Most leaders are chasing short-term wins and missing the long game.

In this episode, Chip Conley talks with Rand Stagen, founder of the Stagen Leadership Academy, about what’s quietly breaking leadership today and how to lead with purpose, perspective, and staying power.

Rand shares hard-earned insights from decades of working with CEOs and entrepreneurs who want more than success, they want meaning.

You’ll learn:

- Why short-term thinking undermines great leadership

- What it means to play the infinite game

- How awareness creates better choices

- Why the best leaders think in decades, not quarters

If you’re leading others, or rethinking your own direction, this conversation offers a clear, grounded reframe.

👉 Watch now and start playing the long game.

Timestamps:

05:51 Rand Stagen personal leadership journey

07:47 The advice for young entrepreneurs

10:17 Entrepreneurial roots and early influences

12:43 Founding the Leadership Academy

16:50 Structure of the leadership program

22:23 Integral theory explained

26:18 Leadership and polarization

35:57 Practical advice for leaders

41:45 Conscious Capitalism principles

45:41 Short term versus long term thinking

52:01 Workshop goals and takeaways

56:18 Who the workshop is for

58:12 Leadership wisdom and closing insight

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

#LeadershipDevelopment, #ConsciousLeadership, #LongTermThinking, #LeadershipMindset, #PersonalGrowth, #ExecutiveLeadership, #PurposeDrivenLeadership, #InfiniteGame, #MidlifeLeadership, #SelfLeadership, #LeadershipPodcast, #AwarenessAndChoice, #ModernLeadership, #LeadershipWisdom, #ChipConley

Most companies are racing toward AI, efficiency, and scale while quietly losing the one advantage that actually sustains great leadership: wisdom.

In this Wisdom Wednesday episode, we reveal why culture, lived experience, and human judgment matter more than ever. Chip draws on decades of leadership experience to explain why many organizations are losing their edge and what they can do to reclaim it.

In this episode, you’ll learn:

- Why leadership is a practice, not a personality trait

- How culture is shaped when leaders aren’t in the room

- What companies lose when institutional wisdom disappears

- The difference between knowledge workers and wisdom workers in the AI era

As technology accelerates, human skills become the real competitive edge.

👉 Watch now and discover how wisdom future-proofs leadership and culture.

Timestamps:

00:13 Leadership as a practice

02:29 Culture leaders overlook

05:18 Defining real company culture

08:57 Institutional wisdom loss

13:47 Knowledge workers vs wisdom workers

18:30 AI impact on early careers

22:22 Humanities and philosophy comeback

22:44 Wisdom at Airbnb

25:53 Informal mentors and EQ

27:57 Leading yourself first

28:18 Resources and upcoming workshop

30:12 Closing thoughts

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

#LeadershipWisdom #WisdomAtWork #FutureOfLeadership #AIAndLeadership #CompanyCulture #EmotionalIntelligence #KnowledgeVsWisdom #HumanSkills #MentorshipMatters #InstitutionalWisdom #LeadershipDevelopment #WisdomWednesday #LeadershipCulture #AIImpact #ModernLeadership

Have you ever reached a point in life where what once worked… suddenly doesn’t?

In this warm conversation with Chip, Ben Katt, MEA’s faculty in residence and author of The Way Home, offers a hopeful reframe of midlife. Rather than seeing it as a breakdown, Ben invites us to see this season as a meaningful transition, one that asks us to let go of old roles and reconnect with who we truly are.

In this episode, you’ll discover:

- Why midlife often feels disorienting, even when life looks “successful” on the outside

- How releasing familiar identities creates space for deeper purpose and wholeness

- Why stillness, reflection, and meditation are essential during times of change

- How community and support help us move through transitions with more easy

If you’re feeling restless, uncertain, or quietly asking “What’s next?”, this conversation offers clarity, comfort, and a sense of direction.

👉 Watch now and explore what this chapter of your life is gently calling you toward.

Timestamps:00:35 The Hero’s Journey and The Way Home

04:49 Ben’s five-year soul journey

07:20 Achievement perfectionism and people pleasing

09:44 Meditation and inner balance

13:19 Phase 1: Leaving the familiar

15:46 Phase 2: Falling into the unknown

18:30 Dark night of the ego

20:51 Wander in the wild

23:56 Support and community

29:52 Phase 3: Rising to wholeness

33:46 Stillness and begin again

38:58 Teaching wisdom without religion

44:13 The wisdom well metaphor

47:21 Why wisdom matters now

50:28 Wisdom bumper sticker

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

Find Ben Katt at https://benkattofficial.com/

#MidlifeTransition #MidlifeCrisis #MidlifeTransformation #HeroJourney #FindingPurpose #MidlifeWisdom #LifeTransitions #PersonalGrowth #MidlifeAwakening #SecondHalfOfLife #InnerWork #MeaningInMidlife #JosephCampbell #WisdomTraditions #MidlifeChrysalis

What if the wellness advice you followed for years stops working after 50?

