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Simon Sinek: If You Feel Lost & Alone Watch THIS! (The KEY to Making REAL Adult Friendships)

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 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: https://simonsinek.com/ https://www.instagram.com/simonsinek https://www.linkedin.com/in/simonsinek https://x.com/simonsinek https://www.facebook.com/simonsinek/ https://www.tiktok.com/@simonsinek https://www.youtube.com/user/SimonSinek https://podcasts.apple.com/us/podcast/a-bit-of-optimism/id1515385282 https://www.instagram.com/jayshetty https://www.facebook.com/jayshetty/ https://x.com/jayshetty https://www.linkedin.com/in/shettyjay/ https://www.youtube.com/@JayShettyPodcast http://jayshetty.me

Simon SinekguestJay Shettyhost
Jun 9, 20251h 33mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:001:02

    Intro

    1. SS

      You start to realize we just treat friends like these disposable things, which I find so upsetting. To have a successful marriage, to have success at work, to be able to manage stress in our lives, friends. They're the ultimate biohack. They fix depression, they fix anxiety, they fix inability to cope with stress.

    2. JS

      Multiple time bestselling author. One of the greatest thinkers of our generation. One of the most impactful voices in the world of leadership. Your best friend thinks the person you're dating is not right for you.

    3. SS

      Sometimes not all our partnerships aren't just stood by our friends. Very often they don't tell you until after you've broken up.

    4. JS

      How should introverts think about friendships differently to extroverts?

    5. SS

      The rules are the same. Every friendship should be additive. They should be worth the time and the energy that we invest.

    6. JS

      What do we do when we feel the people around us don't believe in us?

    7. SS

      Anybody who wants to have an impact on the lives of others has to get used to the idea that not everybody's gonna like you.

    8. JS

      The number one health and wellness podcast.

    9. SS

      Jay Shetty.

    10. JS

      Jay Shetty.

    11. SS

      The one, the only Jay Shetty.

    12. JS

      [laughs]

  2. 1:022:17

    The Universal Truth Behind All Human Problems

    1. JS

      What has surprised you most about human behavior in what you've looked at when it comes to friendships, relationships, romantic or-

    2. SS

      It's all... I, I mean, look, you know this. It's all remarkably consistent. You know, that the problems we have at work are the same problems we have at home, are the same problem we have with our friends. It's all the same thing. You know, I can give advice to somebody who's a leader in an office or a mid-level, uh, uh, middle manager, or, you know, or entry level, and I can give them advice like, "If you get a response that's above a five, it's about something else." Okay? And if I'm giving somebody relationship advice, I can say, "If you get a response that above, that's above a five, it's about something else." You know? Like, it's always the same thing because fundamentally it's just human beings trying to get along with human beings. Now, obviously, the contexts are different, the goals are different, but fundamentally, the breakdowns in communications, the repair that needs to be done, it's all very similar stuff. It's listening. It's how to give and receive feedback. It's how to have an effective confrontation. It's how to hold space. It's all the same.

    3. JS

      Mm.

    4. SS

      And it, it's always funny to me 'cause, you know, I'll work with every industry. I've worked with every single industry, and they all think their problems are unique.

    5. JS

      [laughs]

    6. SS

      And all their problems are the same.

    7. JS

      [laughs]

  3. 2:176:50

    Why We All Really Just Want to Belong

    1. JS

      Yeah. I learned that when I went on my world tour two years ago. We did nearly 40 cities across the world, and everyone was like, "Oh, what was this place like? What was that place like?" Of course, there were local quirks. They were like, Australia had more banter. Like, everyone quipped back if you made a joke. And everyone in Boston was very handsy. Like, everyone would, like, grab me when I walked in the crowd and be like, "Pick my girlfriend, take me out." You know, it was very, like, active. But overall, we laughed at the same things. We cry at the same things. We, we get excited about the same things.

    2. SS

      Mm-hmm.

    3. JS

      We ooh at the same things. Like, there's this... And I wanted to tell people that. I was like, "Wait a minute, I just went across the world," and like you're saying, you went to every industry-

    4. SS

      Mm-hmm

    5. JS

      ... and you saw that. Why is it then belonging and identity feels like it needs to be found in that which is different, right? We find a different football club that gives us a sense of identity. We find, "Oh, I'm in a swim club or a run club or a, I like nonfiction books. I like fiction books." Like, what is then the dissecting of that for finding identity, belonging, community? Where does that kind of come in?

    6. SS

      You know, as an aside, it's really funny 'cause when I do travel around the world, I don't change any of my stories. I don't change any of my cases. They all say, "Please don't use American examples." We-- And I was like, "That's fine."

    7. JS

      [laughs]

    8. SS

      You know? Um, and, uh [laughs] sure, sure.

    9. JS

      Yeah.

    10. SS

      And they, again, they all understand the lessons. They all laugh at the same places. The responses are different. Like, the English, they, they sit there stone-faced, and I'm like, "Am I bombing here?"

    11. JS

      [laughs]

    12. SS

      And at the end, they come up to me like, "That was amazing!"

    13. JS

      Yeah. [laughs]

    14. SS

      I was like, "Well, why don't you give me a little love when I'm on the stage?" Where the Americans, as you, you know, it's, it's all, it's all right there.

    15. JS

      Yeah, yeah.

    16. SS

      What you see is what you get.

    17. JS

      Yeah.

    18. SS

      But we can't belong to everything 'cause then there's no s- no such thing as belonging, and it's not sufficient to say, "Well, we're all human beings." I mean, you know, we're tribal animals, and our sense of safety comes from feeling safe in the tribe. And so the question is, well, what are the definitions of the tribe? And it can come in many different ways, and we can be members of multiple tribes simultaneously. You mentioned some of them. You know, I like this football club. I'm a member of this church, this company, this group of friends. I have this common interest, you know, whether it's a run club or Comic-Con or whatever it is. And we look, we look for those common things so that we feel psychologically safe. And the quickest way to feel ps- psychologically safe is with somebody who looks like me, worships like me, acts like me, has the same, uh, hobbies as me. Those are, those are superficial, and those are easy. And the real close memberships come when we can share values. But it makes perfect sense why we would wanna make things smaller and smaller.

    19. JS

      Mm.

    20. SS

      You know, it's, it's, it's-- Do you remember the Dr. Seuss book The Sneetches? It's like we want, we all wanna belong, and the easiest way, the best way to belong is if we're different from, from them.

    21. JS

      [laughs]

    22. SS

      You know?

    23. JS

      Yeah, yeah, yeah.

    24. SS

      And then I'm belonging-

    25. JS

      Yeah

    26. SS

      ... 'cause I'm different to you, but I'm like them.

    27. JS

      Yeah. It's like that idea of you can only get groups to organize if there's a common enemy.

    28. SS

      Yeah.

    29. JS

      It's like if we know what we're against, then we know what we're for, and it kind of becomes easier to organize humans that way.

    30. SS

      It's easier to know what you're for when you can see what you're against because seeing-- Knowing what you're for tends to be pretty ethereal.

  4. 6:509:26

    Feeling Lonely? You’re Not Alone

    1. JS

      use anymore in society, but there's this feeling around everyone. We know that there's a loneliness epidemic. People are more disconnected. I think I read a statistic that said, like, sixty-five percent of people feel disconnected from others and the world. Definitely purpose is lacking or vision is lacking or clarity. And it's interesting because even though... And, and I don't think we necessarily talk about it in that way to your friend. Like, you don't wake up and call your friend and go, "I have no purpose today." Like, I don't think people really do that on a daily basis. I think people wake up feeling brain fog and exhausted and overworked and burnt out. Like, that's the language that we use.

    2. SS

      Yeah.

    3. JS

      But they're connected.

    4. SS

      Yeah.

    5. JS

      Right? Like, that's kind of the space in which you sit-

    6. SS

      Yeah

    7. JS

      ... which is recognizing that, well, we're dealing with all of these things, but they're actually coming from a lack of all of this.

    8. SS

      I think that's really right, and what we think is the cause of things is, are very often symptoms. Or if we do recognize them as symptoms, we falsely diagnose what the, what the cause may be. So let's take one that you mentioned, which is burnout, right? I'm feeling burnt out. It must be because of my job.

    9. JS

      Mm.

    10. SS

      Right? It must be because of my boss. It must be because of my career, right? It makes sense. It's where I feel it, right? But perhaps it's something else. Perhaps it's a sense of loneliness. In fact, DeeDee Hathill, she came on the podcast and explained this to me. It was amazing. Which is she, she was in the military, and she's got her, her troops, and there was an issue with, with burnout, and people were exhausted. They were struggling, and they all said, "I'm burnt out," and they didn't know what to do, and there's nothing they could do because the, the tempo of the operations, the ops tempos, was intense, and it's not slowing down. So what's a leader supposed to do when the team says, "I'm burnt out and I can't keep up," right? So I'm not even sure what her motivation was. I have to go back and listen, but I, I think maybe it's 'cause the way she felt. She simply asked the room, "How many of you are feeling lonely?" And the number of hands that went up was astonishing. And she realized it wasn't the ops tempo. It was the sense of loneliness that was giving the feeling of burnout and the feeling of overwhelm. And so the way she dealt with people's burnout was not by giving them vacations or giving them days off. Sh- what she did was she did the hard work of helping them not feel alone.

