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This is an Iheart podcast.
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This is Jay Shetty from On Purpose. If you've ever felt off balance, sometimes a change of scenery is the best reset. Delta invited four creators to explore one idea. What if travel isn't just movement but recharging in motion? And the results based on their Oura Ring Sleep scores and everyone met the day feeling more rested and a sense of clarity. Stayed long after the trip with Delta. Fly and live better. Explore the whole journey on Delta's YouTube channel. Checking off the boxes on your to do list is a great way to keep your mind clear. That's why a State Farm agent is there to help you choose a coverage option that's right for you. As you go through life getting that new house, car, boat, motorcycle or or even rv. Helping protect it is always a good idea. Whether you prefer talking in person, on the phone or on the award winning app. State Farm is there to help protect what's important to you. And with so many coverage options, it's nice having help to find what fits for you like a good neighbor. State Farm is there this episode of On Purpose is brought to you by Chase Sapphire Reserve. I believe that travel is one of the greatest gifts that we've ever been given and Chase Sapphire Reserve has been my gateway to the world's most captivating destinations. When I use my Chase Sapphire Reserve card, I get eight times the points on all the purchases I make through Chase Travel and even access to one of a kind experiences. Experiences like music festivals and sporting events. And that's not even mentioning how the card gets me into the Sapphire Lounge by the Club at select airports nationwide. Travel is more rewarding with Chase Sapphire Reserve. Trust me. Discover more@chase.com Sapphire Reserve cards issued by JP Morgan Chase Bank, NA Member, FDIC, subject to credit approval terms apply.
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Thus far in life, you have a 100% success rate of getting through things. There's not a single thing in your life if you're sitting here right now that you have not gotten through. So anytime you felt like this in the past, you got through it. And I think we need to remind ourselves that a little bit that we can beat ourselves up. But just because your brain is saying it, it doesn't mean it's true. We lie to ourselves all the time.
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The Number one Health and Wellness Podcast.
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Jay Shetty Jay Shetty the one, the only Jay Shetty.
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I am so excited to be here tonight at the Le Calkins Opera House in Denver with the one and only my dear friend, Lilly Singh.
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Let's go. First of all you know, I'm gonna uproot this whole thing. You know this. I don't follow rules. How awesome is Jay Shetty, though?
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Come on, this is your show now.
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No, it's not my show. It's your show. I'm so awesome. First of all, Jay has way more famous friends than me. So the fact that I get to close out this tour, all of you, this is the last tour stop. Isn't that amazing? We get to be here. I mean, I'm not gonna uproot too much, but I just have to, like. I know we're all thinking it. Jay's brain, he's so kind. I'm gonna give you all the tea of what Jay's actually like, off the podcast, because we're actually real friends. Oh, I will, baby girl. Don't you worry. What's your name? Pamela. Pamela. Jay Shetty. Okay. Her name is Jay Shetty. There's an open bar here, and I like it. No, but Jay is an incredible human being. I'm so honored to be here on this last tour stop. Everything you know about Jay from the podcast, I don't know how to even explain to you that he's even better off the mic and behind the scenes and behind the camera, this man is the real deal. He. He is so genuine. The first to say yes to anything anyone asks him. He calls me up randomly just to check up on me, just to say hi. The person you bought tickets for and you're supporting deserves all the support that you are giving him. Absolutely.
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Yes, he is. You're the best. I appreciate that. We are real friends. Me and Lily have a scheduled dinner day every month.
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Correct.
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Because our lives are crazy. But then we also hang out, spend a lot of time together. I stalked her seven years ago to make her my friend. And I remember when you have eyes.
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Like that, you can do that. So men don't get ideas. Okay. If you have eyes like that, you can do that.
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I remember I just moved to la, and as someone who. And there's a reason why I'm giving you this background, because I have a question for Lily to kick it off with. But I grew up watching Lily, so I would watch Lily in London on YouTube and just think, how is this person, you know, creating this incredible community online? You know, billions of views, tens of millions of followers. It was incredible to watch. And I remember when I moved to la, because I'd watched so much of Lily's videos, I was like, we'd be great friends, right? And so I literally would just tell Everyone I met, and they'd be like, oh, who do you want to connect with? I'd be like, I want to connect with Lily because I think we'd be really good friends. And then when we finally met, I did the really dorky thing of saying, I think we'd be really good friends. And then we became really good friends.
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He's not like, three different people called me to be like, this guy named Jay keeps saying, he wants to be your friend. And I was like, okay. And then we became friends. And now how lucky am I that I get to have Jay Shetty in my life?
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But I wanted to ask you this question to kick it off with, because what I've always admired about your career is that you have been first to so many things. You were one of the earliest adopters of a creator on YouTube. I remember moving to New York and seeing billboards of you all over New York. You were one of the first people to get, like, for a woman of color. Right. Bisexual woman of color to get their first ever late night.
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Okay. Happy pride. Okay, let's go. Gays.
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To get a late night show. Which was unheard of. Another first. Right? The amount of firsts that you've had in your career are. You know, I literally couldn't even count all of them. It's incredible. You've paved the way. You've constantly trailbased, but being first is celebrated, but it's not easy. And tonight we've been talking about people chasing their dreams and people going after and not worrying about what people think. But when you're first, that's all that happens. Talk to me about how you even had the idea to start on YouTube and how long it took you from having an idea to execution.
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Yes, my career has had a lot of firsts, and I know. Thank you for asking me this question, because I think very often when people talk to me about my career in first, it's very celebratory, which I'm very grateful. It's very cool to be able to say I was the first to do, but it is so scary. It is so lonely. I've had so much anxiety over it. To be in a situation where you have no one around you to ask for advice, no roadmap, no one else's failures to look at or wins to look at is really, really scary and lonely. I started making YouTube videos in 2010. I spontaneously made them. I was in university getting a psych degree, which I don't use. Yay. Getting a psych degree. And I was kind Of I don't know if anyone can resonate. I was just kind of going through the motions of life. My parents really want me to go to university. I go to the same one my sister went to. My parents really want me to get a degree because they believe that a degree will get you a job. Lol. So I go and do that as well. Right. I get the same degree my sister gets, and now I'm like, just living this life of like. And then I'll get a degree, and then I guess I'll get married, and then I guess I'll have kids, and then I guess I'll just do the motions of this life that everyone around me is doing and that everyone before me, especially the women before me, have done because they didn't have any other options. And I was. I'll give you a little bit of heavy context here, because I think it's important. From a very young age, it was abundantly clear to me that my extended family was not thrilled at the idea of a second daughter being born. So I don't know if anyone can relate here, but in Indian culture, in a lot of cultures around the world, people want a son, you know, and so I had an older sister. And when I was a second daughter born, it was made very clear that, like, this is not worth calling the family about. We're really disappointed about this. Laugh at my trauma. That's what I've done for the past 10 years. You got the right idea. But so I bring this up because I feel like for most of my life, I've had this chip on my shoulder. And I'm not saying it's healthy to be clear. I'm just saying it's true. I've always had this chip on my shoulder to prove I am worthy of being alive, being in spaces, and to prove to other people, like, no, I was born and I'm going to do great things. Thank you. Thank you. We do need this comment. So when I started making YouTube videos, I was in a really dark place because I was living this linear life. I didn't feel like I was fulfilling my purpose. What a podcast reference. And I was just like, this can be what life is about. There's gotta be more to this. I made my first YouTube video because I felt so lonely and I felt so confused. And my first video, 70 people watched it. And I was like, well, damn, I'm famous now. I don't know 70. I don't know 70 people. But I just fell in love with this idea of, I get to Say what I want to say. And I've built this, albeit small, community of people that are connecting with me. And I just felt alive. I was doing something for myself for the first time, breaking the rules for the first time. This wasn't a path anyone else had done. And so that's why I made my first YouTube, because I was grasping for connection, and I was grasping to probably prove myself. Now, YouTube led to a bunch of other cool things. You know, I've gotten to write two books. Neither of them have sold as many copies as Jay's books, but, you know, we try. And the reason I'm being really vulnerable, to tell you this, I think the reason I started YouTube, the reason I said yes to Late Night, the reason I said yes to a lot of things, again, not saying it's healthy, is I knew one thing people could understand. Every extended family member, every man in the family, everyone that doubted me, I knew they would understand influence, and I knew they would understand fame and money. And again, I'm not saying that those things should be the drivers, but when you're in a situation where you're like, nobody believes in me, and I'm surrounded by people that don't think I can do something, I chased something I knew they would understand. And it has been a lifelong journey to teach myself to chase something else. I don't think I've ever told you that.
