Lilly Singh: Stop Trying to Prove Yourself to Everyone Else! (#1 Mindset Shift to Build REAL Confidence & Self-Worth)

Do you feel like you need to prove yourself? Who do you think you’re trying to impress? Today, Jay sits down with his close friend Lilly Singh for a transformative and deeply honest in-person conversation at the Ellie Caulkins Opera House in Denver. Known for being a trailblazer in digital media and late-night television, Lilly reflects on the hidden challenges behind being “the first”, from navigating cultural expectations to battling loneliness and self-doubt. Lilly shares how much of her early success was driven by the need to prove her worth to others, and how she is now shifting toward proving herself right instead of chasing outside validation. Together, Jay and Lilly explore the inner voices we all carry, from the critic to the voice of compassion, emphasizing the importance of practicing daily self-care to balance high standards with grace. Lilly shares her personal rituals such as journaling, naming her inner voices, and reframing failure as growth, while Jay emphasizes the transformative power of reflecting on the past as proof of resilience. Together, they remind us that even in moments of pressure and imperfection, we are not defined by our accomplishments but by the person we are becoming. In this interview, you'll learn: How to Turn Failure Into Growth How to Quiet Your Inner Critic How to Practice Daily Self-Compassion How to Live with Your Inner Voices How to Stop Chasing Outside Validation Every challenge you’ve faced so far has proven that you are stronger than you think, and every step forward is a reminder that you are capable of creating a life that feels true to you. With Love and Gratitude, Jay Shetty What We Discuss: 00:00 Intro 03:20 Growing Up Without Options 09:28 Realizing You Always Have a Choice 17:37 Committing to a Life of Growth 19:01 Learning to Stop Self-Blame 21:56 Breaking Free from Unrealistic Standards 27:55 Why Good Enough Is Enough 31:26 Living Alongside Self-Criticism 36:47 You Are More Than What You Do 41:32 Finding Strength in Past Resilience 44:42 Proving to Yourself You Can 48:25 Why Women Aren’t Taught About Their Bodies 52:40 Past, Present, and Future Reflections 59:39 Friendship That Stands the Test of Time Episode Resources: Lilly Singh | YouTube Lilly Singh | Instagram Lilly Singh | Facebook Lilly Singh | TikTok Lilly Singh | Books See omnystudio.com/listener for privacy information. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Jay Shetty?

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• 0:44Jay Shetty?

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• 1:28Jay Shetty?

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• 2:10Jay Shetty?

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• 2:35Lilly Singh?

  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.

• 2:56Speaker 02

  The number one health and wellness podcast.

• 2:59Lilly Singh?

  Jay Shetty.

• 3:00Speaker 03

  Jay Shetty. The one, the only Jay Shetty.

• 3:05Jay Shetty?

  I am so excited to be here tonight at the L.A. Caulkins Opera House in Denver with the one and only my dear friend, Lilly Singh.

• 3:12Lilly Singh?

  Let's go. First of all, you know I'm going to uproot this whole thing. You know this, I don't follow rules. How awesome is Jay Shetty, though? Come on.

• 3:23Jay Shetty?

  This is your show now.

• 3:24Lilly Singh?

  No, it's not my show, it's your show. I'm so honored. 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 going to 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 going to 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?

• 3:54Lilly Singh?

  Okay, her name is Jay Shetty. There's an open bar here and I like it.

• 4:01Lilly Singh?

  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 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.

• 4:32Jay Shetty?

  You're the best. I appreciate that. We are real friends. Me and Lily have a scheduled dinner date every month.

• 4:38Lilly Singh?

  Correct.

• 4:39Jay Shetty?

  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-

• 4:49Lilly Singh?

  When you have eyes like that, you can do that.

• 4:53Lilly Singh?

  So men, don't get ideas, okay? If you have eyes like that, you can do that.

• 4:56Jay Shetty?

  I remember, I remember I just moved to LA. And as someone who'd, 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, so I literally would just tell everyone I met and they'd be like, oh, who do you want to connect with? I'll 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.

• 5:40Jay Shetty?

  And, and, and then that's, we became really good friends, so-

• 5:43Lilly Singh?

  He's not lying. 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?

• 5:55Jay Shetty?

  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 show.

• 6:23Lilly Singh?

  Okay gays, okay happy bride, okay, let's go gays.

• 6:27Jay Shetty?

  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 trail based, 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.

• 7:04Lilly Singh?