In this episode, wellness pioneers Jeff Krasno, co-founder of Wanderlust, and Schuyler Grant, founder of Kula Yoga Project, share how their approach to health quietly but radically shifted in midlife, and why many popular wellness habits fall short as we age.

With decades spent in yoga, wellness festivals, and lived experience, they share what actually matters now.

They share insights on:

- Why yoga alone isn’t enough after 50

- How muscle and strength shape metabolic and brain health

- The importance of diverse movement, not extremes

- How simple habits and presence support long-term well-being

This is a grounded, honest conversation about aging well — without hype or shortcuts.

👉 Watch now and rethink what midlife wellness really requires.

Timestamps:

01:22 Skylar’s yoga studio near Ground Zero

05:54 The origins of Wanderlust

09:47 Early resistance to the festival idea

11:28 Wellness hotels and business travel

14:32 Challenges of working with a spouse

20:52 What wellness means after 50

20:52 Muscle, metabolism, and aging

26:30 Yoga versus strength training

29:43 Muscle health and brain health

31:37 Diversity of movement in midlife

34:38 Curiosity, learning, and discomfort

37:34 Habit stacking explained

40:27 Wellness and politics

45:49 Upcoming Baja workshop

49:27 Wisdom bumper stickers

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

#WellnessAfter50 #MidlifeWellness #HealthyAging #StrengthAfter50 #MuscleAfter50 #AgingWell #Over50Health #MidlifeHealth #LongevityLifestyle #FunctionalFitness #WellnessPodcast #HealthyMidlife #MindBodyHealth #HabitsForHealth #LifeAfter50

Why most New Year’s resolutions fail before February? In this episode of Wisdom Wednesday, we take an honest look at why good intentions fade quickly and share a simple, practical framework for building habits that last. Drawing from real-life experience, we break down how to turn good intentions into daily actions, without relying on motivation alone.

In this episode, you’ll learn:

- Why most resolutions fail

- How habit stacking makes change automatic

- The “Four Ps” that make goals stick

- Why public accountability matters

- How to build habits that last beyond January

If you’re done repeating the same resolutions every year, this episode will help you do it differently.

👉 Watch now and start the year with habits that actually stick.

Timestamps:

00:44 Morning people and Baja midnight

01:39 Why New Year’s resolutions fail

02:07 Common resolutions and lack of a plan

03:30 Habit stacking explained

05:10 Turning resolutions into daily practice

06:10 The four Ps framework

07:45 Pairing and social accountability

08:39 Passion versus accountability

09:50 Why fewer goals work better

11:03 Learning from past resolutions

11:50 Personal resolutions and alcohol

13:10 Family time as a long-term priority

14:14 Final reflections for 2025

15:02 Age, milestones, and perspective

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

#NewYearsResolutions #HabitBuilding #HabitsThatStick #PersonalGrowth #MidlifeWisdom #BehaviorChange #GoalSetting #Accountability #HabitStacking #Mindfulness #SelfImprovement #Longevity #Wellbeing #LifeDesign #WisdomWednesday

Midlife can feel confusing, even when life looks good from the outside. Careers change, relationships shift, and the way we see ourselves starts to evolve, leaving many people feeling stuck in between what was and what’s next.

In this episode, Kari Cardinale, Chief Content Officer and partner at Modern Elder Academy, explains why these moments aren’t breakdowns but transitions, and why learning to navigate them is an essential life skill. Through her work on Transitional Intelligence, Kari shares what’s really happening during midlife change and how to move through it with greater clarity and confidence.

You’ll learn:

• Why most midlife “crises” are actually misunderstood transitions

• The three stages of change: endings, the messy middle, and new beginnings

• Why the messy middle feels so hard — and why it matters

• How rituals, community, and small “glimmers” guide what comes next

If you’re feeling stuck or sensing a shift in your life, this episode will help you understand where you are and how to move forward.