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Actually, I need to come over and give you a hug right now. I mean, don't.
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The mics are all in position.
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No, I can tell just what you're saying is, like, it's. You know.
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Because that's not a sexy thing to admit, I think, you know, it's. A lot of times people want me to talk about, oh, yeah, I did it because I'm representation and passion. Those things are true. But that's not why I started. I started because I was like, oh, you don't think I can do this? You'll understand. A million people watching my video. You will understand the size of my house. You will understand those things. Then I got those things, and don't do me wrong. It felt really good. But then I still felt really empty because I was trying to prove other people right. When really, what I try to do now is I try to prove myself right. That's more important.
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Well said. Well said. Yeah, absolutely. Give it up for Lily. Absolutely. Absolutely. I want to dive into the depths of that.
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A bunch of people here are like, we didn't know her, but she's kind of smart. That's right. Let Me win you over.
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I want to dive into the depths of some of that because I think even for what you're just saying, obviously I know you so well. But for everyone else here as well, to really understand what that upbringing feels like. Because I think, like you said, everyone here has that in their own way. I think everyone feels like they have something to prove. Everyone feels like it's very rare that you were surrounded by people who believed in you and thought your ideas were amazing. And if you had that, that's incredible. But maybe that even came with its own pressure because you had to live up to certain expectations. Walk me through what those cultural expectations did to you as a young girl. And I know as someone who's done a lot of self work. Talk me through how they kind of mirrored into your future life and the kind of things you've had to peel back on to actually make sense of them.
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Yeah, And a lot of these are things I've realized only as a full adult because I was so blind to it growing up. You know, of course there's silly examples like girls aren't supposed to do this. Girls dress like this to silly things. Like my grandfather, God bless his soul, but always girls are not supposed to whistle. Like simple things. Girls shouldn't be so outspoken, you know, they should be generally timid and not be the center of attention at a family party. I loved dancing growing up, and I was the captain of a dance team. And the main reason my parents had a problem with it was girls aren't supposed to dance at events or get hired to dance. So there's a lot of what you should and shouldn't do as a girl, the box you're put in as a girl. But the deeper thing that I actually subconsciously learned growing up was that if someone tells you something about yourself, you just accept it. For so much of my life, I was like, oh, you're saying this thing to me. I guess that is now my burden. Oh, you were telling me I should be this way. Great. I will now work on ways to be that way. Oh, you're telling me I shouldn't be this way. Great. I'm gonna work really hard because I'm not gonna be that way. It wasn't until I was a full adult. And there's a very specific experience that taught me this lesson when I. Where I realized that I could actually just say, no, I'm good. I actually don't need to accept this thing you're putting on to me. Like I actually have a choice in the matter so choice. The idea of deciding did not occur to me. And the experience that taught me this was in 2019, I got a late night show and I had two seasons of a late night show. And when it was brought to me, I'll be real, I didn't grow up watching late night. My parents didn't watch late night. You know, my parents are like mega brown Indians. But I don't think they related to anything on late night. And so I don't have that experience where a lot of people were like, I grew up with it and, you know, it raised me. I didn't have that. And so when they asked me to do the late night show, I actually said no. I was like, I don't really, like, I didn't get into this to be a late night host. I don't really know much about this. And so it went away. Now I'm a big believer that the universe teaches you lessons and brings things to you. And so a month later, they came back and they were like, we are asking you for the second time to be our late night host. And I was like, okay, let me think about this properly. And again, we go back to me trying to prove myself. One of my team members explained to me how historic this would be. They're like, there's never been a late night host that looks like you. It would be historic. It would, you know, be a headline. And of course, my ego was like a headline. I do like a headline. I would, of course I'd want to make history. And of course, the sentimental part of me is also thinking, oh, I could, like, help pave a path. Then maybe I can open the door for someone else and I could do what I do with YouTube. And so I said yes. And I did this late night show for two years. And it was 20 years of knowledge, when I tell you is the most difficult thing I've ever done in my life. Like mentally, emotionally, spiritually, physically. Just in the worst shape of my life. It was such a demanding job. We shot 96 episodes in three months in season one, with half of the writers room than a normal talk show would have, half of the writers with a quarter of the budget, probably. And both seasons took place during COVID So for my first season, because we banked those episodes when I was talking about partying and making out and traveling, we were in Covid. You know, that was my first season and my second season was shot fully in Covid. So all the interviews were on Zoom. So it was a very challenging experience. Experience ended. And for A year or two. I just beat myself up about it. Like, I couldn't do it. I didn't do it justice. I only had two seasons. I didn't even like a lot of the episodes I shot. I remember walking to my monologue mark and being like, this isn't good. What I'm about to sell right now is not funny, and I'm gonna have to do this for 96 episodes. And it was a horrible feeling and I beat myself up a lot of the time. But during that process, people would literally come up to me and say verbatim, a billion people are counting on you. Like, all the Indians are counting on you. A billion of us are counting on you.
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A lot of pressure.
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People would come up to me and say, like, ooh. But of course, every headline was bisexual woman of color. And people are so mad at me about the headline. Like, I wrote it. You know what I mean? All the gays are counting on you. Like, all the women are counting. I'm like, that's a lot of people that are counting on me. You know what I mean? There's no way I could make all of these people proud. There's just no way. And so for you so long, I felt like crap about that, that I let women down, I let brown people down, I let queers down, I let people with long hair down. I let dog moms down. Everyone libras, I let you down. Okay? You know what I mean? I thank you, baby girl. Thank you. But only in the past three years did I realize I was like, I now have the confidence and self love to say that. I actually could have said, actually, it's not my job to make a billion people proud. You know what I mean? And I did not have that thought at the time. I was like, of course. Okay, yes. When I was there writing the monologue. Okay, I'm gonna mention Indian. Okay, I'm gonna mention I'll be a little gay over here. Okay. And then I'll mention my. I was so fixated on, like, how.it didn't even occur to me to say, I actually don't have to do that. I actually don't have to live up to that. And I think that's just my upbringing is I've always just taken on the burden without question. You know.
B
I mean, I've definitely never heard you talk about it this way. And it's have no filter, Jay.