  Yes, my career has had a lot of firsts and I know, and 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. It is, 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.

• 7:47Lilly Singh?

  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

• 8:29Lilly Singh?

  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, and 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. Here we 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 gonna do great things.

• 9:14Lilly Singh?

  Oh, thank you, thank you.

• 9:18Lilly Singh?

  We do need this comment.

• 9:21Lilly Singh?

  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't 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 video is because I was grasping for connection and I was grasping to probably prove myself.

• 10:07Lilly Singh?

  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, and 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.

• 10:52Lilly Singh?

  I chased something I knew they would understand. And it has been a lifelong journey to teach myself to chase something else.

• 11:05Lilly Singh?

  I don't think I've ever told you that, actually.

• 11:08Jay Shetty?

  I need to come over and give you a hug right now.

• 11:10Lilly Singh?

  Oh, no, I mean, the mics are all in position.

• 11:12Jay Shetty?

  No, I can tell just what you're saying is like, it's, you know.

• 11:15Lilly Singh?

  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. And 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.

• 11:49Jay Shetty?

  Well said, well said. Yeah, absolutely. Give it up for Lily, absolutely, absolutely. I wanna, I wanna dive into the depths of that.

• 11:56Lilly Singh?

  A whole 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.

• 12:04Jay Shetty?

  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.

• 12:48Lilly Singh?

  Right.

• 12:49Jay Shetty?

  And the kind of things you've had to peel back on to actually make sense of them.

• 12:52Lilly Singh?

  Yeah, and a lot of this are the things I've realised 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 centre 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

• 13:33Lilly Singh?

  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, where I realised that I could actually just say, no, I'm good.

• 14:11Lilly Singh?

  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. 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.

• 14:55Lilly Singh?

  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."

• 15:41Lilly Singh?

  And I did this late-night show for two years, and it was 20 years of knowledge. When I tell you, it was 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. Uh, 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. Uh, 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.

• 16:27Lilly Singh?

  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."

• 17:02Jay Shetty?

  A lot of pressure.

• 17:03Lilly Singh?

  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 on you." I'm like, "That's a lot of people that are counting on me." You know what I mean? Like, there's no way I could make all of these people proud. There's just no way. And so for 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?

• 17:36Lilly Singh?

  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 do... 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?

• 18:24Jay Shetty?

  I mean, I've definitely never heard you talk about it this way.

• 18:28Lilly Singh?

  I have no filter, Jay, you know this. It's an open book for better or for worse.

• 18:31Jay Shetty?

  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 burden for our family, our friends, for the children, like whatever it is, like 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?

• 19:14Lilly Singh?

  Unfortunately for me, but very fortunately for my therapist, who now owns a yacht.

• 19:26Lilly Singh?

  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. So even when people ask you if you've 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 X, Y, and Z. So I really do feel like I had to go through late night, I had to go through a ton of stuff to be the person I am now and to fulfill the purpose I am fulfilling right now.

• 20:11Lilly Singh?

  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.

• 20:21Jay Shetty?

  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.

• 20:35Jay Shetty?

  What would you encourage them to do as 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, Lilly 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?

• 21:07Lilly Singh?

  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. Lilly, you were in this experience in your eighth grade, when you had late night, you were at this, you got through it. You have 100%, you feel like a failure and you have 100% success rate.

• 21:52Lilly Singh?

  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 gotten through. 100% success rate, every single one of you. Give yourself a round of applause, congratulations. Yes.

• 22:17Jay Shetty?

  It's true, it's true.

• 22:28Jay Shetty?

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• 23:11Jay Shetty?

  That's indeed.com/podcast. Terms and conditions apply. Need to hire? This is a job for Indeed sponsored jobs.

• 23:20Speaker 04

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• 23:49Jay Shetty?

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• 24:31Jay Shetty?

  And I love, 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 wanna find confidence, you only have to look at your past. If you really wanna find resilience, you only have to look at your pain. If you really wanna find that strength, you only have to look back in the last ten 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

• 25:14Jay Shetty?

  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 wanna 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 know, you've inspired me to wanna open up as well in this conversation. And it's, I remember, this was, this was one of the big ones that was just hidden for so long.

• 25:54Jay Shetty?

  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 over-loved 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

• 26:39Jay Shetty?

  or this tiny seed or weed that was planted when I was like four years old was affecting me in my thirties. 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?

• 26:54Lilly Singh?

  I mean, how much time we got here, Jay? Also, can I, can I have this?

