Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements | E136

1. 0:00 – 1:27

   Intro

   1. SBSteven Bartlett0:00

      Could you do me a quick favor if you're listening to this? Please hit the follow or subscribe button. It helps more than you know, and we invite subscribers in every month to watch the show in person.

   2. LSLilly Singh0:08

      I wanted to be powerful and have influence because I wanted to prove people wrong. You can't surf the internet for very long without stumbling upon Lilly Singh. Lilly Singh. Lilly Singh! I was born into the reality of being a disappointment right away. There were rules about being a woman. My mom did not grow up with queer culture, so for me to expect her to operate from a place of my lived experience, how was that math ever gonna add up? Welcome to the first episode of A Little Late with Lilly Singh.

   3. SBSteven Bartlett0:39

      You got given a, a late night sh- when I said that, you said, "I'm so sorry." Tell me why you said that.

   4. LSLilly Singh0:43

      'Cause I don't think the thing was good. The community that I did this show for is pissed at me because I nervously made a joke out of context, and that broke my heart every day.

   5. SBSteven Bartlett0:55

      Did you have anxiety at the time?

   6. LSLilly Singh0:56

      I developed it during season one of the show. Is the struggle worth it? For me, yes it is. I believe in what I believe so much more than the hurt that I feel.

   7. SBSteven Bartlett1:06

      So without further ado, I'm Steven Bartlett, and this is the Diary of a CEO USA Edition. I hope nobody's listening, but if you are, then please keep this to yourself. Lilly, thank you for being here. It's a real

2. 1:27 – 7:00

   Early Years - Having to prove I was worthy

   1. SBSteven Bartlett1:27

      honor, and, um, we've got a mutual friend in Jay Shetty-

   2. LSLilly Singh1:29

      Yes.

   3. SBSteven Bartlett1:29

      ... who's really spoken so incredibly highly of you. And then when I got a chance to delve into your story, I became pretty fascinated by many things. I wanna start, 'cause I always, I always believe that the foundation of everybody that I sit here with, and also myself, having studied some childhood psychology, is their childhood. So I guess the question I had for you is, when you think about 10-year-old Lilly-

   4. LSLilly Singh1:51

      Mm-hmm.

   5. SBSteven Bartlett1:52

      ... and the lessons she had learnt by that age about the world and life, what were those lessons and where did she learn them from?

   6. LSLilly Singh1:58

      The lessons at the age of 10 I don't think were necessarily beneficial ones. Um, I was born into the reality of being a disappointment right away, being the second daughter in an Indian family. I was told (laughs) in my adult, adult life that my grandparents, great-grandparents in India didn't find out about my birth for about two weeks, because they had said, "If it's not a son, it's not worth calling home about." So that really colored in a lot of my childhood, because whether it was ridiculous things like, "Oh, you know, girls aren't supposed to talk that much," ridiculous things like, "Girls aren't supposed to whistle," whatever girls weren't supposed to do was very apparent to me from a really young age. So the lessons I was taught that there were rules about being a woman. There was expectations about being a woman, and I had to f- fit that mold if I wanted to be, not, not even accepted, but if I wanted to make people proud, I think, more than anything. I think I, I never felt like I wasn't accepted, but if I wanted to be extraordinary in the eyes of people that were disappointed in me, I had to fit the mold. And so a lot of my upbringing was a little bit of this, uh, simultaneous, "I need to fit the mold," but then this rebellious side of me being like, "But I don't want to!"

   7. SBSteven Bartlett3:13

      Mm.

   8. LSLilly Singh3:13

      And kind of negotiating that balance.

   9. SBSteven Bartlett3:16

      What you said about your grandparents-

   10. LSLilly Singh3:17

       Mm-hmm.

   11. SBSteven Bartlett3:17

       ... wanting a boy, and generally in an Indian culture-

   12. LSLilly Singh3:19

       Yeah.

   13. SBSteven Bartlett3:19

       ... there being a desire to have a boy, how did that impact you? I, I read that you were a tomboy growing up.

   14. LSLilly Singh3:25

       Yes.

   15. SBSteven Bartlett3:25

       Yeah.

