On Purpose with Jay Shetty

Episode: I Reached a Major Milestone! 8 Life-Changing Lessons I’ve Learned From Incredible Guests Along the Way

Air Date: November 26, 2025
Host: Jay Shetty

Overview

In this milestone episode, Jay Shetty celebrates reaching 5 million YouTube subscribers by reflecting on the most potent lessons shared by extraordinary guests throughout the five-year journey of his podcast. Jay curates powerful, heartfelt conversations about growth, resilience, sobriety, love, self-knowledge, spirituality, and community — all aimed at supporting listeners in living happier, healthier, and more authentic lives. Each segment revisits an iconic guest, distilling the wisdom that shaped both the show and its massive community.

Key Discussion Points & Insights

1. Sobriety and Self-Discovery with Tom Holland

• Segment Start: [02:54]
• Core Theme: The courage to embrace sobriety and find clarity in self-examination.
• Key Insights:
  • Tom Holland shares his journey of quitting alcohol, revealing both the struggle and the transformational benefits.
  • The process started as a “Dry January” but became an exploration into his relationship with drinking, leading to a lifestyle change.
  • He underscores the value of supportive friends and finding meaningful replacements for old habits.
  • Both Tom and Jay normalize addiction struggles, championing honesty and self-compassion.
• Notable Quotes:
  • “By the time I had got to June 1, I was the happiest I've ever been in my life...I can't believe the difference that I feel from not drinking.” — Tom Holland [06:08]
  • “There was something that we called the higher taste...you can never give up a lower taste unless you add a higher taste...” — Jay Shetty [17:17]
  • “If I could encourage someone to drink less, then that's great...I went on my own little journey.” — Tom Holland [06:46]
• Memorable Moments:
  • Both Jay and Tom reflect on their former party-loving personas, opening up about social anxiety and the pressure to drink.
  • Tom’s realization about the real impact of alcohol, aided by tracking his sleep patterns, marked a turning point.

2. The Mamba Mentality and Mastery with Kobe Bryant

• Segment Start: [19:26]
• Core Theme: Excellence through discipline, emotional awareness, and consistent effort.
• Key Insights:
  • Kobe Bryant discusses “the Mamba mentality,” dissecting how greatness is built from discipline, obsession, and showing up each day.
  • Emotions must be acknowledged—not suppressed—so one can act with clarity rather than fear.
  • Results aren’t the focus; rather, constant curiosity and iteration lead to actual growth.
• Notable Quotes:
  • “Emotions come and go. The important thing is to accept them all... then you can choose to do with them what you want versus being controlled by emotion.” — Kobe Bryant [19:28]
  • “The results don't really matter. It's the figuring out that matters.” — Kobe Bryant [22:18]
  • “Every day is just constant improvement, constant curiosity, constantly getting better.” — Kobe Bryant [21:50]
• Memorable Moments:
  • Jay and Kobe break down the fear of failure, emphasizing unpacking emotions to move past superficial anxieties.
  • Kobe’s reflections on his upbringing, self-imposed development timelines, and patience in catching up to more physically-gifted peers.

3. Self-Knowledge & Wholeness in Love with Emma Watson

• Segment Start: [27:57]
• Core Theme: Building relationships from a state of wholeness rather than need.
• Key Insights:
  • Emma Watson shares her evolution from seeking relationships out of uncertainty to choosing them from self-understanding and peace.
  • She poses and answers some of life’s hardest questions: “Are you really happy?” “Are you living your values?”
  • The courage to leave things that look good outwardly but don’t feel right inwardly is celebrated.
• Notable Quotes:
  • “You want to be with someone because you want them, not because you need them.” — Emma Watson [29:56]
  • “Can you live with your truth? Can you accept the fact that for most other people, your truth is pretty confusing and unpalatable?” — Emma Watson [33:20]
  • “If you don't know what your baseline happy is, then...you've got no idea of knowing what's going on at all.” — Emma Watson [31:08]
• Memorable Moments:
  • Emma’s candid discussion about walking away from what the world sees as a dream life.
  • Jay’s vow to his wife — if love fades, to please tell him, rather than stay incomplete out of duty.