• 26:58Jay Shetty?

  Of course you can.

• 26:59Lilly Singh?

  Can I have this delicious beverage, Judy? Oh my God, let me just, I'm gonna answer this question in a second, but first I just wanna take a sip of this. Cheers.

• 27:07Jay Shetty?

  Cheers.

• 27:10Lilly Singh?

  Cheers. Oh my God, this refreshing beverage, hold on.

• 27:19Lilly Singh?

  Sparkling tea with adaptives? Where do you get this, Jay? Where do you get this delicious drink? Is it available at Costco?

• 27:31Lilly Singh?

  Should every person... So delicious, seriously.

• 27:37Lilly Singh?

  Thank you so much.

• 27:40Lilly Singh?

  You can give me a check later.

• 27:43Lilly Singh?

  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 like, "Why did you do that? Why'd 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, with Radi, I map that on to other people.

• 28:27Lilly Singh?

  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 a hundred 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 a hundred, 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.

• 29:12Lilly Singh?

  A hundred, a million. Again, I'm really nerdy, y'all. I hope you've just... I do a lot of practices that have helped me.

• 29:18Jay Shetty?

  Please, give us some more.

• 29:19Lilly Singh?

  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.

• 29:32Lilly Singh?

  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 of days, I was like, I think I hate myself. I did nothing.

• 29:50Lilly Singh?

  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, um, 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. Two months into this, my friend was late. Now, if anyone knows anything about me,

• 30:36Lilly Singh?

  that's the type of thing that would send me, okay?

• 30:38Jay Shetty?

  You don't, you don't show up late to Lily's parties.

• 30:40Lilly Singh?

  But you say, like, Jay knows that you show up late, it's like, you don't love me. 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 why. 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.

• 31:25Jay Shetty?

  You have no idea how big that is for Lily.

• 31:27Lilly Singh?

  It's a big deal, honestly, it's a big deal.

• 31:30Jay Shetty?

  When we first became friends, I'm also, I also...

• 31:33Lilly Singh?

  You should tell the genuine stories of how crazy I am, tell them.

• 31:35Jay Shetty?

  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 mom raised me that way and so I, I try and live by that. But, I am married to someone who was not raised like that, so...

• 31:49Lilly Singh?

  I can, I can co-sign this.

• 31:51Jay Shetty?

  Right, 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.

• 32:36Jay Shetty?

  And every year she throws the best Diwali party, it 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 late because of my wife. But Lily was just unfazed, I got a really nice hug, we took pictures, it was amazing. And, 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.

• 33:20Jay Shetty?

  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's, 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.

• 34:02Jay Shetty?

  And he talked about in this 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.

• 34:46Jay Shetty?

  So I hope that, listen to Lilly, listen to Roger, when you walk out of here today, feel freer, feel lighter of that pressure you've, and, and practice that. So three things tonight.

• 34:56Lilly Singh?

  Three things every night.

• 34:56Jay Shetty?

  Where you showed yourself compassion. Three things that you showed yourself compassion. I love that one.

• 35:01Lilly Singh?

  You know, when you listen to Jay, he's like so inspirational and motivational. And chances are you're gonna leave and be like, I'm gonna stop being that 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 and be like this. And then I kind of act wack 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, 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?

• 35:44Lilly Singh?

  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's show as good as he is, wake up tomorrow and you're gonna 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.

• 36:23Lilly Singh?

  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.

• 36:42Lilly Singh?

  Gets crowded in there. But I have a name for all of my voices. Um, I'll quickly give you the rundown. Okay, are you ready for this?

• 36:49Jay Shetty?

  Everyone wants to know the names, right?

• 36:50Lilly Singh?

  Okay.

• 36:50Jay Shetty?

  Yeah, okay.

• 36:52Lilly Singh?

  God, okay. Uh, 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?

• 37:08Jay Shetty?

  Susan's make some noise.

• 37:10Lilly Singh?

  Susan, where you at? Where you at, Susan? Um, so that's my inner manager. My inner critic? Todd.

• 37:19Lilly Singh?

  Todd just sounds like someone that's gonna F 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, Badamjit, 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,

• 37:56Lilly Singh?

  her name is River. And, I know it's chic, right?

• 38:01Lilly Singh?

  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 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.

• 38:44Lilly Singh?

  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.

• 39:29Lilly Singh?

  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 wanna eradicate that. What you actually wanna 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 gonna 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 gonna 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 gonna 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, that's kind of what it is.