    11. JS

      Mm.

    12. SS

      Checking in with them as human beings. And I think people's burnout started to subside when somebody was doing the hard work of making sure they knew that they were-- they weren't alone in this world.

    13. JS

      I mean, I love that example

  5. 9:2618:00

    Why Community is Disappearing & Why It Matters

    1. JS

      because it completely shifts your perspective because you're over here trying to solve this problem.

    2. SS

      Yeah.

    3. JS

      And then you realize, oh, it's actually over here. There's almost more places to belong, but there's less bigger places to belong.

    4. SS

      Yeah.

    5. JS

      So in the past, like you said, you'd have church or your place of worship. The company was a big part of your identity, and then family was big, and now families are spread over. Even myself, like, my wife and I don't live anywhere near our family. You don't live that close to your family. So that's kind of broken over time. Places of faith, some people have them, but they're not as popular in some places as it used to be.

    6. SS

      Church, church, church membership is down. Yeah.

    7. JS

      Yeah, exactly. So that's there as well. And then on top of that, you have the breakdown in company in terms of people not necessarily-- People either love where they work or they absolutely hate it and it's a chore. So you're losing these very big places of belonging.

    8. SS

      Mm-hmm.

    9. JS

      Or at least if you see the words on a wall, you don't believe that they're lived.

    10. SS

      Mm-hmm.

    11. JS

      And so there's a disconnect.

    12. SS

      Mm-hmm.

    13. JS

      Should we be relying on our friends now? Is that where we have to go? Or where do you go when you see these big symbols of belonging kind of disconnected?

    14. SS

      So I mean, you're touching on something which if you go back to, like, the 1950s, right? Which is we went to church for our sense of values. Work was just a place to make a living. They took care of us, and we took care of them, and we would work decades at one company. That was considered normal. You know, you got your sense of community from the bowling league, and you knew your neighbors, and sometimes you even had barbecues with your neighbors on the weekends. That was-- And so there were these-- There was a sense of community, and there were many communities to which we were able to partake, with w- with whom we were able to partake. And then things change. The world changes for w- various reasons. The bowling clubs went away. Church membership declined. Don't really know the neighbors anymore. And all of a sudden, we started putting pressure on work to fill all the voids. Now I want my l- my work to give me a sense of values and purpose, and I want work to provide my social life, and I want work to provide my sense of community, my sense of belonging. And now let's throw politics in. I want my work to match my politics as well. And it's not a good thing or a bad thing. It just is, is an is. And most companies are ill-equipped to even know what to do there. You can't push back because it's the world we live in. And so companies now actually do have to make some decisions where and how they want to play.

    15. JS

      Mm.

    16. SS

      And we do have to offer some sense of belonging and community and set of values because that's-- where else are people gonna get it? And when you ask about friends, you know, I find friendship and the concept of friendship super fascinating. You know, if you ask most people, "Are you a good friend?" Most people say, "Yeah, I'm a good friend." And if you peel the onion just one layer, you find out that most of us are not great friends, right? Would you cancel on a friend for a meeting, or would you cancel on a meeting for a friend? Oh, but my friend would understand. You know, we sort of take our friends for granted that way. You know, if your, if your marriage is struggling, what do you do?You go for couples counseling because you don't want to just throw the relationship away. We've invested this amount. We're gonna do the work first, and if we can't do the work, then okay, but we're gonna do the work. Why aren't there f- friendship counselors? Why is there no friendship therapy? I, I s- I saw it happen just two weeks ago. Two people who defined each other as best friends, they talked every day. Something happened. They both blame each other, but there was, there was a, a fight. They haven't talked since, and I've, I've talked to them and said, "What's going on?" They're like, "The friendship is over." And I was like, "Well, isn't it worth... What about the friendship leading up to it? How can you just walk away?" They thought, "Maybe I was wrong. Maybe, maybe they were never my friend," which of course is complete nonsense.

    17. JS

      Mm.

    18. SS

      You know? And it was just so upsetting to me the, the, the fragility of the friendship and how, how we treat friendships so differently. And the skills of good friendship are the same skills, we've talked about it before, relationships, relationships, are the same skills as marriage or any kind of romantic relationship. You know, do your friends know how to hold space for you when you're struggling? Do your friends know how to listen to you when you just need somebody to listen, not fix? And, I mean, I'll tell you from personal experience, you know, I was accused by many of my friends that I was a terrible listener.

    19. JS

      [laughs]

    20. SS

      And I would say, "You do know what I, I do for a living, right?"

    21. JS

      [laughs]

    22. SS

      Like, "You do know, right? I'm a, I'm a great listener."

    23. JS

      You're a professional listener.

    24. SS

      I'm a great listener. And then I took this listening class, and what I learned was that I am a fantastic listener with people I will never talk to again for the rest of my life, but when it came to my intimate relationships and my close friends, terrible.

    25. JS

      Wow.

    26. SS

      Terrible.

    27. JS

      That's a great realization.

    28. SS

      Terrible. And just 'cause I had the skills, I wasn't applying them-

    29. JS

      Yeah

    30. SS

      ... to the place that was actually more important than anywhere else. The first thing I did after I got out of this class is I called [chuckles] all my close friends, and I was like, "I just found out I'm a bad listener, and I owe you an apology." They're like, "Yeah, what took you so long?" Right?

  6. 18:0021:40

    Do Kids Really Need a Village?

    1. JS

      It's interesting. I observe two types of people. One type of person was never that close to their family, and therefore friends became their family.

    2. SS

      Yeah.

    3. JS

      And then there's the other type of person that's so close to their family that they rely less on their friends. So when I look at my wife, she's really close with her mom, and she's really close with her sister, and they are her friends. They act as her friends in all of the ways you mentioned. And when I look at me, someone who was less close with my family or my family unit, even though me and my sister are good friends and my mom is too, my friends became my family.

    4. SS

      Sure.

    5. JS

      So I'm veryFocused on developing community beyond family-

    6. SS

      Yeah

    7. JS

      ... because that's what I've always had to rely on. And, and so it's interesting when you look at that because you're like, all right, well, is it that those of us who have family don't invest in friendships as much because we don't need them?

    8. SS

      I think it's a good question.

    9. JS

      Yeah.

    10. SS

      I don't think it's an either/or. I think it's a both.

    11. JS

      Yeah.

    12. SS

      And again, remember, if you go back to how we evolved, you know, we're tribal animals. We lived in, in groups never bigger than about 150-ish, you know, plus or minus. And what worked was you had your family, of course, but the community helped raise your kids. Uh, I- it's really funny if you look at just, you know, r- rich and poor, right? Those who have and those who don't. Like, if you go to sort of a, a poorer neighborhood, people sit on the front porch, and their kids play in the front, and they, they raise each other's kids. And as soon as you start having any kind of wealth, you move to the back.

    13. JS

      Wow.

    14. SS

      And you put up-

    15. JS

      That's a great point

    16. SS

      ... you put up fences, and you have to raise your own kids. And, you know, the idea that w- that the community looks out for the kids is actually correct. Like, that's how, how we sort of work together. So I don't think it's an either/or. I think it's a both.

    17. JS

      Mm.

    18. SS

      I mean, y- I, I don't know if you've ever had... Did you ever have the chance to go to Dharavi in Mumbai?

    19. JS

      No. No, no, no.

    20. SS

      So Dharavi, Dharavi's the largest slum in Bombay, in Mumbai. And just to give you a sense of scale, right? Um, Manhattan is 13 miles long, two miles wide. It's about 26 square miles. And the island of Manhattan, the residents are about 1.5 million. 1.5 million people live on the island of Manhattan. So if you've ever visited Manhattan or seen pictures of Manhattan, you can get a sense of population density. Obviously, the population goes up during the day during work, but you can get a sense of the density over 26 square miles, okay? Dharavi is one square mile, and there's about 750 to a million people that live there.

    21. JS

      Mm.

    22. SS

      They're not 100% sure about the exact number. So you can just imagine the intensity and the density, which is why when disease shows up, it just r- it runs rampant, right? Because it's just so close. And you walk around Dharavi, and it's, it's not sanitary, and there's, like, live electric wires hanging down. If you touch one by accident, you're a goner. And kids are just running around by themselves or with their friends because the community looks out for them.

    23. JS

      Mm.

    24. SS

      You know? It is an amazing feeling of looking out for each other.

    25. JS

      Mm.