👉 Navigating Transitions online course from Modern Elder Academy offers a supportive, step-by-step way to work through change with clarity and confidence, starting March 2: https://www.meawisdom.com/navigating-transitions-online/

Timestamps:

01:20 What is transitional intelligence

03:58 The three stages of transition

06:02 Voluntary and involuntary change

08:02 Why transitions take longer than we expect

11:50 The role of ritual in midlife

15:54 The messy middle and uncertainty

17:53 Glimmers and new beginnings

21:44 Growth mindset in midlife

24:28 Kari’s personal transition story

28:37 The birth of Modern Elder Academy

31:36 Love and relationships in midlife

34:48 What truly gets better with age

37:23 Building community and belonging

42:31 Wisdom bumper sticker

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

#KariCardinale #MidlifeTransitions #MidlifeChange #MessyMiddle #LifeTransitions #PersonalGrowth #MidlifeWisdom #ModernElder #TransitionalIntelligence #EmotionalIntelligence #MidlifePurpose #NewBeginnings #GrowthMindset #MidlifeJourney #InnerWork

He didn’t plan on being successful. He just followed what pulled at him and kept letting go when it stopped working. In this episode, Stacy Peralta, legendary skateboarder, filmmaker behind Dogtown and Z-Boys, and modern elder, shares how a life built on passion, curiosity, and vulnerability led him from skateboarding to filmmaking to painting, without clinging to any single identity.

Rather than chasing security or certainty, Stacy reveals why reinvention requires becoming a beginner again and why midlife may be the most powerful time to do it.

In this conversation, Stacy explores:

- Why holding onto past identities quietly blocks your future

- How embracing vulnerability and being a “kook” unlocks growth

- The difference between loving something and knowing when to let it go

- How intuition, not logic, often guides the most meaningful transitions

- Daily practices that keep creativity, curiosity, and vitality alive

👉 Watch the full episode now and discover why letting go might be the most powerful move you can make.

Timestamps:

00:58 Early life mischief and finding skateboarding

03:32 Understanding transitions and success

05:57 Realizing it was time to leave skateboarding

06:38 Becoming a beginner in filmmaking

10:46 Family influence and unconventional paths

13:16 Work ethic creativity and self reliance

15:19 Learning from surfer elders

16:59 Following what you love in midlife

18:41 Giving your gift and letting it go

20:00 Embracing vulnerability and being a kook

24:10 Facing fear of being too old

28:00 Flow challenge and skill

31:10 MEA workshops experience

34:25 Quiet rebellion and midlife dreams

37:05 Listening intuition and creating space

39:05 Letting go of control

41:23 Daily practices for vitality

42:46 Harmonizing heart and mind

43:07 The power of listening

44:51 Closing reflections and gratitude

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

#StacyPeralta #MidlifeReinvention #ModernElder #PersonalReinvention #MidlifeTransition #GrowthMindset #CreativeLife #LettingGo #SecondAct #PurposeInMidlife #LifeTransitions #DogtownAndZBoys #SkateboardingLegend #BecomingABeginner #Intuition

In this Wisdom Wednesday episode, Chip Conley, entrepreneur, author, and founder of MEA, opens up about the quiet disappointment many high achievers feel after they’ve “made it.”

Through stories from building iconic companies, guiding Airbnb’s founders, and navigating midlife reckoning, Chip explores the success treadmill, and why chasing the next win so often leaves us unsatisfied.

In this conversation, you’ll learn:

- Why success can feel addictive but never fulfilling

- The crucial difference between happiness and joy

- How a simple gratitude practice can change how life feels day to day

- What midlife teaches us about meaning, ego, and impact

Thoughtful, honest, and deeply human, this episode is an invitation to pause, reflect, and reconnect with what actually matters.

👉 Watch now and step off the success treadmill.

Timestamps:

01:00 Holiday plans and family time

01:51 MEA Film Festival vision and growth

04:28 Defining success and ambition

06:30 Happiness vs. Joy

10:03 Making gratitude intentional

11:27 Realizing the success treadmill

15:21 Ego shift at Airbnb

16:32 Getting off the treadmill sooner

16:50 Near death experience and perspective

18:30 Service as gratitude practice

19:40 Facing illness and loss

21:33 This too shall pass

21:49 Collective gratitude and closing

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

#SuccessTreadmill #GratitudePractice #MidlifeWisdom #FindingMeaning #HappinessVsJoy #PersonalGrowth #MidlifeTransformation #RedefiningSuccess #LifePurpose #InnerFulfillment #ChipConley #MidlifeCrisis #SelfReflection #LifeLessons #MindfulLiving