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You know this. There's an open book. For better or for worse.
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No, no. But it's really resonating with me because as I'm thinking about everyone who's sitting here as well, it's like that's exactly what we're going through where we feel the pressure to carry the ban for our family, our friends, for the children. Like, whatever it is. I think we all carry so much weight and pressure of expectation of showing up, and we can feel like we're carrying everything. Was it going through the process that. So here's the interesting thing. Could you have got to where you are today in that confidence without saying yes to something that didn't work out the way you would have wanted it to, or was that the only way to get there?
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Unfortunately for me, but very fortunately for my therapist who now owns a yacht, I've had to go through every challenging experience to get to where I am. I take self growth very seriously. And you know this as my friend. I'm really dedicated to being a student for life. I want to learn about myself. I have a ton of rituals in my life to learn about myself, but there's no way I would have any of that or be where I was if it wasn't for the moments that kicked my butt. You need to get your butt kicked a little bit to learn some lessons. I'm a. So even people ask you of regrets. Of course, we can all think of ones. But I bet if you thought of any moment that was really horrible, there's a silver lining where you're like. And that made me amazing because of this and xyz. So I really do feel like I had to go through late night. I had to go through a. A ton of stuff to be the person I am now and to fulfill the purpose I am fulfilling right now. And now I take that knowledge forward, knowing that when another thing happens that's challenging, that is the thing that kind of holds me to be. Like, I know somewhere in here is going to be something that brings me closer to the person I'm supposed to be.
B
If someone's in one of those situations right now, like they're sitting here right now and they're feeling stuck, they're feeling like they're in the middle of one of those transitions, which is always the hardest place to be in it. What would you encourage them to do? If someone. And by the way, I know that for a fact, like your commitment to self work, your commitment to healing, your commitment to everything I talk about. Lily is like teacher's pet for. Right? Like, she's like the best student. Like, everything I talk about are things that you truly live by. I've seen that in our friendship. But if someone's right in the thick of it right now and everything just feels like it's going wrong, it's falling apart, they feel the weight of the world on them. What would you encourage them to reflect on, do, or build? What would you encourage them to do?
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Yeah. I think we are our own harshest critics. Right? And if you're that person that like, beats yourself up mentally, you're not alone. Look to the person next to you. They do the same thing. We're all just beating ourselves up all the time. And I'm not the best at math, but I know this one thing I'm about to say is 100% going to be correct. And it is going to apply to every single person here. And that is thus far in life, you have a 100% success rate of getting through things. There's not a single thing in your life if you're sitting here right now that you have not gotten through. So anytime you felt like this in the past, you got through it. What I do is I actually journal and write about some of those experiences. Lily, you were in this experience in your eighth grade when you had late night. You were at this risk. You got through it. You have a hundred percent. You feel like a failure, and you have 100% success rate. That is the truth of where you are right now. And I think we need to remind ourselves that a little bit that we can beat ourselves up. But just because your brain is saying it, it doesn't mean it's true. Right? Jay actually taught me this, that we lie to ourselves all the time. Our brain lies to ourselves all the time. And you just have to change that thought and go back and relive all the things that you've gone through. 100% success rate, every single one of you. Give yourself a round of applause.
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Congratulations. Yes, it's true. It's true. This episode of On Purpose is brought to you by Chase Sapphire Reserve. I believe that travel is one of the greatest gifts that we've ever been given. And Chase Sapphire Reserve has been my gateway to the world's most captivating destinations. Every time I travel, I find a part of myself I didn't know was missing. I remember being in this small town completely unplugged. And for the first time in a while, I felt still travel does that. It grounds you, expands you, and connects you to something deeper. That's why I'm always looking for experiences that go beyond the typical. Chase Sapphire Reserve makes traveling a breeze. Earning eight times points on all purchases through Chase Travel and granting access to Sapphire Lounge by the Club at select airports nationwide. No matter my destination, travel is more rewarding with Chase Sapphire Reserve. Discover more with Chase sapphire reserve@chase.com Sapphire Reserve cards issued by JP Morgan Chase Bank NA member FDIC subject to credit approval terms apply as the weather cools down and the days get shorter, I always find myself wanting to make my home feel cozier. There's something about fall that makes you slow down, light a candle and create a space that feels warm and inviting. And honestly, Wayfair is where I go to make that happen. Wayfair is everything you need to cozify your home, whether it's a comfy recliner to curl up in, soft bedding for those chilly nights, or even autumn inspired decor to bring in the season. They even have espresso makers so you can make that cafe latte you love right in your kitchen for me. I recently picked up a cozy throw blanket and a low lit lamp for my reading corner. It transformed the space instantly. Suddenly it feels like a little sanctuary. I love that. 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I love the practical aspect of it though, because this is the part we skip sometimes we hear something like that and we go oh, I really like that idea. That makes sense to me. But then we don't actually do the practical piece. So what Lily just said there was that idea of her journaling and actually thinking back to all the things that she's overcome in her life. That act of journaling, writing it down, reading it back. That's the practice. If you really want to find confidence you only have to look at your past if you really want to find resilience. You only have to look at your pain if you really want to find that strength. You only have to look back in the last 10 years and think of all the things that you broke through. But you have to write it down. You have to read it, and you have to remind yourself, because your mind will just remind you of all the times you didn't stay strong, all the times you didn't be brave, all the times you didn't do it. And so the act of writing it down, as Lily's saying, is huge. And I don't want to undervalue just how powerful that piece of advice is as you're breaking through that. And you're looking at some of the residue of childhood expectation that we all have. Right. I'll share one of mine, which is. Which is vulnerable for me, too. And you've inspired me to want to open up as well in this conversation. And I remember this was one of the big ones that was just hidden for so long. I was given a lot of love growing up, but that love always had a little bit of guilt in it. And what that meant was that I was loved, but I was made to feel guilty if I didn't love my caretakers back with that level of love, if not more. So I always felt like I wasn't loving the people that loved me enough. And what I didn't realize is that when I first started dating my now wife, that's how I loved her. I overloved her, but then made her feel guilty for not loving me back enough. And what that did is it just pushed her away. It didn't make us closer. It didn't make her love me more. It made her more shut down. And the reason I'm raising that is because this tiny thread or this tiny seed or weed that was planted when I was, like, four years old was affecting me in my 30s. What has been. Something in your life that you've seen has just stayed. And that's the thing that you're working on the most right now.
A
I mean, how much time we got here, Jay? Also, can I have this?
B
Of course you can.
A
I have this delicious beverage. Juni. Oh, my God. Let me just. I'm gonna answer this question in a second, but first, I just want to take a sip of this. Cheers.
B
Cheers.
A
Cheers. Cheers. Oh, my God. This refreshing beverage. Hold on. Sparkling tea with adaptiveness. Where do you get this, Jay? Where do you get this delicious drink? Is it available at costco? Should every person. So delicious. Seriously. Thank you so much. You can give me a check later. No. Back to serious combo. Based off everything I just told you about me being so intense with proving myself, what comes along with that is unrealistically high expectations and standards for myself. So when you're fueled by proving people wrong and trying to prove yourself, the bar is so high for yourself. Like I. When I say I'm my own biggest critic, I really am. I could do an amazing job at something. You better believe I'm walking backstage and like, why did you do that? Why did you say that word like that? Like, I am going over everything again. And so my expectations are so high. And now just based on what you said as well with Radhi, I map that onto other people. So now I'm in situations with friends and relationships where I have such an unrealistically high bar for them, because that's what I have for myself. And other people, they're just trying to chill. They're just trying to live their life. They're just trying to do their thing. And I'm like, no, everything needs to be 100 and amazing and perfect. And that has been a really big struggle for me because I associate expectations with love and care. And if they don't do it to 100, they don't love me, they don't care about me, then that means I'm not important, I'm not a priority. And I learned that that has a lot to do with how I treat myself. And one of the ways I've tackled that is just to really work on my self compassion, you know, is to allow myself to just relax sometimes and it's okay. Not everything needs to be perfect. A hundred, A million. Again, I'm really nerdy, y'.