    26. SS

      And I-- and when you talk about belonging, and 'cause we, we do. We look, we look for it. When, when-- we, we look for, for things to join, and we push our kids to join things, so they have these, these friends. And it's easier for kids 'cause they're at school, right? So kids go to school. They're about the same age. They have the same similar stresses, the same teachers, the same homework, same, same, same, same, same, same, same. And so common experience is real-- the same stresses of adolescence and growing up, and, like, they have very common experiences. It's very easy to connect. Soon as you leave school, still pretty easy 'cause you're entry level with all the other entry levels, uh, all bumbling and fumbling, trying to make a career. And then all of a sudden, it starts to separate. Your friends start at different ages, and now you don't have common experience. And, and I think friendship actually gets more difficult as we get older, not less-

    27. JS

      Absolutely

    28. SS

      ... not, not less difficult.

    29. JS

      Absolutely. And, and, and that's why I wanna dig

  7. 21:4023:45

    Why We All Crave Safety

    1. JS

      into it because I couldn't agree with you more, especially for people who've moved. I remember the first time I interviewed a Brit on the podcast.

    2. SS

      Yeah.

    3. JS

      And it was different. It was this really different experience.

    4. SS

      You connected with them?

    5. JS

      So much because-

    6. SS

      Yeah, that makes sense

    7. JS

      ... yeah, but I hadn't-- it didn't, like, register until I did that, where I was like, "Wait a minute. Why do we have so much chemistry?"

    8. SS

      Yeah.

    9. JS

      And I was like, "Oh, wait a minute. Of course, we both talk about football, both grew up in some part of London, like-"

    10. SS

      Yeah

    11. JS

      ... had similar types of friends."

    12. SS

      It makes sense.

    13. JS

      And it makes sense, but it didn't register because I'd been interviewing Americans for so long or, or-

    14. SS

      I'll, I'll give you a funny analogy, right?

    15. JS

      Yeah.

    16. SS

      Just, just to, just to drive the case home.

    17. JS

      Please.

    18. SS

      'Cause beating a dead horse is kinda my thing.

    19. JS

      [laughs]

    20. SS

      The-- So are you friends with everybody, uh, in California?

    21. JS

      Not everybody.

    22. SS

      And you live in California.

    23. JS

      Yeah, not everybody.

    24. SS

      Are you friends with everybody in California?

    25. JS

      Not everybody.

    26. SS

      No, of course not, right?

    27. JS

      Yeah.

    28. SS

      It's ridiculous.

    29. JS

      Yeah.

    30. SS

      But if you go to Michigan, and you meet somebody from California, you're like, "Hey, we're from-"

  8. 23:4527:40

    How to Find People Who Share Your Values

    1. JS

      Yeah. Is there, is there a way-- do you believe there's a way to feel that way with more people if we're feeling disconnected, or can it only happen when it's correlated in the way you're saying?

    2. SS

      Great question. So as we-- goes right back to what we said before, which is we, you know, the tangible stuff is just easier 'cause I can see it, right? So it makes sense why neighborhoods look the way they do. You know, it, it makes sense, right? We wanna live and hang out with people who worship like us, look like us, sound like us, live like us, whatever it is, right? And that can be based on anything.

    3. JS

      Mm-hmm.

    4. SS

      But it's superficial, which means the connections aren't necessarily there, and once you're in the neighborhood, it kind of disappears anyway, right?

    5. JS

      Mm-hmm.

    6. SS

      You asked the question right at the beginning, you know, somebody who sort of applied my work, what would their life look like? Well, this is what happens when you learn to start with why. Because when you learn to stop thinking about your life in terms of what I do, what I look like, what I sound like, what I, you know, all of these superficial things, and you start thinking of yourself in terms of who I am, why I'm on this planet, what are my values, and more important, you learn the language of how to express those things, you will more efficiently and more quicklyFind people who actually view the world and live the world like you.

    7. JS

      Mm.

    8. SS

      So, and this is, you can do it in a personal context, you can do it in a business context, and I'll give you a real-life example. So when I first learned my why, I didn't know how to tell people about it. And so I stopped asking the question, "What do you do? What do you do?" I would tell people what I believed, right? What do you do is really easy, you know? I'm a doctor, I'm a lawyer, I'm a consultant, whatever, right? You're sitting on a plane and somebody says, "What do you do?" And you go, "Oh, I'm a doctor." Unless they need a doctor, you- the- nobody cares, right?

    9. JS

      Yeah.

    10. SS

      And so I started saying what I believed, and it took a probably 100, 150 tries of me bumbling and fumbling different ways of saying it so that I-- people wouldn't look at me like I had three heads, right? And eventually I had the perfect elevator pitch where so I'd sit on a plane, and you know, this is pre-internet, you know, we actually talk to people. And somebody would say, "What do you do?" And I would say, "I teach leaders and organizations how to inspire people."

    11. JS

      Mm.

    12. SS

      The people who believe what I believe would say, "Inspire, cool. How do you do that?" We're talking about me for the next two and a half hours. We're connecting, we're becoming friends. I mean, instantaneously, right? We, we like really get along. The people who don't believe what I believe would say, "What kind of companies?"

    13. JS

      Mm.

    14. SS

      It was a, it was a filter instantaneously because I was presenting my beliefs.

    15. JS

      Yes.

    16. SS

      And those relationships, some of them I made friends on planes.

    17. JS

      [laughs]

    18. SS

      And some of my friends today, believe it or not, I met them on random flights-

    19. JS

      Yeah

    20. SS

      ... years ago. And it's one of the reasons that we connect with some professions more than others, right? So I tend to have really good relationships with folks who serve in the military 'cause I'm pretty open about my sense of service, that I believe true purpose is the opportunity to serve those who serve others. They kinda l- live their lives very similarly, so the minute we show up we're like, "Gotcha," you know? And so there's at least a common thing. I don't necessarily like them all. They don't necessarily all like me. But there's a good foundation to make-

    21. JS

      Mm

    22. SS

      ... make a real friendship.

    23. JS

      Mm.

    24. SS

      And so I, the, I think the opportunity to understand one o- one's own values and beliefs and to say them often. You know, I mean, you know, when I blurb a book, for example, I'm really sort of s- strict about it. Like, if somebody asked me to blurb their book, I always insist that the way they list me is it's Simon Sinek, optimist, and blah, blah, blah, blah, blah, blah, blah. I list all the things I've done after I tell you who I am.

    25. JS

      Mm.

    26. SS

      'Cause if you cut that list off after w- who I am, I don't care what goes after it. And the number of people who are like, "Author, New York Times bestselling, p- host podcast," blah, blah, blah, which is fine, but that's not who you are. That's just stuff you do.

    27. JS

      Mm-hmm.

    28. SS

      That doesn't make anybody connect with you. They just go, "Oh, I know the podcast."

    29. JS

      Yeah.

    30. SS

      "Oh, I, I read the book," you know? And our identity doesn't come from our credibility.

  9. 27:4030:11

    Understanding the Journey vs. the Goal

    1. SS

      Our identity comes from our beliefs.

    2. JS

      I remember the first time I went on television, and they were like, "What do you want the-

    3. SS

      Yeah, the chyron

    4. JS

      ... official lower third?"

    5. SS

      Yeah.

    6. JS

      The chyron, the thing to say. And, and I was like, "I don't... I want it to say, 'Dedicated to helping billions of people find their purpose.'"

    7. SS

      Yeah.

    8. JS

      Something like that.

    9. SS

      Yes.

    10. JS

      Something like that.

    11. SS

      See?

    12. JS

      And I was like, "That's what I want." And they were like, "No, but Jay, like, that isn't..." And I'm like, "But that is who I am."

    13. SS

      Yes.

    14. JS

      Like, and, and I relate, I so relate to what you're saying because I never set out to be a social media creator or to be an author or to be a podcaster. To me, these are just vehicles. They're just-

    15. SS

      Exactly right

    16. JS

      ... formats of distribution-

    17. SS

      Exactly right

    18. JS

      ... and mediums. They've got nothing to do with-

    19. SS

      It's nothing to-

    20. JS

      ... how I see myself

    21. SS

      ... which, which is one of the reasons why-

    22. JS

      Yeah

    23. SS

      ... I can speak for you, I think, but for me for sure, which is I re- I'm super flexible as to how I get my message out.

    24. JS

      Yes.

    25. SS

      You know, what got me here won't get me there.

    26. JS

      Yes.

    27. SS

      And I'm not-- I don't define myself as a speaker or a writer or whatever. M- everything I've done, I never thought I'd write a book. I never thought I'd have a podcast.

    28. JS

      Yeah.

    29. SS

      I never thought I'd be a public speaker. And so for me to walk away from any of those things is super easy because it's not who I am.

    30. JS

      Yeah.