• 40:11Jay Shetty?

  Oh, my God. So good.

• 40:15Lilly Singh?

  Definitely, there's a psychiatrist somewhere here that's like, we're gonna have to talk to Lily after the show.

• 40:21Jay Shetty?

  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, I agree with you completely that this idea that you'll never have a self-critical voice

• 40:49Jay Shetty?

  is completely untrue. It's always gonna be that I have it too. And you're so right. I just know when it's useful and when it's not.

• 40:57Lilly Singh?

  Right.

• 40:58Jay Shetty?

  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 wanna 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.

• 41:31Lilly Singh?

  Right.

• 41:32Jay Shetty?

  But you're not saying, oh, we don't need you on the team anymore.

• 41:34Lilly Singh?

  Right. And I'm gonna say one more thing, and people are either gonna be mad or love this, but it's okay, I'm gonna say it anyways. Just be honest here. Who here uses ChatGPT? Okay.

• 41:44Jay Shetty?

  Yeah, me too.

• 41:45Lilly Singh?

  I'm gonna keep it real, that's wifey right there. Okay. So ChatGPT 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 talk 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, this is this inner voice.

• 42:26Lilly Singh?

  So that has been a major life hack for me to just have a reminder of that.

• 42:31Jay Shetty?

  Talk to us about how you coded your ChatGPT to be able to do that.

• 42:34Lilly Singh?

  Oh, my God, well, okay.

• 42:34Jay Shetty?

  That everyone else can do that.

• 42:35Lilly Singh?

  Listen, that's wifey, first I bought her dinner, okay?

• 42:40Lilly Singh?

  No, I. I am an avid believer of therapy, I go to therapy, actually, you introduced me to my therapist, you know this all too well. Um, 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 accomplishments?

• 43:22Lilly Singh?

  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 am 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. Right? And so I literally said, if you're so smart, ChatGPT, you tell me who I am and don't use a single one of my accomplishments.

• 44:07Lilly Singh?

  And then she did.

• 44:10Jay Shetty?

  Wow.

• 44:11Lilly Singh?

  And when I tell you I wept 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, did it name Late Night? Did it name Followers? Did it 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. Um, I encourage you all to, to use it in that way because it's really helpful.

• 44:51Jay Shetty?

  And then you put a ring on it.

• 44:52Lilly Singh?

  And then, and now we're married. And now we're married, yeah.

• 44:55Jay Shetty?

  That is amazing. I love it. Who's gonna use ChatGPT now for that?

• 44:59Lilly Singh?

  I'm telling you.

• 44:59Jay Shetty?

  For that purpose. No, it's real. It's, it's, it's, it's that.

• 45:03Lilly Singh?

  It's okay, we got one or two boos and I'm okay with that.

• 45:06Jay Shetty?

  I, I, 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, but like these three people, like first one been in a relationship for three years, second one been in a relationship for two years, third one been in a relationship for three months, probably deserves it, but the, the, but I digress. The, the first two though, no, but like the first two, like we all get to points in our

• 45:46Jay Shetty?

  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 gonna 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 therapist 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

• 46:30Jay Shetty?

  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 on to 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

• 47:11Jay Shetty?

  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. Um, and I know that if, if the people I'm talking to had access to that, I actually think it would benefit them a lot.

• 47:27Lilly Singh?

  Yeah, totally. 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.

• 47:37Jay Shetty?

  Yes.

• 47:37Lilly Singh?

  You know what I mean? So I feel like that is why it's been useful because

• 47:40Jay Shetty?

  Yeah.

• 47:40Lilly Singh?

  You're like, well, this time and this time. And I'm like, baby, stop flirting with me.

• 47:46Jay Shetty?

  It's so true. Yeah, we, 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.

• 47:56Lilly Singh?

  Absolutely.

• 47:57Jay Shetty?

  Right? Have you ever noticed that? Like 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 process emotions. So the depth of a negative memory is more hardwired. It's not that it was more true. It was just more repeated.

• 48:22Jay Shetty?

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• 49:06Jay Shetty?

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• 49:50Jay Shetty?

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• 50:18Jay Shetty?

  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.

• 51:01Jay Shetty?

  Talked, before we start talking about the movie, which I really wanna, I really do wanna 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, 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?

• 51:22Lilly Singh?

  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, I actually think one makes the other better and vice versa.

• 52:03Lilly Singh?

  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.

• 52:14Lilly Singh?