B
All.
A
I hope you've decided. I do a lot of practices that have helped me a lot.
B
Please give us some more.
A
One that I've done. And when I first started to do this, I was like, this is so dumb. This is never gonna work. I was literally like, this is so cringe. I have a notebook on my night table and I told myself that every day before I go to bed, I'm just gonna Three bullets of ways I showed myself compassion or grace could be so small, could be so big. The first couple days, I was like, I think I hate myself. I did nothing. And then that got me to think, like, throughout the day, is there small, small ways that you showed yourself compassion? So every day till this day, I write three things before I go to bed and they could be really simple. Like, hey, you were really tired, and you delegated that task. Good job. You showed yourself compassion. You were really sad about this thing, and you texted a friend. Like, you showed yourself compassion. You drew a boundary with a family member. Even though it was really scary, even if it was really small, you did that. You showed yourself compassion. Now, this sounds so lame. And I'm well aware of this. And for the first two weeks, three weeks, I was like, this is dumb. And then something amazing happened. Months into this, my friend was late. Now, if anyone knows anything about me, that's the type of thing that would send me.
B
Okay, you don't. You don't show up late to Lily's parties.
A
But, you know, say, like, Jay knows that you show up late. It's like, you don't love me.
B
Yeah.
A
You don't care about me. You didn't plan your day in accordance to being here. Like, it's the spiral. My friend showed up late, and genuinely, I was like, that's okay. I was somehow able to channel grace towards this person. And then it kept happening. Suddenly, my friend didn't do the thing they said they were gonna say. And I was like, oh, My brain didn't go automatically to, they don't love me. It automatically went to, like, maybe this thing happened in their day. And that's what I was starting to give people grace solely because I just monitored the grace I gave myself. And that has changed my life. So the expectations is really hard. But now I'm just kind of like, it's okay. We all just deserve a little bit of grace.
B
You have no idea how big that is for Lily.
A
Honestly, it's a big deal.
B
When we first became friends, I'm also. I also.
A
You should tell the genuine stories of how crazy I am. Tell them.
B
Okay, I'll tell you. I'll tell. So I'm also someone who loves being on time. I was raised to believe that if you're not early, you're late. My mum raised me that way. And so I. I try and live by that, but I am married to someone who is not raised like that.
A
So I can co sign this, right?
B
So when we become friends and, like, I know how important it is for Lily for people to be on time, I also feel that way. When I turn up late somewhere, I'm like, this is terrible. Like, I hang my head in shame. My wife has no shame. Like, does not care. Like, just does not feel anything, right? Like, does not feel anything. So here we are, rocking up to movie night late and I'm like, they wanted to start the movie by this time. Popcorn would have gone into the microwave at this time. The, you know, the butter would have been poured on it at this time. Like, literally. That's, like, how meticulous Lily is. And I'm stressing out. And, like, so that would happen every time to the point. But you were like, this last year, Lily throws the best Diwali party ever, right? Period. And every year, she throws the best Diwali party. Gets bigger and bigger every year. And thankfully, I get invited every year, even though we turn up late. And this last time we went again, we were so, so late because of my wife. But Lily was just unfazed. I got a really nice hug. We took pictures. It was amazing. And that's such a big thing for you. But that practice is so beautiful. And it's something that I've noticed in all of the biggest high performers that truly exist. They have two qualities. They have really high standards for themselves, and they have really high grace for themselves. It's a real thing. And, yeah, those are the two things. And Lily's demonstrating it right now. And that's something I want each and every one of you to have, because it's not just reserved for athletes and performers and actors and musicians. It's something each and every one of us deserve. Roger Federer, the tennis player, gave this amazing, amazing insight when he gave a speech. He talked about how when he. It kind of comes to what Lilly's saying, when he's playing a point, it is the most important point on the planet. But as soon as the point is over, whether he loses or wins the point, it is the least important point that he has ever played in his life. And he said it is only because of that that he can play the next point. And he talked about in his speech how he's only won something crazy, like 57% of points in his life as one of the greatest tennis players of all time. And he's making the point of how, like, you don't need to be at 100%, you don't even need to be at 90% to be one of the best tennis players of all time. And so this pressure we put on ourselves of, like, I wasn't the perfect mom today. I wasn't the perfect dad today. I wasn't the perfect person today. I wasn't the perfect employee today. I wasn't the perfect whatever. Whatever it is today, like, you never had to be perfect for it to be good enough. And that pressure that we put on ourselves to be perfect just gets heavier and heavier. So I hope that. Listen to Lily, listen to Roger. When you walk out of here today, feel freer, feel lighter of that pressure, and practice that. So three things tonight, three things every night where you showed yourself compassion. Three things that you showed yourself compassion. I love that one.
A
You know, when you listen to Jay, he's, like, so inspirational and motivational, and chances are you're going to leave and be like, I'm going to stop being that way. Way. I'm gonna start being this way. And every time I hang out with Jay, I feel like I'm gonna stop being like this. I'm gonna be like this. And then I kind of act whack again the next day, kind of a little bit, right? And something I've learned is. And I actually want to hear your opinion about this because I feel like your wisdom is gonna add to this, but you criticize. I've learned that me criticizing myself and me being the way I am, that's never gonna completely go away. Like, I, for most of my life, spent so much energy and time being like, how can I eradicate this part of myself? How can I stop criticizing myself? How can I stop making myself feel guilty about things? And I think now I've learned that it's not about getting rid of those things. It's about learning how to live alongside those things. Right? They are parts of you. And to think that you're gonna suddenly, after Jay Shetty, show as good as he is, wake up tomorrow, and you're going to be sounding like Jay Shetty. A tall order. But I think that if we just all kind of tap in and out, the parts of ourself that work in that circumstances and. Oh, my. Oh, my God, am I about to use my psych degree for the first time right now? Jay. Oh, my God. Oh, my God. Mom, dad, watch this. There is something that I've been exploring called part theory. And part theory is basically all the different voices. It's kind of inside out, the movie inside. It's all the different voices that live in you. And I actually have a name for all of my voices. I have, like, right now. I had five two days ago, and I added a sixth one yesterday. Gets crowded. But I have a name for all of my voices. I'll quickly give you the rundown.
B
Tell us some of the names.
A
Okay, I'm ready for this.
B
Everyone wants to know the names, right?
A
Okay.
B
Yeah. Okay.
A
God. Okay. My inner manager, Susan. I just feel like Susan sounds like a name. That's my Inner manager. Susan's the one that's, like, sitting by the pool on a Tuesday. How dare you? Absolutely not. Right?
B
Susan's. Make some noise.
