Why do so many relationships lose intimacy over time, even when love is still there?

In this episode of Midlife Chrysalis, Chip Conley talks with renowned couples therapist Terry Real, creator of Relational Life Therapy and bestselling author of Fierce Intimacy and The New Rules of Marriage. For decades, Terry has helped couples understand why connection fades—and how to rebuild it.

In this conversation, he explains:

• Why love requires skills most people were never taught
• How childhood patterns quietly shape adult relationships
• Why traditional masculinity often blocks emotional intimacy
• How couples can reignite connection in midlife

Terry argues that relationships don’t fail because people stop caring, they fail because no one teaches us how to do intimacy well.

Watch the episode to learn the relationship skills that can change everything.

Timestamps:

01:30 Terry Real joins from Anguilla

03:01 What is Relational Life Therapy (RLT)

03:54 Why RLT takes sides in couples therapy

06:18 The core principles of RLT

08:14 Trauma triggers and childhood patterns in relationships

11:59 What holds men back in relationships

15:04 Redefining masculinity for intimacy

16:25 Patriarchy and the modern relationship crisis

18:23 Relational joy vs gratification culture

22:44 Reigniting intimacy as empty nesters

27:03 Why couples must confront resentment

29:46 Independence vs connection in long-term relationships

33:24 Are you really happy in your relationship

36:53 Why relationships require practice and skill

40:08 Wisdom bumper sticker

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

#midliferelationships #relationshipadvice #intimacy #modernrelationships #couplestherapy #loveskills #relationshipskills #midlifechrysalis #emotionalintimacy #terryreal #relationshipgrowth #relationshipproblems #communicationinrelationships #longtermrelationships #midlifelove

The moment that breaks your life can also be the moment that transforms it.

In this episode of Midlife Chrysalis, Chip Conley sits down with comedian and writer Pete Holmes for a deep and surprisingly funny conversation about heartbreak, spirituality, and the search for meaning. Pete shares how a painful divorce in his twenties pushed him to fully commit to comedy and set him on a journey into consciousness, psychedelics, fatherhood, and what it really means to live a good life.

In this episode, Pete reveals:

• How his divorce became the turning point that changed his life and career
• Why humor may be one of the most powerful tools for healing
• What psychedelics taught him about consciousness and awareness
• Why midlife can actually be the most meaningful chapter of life
• The life-changing idea: don’t believe everything you think

Warm, honest, and thought-provoking, this conversation explores how laughter and self-awareness can transform even life’s hardest moments.

👉 Watch the full episode to hear Pete Holmes’ story and discover why humor might be the secret to a better life.

Timestamps:

03:46 Is Pete Christian Comedian?

06:25 Was Jesus Funny?

09:04 Humor Humility and Getting Older

10:44 Can You Train Your Sense of Humor?

13:41 Why Midlife Is Actually Better

15:36 Fatherhood and Life in His 40s

19:52 Turning 47 and the Happiness Curve

20:59 Divorce at 28 and the Turning Point

26:17 Why Comedy Exploded After 9/11

30:42 Humor as Healing for Pain

31:54 Comedy Is Saying What Everyone Thinks

35:46 Aging What Gets Worse and What Gets Better

39:50 Psychedelics and Spiritual Awakening

46:39 Bringing Spirituality Into Comedy

49:48 Pete Holmes’ Best Life Advice

54:33 Relationship Advice That Actually Works

56:19 Final Thoughts and Richard Rohr

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

#PeteHolmes #MidlifeChrysalis #MidlifeWisdom #ComedyPodcast #PeteHolmesInterview #StandUpComedy #SpiritualityAndComedy #MidlifeGrowth #PersonalGrowthPodcast #PsychedelicInsights #RichardRohr #LifeLessonsPodcast #ConsciousComedy #SpiritualAwakening #SelfDiscovery

What if the most powerful move you could make at midlife… is to pause?

In this episode of Wisdom Wednesday, Derek sits down with Chip Conley to explore the rise of the midlife sabbatical and why more people over 50 are choosing a reset instead of racing toward retirement.

Chip challenges the old “learn, earn, retire” model and introduces a new idea: the midlife pit stop — a courageous break to refuel before the next chapter.

In this conversation, you’ll learn:

• Why a sabbatical isn’t a vacation. It’s renewal
• How stepping away can strengthen your career and relationships
• What Chip discovered during his own two-year break
• How to design a meaningful month off, even if a year feels impossible

Midlife isn’t about slowing down. It’s about getting intentional.

If this resonates, share it with someone who might need a reset and subscribe for more Wisdom Wednesday insights.

Timestamps:

00:05 Spring Travel Chat & Baja Living

05:34 The Rise of the Midlife Gap Year

11:20 The Midlife Atrium Concept

13:15 Why Employers Should Support Sabbaticals

17:14 Starting Small with a Gap Weekend

18:07 Chip’s Two-Year Sabbatical Experience

23:13 Ego, Curiosity, and Deepened Friendships

24:31 How to Design a One-Month Sabbatical

26:58 Saving for a Midlife Pit Stop

29:19 Escaping One-Dimensional Living

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

#MidlifeReset #MidlifeSabbatical #MidlifeGapYear #SecondAct #LifeAfter50 #CareerBreak #SabbaticalLife #WorkLifeBalance #RetirementRedefined #PersonalGrowthJourney #EmptyNestLife #ReinventYourLife #MidlifeTransformation #PurposeAfter50 #ChipConley