, and PMDD

50:19 Modern Elder Academy experience

53:37 Focusing on presence and meaning

55:42 Introverts, extroverts, and integration

58:17 Feminine energy as a superpower

59:42 Wisdom bumpersticker

1:02:26 Chip’s final thoughts

Learn more about MEA at ⁠https://www.meawisdom.com/

#SarahBlakely #Spanx #FemaleEntrepreneur #WomenInBusiness #EntrepreneurLife #BusinessSuccess #Motivation #Inspiration #FounderStory #StartupJourney #MindsetMatters #SuccessTips #BusinessAdvice #SelfMadeWoman #EntrepreneurMindset #ChipConley #MidlifeChrysalis

What if midlife isn’t a breakdown—but a breakthrough?

In this powerful conversation, world-renowned writer Pico Iyer shares the surprising lessons he’s learned from 50 years of friendship with the Dalai Lama, losing everything he owned, and finding stillness in the chaos. From walking away from success in New York to building a soulful life in Japan, Pico reveals how true freedom comes not from having more—but from letting go. This episode is a masterclass in finding purpose, inner peace, and meaning in the second half of life.

Timestamps:

00:00 Intro

01:13 Meet Pico Iyer

02:02 Why TED Keeps Inviting Pico Back

02:50 Pico’s favorite TED talk

04:04 Early Life Across Continents

05:17 What “Home” Really Means

07:21 Stillness and the Midlife Chrysalis

12:33 Moving from Park Avenue to Kyoto

15:31 The Value of Being an Expat

18:10 Inner Calm in a Chaotic World

22:31 Everyday Stillness Practices

29:24 A Lifetime with the Dalai Lama

37:34 Living in Absence of Answers

42:29 Pico’s Anticipated Regret

46:11 What Makes MEA So Special

50:47 Awe, Community, and Transformation

53:27 Pico’s Wisdom Bumper Sticker

56:27 Episode Key Takeaways

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeChrysalis #PicoIyer #ChipConley #MidlifeTransformation #ModernElder #Stillness #InnerWisdom #SpiritualGrowth #LifePurpose #DalaiLama #HomeAndSoul #ExpatLife #GratitudePractice #Resilience #MindfulLiving

What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?

In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age.

What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age.Feeling your own shift? Subscribe to The Midlife Chrysalis and explore Modern Elder Academy’s workshops designed to help you thrive in midlife and beyond.

Timestamps:00:00 Intro00:41 Chip’s Relationship With His Dad 08:28 A Prolific Film Career09:38 Working with Clint Eastwood10:51 Carving His Own Path13:54 New Projects & Genre Exploration15:52 Masculinity in Modern Culture18:09 Growing & Maturing as a Man19:26 Questioning & Redefining Midlife21:32 Childhood Dreams & Creative Shifts24:05 Aging, Directing & Creative Control27:1 Time, Regret & Following Your Gut31:51 The Outpost Movie & Hyperbaric Healing35:07 Real Wellness, Not Wellness Trends37:16 Life Lessons & Emotional Maturity39:44 How Scott Hopes to Be Remembered41:31 Lessons from Mom & Dad43:20 Having Mentors & Becoming One44:13 Scott’s Wisdom Bumper Sticker49:13 Healing a Father-Son Relationship

Learn more about MEA at ⁠https://www.meawisdom.com/

#ScottEastwood #MidlifeChrysalis #ChipConley #ClintEastwood #MasculinityToday #ActorLife #FilmIndustry #PersonalGrowth #LegacyAndIdentity #MidlifeReflection #LifeLessons #EmotionalMaturity #CreativeJourney #WellnessWisdom #FollowYourGut