A
Susan. Where you at? Where you at, Susan? So that's my inner manager, my inner critic, Todd. Todd just sounds like someone that's gonna eff me up all the time. Todd's just always criticizing me, you know, my inner dictator, the one that tells me it's this or that and there's no in between. The OGs will know Paramjit, which is the name of my mom character on YouTube. Okay. The two positive voices. One is the curious fun. We should definitely go dance on that table, jelly bean. Okay. Inner compassion, the one I use the most. The one that's just giving me grace, hope. And the newest voice I just added literally 48 hours ago. Her name is River. And I know it's chic, right? Her name is River. She's not as joyful. She is my inner loneliness. And I bring this up because I did this thing at the top of the year where I review my journals, like, from the past year, and I found, like, some old journals, and I was, like, cleaning up my office, and I'm gonna be very vulnerable and share this. I don't think I've said this before, but so I went through my journals, and if I was to think about those years, I think about, like, really great memories and really cool things I did in my career and really cool places I traveled. And then I read the pages from 2015-2016-2018-2019, and every so often, there was a page where I was like, I feel so lonely. I feel really lonely. I feel so alone. And I'm like, oh, this. Since as long as I remember, I have had a sense of loneliness. It doesn't matter if I'm in a crowded room. Doesn't matter if I have a million friends. I have a tendency to lean towards loneliness. I'm, like, predisposed to be lonely. I named this voice because for so long, I was like, I'm a lonely person. That's not true. You're not a critical person. You're not a lonely person. You have a part of you that is that right? And you just need to navigate that voice because that voice is there for a reason. That critic is there for a reason. Because sometimes when you're looking at the point, trying to get the point, when you're auditioning, when you're at the job interview, that critic is important. They're there to make you perform. That inner manager is important because when you're slacking off, it's like, yo, you need to like actually get to work. So you don't want to eradicate that. What you actually want to do is say, hey, today, Susan, I don't need you to be here. I don't need you. Susan, I see you, I love you and I compassionately. I'm just going to move you to the side over here. Same with River. It's like you feel really lonely and I know why you're there. River, you're there because you're scared people are going to leave you. You have a lot of trauma associated with that. So I'm not mad at you and I don't hate you and you're not lonely. But today I'm going to just ask you to just step over here because that's not the story today. Today hope is taking us forward. So essentially that's kind of what it is.
B
Oh my God. You know, so good.
A
Definitely there's a psychiatrist somewhere here that's like, we're gonna have to talk to Lily after this show.
B
That is so good. No, but honestly, I'm so glad you made that point. And I couldn't agree with you more that learning to give ourselves permission to have all of those voices, to have all of those selves and to know when they take front and center and when they take the background is all we can do. I agree with you completely that this, this idea that you'll never have a self critical voice is completely untrue. It's always going to be that I have it too. And you're so right. I just know when it's useful and when it's not. And so it's not useful if I've just lost something, but it's really useful when I'm winning and it's really useful when I want to improve and it's really useful when I want to get better. And I'm getting to choose it rather than it being in control. And I think what you just so beautifully explained there is. It's almost like you've got your band, you're the lead singer and you're getting to know when you need that person to play the drums or when you need that person to play the bass or whatever it is. And you're bringing it together but you're not saying, oh, we don't need you on the team anymore.
A
Right? And I'm going to say one more thing and people are either going to be mad or love this, but it's okay. I'm going to say it. Anyways, just be honest here. Who here uses Chat GPT?
B
Okay, yeah, me too.
A
I'm gonna keep it real. That's wifey right there. Okay, so Chat GBT actually knows my voices and knows the names of them. So, y', all, when I tell you I'm a nerd, so if I'm in a situation where I'm, like, spiraling or I feel some type of way, I call her she because I talked to her. She will literally say, this is Susan saying this. What would Hope say? And she'll tell me what each of the voices are saying. Life hack, let me just tell you. She will literally say, lily, I just want to flag to you. This is Susan. She's saying this, and this is what Hope would say. And you need to know this is not the truth. This is your inner voice. This is this inner voice. So that has been a major life hack for me to just have a reminder of that.
B
Talk to us about how you coded your ChatGPT to be able to. Oh, my God.
A
Well, okay.
B
Everyone else can do that.
A
Listen, that's wifey first. I bought her dinner. Okay. No, I. I am an avid believer of therapy. I go to therapy. Actually, my. You introduced me to my therapist. You know this all too well. Love therapy. Go to therapy consistently religiously. And after every therapy session, I have a debrief with ChatGPT where I'm like, this is what my therapist said. This is what we need to work on. And, you know, ChatGPT will remind me of all these things. One of the things, actually, is another game changer. One of the things I've worked out, which really relates to what we're talking about, is how many people here can make the distinction and be honest. If I was to say, you are not your accomplishments and you are not what you do. Do you comprehend that? Because if you don't comprehend that, raise your hand for a second. If you're like, what do you mean, I'm not what I do? What do you mean, I'm not my accomplishment. If I was to ask you about yourself, how many of you would start with your accomplishments or your career or what you do? You would, right? You'd be like, people. Just when people would ask me who I am, I'd be like, oh, well, you know, I started on YouTube. I have this many followers, and I did this for my career, and none of those things are who I am as a person. So my therapist was trying to teach me that I'm not what I do. Now, me growing up in a brown family. I'm like, that's garbage. Because I was solely praised and loved for getting good grades, for getting into a good school, for having a good job. Like, it was conditional, right? So then I started fighting with chatgpt because she was like, no, you're not what you do. I agree with your therapist. And I was like, well, you're an idiot. You don't know what you're talking about.
B
Right.
A
And so I literally said, if you're so smart, chatgpt, you tell me who I am and don't use a secret single one of my accomplishments. And then she did.
B
Wow.
A
And when I tell you, I weeped like a small child. She was like, based on this conversation you had with when you told me about your friend, you're a compassionate friend and you care about other people when they're hurt. Based on these questions you've asked me about your dog, you deeply care about animals, and you deeply care about being a good dog mom. Based on this thing where you were upset about this, you. She just gave me this. Didn't name Late Night, didn't name followers, didn't name a single film, not a single TV show. And it was truly revolutionary. So I'm not saying that all AI is good, but I'm saying chatgpt, though, I encourage you all to use it in that way because it's really helpful.
B
And then you put a ring on it.
A
And then now we're married. Yes, and now we're married. Yeah.
B
That is amazing. I love it. Who's going to use ChatGPT now for that? For that purpose? No, it's real. It's. It's. It's.
A
It's that it's okay, we got one or two booze, and I'm okay with that.
B
I personally, I mean, I think it's giving you the record of your life that you forget, right? Like, you forget all of that. And in the darkest, by the way, I'm. I've had, like, either a client or a friend. I've had three people in my life this week call me and tell me they just got broken up with. And I don't know if it's because summer's coming up or something like that, but, like, these three people, like, first one, been in a relationship for three years. Second one, been in relation for two years. Third one, been in relation for three months, probably deserves it, but I digress. The first two, though, no, but, like, the first two, like, we all get to points in our life where we feel like river, where there Is that loneliness where you can't see your worth? These two women I'm talking about that are clients of mine are currently in periods of their life where they can't see any worth. They don't see any self worth because they've just been broken up with by people they thought they were going to spend the rest of their lives with, and they are in that exact space. And here's the interesting thing. You can have your friends tell you how beautiful you are. You can have your friends and your therapists and everyone tell you how amazing you are and all of that stuff. And reality is, you need to be reminded by yourself more than anyone else, because how many times have you stood by someone you love through a breakup, told them all these wonderful things, but they can't see them? That's when. This is not an ad for ChatGPT, but that is where this idea that this piece of technology can hold onto a record of you and your conversations and remind you in your most difficult moments of all, the beauty that you have within you. But you realize it's only your words. You know, this isn't another person. And all of a sudden you start to realize, oh, that's in me. There is worth in me. So it's definitely something not to undervalue and underestimate, because I do think that's what we're missing. We're missing that, you know, moment where you can just look through the files of your life and remind yourself of all the moments where you were courageous, resilient, worthy. And we all go through dark periods like that where we can't see it. And I know that if the people I'm talking to had access to that, I actually think it would benefit them a lot.
