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.

Have you ever found yourself holding onto someone who couldn’t fully open up to you?

Have you ever stayed in a relationship longer than you should have, hoping things would finally get better?

In today’s episode, I’m doing something a little different. My good friend Lisa Bilyeu flips the script and interviews me. Lisa is the co-founder of the billion-dollar company Quest Nutrition, founder of Women of Impact, and one of the most honest, fearless voices I know when it comes to growth, relationships, and empowerment. Together, we unpack some of the most misunderstood truths about relationships, from why we settle to how we can start making choices rooted in self-worth rather than fear.

We talk about how to stop crowd-sourcing your most important life decisions and why learning to listen to your own voice—without all the outside opinions—is one of the most healing things you can do. I share the real reason many of us struggle with being alone, how to break the cycle of chasing emotionally unavailable partners, and why true love should feel like peace—not anxiety dressed up as passion.

This episode is about so much more than dating. It’s about rebuilding your self-worth one choice at a time. I walk you through my 5 daily habits that help me build inner confidence, how to tell when you’re compromising in love versus losing yourself, and the honest questions you need to ask before deciding whether to stay—or walk away.

In this interview, you'll learn:

How to Stop Settling and Start Choosing From Confidence

How to Trust Your Intuition Without Second-Guessing Yourself

How to Break Free From the Fear of Being Alone

How to Create Peace In Order to Attract a Healthy Relationship

How to Know If You’re Compromising or Abandoning Yourself

How to Build Self-Worth With 5 Simple Daily Habits

I’m so grateful to Lisa for creating this space. I hope it brings you a deeper sense of direction, healing, and the reminder that you are always worth choosing—especially by yourself.

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.

What We Discuss:

00:00 Intro

01:21 The Three Reasons We Settle in Love

04:24 We All Have a Different Take on Love

06:36 The 7-Day Opinion Fast

13:15 Why Do We Keep Chasing the Wrong Person?

17:29 The Technique Men Use to Flirt with Women

23:44 The Difference Between Adapting vs. Diminishing Yourself in Relationships

28:39 This is the Biggest Reason for Breakups & How to Avoid It

31:50 Promoting a Healthy Relationship Through 'US' and 'WE'

34:52 Never Say these Two Words During An Argument

36:41 Is it Love or Just Lust?

38:24 Are You Comfortable or Complacent in Your Relationship?

45:24 Don't Let Your Insecurities Affect Your Current Relationship

48:06 The Three People You'll Fall With in Love in Your Life

53:29 Why Trust Should Be Given Easily

56:02 Fixing Someone Isn't Your Responsibility

01:00:39 Three Ways to Adapt to Your Partner's Personality

01:06:23 You Can't Live on Someone Else’s Timeline

01:12:29 This is the Type of Conversation You Should be Having With Your Partner

01:16:16 5 Daily Habits to Build Self-Worth

01:22:47 Best Nighttime Routine to Block Negative Thoughts

01:25:25 Jay's On Tour Update

Episode Resources:

Lisa Bilyeu | Website

Lisa Bilyeu | Instagram

Lisa Bilyeu | TikTok

Lisa Bilyeu | Facebook

Lisa Bilyeu | YouTube

Lisa Bilyeu | X

Lisa Bilyeu | LinkedIn

Women of Impact Podcast

Radical Confidence: 11 Lessons on How to Get the Relationship, Career, and Life You Want

See omnystudio.com/listener for privacy information.

Do you believe our thoughts can shape our reality?

Have you ever had a moment where something you visualized came true?

In this special compilation episode of On Purpose, Jay Shetty brings together a powerful lineup of voices—including Roxie Nafousi, Dr. Tara Swart, Big Sean, and Will Smith—to explore how manifestation can be truly transformative when rooted in clarity, alignment, and intentional action. Through candid conversations and personal reflections, Jay and his guests break down the mindset shifts and daily habits that turn dreams into reality.

This episode challenges common misconceptions, revealing that manifestation isn't about wishful thinking but about cultivating a deep sense of self-worth and purpose. Listeners will discover how to harness the power of visualization, overcome limiting beliefs, and align their actions with their deepest desires. The discussions emphasize the importance of consistency, gratitude, and resilience in the journey toward personal fulfillment.

Whether you're new to the concept or seeking to deepen your practice, this episode offers practical insights and inspiring stories to guide you on your path. It's a reminder that with the right mindset and intentional effort, you can create the life you've always envisioned.

In this episode, you'll learn:

How to Shift from Passive Wishing to Active Creating

How to Build Unshakable Self-Trust

How to Visualize and Embody Your Desired Outcomes

How to Stay Motivated and Bounce Back from Setbacks

How to Align Daily Actions with Long-Term Vision

Manifestation is more than a buzzword, it's a commitment to living with purpose and intention. Tune in to uncover the tools and perspectives that can help you turn your aspirations into tangible realities.

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

01:10 This is Why You Attract Rejection and Negativity

04:40 Stop Manifesting the Wrong Things

08:19 Manifesting the Life You Want Isn't a Trend

12:06 Start Small to Grow Big Long Term

15:04 The Impact of Micro Changes to Make Your Life Better

17:57 Why is the Brain Wired to Avoid Risk?

24:45 How Acceptance Can Help You Move Forward

28:52 Stop Chasing, Start Attracting

30:29 Focus on the Things You Can Control

33:08 The Price of Having the Wrong Success Mindset

36:02 How to Live Your Life in Love and Service

See omnystudio.com/listener for privacy information.