  10. 30:1132:31

    Knowing When to Persevere vs. Let Go

    1. JS

      Yeah. Absolutely. And you don't get, you don't get disappointed. I was just talking to someone this morning on a Q&A. You don't get disappointed when the platform doesn't reciprocate. So what I mean by that is if your why is what you just beautifully said is to, I'm paraphrasing completely, but to help people using the skills you have, if you get rejected, you don't think it's no to what you're committed to. You just realize that's just not where it's gonna be disseminated, and you can continue-

    2. SS

      Yeah

    3. JS

      ... to try and find-

    4. SS

      Right

    5. JS

      ... a new place for it to be distributed.

    6. SS

      Right.

    7. JS

      Whereas when you think, "Oh, this is a rejection of my idea"-

    8. SS

      Right

    9. JS

      You actually let go of the idea that you so deeply cared about

    10. SS

      Right. So if I decide that the best way for me to advance my message is for me to join the NBA-

    11. JS

      Yeah

    12. SS

      ... and become a professional basketball player, I will learn very quickly that that's not gonna go well.

    13. JS

      Yeah.

    14. SS

      Right? And so do I go home depressed, or do I say, "Well, maybe basketball is not the best way"?

    15. JS

      Yeah.

    16. SS

      You know?

    17. JS

      Exactly.

    18. SS

      And it's, it's an interesting rabbit hole to go down because it raises the question, and I, and I can't remember if you and I have talked about this before, but knowing when to quit.

    19. JS

      I think we did on yours.

    20. SS

      Yeah.

    21. JS

      Yeah, that idea.

    22. SS

      Which in-- 'cause, you know, there are some people that say, "Nope, you never quit. That's what grit is." And there are some people say, "Nope, there's a time to walk away."

    23. JS

      Yeah.

    24. SS

      And the question is, okay, but when?

    25. JS

      Yeah.

    26. SS

      Like, when, when do you apply grit, and when do you walk away?

    27. JS

      Mm-hmm.

    28. SS

      And my rule has always been, if the sacrifice is worth it, you keep going.

    29. JS

      Mm.

    30. SS

      Right? So I'm exhausted, I'm tired, but is it worth it for what I'm trying to do?

  11. 32:3137:30

    How to Know You've Outgrown a Friendship

    1. SS

      needs to be additive, right? That doesn't mean every single time, but on balance, you, you-- we should all feel that who we're hanging out with, who we're spending time, a non-redeemable commodity. You can spend money, you can lose money, you can make more money, but if you spend time, that's it. That's gone. And so we wanna make sure that the people with whom we spend time, it's additive to our lives. You get to define what additive means. Additive can means you fill me up, you inspire me. Additive can mean I just have a fricking rocking good time with you. Additive can mean you give good advice. You define it however you want. But I think on balance, our friends should be additive. They should contribute something to our lives, to our, and to our wellbeing. And it absolutely happens for n- not necessarily bad reasons, where for whatever reason, you just outgrow each other. Sometimes it's just the natural ups and downs and weirdnesses of life. You know, it's easy to be friends when you're local. Y-your career takes you across the country or around the world, it's just harder, and those friendships sometimes fall away. Nothing personal. Sometimes we outgrow people. That absolutely happens. I had a friend who we were-- we would hang out a lot. We were friends. We would get together. We would talk about how much we hated our bosses and what we hated about work. And I would try and make changes in my life, get new jobs, take myself on, become a better leader. And we would keep getting together, and his problems were always the same. And, you know, a couple of years go by, and I'm realizing I'm having the same conversation with somebody who, for whatever reason, doesn't wanna take themselves on and doesn't wanna listen, and had advice for everybody but couldn't take it. And you realize, I can't be in a friendship if I can't serve my friend.

    2. JS

      Mm.

    3. SS

      I-- yes, I wanna get from my friends, of course, but I also wanna give to my friends, right? It-- there is tremendous joy in being able to hold a friend up.

    4. JS

      For sure.

    5. SS

      You know? And for a friend to deny me the opportunity to serve because they're too fill in the blank to listen, take advice, you know, admit any kind of weakness, at some point, we just drifted apart.

    6. JS

      Mm.

    7. SS

      You know, I just stopped calling, and that's okay.

    8. JS

      And you don't feel there needed to be a definitive ending conversation to-

    9. SS

      In that particular case, no.

    10. JS

      When, when do you need one of those?

    11. SS

      When there's a definitive ending, I think just-- and let's make the comparison to a divorce, right? There has to be work before the definitive ending. So if you feel like the relationship is worth protecting and saving and working on, in that particular case, it seems like neither of us felt like doing the work. We had a good time, and I don't think of it as an ending. I think of it a graduation, right? Like, the relationship was great-

    12. JS

      Mm-hmm

    13. SS

      ... and then we graduated, and we both moved on, right?

    14. JS

      Mm-hmm.

    15. SS

      And that's fine. We graduated, right? I learned what I could learn, and now it's time to go. But if the relationship, if, if it's worth fighting for, and you're doing the, the work, and maybe it's just not working, then I think s- then you have a hard conversation, and you sit down, and you-- just like a divorce or leaving a job. Like, we're, we're trying this, and I'm, I'm struggling, and I don't know, I don't know if it's worth it anymore. Can we end this?

    16. JS

      Mm.

    17. SS

      Um-

    18. JS

      That's a good distinction.

    19. SS

      You know? I, I, I think ghosting is horrible. You know, I'm not talking about you went out w- on one date with somebody, and, like, that's fine, you know? But I'm saying, you know, you hear about whether it's romantic relationships or friendships where you've been hanging out a lot for six months, seven months, a year, and then for whatever reason, you decide you don't want to, and you just stop.

    20. JS

      Mm.

    21. SS

      You ignore the texts. You unfollow on socials, which is an act of unbelievable passive aggression. And some people, it's-- you have to remember what you're doing to somebody when you do that, which is, especially if they can't look on the socials and see that you're fine, there's this horrible sense that something's happened to you. Like, if you got into a car accident or something, the result would be the same. And so the, the, the panic of, "Are you okay?" comes first. Then they may go on social and discover you're fine. They see you out at, you know, out at the club or-

    22. JS

      [laughs]

    23. SS

      ... whatever it is, and then you reach out, and they don't reach back. Now this-- so you've gone through the panic of what's happened. Then you realize they're fine. You realize you're being ghosted. Then the overwhelming sense of, what did I do? The guilt, the no-- you get no closure. You give no closure. You allow someone to stew in their own fears and insecurity and anxieties, which isDebilitating-

    24. JS

      Mm-hmm

    25. SS

      ... and cruel because you lack the courage to say, "I don't know how to say this."

    26. JS

      Yeah.

    27. SS

      "I'm struggling in this friendship. I don't know what to do." You know, again, that's different from friends that just naturally drift apart.

    28. JS

      Mm-hmm.

    29. SS

      And so I think you're right. I think one of the things we have to learn to do is how to have difficult conversations with our friends, even if it means, like, I think at least give somebody a breakup.

    30. JS

      Yeah.

  12. 37:3039:17

    Recognizing Why a Relationship Has Ended

    1. SS

      it with dignity.

    2. JS

      Well, I think your point's well taken because I love the distinction you made, because if you were working on it, if you were both trying to bring some enthusiasm and energy and trying to figure it out, you're more likely to actually have a proper breakup-

    3. SS

      Well, you, you-

    4. JS

      ... and have that conversation

    5. SS

      ... both come to the realization, "I don't think this is working."

    6. JS

      Totally. Totally. And I like that a lot because it's almost like sometimes we have the same expectations for a relationship that we didn't put energy into-

    7. SS

      Yeah

    8. JS

      ... for ones where we did.

    9. SS

      Yeah.

    10. JS

      And you can't really compare the two because-

    11. SS

      Yes.

    12. JS

      Yeah.

    13. SS

      And, and I'll add one final caveat-

    14. JS

      Please

    15. SS

      ... is it's messy.

    16. JS

      Mm-hmm.

    17. SS

      And it's, the reason it's messy is because human beings are messy. We're, we're full of anxieties and ego and pride and fear, and most of us don't have the skills of confrontation and listening.

    18. JS

      Mm-hmm.

    19. SS

      We suck at it. And even if you have the skills, are you good at applying them? And even if you have the skills, when you had a bad night's sleep or you're stressed or you're feeling attacked, are you able to call upon those skills? You and I do this, you know, a lot, and we fail daily.

    20. JS

      All the time.

    21. SS

      You know? And, and it's thrown in our face. "I thought you knew how to." I'm like, "I do, but I'm struggling right now, clearly, because I'm hurt, because my feelings are hurt, and I'm lashing out and being defensive and interrupting you-"

    22. JS

      Yeah, being passive-aggressive. [laughs]

    23. SS

      "... because I'm hurt, and that's not right." But it's messy.

    24. JS

      Yeah. Yeah.