   16. LSLilly Singh3:25

       Yes, yes, yes. I was obsessed with Dwayne The Rock Johnson. I loved wrestling. I wore baggy clothes. I rebelled in every such way because of this expectation that was set upon me. I think in my adult life I have learned, and I don't think I knew this growing up, and I don't think I even knew this years ago, I think this is a quite recent revelation, that experience has put a very heavy chip on my shoulder that I carry in my adult life. And I think for a lot of my life, I was scared to admit that, or I was embarrassed to admit that, because no one wants to admit that they have this chip on their shoulder. But now I fully embrace it. And that chip on the shoulder is from most of my life, I always felt like I had to prove myself in every instance. No matter what it was, whether it was school grades, whether it was my dancing ability, whether it was how I could speak up at a family party, no mat- in every instance, I always felt like I had to prove myself worthy because I was born into this reality where being a girl is lesser in Indian culture. And that has followed me into my adult life. And if you look at the pattern of everything I've done in my career, I've only now connected the dots that the common thread between all of that is proving myself. And so even when I started making YouTube videos in 2010, a lot of people asked me, "Why did you do that?" And I can give you the answer that I think people wanna hear, which was, "I wanted to create a path, and no one else was doing what I was doing." And sure that's all true to some extent, but the real reason was, I wanted to be powerful and have influence because I wanted to prove people wrong. I think that has always been that chip on my shoulder. I wanted to prove that being a girl was worthy of celebration. And so that has been the thing that has followed me. So, so that is truly the chip on my shoulder that now I'm just fully transparent about.

   17. SBSteven Bartlett5:01

       Mm-hmm. When I think about my own insecurities-

   18. LSLilly Singh5:02

       Mm-hmm.

   19. SBSteven Bartlett5:03

       ... and the things I pursued at, like, 18 years old, they were all the opposite of the thing that invalidated me when I was a kid. So when I was a kid, only Black kid in an all white school-

   20. LSLilly Singh5:13

       Mm-hmm.

   21. SBSteven Bartlett5:13

       ... parents with a broke family in a perfect white picket-

   22. LSLilly Singh5:16

       Right.

   23. SBSteven Bartlett5:16

       ... you know, neighborhood. And so my pursuit in life was like, if I had the things that I'd missed as a child, if I had money-

   24. LSLilly Singh5:22

       Mm-hmm.

   25. SBSteven Bartlett5:22

       ... and if I was, I don't know, famous or whatever, then it would be filling some kind of childhood void. I wonder when, when you said then, "I wanted to be powerful and have influence," is that because you, you didn't when you were younger as well? Is that part of it?

   26. LSLilly Singh5:35

       I think it's more so that the people who were the most powerful in my upbringing were men.

   27. SBSteven Bartlett5:41

       Right.

   28. LSLilly Singh5:41

       They were the men in my family, the men at a family party that were in the corn... They got to control the conversation. What they said goes. Men notoriously in Indian culture are the decision makers, the powerful people. And I know one thing that the men in in- and I don't wanna paint all Indian culture men bad. I'm just saying as a kid, it was evident to me that the uncles made the decisions. They got to decide what was acceptable and not acceptable. And so I knew one thing that the men would understand was power, money, and influence. And so I think I strived for a career that would give me those things so I could kind of prove a point to them, being like, "You may not understand my value in any other way aside from money, power, and influence." And to some extent, I was not wrong. I've done a lot of cool things in my life, but the things that really...... made my dad and my uncles go wide-eyed with things like the Forbes list, with things like, "Oh, she's in a headline. She has her own show." Those are the things that they understand to be of value. And I'm not saying that's right or wrong, and I'm not trying to dissect if it's right or wrong.

   29. SBSteven Bartlett6:41

       Mm-hmm.

   30. LSLilly Singh6:41

       I just knew they would understand that. And so for me to have an impact, of course I wanna help people, of course I wanna pave the path. That's all true, but those are not the things that the people that had power as a kid for me would understand. They understand power, money, and influence. So I would be lying to say that that wasn't a driving factor.
3. 7:00 – 13:14

   The reason for starting on Youtube

   1. SBSteven Bartlett7:00

      LA.

   2. LSLilly Singh7:00

      Mm-hmm.

   3. SBSteven Bartlett7:00

      Your YouTube career starts really gaining traction.

   4. LSLilly Singh7:02

      Yeah.

   5. SBSteven Bartlett7:02

      You said a, a second ago that you pursued YouTube because of, you're very honest, power and influence, right?

   6. LSLilly Singh7:07

      Mm-hmm.

   7. SBSteven Bartlett7:07

      But when you're starting YouTube, there's no guarantee of power and influence, right?

   8. LSLilly Singh7:10

      Mm-hmm.

   9. SBSteven Bartlett7:11

      I know your first video did like 70 views or something crazy.

   10. LSLilly Singh7:13

       Yeah. Yeah, yeah, yeah.

   11. SBSteven Bartlett7:14

       Um, so when you started YouTube, a very strange thing to be doing back then, recording yourself-

   12. LSLilly Singh7:19

       Yeah.

   13. SBSteven Bartlett7:19

       ... especially doing, like, funny stuff in your room or whatever.

   14. LSLilly Singh7:22

       Yeah, for sure.

