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

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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.

Antonio Gibson, Reverse Interview w/ @declassifiedwft