    25. SS

      And so, you know, one of the things that you can easily accuse both of us of is sort of oversimplifying all of this stuff.

    26. JS

      Mm-hmm.

    27. SS

      And we do oversimplify it to make the case and hopefully share some lessons that we've stumbled upon over the course of our careers. But it's still hard-

    28. JS

      Yeah

    29. SS

      ... and it's still messy.

    30. JS

      Yeah.

  13. 39:1745:09

    Why Sincerity Beats Perfection Every Time

    1. SS

      conversation with somebody today.

    2. JS

      Mm-hmm.

    3. SS

      You know, like compare that to AI, right? Let's say you have a fight with your wife. You want to get it right. "Hey, ChatGPT, can you tell me what I have to say to get this right?" And ChatGPT, which has been trained with all the best therapy, everything, this thing's a PhD, will give you the exact right thing to say, and you go and say to your wife, you memorize it, and you say to your wife exactly what ChatGPT told you to, and she goes, [tsks] "Thank you. Oh my God, thank you." And then she finds the script in your drawer.

    4. JS

      [laughs]

    5. SS

      And she said, "Did you get this from ChatGPT?" "Yeah." "Did you memorize it?" "Yeah." She's gonna be angry at you-

    6. JS

      Yeah

    7. SS

      ... 'cause there's nothing heartfelt about it. It's hollow. It's not-- And she would rather you bumble and fumble and do it wrong, but at least be yourself and be authentic. Can you imagine giving a 100% ChatGPT written speech-

    8. JS

      Oh my gosh

    9. SS

      ... at a wedding?

    10. JS

      Yeah.

    11. SS

      Best speech ever, and then somebody says, "Oh my God, that speech was amazing. How'd you write it?" I'm like, "No, no, ChatGPT wrote it for me." You know?

    12. JS

      Yeah. [laughs]

    13. SS

      And you'd be like-- And there's just the feeling of like, "Oh."

    14. JS

      Yeah.

    15. SS

      Right?

    16. JS

      Yeah, disappointment.

    17. SS

      I'd rather, I'd rather you give me a worse speech, but I know it's came from the heart.

    18. JS

      Yeah.

    19. SS

      You know?

    20. JS

      Yeah.

    21. SS

      And again, you know, they're silly examples. But the point is, is that imperfect, human, and those two words are synonymous.

    22. JS

      Mm-hmm.

    23. SS

      Those two words mean exactly the same thing. To be human is to be imperfect. To be imperfect is to be human. It is the most beautiful thing in the world.

    24. JS

      Mm-hmm.

    25. SS

      Perfection comes off a factory line. It's the difference between a Pottery Barn mug and a beautiful piece of Japanese ceramic. One is handmade. It is imperfect. It is gorgeous. Versus the thing that comes off a machine. It looks the same as all the other things that come off a machine. It is perfect. It's fine. I like it. Love it? Hmm.

    26. JS

      Yeah.

    27. SS

      And, and I think we forget that in this day and age of incredible technology that can solve all the problems for us-

    28. JS

      Mm-hmm

    29. SS

      ... and answer all the questions for us, it's all there, right?

    30. JS

      Mm-hmm.

  14. 45:0948:16

    Learning to Trust Your Intuition

    1. JS

      the reason why I love it so much-

    2. SS

      [laughs]

    3. JS

      ... is because you're also giving people a, a heightened agency and accountability of feeling the change.

    4. SS

      Just feel.

    5. JS

      Because that's what it is, right? It's like, if I tell you something's a great hike, or i- let's take something really everyone can relate to. If I tell you something's a great restaurant, and it's got two Michelin stars-

    6. SS

      Yeah

    7. JS

      ... it's got 10 star rating-

    8. SS

      Yeah

    9. JS

      ... it's got everything, you could go there and hate the meal.

    10. SS

      Sure.

    11. JS

      None of that means anything in, in that sense. It's, it's your taste. Because you had to feel it, and that was what made the difference. It wasn't the Michelin stars or the rating or the whatever it was, it was you feeling it.

    12. SS

      Yeah.

    13. JS

      And we've lost that ability in a world where we're counting on everyone else and everything else to tell us if we've done it for long enough, short enough, have we lifted for that long enough? You've lost the ability to actually feel. Like, I was talking to my doctor today, I was saying, "Hey, I'm not sure about this whole 150 grams of protein intake. Like, I'm just not feeling good. Like, I just don't feel good when-

    14. SS

      That's a, that's a lot

    15. JS

      ... that, I mean, that's not even as much ... You're meant to do, like, your body weight in protein. And I've tried a hun- I've tried everything, but it's like I don't feel good-

    16. SS

      Yeah, yeah

    17. JS

      ... when I do it.

    18. SS

      Yeah.

    19. JS

      So either, yes, my digestion may not be strong enough, it may need to be strengthened-

    20. SS

      Sure

    21. JS

      ... but at this point in my current strength, it doesn't feel right.

    22. SS

      Yeah. Yeah. I, I mean, you're right. It's ironic, right? Where we trust, we trust the watch, we trust the app, we trust the numbers-

    23. JS

      Yeah

    24. SS

      ... more than we trust ourselves.

    25. JS

      Yeah.

    26. SS

      We trust what we're being told, and we're doubting our own feelings.

    27. JS

      Mm-hmm.

    28. SS

      And so the question is, is A, why are we doing that? And B, uh, shouldn't we learn how to trust our feelings more, right? Now, yes, it feels good when we eat the chocolate cake, but we all know that it feels pretty gross if you do it too often.

    29. JS

      Mm-hmm.

    30. SS

      Right? And so there's also data on this, which is people who stress about eating dessert.

  15. 48:1654:51

    The Most Powerful Relationship Advice You'll Ever Hear

    1. SS

      Especially with hugging.

    2. JS

      Like, even something ... That, I love that example so much because it's like, I love the idea that a kid knows when to let go. Like, that idea of like a ch- only let go when the child lets go.

    3. SS

      Isn't that beautiful?

    4. JS

      It's so beautiful.

    5. SS

      The kid knows.

    6. JS

      It's literally romantic, spectacular, and just, it's-

    7. SS

      The kid knows

    8. JS

      ... it's so beautiful because that's actually what we want. We want someone to hold us for as long as we need to be held.

    9. SS

      And I'll take it a step further, right?

    10. JS

      Yeah.

    11. SS

      So in terms of the kid knows, right?

    12. JS

      Please.

    13. SS

      So, so good parenting advice is like, you know, like, when a k- when it's cold outside and the parent's like, "Put on your sweater." "I don't want to." "Put on your sweater." "I don't want to." "Put on your sweater." "I don't want to." Let the kid go outside in the cold, and very quickly, the kid will either be fine or not fine.

    14. JS

      Yeah.

    15. SS

      The kid knows. The kid will be like, "I'm cold." "Put on a sweater."

    16. JS

      Yeah.

    17. SS

      Right?

    18. JS

      Take the sweater with you, yeah.

    19. SS

      Or they won't.

    20. JS

      Yeah.

    21. SS

      Right? Like, like, there are little things that we knowAnd that goes right back to friendship.

    22. JS

      Mm.

    23. SS

      We've all been in relationships that suck energy from us.

    24. JS

      Mm.

    25. SS

      And we feel like we have to, like s- keep going because, I don't know, we've been friends for a bunch of years, so time is the only bond.

    26. JS

      Mm.

    27. SS

      You don't actually fill each other up anymore. So, you know, people grow up. You are a different person than you were five years ago. I'm a different person than I was five years ago, hopefully better. I definitely know there's some skills that I've got. I'm definitely better, a better friend, I'm a better leader, I'm a, I'm a better boyfriend. Like, I, I worked on those things, you know, and I'm better at it. It's ... You know what it's like? It's like, you know, for a lot of us, we, we left home when we were 18, and we kept growing up. We went to school or we got a job, and we kept learning and growing and taking ourselves on, but our parents knew us up until we were 18.

    28. JS

      Yeah.

    29. SS

      And then they missed the new growth.

    30. JS

      Yeah. [laughs]

  16. 54:511:01:14

    How to Share Your Wins With Friends Who Are Struggling

    1. JS

      Where this is hitting for me is that the challenge I think people are having today is they're struggling to clap for their friends when it's not their turn. So people are struggling to feel joy for someone else's... joy when they're not in a joyful state.

    2. SS

      For sure.

    3. JS

      So I've had real-life scenarios in my life right now, which I'll share, that immediately came to my mind when you were saying this, which I, I love that we're on this conversation, is two examples. One person-- And these are people who are really close.

    4. SS

      Yeah.

    5. JS

      This is not like some fake friendship. Really close. One of them's going through a miscarriage, the other one is expecting a baby.

    6. SS

      Right.

    7. JS

      And the person who had the miscarriage is feeling bad because they had a miscarriage. They're feeling bad because they can't celebrate their friend's win.

    8. SS

      Yep.