   15. SBSteven Bartlett7:23

       What wa- what were you thinking? Like what was the... (laughs)

   16. LSLilly Singh7:25

       Yeah, I was thinking a few things. One was that I was always a very creative kid. I was the kid that wanted to be the center of the dance circle at a family party. I wanted, I watched Ace of Cakes. I wanted to bake cakes. I wanted to be creative through any means necessary. But I think I was convinced that creativity was a phase, that it's something you do as a pastime as a kid. Your career shouldn't be creative. You let go of that. You get a real job, et cetera, et cetera. When I was in university and I discovered YouTube, it was a glimpse of, "I could be creative as an a- as an adult? I could express myself in a way that's, like, on my own terms? There's no gatekeeper, there's no rules?" This was something that I got to make the rules about. I got to decide. I built a little community of people that also were in a little bit of a dark place, so I got this sense of connection that I wasn't getting in real life. Um, and the real, real talk of it is that I'm an obsessive person. Once I started making YouTube videos, I was obsessed with it. I was obsessed with learning how to do it well, l- exploring how else I could be creative, learning how to get more views, learning how to market myself. I, with everything I do, am a very all-or-nothing person, which has been a great pro, but also very detrimental in my life, um, this type of per- obsessive personality.

   17. SBSteven Bartlett8:40

       Especially if you, you become obsessed about something that isn't fully aligned, right?

   18. LSLilly Singh8:44

       Yes.

   19. SBSteven Bartlett8:44

       Which is possible, right? Because there can be-

   20. LSLilly Singh8:45

       Right.

   21. SBSteven Bartlett8:45

       ... two conflicting forces. The force can be, "I wanna be really successful."

   22. LSLilly Singh8:48

       Mm-hmm.

   23. SBSteven Bartlett8:49

       And then the other force can be saying, "Well, this isn't my purpose." And-

   24. LSLilly Singh8:51

       Right.

   25. SBSteven Bartlett8:52

       ... they can surely come into conflict.

   26. LSLilly Singh8:53

       It's also very problematic when you're obsessive over something that is governed by numbers.

   27. SBSteven Bartlett8:59

       Ugh.

   28. LSLilly Singh9:00

       That is a very dangerous combination. When you're obsessive and your success is measured by views and subscribers and stats, that is a bad recipe right there.

   29. SBSteven Bartlett9:09

       Mm-hmm.

   30. LSLilly Singh9:09

       Because I would actually be, th- and this is 2010, before YouTube had a, had very complex analytics. Now you can see and-
4. 13:14 – 16:38

   What helps you when you’re going through pain

   1. LSLilly Singh13:14

      all.

   2. SBSteven Bartlett13:14

      It's really interesting, Mo Gawdat, a guy that came on this podcast, said that when... he used to work at Google, when they interviewed people and said, "Would you erase the most traumatic or difficult moments of your life," um, knowing that it would r- erase all the lessons it taught you as well-

   3. LSLilly Singh13:28

      Mm-hmm.

   4. SBSteven Bartlett13:28

      ... and everything that came with it, would people do it? 99% of people said they wouldn't.

   5. LSLilly Singh13:31

      No.

   6. SBSteven Bartlett13:31

      And there's an interesting thing about how we look back-

   7. LSLilly Singh13:33

      Yeah.

   8. SBSteven Bartlett13:33

      ... on our trauma w- because we also don't know the other outcome.

   9. LSLilly Singh13:36

      Because it's interesting.

   10. SBSteven Bartlett13:37

       You know what I mean?

   11. LSLilly Singh13:38

       It's... and I a- agree, when people ask me in interviews, "What would you say to your younger self and what would you change?" I always say, "I wouldn't change anything." Because even those, like, horrible decisions, those questionable moments, they have all resulted in something really, really great. That's the exchange of the universe and that's just how things work magically. Um, and it's interesting how knowing that, right now I can sit here and tell you that I would not change anything about my past, any trauma, any pain. Even knowing that, I will still sit here today and think that the pain I'm experiencing today is intolerable.

   12. SBSteven Bartlett14:07

       Hmm.

   13. LSLilly Singh14:08

       And not acknowledge that 10 years from now, I will probably say the same thing about the pain I'm experiencing today. (laughs) Something to always keep in mind, w- we have this way of humans, as humans of thinking that whatever pain we're experiencing right now is for sure definitely the worst pain and it cannot get worse. It always does, and we always think that it's still the worst pain. When you were a kid you thought... I remember when I was a kid, my mom, I said I couldn't get this shirt, it said "Backstreet Girls" on it, and I remember thinking, "This is the worst day of my life and my life is never gonna get worse than this." I remember thinking that. "I'm gonna run away. My mom hates me. She won't let me be a Backstreet Girl? How dare her." And then, years, years later, something else happened and I thought that was the worst. And we keep doing that as humans, don't we? We keep thinking that. Whatever this is today, this is the worst.