4. Spirituality as the Compass of Success with Madonna

• Segment Start: [35:24]
• Core Theme: Finding fulfillment beyond ambition through spiritual grounding.
• Key Insights:
  • Madonna discloses that ritual and spiritual practice sustained her through fame and personal challenges.
  • Her path weaved through yoga, Sanskrit study, and eventually Kabbalah, with study and intention becoming anchors.
  • Spirituality doesn’t preclude ambition—instead, it’s a necessary counterpart to lasting fulfillment.
• Notable Quotes:
  • “Success is having a spiritual life, period...You need to be spiritual to be successful.” — Madonna [44:46]
  • “I had everything that people would assume would give you happiness...But I wasn't happy.” — Madonna [35:55]
  • “I just kept going and here I am today. But motherhood or being a parent is really what made me start asking questions...” — Madonna [41:53]
• Memorable Moments:
  • Madonna retells the story of finding Kabbalah while pregnant and needing guidance for her future child.
  • The juxtaposition of public confidence and private search for inner meaning.

5. Mature Love Through Communication and Repair with Benny Blanco & Selena Gomez

• Segment Start: [49:32]
• Core Theme: Relationships thrive not on perfection, but on honest communication and mutual respect.
• Key Insights:
  • Benny and Selena model how couples can handle conflict: taking space, owning feelings, and returning without blame.
  • Validation, physical affection, and respect for each other’s independence strengthen the bond.
  • Both partners bring past lessons into the relationship, using experience to shape a supportive connection.
• Notable Quotes:
  • “We are so cheesy. It's so fun...when she comes back from her day and she tells me what she did...I see the enthusiasm...inspires me.” — Benny Blanco [50:47]
  • “I could never picture myself disrespecting him...I think...I've learned a lot of lessons and I’ve made mistakes and...I just want this to be right.” — Selena Gomez (attributed through Riley Keough) [55:04]
  • “Love is less about avoiding conflict and more about how you navigate it...listening before fixing and validating feelings instead of winning the argument.” — Jay Shetty [61:02]
• Memorable Moments:
  • Benny describes how “guiding the missile, not adding a jetpack” is his approach to handling heated moments.
  • Jay provides a practical tip: “Do you want me to listen, do you want me to fix this, or do you just want me to go through it with you?” [60:06]

6. Presence, Loss, and Family with President Joe Biden

• Segment Start: [61:50]
• Core Theme: The power of showing up and the healing capacity of family and community in grief.
• Key Insights:
  • President Biden reflects on how loss and loneliness are mitigated not by words but by simple acts of presence.
  • Drawing from personal tragedy, he credits family support for his resilience.
  • Availability, daily contact, and the priority of “just showing up” are portrayed as the deepest forms of love and support.
• Notable Quotes:
  • “Sometimes it's just...just touching, just showing up. It just really matters.” — Joe Biden [61:50]
  • “Family is the beginning, middle, and end...no matter what they were doing, they stopped and heard listen to you.” — Joe Biden [65:22]
  • “I think knowing that someone's going to be there for you just to listen, just to...hug you.” — Joe Biden [66:57]
• Memorable Moments:
  • The story of President Biden’s family moving in with him after his wife’s death.
  • Jay and Biden’s mutual recognition that the real gift is just not letting loved ones go through pain alone.

Notable Quotes & Timestamps

• “By the time I had got to June 1, I was the happiest I've ever been in my life…” — Tom Holland [06:08]
• “Emotions come and go...accept them all...then you can choose to do with them what you want…” — Kobe Bryant [19:28]
• “You want to be with someone because you want them, not because you need them.” — Emma Watson [29:56]
• “Success is having a spiritual life, period.” — Madonna [44:46]
• “We are so cheesy. It's so fun...we're inspiring each other...” — Benny Blanco [50:47]
• “Sometimes it's just...just touching, just showing up. It just really matters.” — Joe Biden [61:50]

Lesson Highlights & Takeaways

• Sobriety is a personal journey—find replacements for old habits and strong support systems.
• Greatness comes from diligence, consistency, and emotional honesty—not just talent.
• True love and fulfillment are born from self-knowledge and living your deepest values.
• Spiritual practice is key to sustaining resilience and finding purpose, even amid ambition.
• Healthy relationships embrace differences, communicate boundaries, and repair after conflict.
• Presence and support—being there for one another—are the foundation of emotional healing.

Flow & Tone

Jay Shetty presents the episode with humility and gratitude, employing a storytelling style that honors his guests’ vulnerability and wisdom. The tone is warm, collaborative, and deeply reflective—reminding listeners of their shared humanity and the collective journey toward healing and growth.

Further Listening

Jay closes by encouraging listeners to check out his episode with Michelle Obama on relationship endurance and growth, continuing the theme of introspection and connection.

This episode stands as both a celebration and a heartfelt offering—an invitation to carry wisdom forward on the ongoing journey “On Purpose.”