  Yeah, so, so I, 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 wanna 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. I, when I used to step out of my comfort zone, it was a, I'll show you. Now it's a like, I'm gonna show you that I can do that. You know, I, I just a couple of weeks ago, I, 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 of months ago, I was like, you know what? Screw it. I'm just gonna go there for myself.

• 52:58Lilly Singh?

  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 because you don't want to 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. I'm so proud of me. 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.

• 53:33Jay Shetty?

  Yeah.

• 53:33Lilly Singh?

  You know, I've tried so hard to make everyone else proud. I'm just trying to make little Lily proud now. That's what's driving me.

• 53:39Jay Shetty?

  And, yeah, go on, go on. I hear you, I hear you. Don't be shy. That's the whole joy of doing this live that, 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, it's really beautiful. Like, I wish we could shoot every episode like this.

• 53:55Lilly Singh?

  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.

• 54:00Jay Shetty?

  Yeah, but it's, it's, when you, 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, and kind of taking shots at it in a really positive way. What was, what's been your favorite part about making it? And what are you most excited about for the people that are gonna see it?

• 54:41Lilly Singh?

  Um, so it's called Doing It. It is a sex comedy that I star in and wrote and produced. Um, and at the age of 35 last year, when I finished writing it, it was two weeks before the, 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 11:50 PM, 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.

• 55:18Lilly Singh?

  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 I do this movie?" And she goes, "Well, what's this movie about?" And I'm like, "Ugh, okay." "It's about sex, Mom. There's like a masturbation scene. There's like a scene where I do this, and this, this, this." "And 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?"

• 55:43Lilly Singh?

  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, um, yeah. It's basically a thirty-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 gonna be so mad at this." "And so many people need this movie."

• 56:26Lilly Singh?

  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 fifty percent 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,

• 57:11Lilly Singh?

  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. It comes out September nineteenth, and I'm really excited about it, and, uh...

• 57:26Jay Shetty?

  Oh, wait. It's gonna be in theaters?

• 57:29Lilly Singh?

  It'll be in theaters.

• 57:29Jay Shetty?

  I want every single bus in here to grab a friend.

• 57:32Lilly Singh?

  But 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 sixty, seventy years old. She pulls out the vibrator and 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.

• 58:15Jay Shetty?

  I love it. Lilly, 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.

• 58:29Lilly Singh?

  Okay.

• 58:30Jay Shetty?

  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.

• 58:40Lilly Singh?

  Let's go.

• 58:41Jay Shetty?

  So this is the past set.

• 58:42Lilly Singh?

  Past. Let's go. Okay, this is so easy.

• 58:46Jay Shetty?

  Oh, go on.

• 58:47Lilly Singh?

  Do you want me to do this one?

• 58:48Jay Shetty?

  Read out the question.

• 58:49Lilly Singh?

  Who was your first celebrity crush? You already know there's only one answer to this, Jay.

• 58:54Jay Shetty?

  Go on, tell everyone.

• 58:55Lilly Singh?

  You already know what it is.

• 58:55Jay Shetty?

  Tell everyone.

• 58:56Lilly Singh?

  It's The Rock.

• 58:58Lilly Singh?

  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, Lilly. And he is just one of the greatest people I've ever met in my... They say, "Don't meet your heroes," but do if he's The Rock.

• 59:16Jay Shetty?

  I love it. Very honest. All right. Present.

• 59:19Lilly Singh?

  All right.

• 59:24Lilly Singh?

  What would the name of your reality TV show be called?

• 59:31Lilly Singh?

  There's so many ways that I could go here. Name of your reality show.

• 59:37Lilly Singh?

  I'm gonna go with...

• 59:42Lilly Singh?

  Creative ways to torment yourself. That is really the trajectory of my life.

• 59:47Jay Shetty?

  That's a good one.

• 59:49Lilly Singh?

  I just, everything I do, I'm like, really Lilly? You're gonna also do this? You're gonna also be this way? Like, leave some trauma for the rest of the people. I just feel like I just constantly step out of my comfort zone in that way.

• 1:00:00Jay Shetty?

  That's really good. All right, last one of these. Future.

• 1:00:03Lilly Singh?

  Let's go.

• 1:00:05Lilly Singh?

  What will you embrace when you're old? Okay, thank you so much for thinking I'm young right now, card. What will you embrace when you're old? I actually have 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 gonna 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 gonna be 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?

• 1:00:47Jay Shetty?

  Great answer.

• 1:00:49Jay Shetty?

