Scroll down

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

What We Discuss:

00:00 Intro

01:02 The Universal Truth Behind All Human Problems

02:17 Why We All Really Just Want to Belong

06:50 Feeling Lonely? You’re Not Alone

09:26 Why Community is Disappearing & Why It Matters

18:00 Do Kids Really Need a Village?

21:40 Why We All Crave Safety 

23:45 How to Find People Who Share Your Values

27:40 Understanding the Journey vs. the Goal

30:11 Knowing When to Persevere vs. Let Go

32:31 How to Know You've Outgrown a Friendship

37:30 Recognizing Why a Relationship Has Ended

39:17 Why Sincerity Beats Perfection Every Time

45:09 Learning to Trust Your Intuition 

48:16 The Most Powerful Relationship Advice You'll Ever Hear

54:51 How to Share Your Wins With Friends Who Are Struggling 

01:01:14 Stop Letting Insecurities Define Your Behavior

01:06:58 Can You Be Friends with People You Envy?

01:09:01 How to Respond to Skeptics with Grace

01:12:09 Your Worth Isn’t Measured by Numbers

01:15:08 Tune Into Your Needs, Not Others' Expectations

01:17:51 What Social Awkwardness Really Means

01:22:16 Real Communication Is About Understanding, Not Winning

01:29:00 Embracing Imperfection Is What Makes Us Human

01:30:59 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

“Love this podcast!”
By SHU12323
Love this podcast!
Jay, and everyone else who works on this podcast, thank you. Your energy and passion is contagious and helpful. Thank you so much!
By SHU12323
“Amazing and life changing podcast”
By ChrisAlan83
Amazing and life changing podcast
I was not a fan of podcasts, however after listening to a few of Jay Shettys podcasts I’ve quickly become a fan of podcasts in general but primarily this one. It genuinely gives sincere positive life changing habits that I personally have incorporated into… life and often share with my own friends… and family. Like many of us, I sometimes struggle with anxiety, and the many tips and mindful habits on this podcast truly help.
By ChrisAlan83
“Jay has a special energy that draws people towards him, and a talent at taking people on a journey”
By ChrisAlan83
Jay has a special energy that draws people towards him, and a talent at taking people on a journey
By ChrisAlan83
“Fantastic”
By Kshaq87
Fantastic
Thank you for sharing your insight and knowledge as you fulfill your purpose in life in making wisdom go viral. I really enjoy your podcast.
By Kshaq87
“2020 Vision & Purpose”
By Scottie4488
2020 Vision & Purpose
He has some much good interesting information. I like how he uses facts and information behind what he talks about. I am glad I found him in 2020 because he was just what I was looking for. I would love to meet him and keep up the great work. I am looking forward to your book. Not sure what to expect but listening to everything you said so far has been great. I can’t wait to see what it has in store for us. Thank you for being a positive person and shedding light on things. I’m glad your not a lawyer or doctor! I’m glad you found your passion and helping others. I am looking for that as well. I feel stuck and hope your content gets me passed that!
By Scottie4488
“Amazing and life changing podcast”
By ChrisAlan83
Amazing and life changing podcast
I was not a fan of podcasts, however after listening to a few of Jay Shettys podcasts I’ve quickly become a fan of podcasts in general but primarily this one. It genuinely gives sincere positive life changing habits that I personally have incorporated into my life and often share with my own friends and family. Like many of us, I sometimes struggle with anxiety, and the many tips and mindful habits on this podcast truly help.
By ChrisAlan83
“Every episode is an opportunity!”
By Gloraya
Every episode is an opportunity!
Life is beautiful when you find the right words and the right person who motivates you to keep growing, learning , going deep in our feelings and become a better version of ourselves ...Thank you Jay for been part of my journey and teaching me how to embrace the chaos with a better understanding. I was addicted to chocolate, now is chocolate and “On purpose”
By Gloraya
“Life changing”
By wesbacher
Life changing
This podcast is by far the best I’ve ever listened to. Jay goes deep into what it means to live a healthy life in all aspects and causes you to truly reflect on your own life and where you’re at. Thank you for the life changing content, Jay!
By wesbacher
“Great Perspective”
By Steelborne
Great Perspective
“The world we see is what we give it, nothing more than that. As a man thinketh so does he perceive. Therefore, seek not to change the world, but choose to change your mind about the world.” So far I would say the above quote from “A Course in Miracles,” sums up Jay’s podcast the best. If you want to live a purposeful life in service of others, as I do, you need to change your mind - your perception; not work to change others or the world. Work authenticity in what you are. Jay does this extremely well. Fantastic messages for a purposeful life. I will certainly listen to every episode.
By Steelborne
“Inspiring”
By Shocked and Offended
Inspiring
