Are you keeping this friendship out of habit or love? If they weren’t in your life today, would you try to be friends again? In this profoundly insightful episode of On Purpose, Jay Shetty sits down with Simon Sinek, renowned leadership expert, bestselling author, and host of the podcast, A Bit of Optimism. Jay and Simon share a deeply vulnerable and powerful conversation about what it truly means to be human in a world that’s more connected than ever, yet so emotionally disconnected. Together, they explore the foundational role of friendships, belonging, and purpose in building meaningful lives and relationships. Jay opens up about his own transformation and the early influence of Simon’s book Start with Why, while Simon reflects on the personal journey behind his body of work, emphasizing that all leadership is, at its core, about human connection. They speak candidly about how burnout often stems from loneliness, the fragile nature of adult friendships, the difficulty many have in celebrating others’ success, and the healing power of emotional honesty in relationships. With wisdom, humor, and emotional clarity, Simon breaks down how we can show up more authentically for ourselves and for those we love—even when it’s uncomfortable. In this episode, you'll learn: How to Support a Friend Without Trying to Fix Them How to Know When It’s Time to Let a Friendship Go How to Create Belonging When You Feel Disconnected How to Celebrate a Friend’s Win Even When You’re Struggling How to Communicate When You Don’t Know What to Say How to Recognize Burnout as a Sign of Loneliness This episode is a powerful reminder that being imperfect is what makes us human, and that real connection isn’t built on perfection, but on the willingness to be present, authentic, and compassionate.  With Love and Gratitude, Jay Shetty Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here.  Join Jay for his first ever, On Purpose Live Tour! Tickets are on sale now. Hope to see you there!  What We Discuss: 00:00 Intro 02:26 How to Truly Connect with Others 03:45 The Universal Truth Behind All Human Problems 05:45 Why We All Really Just Want to Belong 09:33 Feeling Lonely? You’re Not Alone 12:10 Why Community is Disappearing & Why It Matters 18:33 Do Kids Really Need a Village? 22:17 Why We All Crave Safety  24:22 How to Find People Who Share Your Values 28:19 Understanding the Journey vs. the Goal 30:49 Knowing When to Persevere vs. Let Go 32:46 How to Know You've Outgrown a Friendship 35:22 Recognizing Why a Relationship Has Ended 38:08 Why Sincerity Beats Perfection Every Time 45:46 Learning to Trust Your Intuition  48:52 The Most Powerful Relationship Advice You'll Ever Hear 55:27 How to Share Your Wins With Friends Who Are Struggling  01:03:10 Stop Letting Insecurities Define Your Behavior 01:06:21 Can You Be Friends with People You Envy? 01:09:35 How to Respond to Skeptics with Grace 01:12:44 Your Worth Isn’t Measured by Numbers 01:15:45 Tune Into Your Needs, Not Others' Expectations 01:19:01 What Social Awkwardness Really Means 01:22:59 Real Communication Is About Understanding, Not Winning 01:29:44 Embracing Imperfection Is What Makes Us Human 01:31:40 Simon on Final Five Episode Resources: Simon Sinek | Website Simon Sinek | Instagram  Simon Sinek | LinkedIn Simon Sinek | X Simon Sinek | Facebook Simon Sinek | TikTok Simon Sinek | YouTube A Bit of Optimism See omnystudio.com/listener for privacy information.