    9. JS

      And they're now feeling bad that they don't even want to be around their friend-

    10. SS

      Yeah

    11. JS

      ... because their friend's actually expecting. And now that friend's feeling guilt because they're having a baby, and they're like, "Well, how do we share this with that person who's just lost a baby?" And it's real.

    12. SS

      Yeah.

    13. JS

      Right? Like, it's really real, and this applies to people getting married before you. The kids one is probably the most, one of the most extreme forms of it. Uh, but it's people getting married, people getting engaged before you-

    14. SS

      Oh, your career doing great, somebody else's career hitting the skids.

    15. JS

      Totally. There's so many versions of it.

    16. SS

      All, all of it.

    17. JS

      But the most extreme one being, or le- that I've heard so far is this, that-

    18. SS

      Yeah, that's a good one

    19. JS

      ... I've just lost a child, and you're having a child, and we're best friends, and we were gonna be having children at the same time, and we were gonna share that together-

    20. SS

      Yeah

    21. JS

      ... and we were gonna raise our kids together.

    22. SS

      Yeah.

    23. JS

      Now I don't even... You know? So how-- What do we do when we can't share our win with our deepest friend because they're losing, and they're scared to share space with us because they're threatened by your win in that context?

    24. SS

      Communication, right? And this is the thing. We avoid the communication because it's uncomfortable. I don't know what to say. I don't know what to say. You know, one person's the happiest they've ever been, the other person's the saddest they've ever been, and neither knows what to say, and both are consumed with guilt. Both are consumed m-maybe there's a little bit of anger. I mean, there's all kinds of feelings, and feelings are messy, and they flow and, you know? And the other one's success or achievement or, in this case, pregnancy just reminds me of what I'm going through. It makes, it just makes it feel worse. I don't want to be reminded right now. And it's kinda like when something bad happens in someone's life. You know, sometimes we don't do anything 'cause we don't know what to say, and we don't want to say the wrong thing. And so sometimes that's the best thing to say. "Hey, I don't know what to say. I don't want to say the wrong thing. But I want you to know I love you. I can't imagine what you're going through, and it must be the worst thing in the world. I'm here when you need me. Take the space you need."

    25. JS

      It's better to say-

    26. SS

      Just say something.

    27. JS

      Say something.

    28. SS

      Say something incomplete. And when you say-- Don't have to worry about getting it right. Just say the thing you're feeling, and the feeling is, "I don't know what to say."

    29. JS

      Yeah.

    30. SS

      You know, I had a friend recently-

  17. 1:01:141:06:58

    Stop Letting Insecurities Define Your Behavior

    1. JS

      The most important thing about that is saying something is better than saying nothing, and the saying something partSpeak your intention. Like, that's, that's what I feel. Like, it's like when I'm sharing my confusion and I'm sharing my feelings and I'm scared to share them because they're messy, going back to your earlier point, being human is messy, and you're right. Sometimes I get a message like that too, and I'm like, "I don't really know what to say." And not saying anything is way worse than saying, "Hey, I'm really sorry. I'm here if you need me. Let me know how you-

    2. SS

      I don't know what to say, and I don't know what you need

    3. JS

      ... Exactly. And tell me-

    4. SS

      T- i- if, if you feel up to it, please tell me.

    5. JS

      Exactly.

    6. SS

      Right? But I'm here. Just know one thing. One thing 100% sure is I'm here.

    7. JS

      Exactly.

    8. SS

      You know?

    9. JS

      Yeah.

    10. SS

      And that's sometimes all people need is to feel not alone. That's-

    11. JS

      Most- mostly

    12. SS

      ... Mostly, yeah. And I think we're also afraid of triggering somebody or saying the wrong thing or doing the wrong thing, and it's our own fears.

    13. JS

      Mm-hmm.

    14. SS

      And that's our own insecurities, and it goes back to the ghosting. It's my fear of discomfort that's making it worse for somebody else.

    15. JS

      Yeah.

    16. SS

      You know? And it goes back to what the definition of a leader is, right?

    17. JS

      Mm-hmm.

    18. SS

      The l- a leader is the person who accepts the awesome responsibility to see those around us rise.

    19. JS

      Mm-hmm.

    20. SS

      It's about caring for people, right? And it's a very leadery thing to do to just be the person who says, "I don't know-

    21. JS

      Yeah

    22. SS

      ... but here it is."

    23. JS

      Yeah. I remember this a while ago. There was someone that I knew that told me one of their friends came up to them and said, they said exactly how they feel, but it was different. It said, "I'm envious of you."

    24. SS

      I kind of respect that.

    25. JS

      Yeah, it was, but it was hard for that person to hear it-

    26. SS

      Yeah

    27. JS

      ... because they, they felt it created a distance even though to me that person was being courageous.

    28. SS

      There's a way to do it, though.

    29. JS

      Yeah.

    30. SS

      I, I wouldn't recommend going up to somebody and being like, "Dude, I'm really envious of you," 'cause you don't know the context. You don't know-

  18. 1:06:581:09:01

    Can You Be Friends with People You Envy?

    1. JS

      um, I had a friend say to me the other day, they said, "Jay, you know, the thing I love about you is that you've stayed the same despite your success."

    2. SS

      You're taller.

    3. JS

      A friend, yeah. [laughs]

    4. SS

      [laughs]

    5. JS

      A friend said that to me, and it was just like... And I said, "You know, the reason why I've been able to be the same with you is because you've stayed the same with me." And it was this really interesting... Not that we haven't changed or grown. Of course, I've learned new skills, so have they, but that they didn't think I was changing negatively.And that allowed me to continue to be who I wanted to be with them

    6. SS

      You only get half the credit on that, right? The other half of the credit is that I guarantee you that other people in your life, other friends, will give me a different answer. That they will say, "Now that Jay's all successful and, you know-

    7. JS

      No, but that's the point of my-- what I'm saying

    8. SS

      ... like, like he, he's like aloof now, you know, like doesn't-

    9. JS

      No, but that's the point. Yeah, yeah. So my point is that's exactly what I'm saying, that maybe I didn't explain it well. He's saying that, and I'm giving him the credit back.

    10. SS

      Oh, yeah, yeah, yeah.

    11. JS

      Because I'm saying you didn't change what you viewed of in me.

    12. SS

      Right.

    13. JS

      So I never-

    14. SS

      It's, it's hi- it's he, he's done the work.

    15. JS

      Correct.

    16. SS

      Yeah.

    17. JS

      Yeah, because he's allowed me to-

    18. SS

      Yeah

    19. JS

      ... continue to be me without judging me-

    20. SS

      Yeah

    21. JS

      ... comparing the-

    22. SS

      And, and you-

    23. JS

      And you're right. You're right. It is only half the credit, for sure.

    24. SS

      It, you know, and you, you may have changed.

    25. JS

      Totally.

    26. SS

      And you may be more aloof, you know? And you may be more cynical, and you may be more guarded. All of that's-

    27. JS

      100%

    28. SS

      ... true.

    29. JS

      100%.

    30. SS

      And some people who may experience you as different-

  19. 1:09:011:12:09

    How to Respond to Skeptics with Grace

    1. JS

      but I was thinking about another thing that I feel a lot of people are struggling with, friendships that I at least hear right now, are people who are wanting to, kind of like where you were actually, where you're wanting to grow. You're wanting to pivot into a new business. You're wanting to start something. And what I've noticed is we're not scared of what people think on the internet. We're scared of what people around us think when you're starting something. Like when you're trying to begin something, you're not really scared about what some anonymous person says on the internet. That's not even on your mind. You're scared about what your friend from college is gonna say about that video you made, or you're scared of what your friend from, uh, high school is gonna say about the business you're about to start. You're scared of the LinkedIn update that goes out to your former colleagues.

    2. SS

      Yeah.

    3. JS

      Right? Like, that's the thing you're worried about. What do we do when we feel the people around us don't believe in us, are the most cynical, the most skeptical, are the most negative about our ideas?

    4. SS

      That's interesting.

    5. JS

      Even a person.

    6. SS

      For anybody who wants to accomplish anything of value in the world, and when I think of value, I think of impact, right? That's how I define it, right? I- if you wanna operate at a scale that's bigger than yourself, and if you wanna... And, and when I say bigger than yourself, it could be three people, right? Meaning I wanna have an impact in, in three people's lives around me. I wanna be the best parent in the world, right? My point is more than you, right? So I think we confuse when we think bigger than ourselves. We don't necessarily mean national stage. Bigger than yourself can, just means more than one, right?

    7. JS

      Mm-hmm.

    8. SS

      Anybody who wants to have an impact in the lives of others has to get used to the idea that not everybody's gonna like you, right? You just have to get used to that idea. And for me, I have rules, which is if you don't like me because you disagree with me, I'm cool with that, right? If you don't like me because somehow I make you uncomfortable, I'm okay with that too. But if somebody I respect doesn't like me, now I've got a problem.