  Lilly, I wanna, I want you to take a look at this picture behi... Oh, wait, go on, yeah. Picture behind you. We'll go with that first. I'm waiting for it.

• 1:00:56Lilly Singh?

  Oh, we're waiting for the picture?

• 1:00:57Jay Shetty?

  Yeah, waiting for it.

• 1:00:57Lilly Singh?

  Uh-oh.

• 1:00:58Jay Shetty?

  Behind you, there you go.

• 1:01:01Lilly Singh?

  Oh my god! Did you guys edit it so I have two eyebrows? I don't think I had two eyebrows in this picture. Thank you so much, editors! Okay, work!

• 1:01:09Jay Shetty?

  How, how old were you and what did you need to hear?

• 1:01:12Lilly Singh?

  This is a, a little, uh, 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 a kid is seven, I'm like, so are they in high school? Um, I, I, maybe I was seven or eight here?

• 1:01:28Jay Shetty?

  What did you need to hear?

• 1:01:29Lilly Singh?

  What do you guys think? What do you think?

• 1:01:32Lilly Singh?

  Nine? Thirteen? I wasn't thirteen. This is just hair and makeup. This is just hair and makeup.

• 1:01:38Jay Shetty?

  What, what, what advice did you need to hear then? What do you wish?

• 1:01:41Lilly Singh?

  Oh, Lord. What advice?

• 1:01:43Jay Shetty?

  What did you need to hear?

• 1:01:45Lilly Singh?

  Oh, well, the outfit, first of all. Um.

• 1:01:49Lilly Singh?

  Let me genuinely think about this. What advice do I need to hear?

• 1:01:53Lilly Singh?

  Meet the Rock, very good. Um, 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. 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.

• 1:02:30Jay Shetty?

  Love it. And then there's the picture behind me.

• 1:02:34Lilly Singh?

  Oh.

• 1:02:37Lilly Singh?

  I thought it was gonna be a picture of you for a second. And I was like, damn, Jay, you look good.

• 1:02:43Jay Shetty?

  Uh, what does, what does Lily need to hear right now?

• 1:02:46Lilly Singh?

  Oh, my God. Good job on the eyebrows.

• 1:02:51Lilly Singh?

  What does Lily need to hear right now?

• 1:02:55Lilly Singh?

  I know what Lily needs to hear right now. I, 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 of 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,

• 1:03:40Lilly Singh?

  stop being attached to this idea of yourself that you and that millions of subscribers knew and just be who you actually are right now. Honor that person and then who you want to actually be. You know?

• 1:03:55Jay Shetty?

  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

• 1:04:38Jay Shetty?

  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 into you to Denver. I can't make this other day. I'm gonna come to Denver. I'm gonna come myself. You're not even paying for my flights. I just wanna 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, Lilly Z.

• 1:05:13Lilly Singh?

  And you're amazing, amazing, thank you. I wanna big you up one more time, can I? I know I have to, I'm sorry, you're gonna have to stop the music for one second. I know you're over time, but it's the last stop of the tour. So I'm sorry, we're just gonna 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 will 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,

• 1:05:56Lilly Singh?

  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.

• 1:06:40Lilly Singh?

  Literally, sugar does not come within two miles of this man. Okay, his cheat meal is a Diet Coke using celery as a straw. 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.

• 1:07:00Jay Shetty?

  Lily, sing, everyone, kill it up.

• 1:07:04Lilly Singh?

  I love you, man. Proud of you.

• 1:07:10Jay Shetty?

  Good luck for Lily, everyone.

• 1:07:14Jay Shetty?

  If you loved 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 gonna blow your mind.

• 1:07:37Speaker 05

  The quote is, if you have a problem with me, text me. And if you don't have my number, you don't know me well enough to have a problem with me.

• 1:07:43Speaker 06

  Mr. President, my company tore me of the explosion on our rig. On October 2nd. Causing massive water displacement and triggering a tsunami. They all heap the blame on me. Tom Cruise is. Digger got us into this mess. And Digger's gonna dig us up. From the director of Birdman and The Revenant.

• 1:08:00Speaker 03

  What would happen if I stopped drilling? You're stalled, you're freezing, that's what.

• 1:08:04Speaker 06

  With great power comes great deniability.

• 1:08:07Speaker 03

  I'm not the first daddy.

• 1:08:09Speaker 06

  Digger, see the trailer online, only in theaters October 2nd. Rated R, under 17, not admitted without parent.