Simon Sinek: Not Every Friendship Is Meant to Last—And That’s Okay! (THIS is How to Know If It’s Time To Walk Away From Adult Friendships That No Longer Fit)
from On Purpose with Jay Shetty
by iHeartPodcasts
Published: Mon Jun 09 2025
Show Notes
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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What We Discuss:
Intro
How to Truly Connect with Others
The Universal Truth Behind All Human Problems
Why We All Really Just Want to Belong
Feeling Lonely? You’re Not Alone
Why Community is Disappearing & Why It Matters
Do Kids Really Need a Village?
Why We All Crave Safety
How to Find People Who Share Your Values
Understanding the Journey vs. the Goal
Knowing When to Persevere vs. Let Go
How to Know You've Outgrown a Friendship
Recognizing Why a Relationship Has Ended
Why Sincerity Beats Perfection Every Time
Learning to Trust Your Intuition
The Most Powerful Relationship Advice You'll Ever Hear
How to Share Your Wins With Friends Who Are Struggling
Stop Letting Insecurities Define Your Behavior
Can You Be Friends with People You Envy?
How to Respond to Skeptics with Grace
Your Worth Isn’t Measured by Numbers
Tune Into Your Needs, Not Others' Expectations
What Social Awkwardness Really Means
Real Communication Is About Understanding, Not Winning
Embracing Imperfection Is What Makes Us Human
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
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