    9. JS

      Mm.

    10. SS

      Right? Because I'm not so blind and pig-headed to be like, "Screw the world. It's me. You know, if you don't like it, you can, you know, you can eat it," right? My eyes are open. And if there's a friend I care about who's, "Mm, Simon," okay, I gotta take that seriously. 'Cause now I'm getting too big for my britches, or now I'm not listening, or now I'm ignoring my blind spots. And now I got a problem.

    11. JS

      Mm.

    12. SS

      Right? But if somebody just disagrees with me, I mean, what am I supposed to do? I'm, I don't get everything right. Sometimes things come out wrong. Give me some grace, you know? But if you just disagree with me, like, what am I... Like, I don't know what, I actually don't know what to do. It's like the, the gold dress, blue dress. Remember that?

    13. JS

      [laughs] Yeah, I do. Yeah.

    14. SS

      It's like the, the dress is blue. You're an idiot. It's gold.

    15. JS

      Yeah.

    16. SS

      I'm like, what am I supposed to do? I see it as blue.

    17. JS

      Yeah, yeah.

    18. SS

      I don't know what to do. [laughs]

    19. JS

      [laughs]

    20. SS

      That's what it is.

    21. JS

      That was the funniest line, yeah.

    22. SS

      Right?

    23. JS

      Yeah.

    24. SS

      It's hard. Everybody wants people to like y- you know? I, I have a lot of respect for people who, like, literally don't care.

    25. JS

      Yeah.

    26. SS

      I don't have that.

    27. JS

      Well, it goes back to what you were saying earlier, that

  20. 1:12:091:15:08

    Your Worth Isn’t Measured by Numbers

    1. JS

      we're looking for people to affirm, confirm, and join. So it's like when you have that idea-

    2. SS

      Yeah

    3. JS

      ... and everyone around you who you thought supported the same football club and had the same values doesn't agree with you, it kind of feels like there's something wrong.

    4. SS

      You're kind of raising something that's quite ins-

    5. JS

      Yeah, please

    6. SS

      ... that's quite insidious. We can't help but think about, like, likes and views-

    7. JS

      Mm-hmm

    8. SS

      ... on a post that, you know, we get our sense of self from how many likes we get, and this video got more likes. I'm, boy, period, I'm, I'm awesome. This video got no likes. Oh my God, I'm worthless. Uh-

    9. JS

      It's a daily occurrence.

    10. SS

      Yeah. Like, or how many views it gets. And that's sort of the macro social media version of what you're talking about-

    11. JS

      Mm-hmm

    12. SS

      ... which is if people like me, I must be a good person. If people don't like me or aren't giving me a lot of views, I m- I must, I must not be a good person.

    13. JS

      Yeah.

    14. SS

      And how to disconnect a like or a view or a comment from what I'm trying to do here-

    15. JS

      Yeah

    16. SS

      ... and what I'm putting out in the world. And the problem is it's, it's the incentive structure, right? Because if you're making money from views, if your sense of value in the world comes from those numbers, that's the insidious version of what you're saying.

    17. JS

      Yeah.

    18. SS

      And how do you get comfortable? Like, some will do well, and... Like, I can tell you, I've won the internet lottery more than once.

    19. JS

      Yeah, you have. Yeah.

    20. SS

      I have won the internet lottery more than once, and I have had multiple things that I have put out there go very viral. None of themDid I predict

    21. JS

      Mm-hmm

    22. SS

      The videos that I thought would do well [laughs] fine

    23. JS

      Yeah

    24. SS

      And the videos that I had no clue

    25. JS

      Yeah

    26. SS

      Went, you know

    27. JS

      Ballistic, yeah

    28. SS

      And they went ballistic, and it wasn't because of the production quality, and it wasn't... I didn't, just didn't know. Something connected. You know, that's why I call it virals. I, I was at a dinner once, and a guy, I'm like, "What do you do?" He's like, "I make viral videos." I'm like, "No, you don't. You make videos, and you hope they go viral."

    29. JS

      Yeah

    30. SS

      And that's why this stuff is hard.

  21. 1:15:081:17:51

    Tune Into Your Needs, Not Others' Expectations

    1. JS

      But yeah, no, that, that point that you're making, to me, that micro version is that I don't feel value. Like, for example, when I put out my first video, the people closest to me or maybe second closest to me were like, "You talk too fast. The editing's bad. The music's off." And the funny thing is they were right. Like, it, the, all of that was true, but it resonated with someone, right? [laughs] It was, like, a weird... It was, like, this weird thing where... And, and I've seen that with people. When they're trying something new, it's like the people around them will be the most cynical, the most skeptical. And if you use that as feedback, it could get better. Or if you use it as like, "Hey, you're not really an expert on that. You don't know much. I'm just gonna get on with it," right? That's what I'm trying to get at is like how does, how does someone deal with the discomfort of just your best friend thinks your business idea sucks or, like, your, your best friend thinks the person you're dating is not right for you?

    2. SS

      You're conflating a lot of stuff there.

    3. JS

      I like the best friend doesn't like the person you're dating.

    4. SS

      That's a hard one.

    5. JS

      Yeah.

    6. SS

      Very often they don't tell you until after you've broken up.

    7. JS

      Why do our friends feel like they have to wait till we break up?

    8. SS

      'Cause it's really uncomfortable to say, "I don't like your partner."

    9. JS

      Could we do something better about that to create honesty?

    10. SS

      Can I have a really uncomfortable conversation with you, you know?

    11. JS

      Could we do something better to help our friends have uncomfortable conversations with us?

    12. SS

      You know, at the end of the day, sometimes not all our partnerships are understood by our friends too. I've definitely been in partnerships that people are just like, "Really?" I'm like, "No, no, no. You don't understand the value that this person gives to me, and this person is the exact right person I need to date for the place I'm in right now." You know? I mean, I had a girlfriend many years ago who nobody could... Like, they looked at us walking down the street, and people just like... Like, I mean my friends. Like, they're like, "What?" Like, they couldn't understand this relationship. And what they didn't understand is I, who I was and what I needed in that time. She was magical, and we're still friends. But nobody, nobody got it. And she was socially awkward, and like... So, like, if you've got friends with big personalities, and, you know, we go out, and she's just quiet the whole night. And, like, my friends didn't get it. And that's the other thing I've learned, which is to do people not like the girl I'm dating or do they just want somebody who's the life of the party?

    13. JS

      Mm.

    14. SS

      You know?

    15. JS

      That's a great point. Yeah.

    16. SS

      And if they're looking for somebody who's the life of the party, that's not who I'm dating. She's the rock. She's not the fireworks. She's stable, and that's what I need.

    17. JS

      No, I like that. I like that because I think you're right. I mean, introverts in general-

    18. SS

      Yeah

    19. JS

      ... in friendships-

    20. SS

      Yeah. My-

    21. JS

      ... in group settings

    22. SS

      Like, my, my family, my parents, have never liked, quote, unquote, "any introvert I've ever dated." They love the extroverts.

    23. JS

      [laughs]

    24. SS

      'Cause the extroverts are fun.

    25. JS

      Yeah.

    26. SS

      And the introverts are awkward. That's pretty much it.

    27. JS

      Yeah. It is funny. No,

  22. 1:17:511:22:16

    What Social Awkwardness Really Means

    1. JS

      because I'm... I think everyone who's listening right now and watching, me included, is thinking of someone in my life right now-

    2. SS

      Yeah

    3. JS

      ... that I don't enjoy being around because they're introverted.

    4. SS

      Yeah.

    5. JS

      And even though I can be very introverted in certain group settings-

    6. SS

      Yeah, in certain group settings, certain groups-

    7. JS

      In certain groups saying I'm the biggest introvert there is.

    8. SS

      Yeah.

    9. JS

      And then in certain group settings-

    10. SS

      And I'm the awkward one sometimes where people are like, "I don't get it."

    11. JS

      Same.

    12. SS

      You're dating him?

    13. JS

      [laughs]

    14. SS

      He's so vivacious on stage and on camera.

    15. JS

      Yeah.

    16. SS

      And at dinner he was quiet and grumpy.

    17. JS

      How should introverts-

    18. SS

      [laughs]

    19. JS

      ... think about friendships differently to extroverts?

    20. SS

      Uh, I don't think they should think about friendships differently. I think they're all the same. Uh, the rules are the same. You know, the, the... I think we confuse introversion, extroversion, and social awkwardness.

    21. JS

      Mm-hmm.

    22. SS

      There's a s- there are socially awkward introverts. There are socially awkward extroverts.

    23. JS

      Oh, definitely, yeah.

    24. SS

      There are socially functional introverts, and there are socially functional extroverts. I'm a socially functional introvert, right?

    25. JS

      Yeah.