Great pearls of wisdom in each episode. Always motivates me to make changes in my life. Finally consuming content that increases your emotional intelligence and asks you to be better for your community. Keep a pen and notebook handy while listening. Lots of helpful and actionable steps for you life.
By Shocked and Offended
“Life changing”
By BeChDu
Life changing
Thank you so much for your enlightenment. It is so easy to listen and realize what direction I wanted to go but didn’t know the steps to take. The podcast on how to not fall in love fast hit me like a brick. Words and their definitions such as what love means to me, values, priorities and preferences, etc. All of it is pure gold!!! Thank you Jay!
By BeChDu
“The most Transformational podcast”
By LD504
The most Transformational podcast
This podcast will become a mirror to your life, you will begin to have moments after listening that are constantly reflecting situations in your everyday and it gives you the tools and inspiration to make great choices! Jay is truly one of a kind. His messages and content services all walks of life.
By LD504
“Podcast is great!”
By Bradley0414
Podcast is great!
This is an amazing podcast! It really has helped me to set my intentions for my day and to make decisions in alignment with my purpose! I really appreciate the thoughtfulness of your choices and the fact that it forces me to think deeply about my life and my choices! Thank you so much for all you do!
By Bradley0414
“Podcast is life changing”
By Dejalovesyou670
Podcast is life changing
Jay Shetty podcast is what has literally changed my life. Just buy listening everyday I have seen have much I have grown and healed myself as a person. I can’t thank him enough for all his love, compassion, and knowledge. It’s what’s truly helped me be the person I am today and constantly wanting to grow into the best version of myself.
By Dejalovesyou670
“Meaningful content!!”
By Marmeduke puke
Meaningful content!!
Thank you, Jay, for your podcast! I love the content and find myself regularly sharing the insights with people in my life. Many times I will listen 2 to 3 times per episode. Once while doing tasks, again to take notes, and a third time to really let it sink in. Listen, meditate, contemplate. Thanks again to you and your team.
By Marmeduke puke
“Gratitude for sharing knowledge”
By BrotherRidhu
Gratitude for sharing knowledge
We human beings come across those souls so fortunately, yet so rarely, that generate a spark within us to see what the naked eye cannot. You have changed the rarity of such meaningful friendships by instigating that self-love, self-awareness, and self-care in every person who’ve had the chance to hear and see you. Knowledge is power, but when shared with others it becomes powerful. Thank you for sharing with the world your lessons and your insights. I’ve embarked on this journey of self discovery and your voice has been a powerful guide. I’m hoping to have a chance to connect with you personally some day, but until then I look forward to hearing from you every week to inspire me to make an impact in my own life for a better present.
By BrotherRidhu
“Mentor I hope to meet someday”
By Hidef53
Mentor I hope to meet someday
This is one of my favorite podcasts I listen to every week. I look forward to it and know I’ll always go away learning something new, a new perspective on a subject I never considered. As I learned from Jay that you can be mentored by someone you haven’t met and he is def someone I consider a mentor (hopefully I’ll meet someday). This is a must listen, consider it a self care item.
By Hidef53
“Love this podcast!!”
By Shui2323
Love this podcast!!
Jay, and everyone else who works on this podcast, thank you. Your energy and passion is contagious and helpful. Thank you so much!
By Shui2323
“Thank you!!!”
By madhatter96
Thank you!!!
Thank you so much Jay for creating this podcast and providing weekly content! I listen whenever I have some down time during the day and it’s such a nice way to reflect and stay motivated and grounded throughout the day.
By madhatter96
“Wow!”
By RollTideDLCC
Wow!
Jay has an amazing gift and an even more amazing heart! I love what he is doing in the world and has made me a better person through his insights and kindness! Thank you Mr. Shetty
By RollTideDLCC
“Fantastic”
By Kshaq87
Fantastic
Thank you for sharing your insight and knowledge as you fulfill your purpose in life in making wisdom go viral. I really enjoy your podcast.
By Kshaq87
“Jay is life-changing!”
By Naty0210
Jay is life-changing!
Listening to Jay Shetty during my commute early in the mornings has changed my life! He’s wise yet so simple in delivering his message. I’m a fan and I’m so thankful for his insights in life, love and everything in between!
By Naty0210
“Thank you Jay Shetty for your spiritual wisdom and insight. ”
By PearlJelly9
Thank you Jay Shetty for your spiritual wisdom and insight.
Thank you Jay Shetty for your spiritual wisdom and insight. I am on a spiritual journey currently and I’ve been searching for answers and teachings that are deeply connected spiritually. There’s a higher calling on my life. I thank you again for all of your teachings.
By PearlJelly9