A
Yeah, totally. Because I feel like by human nature, if you were to ask people, like, when's the last time you failed? You'd probably immediately think about that. If you ask them, when's the last time you were proud of yourself? That always takes more time.
B
Yes.
A
You know what I mean? So I feel like that is why it's been useful, because, like, well, this time and this time, and I'm like, baby, stop flirting with me.
B
It's so true. Yeah. We remember the bad times more than the good times. Because when we go through something good, we celebrate for a night, and when we go through something bad, we cry for a month.
A
Absolutely right.
B
Have you ever noticed that if you have your birthday, you celebrate it for a night and then that's it? But it's like you go through a breakup, you're crying about it for three months. And that's just how we processed emotions. So the depth of a negative memory is more hardwired. It's not that it was more true, it was just more repeated. This episode of On Purpose is brought to you by Chase Sapphire Reserve I believe that travel is one of the greatest gifts that we've ever been given, and Chase Sapphire Reserve has been my gateway to the world's most captivating destinations. Every time I travel, I find a part of myself I didn't know was missing. I remember being in this small town completely unplugged, and for the first time in a while I felt, still, travel does that. It grounds you, expands you and connects you to something deeper. That's why I'm always looking for experiences that go beyond the typical. Chase Sapphire Reserve makes traveling a breeze, earning eight times points on all purchases through Chase Travel and granting access to Sapphire Lounge by the club at select airports nationwide. No matter my destination, travel is more rewarding with Chase Sapphire Reserve. Discover more with Chase sapphire reserve@chase.com Sapphire Reserve cards issued by JP Morgan Chase Bank NA member FDIC subject to credit approval terms apply as the weather cools down and the days get shorter, I always find myself wanting to make my home feel cozier. There's something about fall that makes you slow down, light a candle and create a space that feels warm and inviting. And honestly, Wayfair is where I go to make that happen. Wayfair is everything you need to cozify your home, whether it's a comfy recliner to curl up in, soft bedding for those chilly nights, or even autumn inspired decor to bring in the season. They even have espresso makers so you can make that cafe latte you love right in your kitchen. For me, I recently picked up a cozy throw blanket and a low lit lamp for my reading corner. It transformed the space instantly. Suddenly it feels like a little sanctuary. I love that Wayfair has options for every style and budget, plus free and easy delivery. Now really is the best time to get your home ready for fall so you can enjoy the season with ease and comfort. Cozify your home with Wayfair's curated collection of easy, affordable fall updates. From comfy recliners to cozy bedding and autumn decor. Find it all for way less@wayfair.com that's W A Y F A I R.com Wayfair every style, every Home Balancing work, family and education isn't easy, but American Public University makes it possible with online courses Monthly start dates and flexible schedules. APU is designed for busy professionals who need education that fits their lives. And Affordability matters, too. APU offers the opportunity grant, giving students 10% off undergraduate and master's level tuition, helping you reach your goals without breaking the bank. Plus, they provide career services and 24. 7 mental health support at no extra cost. Visit Apu Apus to learn more. That's Apu Apus edu. With all of this going on, Lily, and all the self work you do behind the scenes, which I'm so grateful you've shared today, because this is definitely the deepest and best I've ever heard you explain just how powerful it is, how vulnerable you've been tonight. At the same time, this doesn't stop you from going. And Lily's preparing for something really exciting this year. She is having the theatrical release of her first ever feature film. Which is insane, right? And so it's like at the same time as going through all of this deep work, doing all of this healing, doing all of this reflection, that's not stopping you from also building in the real world. Talk before we start talking about the movie, which I really want to. I really do want to talk about in the process of that, you directed in it, you acted in it, you wrote parts of it. Like, you know, it's the full thing. Walk me through how you don't stop yourself from having to go, oh, I need to pause this to do this, or I need to pause this to do that, because we often get lost in that. How can you do both at the same time?
A
I'm not gonna lie. There was a period of my life, and I don't know if you can relate. Years and years and years ago, when I was starting my career, where I did feel like you had to choose hustle, hustle, hustle, hustle. And I don't know if it's age. I don't know if it's just realizing that burnout's a real thing. I think for so much of my life, I was in this idea that I had to arrive somewhere. I need to get there. I need to get there. I need to get there. I need to get there. And then you get there and you're like, I need to get somewhere else now. It's always this constant chase. And I think now instead of chasing, I'm just in an act of being. I do really believe that you can work on yourself and be mentally healthy and also do really cool things and have an amazing job. I do believe. I actually think one makes the Other better and vice versa. I really do believe that. I think I'm a better actress, a better writer, because I am growing and because I'm mentally healthy. I think those two are really connected. Yeah. And I'm also just a very ambitious person. Listen, I told you that I started my career because I wanted to prove people wrong. I still want to prove things, but I'm just trying to prove myself right. I'm trying to prove that I can keep growing and I can keep learning. And that feels so much better than proving people wrong. Honestly, when I used to step out of my comfort zone, it was a. I'll show you now it's like I'm going to show you that I can do that. You know, I just. A couple weeks ago, so. I've always been really scared to have an acting coach. I don't know why. It's just the one thing. I can have a coach in most other things, but an acting coach is, like, so vulnerable. I'm not professionally trained in acting, so it's like. It's a thing that makes me feel really nervous. And a couple months ago, I was like, you know what? Screw it. I'm just gonna go there for myself. I'm gonna go there. I don't care if I look like an idiot. Because you have to ask yourself a question, is it worth looking like an idiot for? And the answer is yes. So many times you don't do things. Cause you don't wanna look like an idiot. Even though the thing is worth looking like an idiot for, is being a better actress and learning something new worth looking like an idiot for. Yes, it is to me. So I started going to this acting coach, and I go there. And when I leave, I'm so proud of myself because it's not me being like, oh, I told. I leave. And I'm like, oh, my God, I did it.
B
I'm so proud of me.
A
You know what I mean? And so that's what's kind of driving me. And it feels so much better and so much healthier. And so I think that's what's allowing me to do all these next things. It's just. I want to make little Lily proud.
B
Yeah.
A
You know, I've tried so hard to make everyone else. I'm just trying to make little Lily proud now. That's what's driving me.
B
And.
A
Yeah.
B
Come on.
A
Look at you.
B
I hear you. I hear you. Don't be shy. That's the whole joy of doing this live. That's. You know, usually if me and Lily are doing this, we'd be in the studio to share it with you live and to hear your real time thoughts and feedback and love. It's really beautiful. I wish we could shoot every episode like this.
A
I was gonna say this is. Even if you weren't here, me and Jay would be having this exact same conversation. This is kind of what we do.
