What happens when time stops feeling endless and starts feeling real?

In this episode of Wisdom Wednesday, Chip Conley shares how living with cancer reshaped his relationship with time, purpose, and urgency in midlife.

Joined by Derek Gehl, Chip reflects on cancer scans, mortality, and why remembering that life is finite can actually deepen meaning, not fear.

Together they explore:

• Why memento mori can bring clarity, not darkness
• How midlife urgency is about intention, not panic
• What legacy really means beyond achievement

This is a warm, life-affirming conversation about choosing what matters most when you realize tomorrow isn’t guaranteed.

👉 Watch now, and join the conversation by leaving a comment or review.

Timestamps:

00:00 Opening and setup

00:42 Episode introduction

01:00 Workshops and unexpected contrasts

03:12 Ricky Williams and walking away from football

04:28 Cancer scans and living with uncertainty

05:20 Death as a daily presence

06:00 Prostate cancer diagnosis and treatment journey

10:43 Hormone therapy and energy loss

13:46 Feeling mortality in the body

14:16 Memento mori and midlife urgency

16:30 Legacy and ripple of impact

18:24 Near death experience story

22:47 Succession planning and leadership wisdom

23:18 Talking about death without fear

26:10 Purpose usefulness and meaning

28:20 Wisdom bumper sticker on mortality

30:04 Gratitude and closing reflections

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

#MidlifeWisdom #CancerJourney #LivingWithUrgency #MementoMori #MidlifePurpose #FacingMortality #LifeAfterCancer #ModernElder #MeaningfulLife #LegacyAndPurpose #MidlifeReflection #WisdomWednesday #PersonalGrowth #LifePerspective #ChipConley

In this candid and heartfelt conversation, Airbnb co-founder and CEO Brian Chesky joins Chip Conley to explore the hidden side of success. From imposter syndrome to the emotional aftermath of the IPO, Brian shares what midlife has taught him about ambition, belonging, and finally realizing he is enough. In this episode, you’ll hear:• Why success didn’t fix his loneliness• How leadership evolved from control to connection• The wake-up call that followed Airbnb’s $100B milestone• Why midlife is a chance to redefine what truly matters This is a conversation about growth, vulnerability, and choosing relationships over relentless achievement.If you’re navigating success, questioning your next chapter, or redefining what fulfillment means, this one’s for you.Listen in and reflect on what “enough” means in your life. Timestamps:00:00 Reunion and reflecting on 13 years since Airbnb began01:02 How Brian recruited Chip and the early Airbnb vision02:27 Chutzpah and learning from mentors04:00 Discovering hospitality as Airbnb’s true business06:43 Early partnership dynamics and mutual mentorship11:21 Advice to his 26 year old founder self12:20 Imposter syndrome and leadership growth15:42 From creative outsider to Fortune 500 CEO17:26 Childhood, not belonging and ambition22:48 Loneliness after success and the IPO realization27:54 Investing in friendships and rebuilding connection29:00 Founder mode and evolving leadership style37:24 Redefining success in midlife38:17 Hoffman process and realizing he is enough41:35 Fear of intimacy and unfinished business50:03 The Airbnb Open and scaling with soul54:20 Wisdom bumper stickers and life lessons56:04 In you lies unknown potential1:00:48 I am enough and always was Learn more about MEA at ⁠https://www.meawisdom.com/

Midlife isn’t a crisis. It’s an invitation to come alive again.

In this episode of Midlife Chrysalis, Chip Conley is joined by Susan Magsamen, a neuroscientist at Johns Hopkins, and Ivy Ross, Chief Design Officer at Google, for a warm, eye-opening conversation about why creativity is essential to being human, especially in midlife.

Drawing from their book Your Brain on Art, they share how art, play, and sensory experiences quietly support brain health, emotional balance, and a deeper sense of meaning in a world obsessed with productivity and speed.

You’ll hear why:

• Creativity is hard-wired into our biology, not reserved for “artists”
• Midlife is a powerful moment to rediscover curiosity, play, and making
• Small creative acts can reduce stress and help us feel more alive
• Art may be one of the healthiest counterweights to burnout and AI

The second half of life isn’t about doing more, it’s about sensing more, feeling more, and reconnecting with what truly matters.

👉 Watch now and let midlife become a chrysalis, not a cage.

Timestamps:

13:35 Guest backgrounds and journeys

18:36 What Your Brain on Art is really about

21:25 Neuroaesthetics and brain science

23:54 Why creativity is essential for health

24:24 How to rebuild creativity in midlife

29:14 Art, neuroplasticity, and medicine

34:32 Creativity inside Google

39:18 Digital literacy, nature, and balance

41:35 Personal midlife transformation stories

45:30 Resilience through illness and change

49:08 Life wisdom and defining moments

55:51 Final reflections and closing

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

#MidlifeChrysalis #YourBrainOnArt #CreativityAndAging #MidlifeWellbeing #Neuroaesthetics #BrainHealth #CreativityForAdults #MidlifeGrowth #ArtAndScience #HealthyAging #MentalHealthMidlife #PurposeInMidlife #CreativeLiving #SecondHalfOfLife #MidlifeInspiration