    26. SS

      I, I'm okay. You know? I'm, I'm not that awkward, though I can be. My ex would make fun of me. We'd go to a party, and it... Like, all these little groups of conversations, you know? People standing around in threes and fours with their drinks talking, one over there, one over there. And I never knew how to insert myself into one of the... And I know the people. Like, but I never know how to insert myself.

    27. JS

      Yeah.

    28. SS

      And so I just stand by myself with my drink in the middle of the room. And she would always make fun of me that I would just stand there by myself just totally fine, just taking the room in, you know?

    29. JS

      [laughs]

    30. SS

      And I just feel sorry, sorry for everybody else just looking at me going, "I don't even ha- No, people don't know how to talk to me." How do you walk up to an, a g- person just standing in the middle of the room by themselves?

  23. 1:22:161:29:00

    Real Communication Is About Understanding, Not Winning

    1. JS

      do you do in that situation?

    2. SS

      Uh-

    3. JS

      Do you allow it? Do you pretend to be disrespected? Are you offended? I feel like we have such-- we seem to have such big reactions-

    4. SS

      We're a bit-

    5. JS

      ... to such common occurrences.

    6. SS

      I think communication is like lubrication. The more communication there is, the easier the machine goes, and without communication, what you get is friction.

    7. JS

      Yeah.

    8. SS

      Right? Most fights amongst friends-- I just had a fight with a friend just this week. It was based purely on first miscommunication and then total lack of follow-up, and then the tension just grew and grew and grew until one of us was like, "This is ridiculous." It's usually miscommunication and then lack of communication, and so if you can communicate, even badly, that will lubricate the relationship.

    9. JS

      Mm.

    10. SS

      And so what I find is that good relationships talk about the relationship.

    11. JS

      Yeah.

    12. SS

      Like, you see good marriages, and they're like, "Ah, I love how our marriage works so well." And you see good friendships. You know, you're like, "Ah, here's what I love about our friendship. I love that I can tell you everything." I have one friend that almost every time we talk, almost every time, I will say the same thing.

    13. JS

      [laughs]

    14. SS

      "Do you know one of the reasons I love our friendship is because dot, dot, dot, dot, dot."

    15. JS

      Yeah.

    16. SS

      And I say it-- and I even say, "I know I say this every time I talk to you, but it's just how I feel every time I talk to you. I love that we're friends because I can dot, dot, dot," or, "You make me feel dot, dot, dot," every time. And we talk about the friendship. And I think that's healthy. And so it's okay to talk about the friendship. It's okay to say, "Here's what I love. Here's what I..." You know. And I-- and it's okay if we need different things in different moments. And as I said before, if we do the work, it's not the ChatGPT answer. It's if you do the work, you get to earn the serotonin. You get to earn the oxytocin. You get to earn the feeling of the hug because it is natural and not because you counted for it. The serotonin's because it's earned, and you have genuine joy. And if you cannot because you've got your own stuff going on, if you cannot be that person for the time that you know they need you, then simply say so. "I got shit going on in my life. I can't be the person you need me to be right now. I love you, I love you, I love you. I just need to deal with my own shit." 'Cause otherwise people will make up stories. Ninety-nine times out of a hundred, those stories are wrong, and then we will treat people or act based on our version of events or our story.

    17. JS

      Yeah.

    18. SS

      And that's all listening is. Listening is just hearing what the other person's story is just so I have the context for why you've been acting the way you've been acting. The story doesn't have to be right. It's just their story. Just like my story doesn't have to be right. It's right to me, but it's just my experience of something. Like, my friend's like, "You did this, and then you did this, and then you did this." And I was like, "Wow." And I didn't say, "Well, I didn't intend to." I said, "Wow, I'm sorry. Like, I, I'm so sorry. Yes, I did do that. And now I wanna tell you my experience of what happened at the same event."

    19. JS

      Mm.

    20. SS

      "You did this, and you did this, and you did this." And she said, "No, I didn't." And I went, "Oh, da, da, da, da, da."

    21. JS

      [laughs]

    22. SS

      "I'm not telling you I'm right. I just want you to hear how I experienced what went down-

    23. JS

      Mm

    24. SS

      ... so you have context for why I acted the way I acted because now I have context for the way you acted the way you acted." Neither of us is right, and both of us are right. So this is about understanding, not about competing. And the funny thing about-... communication is when somebody gets it wrong or when somebody gets it right, you'll be like, "Thank you for saying that. That's the, that's the best thing I needed to hear."

    25. JS

      Yeah.

    26. SS

      And when they get it wrong, you'll be like, "Don't invalidate my story. Please just listen to my story. Sorry, sorry, sorry. You're right, you're right, you're right."

    27. JS

      [laughs]

    28. SS

      Like, this is the great thing about human beings, is we can actually, like, give people guidance about what they're getting right and wrong in the moment, and it doesn't destroy the moment.

    29. JS

      Mm.

    30. SS

      And you can be like, "You're right. I'm sorry. I'd like to reset. Please, continue." We can do that, and it works.

  24. 1:29:001:30:59

    Embracing Imperfection Is What Makes Us Human

    1. JS

      oh my gosh. It has been such a joy to talk to you. I always feel you're so refreshingly human in all your insights. They're ... Going back to your point on imperfect is, imperfect is human and human is imperfect, it's so refreshingly human to just talk to you about these ideas when sometimes we can end up living in a didactic three ways and two ways and say this and ... And it's true. It's ... All of that's helpful, and it's completely unhelpful because-

    2. SS

      Yeah

    3. JS

      ... the reality is, is-

    4. SS

      It's useful and useless at the same time.

    5. JS

      Exactly, yeah, because the reality is this. I just thank you for showing up in that way because it, I love it. I, I really enjoy it because-

    6. SS

      Well, thanks

    7. JS

      ... it frees you. It's freeing. It's liberating to, to know that, you know, if you can be messy, we all can.

    8. SS

      I think it's important for people to present themselves as they are, which is messy. Because to present yourself as perfect-

    9. JS

      Yeah

    10. SS

      ... sets up an unfair standard for other people to live by.

    11. JS

      Absolutely.

    12. SS

      And usually people present themselves as perfect usually out of absolute fear that they don't want people to know that they're actually imperfect.

    13. JS

      Yeah.

    14. SS

      And I'll say what I said before. To be beautiful is to be human. To be messy is to be beautiful. We don't fall in love with the perfection. We fall in love with the imperfection. We fall in love when somebody lets us be imperfect, allows us to be imperfect, and allows us to love them for being imperfect. You know? We showed up on the first date because of all the perfection. And imperfection is earned. Like, the space to be imperfect is earned. You do not reveal all your imperfections on date one. Too soon, too much. That's overwhelming. And when you do the work and you take the small risks that then become big risks, I want to be my messy self with somebody who loves me for my messy self, and I want somebody to feel that I love them no matter how messy they are. And that is a high standard and a hard thing to find. And if you have a friend like that, you work damn hard to protect that friendship.

    15. JS

      I love it.

  25. 1:30:591:33:28

    Simon on Final Five

    1. JS

      Uh, Simon, we end every episode of On Purpose with a Final Five. These have to be answered in one word to one sentence maximum.

    2. SS

      Okay.

    3. JS

      So Simon Sinek, these are your Final Five. Question number one: what is the best advice you've ever heard or received? Let's do it to do with friendship.

    4. SS

      So the best advice I ever got professionally is three-quarters of an answer is better than an answer and a half.

    5. JS

      That's a good one.

    6. SS

      And I think it actually, I actually think it applies to friendship, too. Sometimes just shut up.

    7. JS

      [laughs]

    8. SS

      You know? One of the best advice I got personally is you don't have to know everything, and you don't have to always be right, and that's a relief.

    9. JS

      Uh, question number two: what is the worst advice you've ever heard or received?

    10. SS

      Trust me, I've been doing this longer than you.

    11. JS

      [laughs] That's a good one.

    12. SS

      [laughs]

    13. JS

      I like that one.

    14. SS

      I try and ignore people who tell me that.

    15. JS

      [laughs] Question number three: define a good friend.

    16. SS

      I believe that friendship is two or more people who agree to grow together. And so a good friend is somebody who we have decided that we're gonna, we're gonna grow together.

    17. JS

      Question number four: how do you define a bad friend?

    18. SS

      A, a, a friend who's trying to extract rather than grow.

    19. JS

      Fifth and final question, we ask this to every guest who's ever been on the show: if you could create one law that everyone in the world had to follow-

    20. SS

      Yeah

    21. JS

      ... what would it be?

    22. SS

      That I would outlaw the harp. Just-

    23. JS

      Why?

    24. SS

      It's a silly instrument. It's good for-

    25. JS

      Really?

    26. SS

      It's good for dream sequences. That's about it.

    27. JS

      No way. You're joking, right?

    28. SS

      No.

    29. JS

      Really?

    30. SS

      Yeah.

Episode duration: 1:33:28

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