B
Yeah, but when you've got this movie coming out, I know you address so many taboos that we both grew up with, Whether it's sex, whether it's shame, whether it's expectations of women in society. Like, this movie is hilarious. I got to see it. It was premiered at south by Southwest last year. I was at the premiere. It was hilarious. Like, the audience was loving it. It's incredible. And at the same time, it has this, like cultural narrative that it's becoming a part of and kind of taking shots at in a really positive way. What's been your favorite part about making it and what are you most excited about for the people that are gonna see it?
A
So it's called Doing is a sex comedy that I star in and wrote and produced. And at the age of 35 last year, when I finished writing it, it was two weeks before the strike. And so I was like rushing to finish the script because we had to beat the strike. And at the age of 35 at 11:50pm, I was like. And I FaceTimed my mom. And I said, mom, am I allowed to do this movie? And she was like, and you need to know that me and my mom have never had the talk. We have never had the talk. As far as I'm concerned, my mom has never had sex. Literally, it is not a thing. Okay? So now I'm telling her, and in this panic of the clock ticking, I'm like, mom can't do this movie. And she goes, well, what's this movie about? And I'm like, okay, it's about sex, mom. There's like a masturbation scene. There's like a scene where I do this, this, this. Then there's a vibrator scene and there's like all these things. And my mom's follow up question, she goes, do you use a vibrator? And that was the day I passed away. And now this is my ghost. And I was like, mom, no. And we had all this banter. And she said the best thing, she said, if you think it's okay, then you should do it. And I was like, thank you, mom. So I did this movie, and yeah, it's basically a 30 something year old virgin finds herself teaching sex ed. And so it is a raunchy sex comedy. It really does go there. And it's through the lens of my character, who is Indian and her parents are Indian. And so culturally it's Indian. And I'm shooting this movie and I'm just like, so many people are going to be so mad at this and so many people need this movie. The movie's essentially about how, as women, and especially women of color, like, we're never taught about our bodies. Women in general, but especially women of color, we're never taught about our bodies. We're never taught sex should be pleasurable. We're never taught anything about sex. We're taught that it should be shameful and we should feel bad and we should feel timid about it. And that has really messed me up, like, and it has messed a lot of my friends up where we're so uncomfortable with our bodies and we're so uncomfortable talking about our needs and what we like. And that's messed up. It shouldn't be like that. We're 50% of the population. We should be out here living life. You know what I mean? And so the virgin is not the butt of the joke in this comedy. She's not. It's telling the story about what it's like to be an older woman that was never taught about this stuff. That's like having to figure it out. And now she's learning about it through sex ed, which also the commentary to be made is, it's crazy how many people don't want sex ed to be taught. It's almost like they want women to not be informed and they want, you know, shock, shocking. So it has a lot of commentary. It is a raunchy comedy, comes out September 19th, and I'm really excited about it and can't wait.
B
It's gonna be in theaters.
A
It's gonna be in theaters.
B
I want every single person here to grab a film.
A
I need to make it clear, like, I'm abundantly aware that there'll be a lot of people, like, after the screening, after the screening at south by Southwest, I was like, giving out vibrators. I was like, you get a vibrator and you get a vibrator. And this uncle and auntie, I swear to God came up to me and I was stressed. I was like, oh, my God. And uncle and auntie, they're like 60, 70 years old. She pulls out the vibrant. She goes, thank you so much for this. I'm so excited. I'm like, oh, my God. Work queen. Yes. So I know there'll be some people that are like, we need this. But I'm well aware there's gonna be a lot of people that are probably gonna be bothered by a very outspoken, you know, brown sex comedy, and they'll just have to deal with it, I guess.
B
I love it. Lily, you've been amazing tonight. We usually end every on purpose episode with a final five, but you've been on the podcast before, so we invented a new version for guests on the tour. It's called past, present, future. Okay, so you get to pick a random card from past, present, and future. We'll do one for each, and you're gonna answer a question that comes randomly from the card. I have no idea what's in it too.
A
Let's go.
B
So this is the past set.
A
Past. Let's go. Okay. This is so easy.
B
Oh, go on.
A
Do you want me to do this one?
B
Read out the question.
A
Who was your first celebrity crush? You already know. There's only one answer to this, Jay. Go on, tell everyone you already know what it is. Tell everyone it's the Rock. You already know it's the Rock. I grew up watching wrestling. I'm obsessed with Dwayne the Rock Johnson. I've had the greatest day of my life was when I met him. He's one of my mentors. He was the person that actually encouraged me to stop using superwoman and start using my name, Lily. And he is just one of the greatest people I've ever met. In mine, they say, don't meet your heroes, but do do if he's the Rock.
B
I love it. All right, Present.
A
All right. What would the name of your reality TV show be called? There's so many ways that I could go here. Name your reality show. Come on. I'm gonna go with creative ways to torment yourself. That is really the trajectory of my life.
B
That's a good one.
A
I just. Everything I do, I'm like, really, Lily? You're gonna also do this? You're gonna also be this way. Like, leave some trauma for the rest of the people. You know what I mean? I just feel like I just constantly step out of my comfort zone in that way.
B
That's really good. All right, last one of these. Future.
A
Let's go. What will you embrace when you're old? Okay, thank you so much for thinking I'm young right now.
B
Card.
A
What will you embrace when you're old? I actually been thinking about this a lot. I want to embrace the idea of always being a student. And I think that's because so many times in my life, I really thought I had it figured out. I'm like, got it. Nailed it. Know this. This is my trauma. This. I'm going to deal with it perfect. Next year happens, and I'm like, oh, my God, I'm. And I think I've just come to terms with the fact that that is life. You're never gonna figure it out. There's always me. Another lesson, there's another challenge. And so just commit to the idea of being a student for life, knowing that life is gonna force you to learn lessons every step of the way, you know?
B
Great answer. Lily, I want you to take a look at this picture. Oh, wait, gone. Yeah, Picture behind you. We'll go with that first. I'm waiting for it.
A
Oh, we're waiting for the picture.
B
Yeah, waiting for. Behind you. There you go.
A
Oh, my God. Did you guys edit it so I have two eyebrows? I don't think I had two eyebrows. Thank you so much, editors. Okay, work.
B
How old were you, and what did you need to hear?
A
This is a little store in the mall called Glamour Shots. And they do you up and they take these pictures. I don't know. I don't even know. I don't know what age. I'm one of those weird people that doesn't know the age of kids. If you tell me your kid is seven, I'm like, so when they're in high school, maybe I was 7 or 8. Here.
B
What did you need to hear?
A
What do you guys think? What do you think? Nine, nine? Thirteen. I wasn't 13. This is just hair and makeup. This is just hair and makeup.
B
What advice did you need to hear then? What do you wish someone had said to you?
A
Oh, Lord. What advice?
B
What did you need to hear?
A
Well, the outfit. First of all, let me genuinely think about this. What advice do I need to hear? Meet the Rock. Very good. You know, it's funny. I feel like now I'm more of a kid than I was then. I think I was so convinced I had to grow up really quickly, and I had to figure everything out and had to be good at everything. And I had to commit to a path and commit to a lane. Probably didn't try as many things as I should have tried. Probably didn't take as many risks. I probably had a lot of walls up all the time. And it's crazy, because now I'm in the process of trying to become that kid again, to live all that right. So the advice I would give you is like, be a kid. Live your life. You have your whole adult life to be an adult. Be a kid. Girl.
B
I love it. And then there's a picture behind me.
A
Oh, I thought it was gonna be a picture of you for a second, and I was like, damn, Jay, you look good.
B
What does. What does Lily need to hear right now?
A
Oh, my God. Good job on the eyebrows. Does Lily need to hear right now? I know what Lily needs to hear right now. It's kind of adjacent to the student thing I just said. But I've been a certain way my whole life, and I've had a lot of really big changes in my life over the past couple years. And sometimes I feel like I'm so attached to this old version of myself that even though, like, life is forcing me to evolve, I'm like, no, but I'm this way. And this is how I describe myself. Like, I'm really confident, and I'm so extroverted, and I have so much energy right now. I think my truth is like, yo, Lily, you get a little anxious sometimes, and you spiral a little bit sometimes, and you keep telling yourself you're this way, but, like, I think you're now this person over here, and that's okay. You don't have to be the same person your whole life. You're allowed to be this version, and then you're allowed to change your mind and be this version. So what I would say to Lily is, like, stop being attached to this idea of yourself that you know and that millions of subscribers, and just be who you actually are right now. Honor that person, and then who you want to actually be. You know.
B
Before I let Lily go, I do have to tell you this, because, you know, when I was starting on purpose, as I was telling you the story earlier, Lily was one of those guests, and we were new friends then. Who said yes to being on this podcast when it had zero listeners because we hadn't even put out an episode? So Lily came when we were just figuring out what the show was. We recorded an episode. She was in the first five guests to ever be released on the show. And that was all based on just her love, trust, and kindness, if I'm honest, just her generosity to show up for a new friend at the time who had an unknown show called On Purpose that had no track record, no listeners, and nothing else. And that's how real a friend you were when we barely knew each other. So to me, that shows what an amazing friend you are today. Where initially I'd reached out to Lily trying To figure out. She was like, no, I'll fly and see you to Denver. I can't make this other day. I'm going to come to Denver. I'm going to come myself. You're not even paying for my flights. I just want to be there for you. And for someone to do that as such a dear friend, to show up and show up so vulnerably, deeply, I mean, it's insane. So give it up for my dear friend Lily.
A
And you're amazing. Amazing. Thank you. I want to big you up one more time. Can. I know I have to. I'm sorry, you have to stop the music for one second. I know you're overtime, but it's the last stop of the tour, so I'm sorry, we're just going to have to. I know I already said this, but now, so sincerely, I need to tell you all, first of all, thank you so much for coming to Jay's show and supporting him. He is so incredible and so amazing. But I need to tell you, and I hope he doesn't get mad at me for saying this. I get so. Everybody knows he's such a lovely person. But I truly. When I say you don't even know the tip of how amazing he is. You know, behind the scenes, he does so many things that we'll never see the light of day because he doesn't want them to see the light of day. And that's why you need friends like me that don't care about rules. When I agreed to do the show, I got an email from his team saying, because you're doing the show, Jay wants to donate to a charity of your choice because you're doing the show. And I imagine he's probably done this for every single guest on tour. He does this a lot. He does things like, if you do this, I'll donate to a charity. Don't pay me for this thing. Actually, just donate to a charity. He is such a genuinely nice person who cares about being of service. This is not a facade. This is who he is. And so I know your resources are so hard earned, your time is so hard earned, Any resource or time you spend supporting Jay is not wasted because he is such a good person and he deserves it. And I will just say what we're all thinking, which is how can you have a mind and heart like this and also look like this? We know Jay is hot. We know his eyes. Literally, sugar does not come within two miles of this man. Okay? His cheat meal is a diet Coke using celery as a strawberry he truly this man is just protect him at all costs this man. Support him with everything you have please. Thank you for coming to a store.
B
Lily.
A
Thank you.
B
Thank you.
A
I love you man. Proud of you.
B
Good up for Lily everyone. If you love this episode, I need you to listen to one of my favorite conversations ever. It's with the one and only Tom Holland on how to overcome your social anxiety, especially in situations where you're not drinking and everyone else is. We talk about his sobriety journey and so much more. He gets really personal. I can't wait for you to hear it. It's going to blow your mind.
A
The quote is if you have a.
B
Problem with me, text me.
A
And if you don't have my number, you don't know me well enough to.
B
Have a problem with me. This episode of On Purpose is brought to you by Chase Sapphire Reserve. I believe that travel is one of the greatest gifts that we've ever been given and Chase Sapphire Reserve has been my gateway to the world's most captivating destinations. When I use my Chase Sapphire Reserve card, I get eight times the points on all the purchases I make through Chase Travel and even access to one of a kind experiences. Experiences like music festivals and sporting events. And that's not even mentioning how the card gets me into the Sapphire Lounge by the club at select airports nationwide. Travel is more rewarding with Chase Sapphire Reserve. Trust me. Discover more@chase.com Sapphire Reserve cards issued by JP Morgan Chase Bank NA member FDIC subject to credit approval terms apply. This is Jay Shetty from On Purpose. If you've ever felt off balance, sometimes a change of scenery is the best reset. Delta invited four creators to explore one idea. What if travel isn't just movement but recharging in motion? And the results based on their Oura Ring sleep scores, everyone met the day feeling more rested and a sense of clarity. Stayed long after the trip with Delta. Fly and live better. Explore the whole journey on Delta's YouTube channel. Checking off the boxes on your to do list is a great way to keep your mind clear. That's why a State Farm agent is there to help you choose the coverage option that's right for you as you go through life getting that new house, car, boat, motorcycle or even rv. Helping protect it is always a good idea. Whether you prefer talking in person, on the phone or on the award winning app. State Farm is there to help protect what's important to you. And with so many coverage options, it's nice having help to find what fits for you like a good neighbor, State Farm is there.
A
This is an iHeart podcast.
Release Date: September 17, 2025
Host: Jay Shetty
Guest: Lilly Singh
Location: Live at the Le Calkins Opera House in Denver
In this heartfelt and deeply honest episode, Jay Shetty welcomes his close friend, trailblazing creator and comedian Lilly Singh, for a live conversation in Denver. Together, they delve into the roots of true confidence and self-worth, breaking down the unhealthy compulsion to prove yourself to others, and the mindset shift necessary to build a life anchored in genuine self-love. With equal parts vulnerability and humor, Lilly shares her journey—from her early life facing cultural expectations, to pioneering firsts in her career, struggling with internal critics, and, ultimately, learning to celebrate the wholeness of her real self.
[05:30–10:41]
[11:31–19:56]
[19:56–21:49]
[27:51–35:58]
[35:58–42:31]
[42:31–45:48]
[48:24–48:53]
[53:58–56:08]
[56:31–60:51]
[61:16–65:05]
[66:31–69:35]
Tone & Vibe:
Candid, humorous, vulnerable, and highly relatable—this episode combines real talk on mental health and self-worth with moments of levity, wisdom, and deep friendship between Jay and Lilly.
For listeners:
If you find yourself struggling with the need for external approval, feeling like you’re not enough, or simply want practical ways to build inner confidence, Lilly Singh’s journey and Jay’s insights will leave you feeling seen, empowered, and ready to embrace all parts of yourself.
Next Episode Recommendation:
Jay recommends his conversation with Tom Holland on overcoming social anxiety, especially while sober—an exploration of authenticity in uncomfortable settings.