   14. SBSteven Bartlett14:49

       That perspective, completely true.

   15. LSLilly Singh14:51

       Mm-hmm.

   16. SBSteven Bartlett14:51

       Completely true. Been through it myself a million times.

   17. LSLilly Singh14:53

       Yeah.

   18. SBSteven Bartlett14:53

       I always say, you know, this is... i- the current crisis always feels like the fatal one until hindsight tells you that the-

   19. LSLilly Singh14:59

       Right.

   20. SBSteven Bartlett14:59

       ... current one is the fatal. (laughs)

   21. LSLilly Singh15:00

       Right.

   22. SBSteven Bartlett15:01

       Um, but what does... even knowing that, it still doesn't seem, in my case, to stop the current crisis feeling (laughs) fa- fatal. It helps a little bit, takes the edge off.

   23. LSLilly Singh15:11

       Mm-hmm.

   24. SBSteven Bartlett15:12

       But when we're in the heart of the storm for whatever reason, what else helps you to gain perspective on the situation? I mean like really. I don't mean like the advice that we give in our books and stuff. I mean-

   25. LSLilly Singh15:22

       Right.

   26. SBSteven Bartlett15:22

       ... what actually helps?

   27. LSLilly Singh15:24

       What actually helps me when I'm going through pain and I can't see myself coming out the other side is truly t- I'm a very logical person in the sense that I always think about things through, to the best of my ability, facts or, like, diagrams, I just have this brain that likes processing things. And so, I think about, "Okay, what is my success rate of getting through things?" It's actually 100% (laughs) right now. I sit here at 100. We all sit here, everyone watching actually, you sit at 100% right now.

   28. SBSteven Bartlett15:57

       A couple of days is, but-

   29. LSLilly Singh15:57

       No matter what. Yeah, 100% is where you sit at.

   30. SBSteven Bartlett15:59

       Mm-hmm.
5. 16:38 – 19:58

   The skill that made you different

   1. LSLilly Singh16:38

   2. SBSteven Bartlett16:38

      You became a, a hugely... I'm gonna leap back to that-

   3. LSLilly Singh16:42

      Mm-hmm.

   4. SBSteven Bartlett16:42

      ... sub-topic in a second-

   5. LSLilly Singh16:42

      Yeah.

   6. SBSteven Bartlett16:42

      ... but to give the listeners a context, you became a hugely, hugely successful social media star, creator, whatever you wanna call it.

   7. LSLilly Singh16:50

      Mm-hmm.

   8. SBSteven Bartlett16:51

      Um, c- built one of the biggest YouTube channels still to, to this day.

   9. LSLilly Singh16:54

      Ah, sure. (laughs)

   10. SBSteven Bartlett16:55

       Some millions and millions of subscribers.

   11. LSLilly Singh16:56

       Yeah.

   12. SBSteven Bartlett16:56

       That is a, that makes you in the 0.0 whatever percent-

   13. LSLilly Singh17:00

       Mm-hmm.

   14. SBSteven Bartlett17:00

       ... anomalies in the world. So, I, I hear the obsessive thing-

   15. LSLilly Singh17:03

       Mm-hmm.

   16. SBSteven Bartlett17:03

       You said about the spreadsheets, I guessed that. I thought, "For her to get there, she must be pretty obsessive."

   17. LSLilly Singh17:07

       I walked in here and you were like, "Ooh, she has Google Doc written all over her." (laughs)

   18. SBSteven Bartlett17:11

       (laughs) Yeah. Well, yeah, like, there's like... but we all, I think, at times in our lives probably look back and think, "Ah, shit, I was also probably toxic ex- obsessive."

   19. LSLilly Singh17:17

       Mm-hmm.

   20. SBSteven Bartlett17:18

       You know, 'cause the things that I was ex-... you know, especially when you're in the numbers business-

   21. LSLilly Singh17:21

       Right.

   22. SBSteven Bartlett17:21

       ... and the metrics business. So, what else about you, when you think about that phase of your life from two thousand and, you know, maybe 13 when you hit a million subs-

   23. LSLilly Singh17:30

       Mm-hmm.

   24. SBSteven Bartlett17:30

       ... to where you hit f- fourteen point whatever seven million subs, what was it about Lilly, outside of the obsessive part-

   25. LSLilly Singh17:38

       Mm-hmm.

   26. SBSteven Bartlett17:38

       ... that made you such an anomaly through that phase of, like, career success on YouTube?

   27. LSLilly Singh17:45

       This has required a lot of reflection because, um, I was trying to think recently what my purpose is, going back to our previous conversation, what is my purpose? 'Cause I, I, I thought my purpose was specific projects I would work on, specific things in the industry and I kept thinking, "That's too small. That's, that's such a in-the-moment purpose. Like, what is your greater purpose?" So I had to go look back through my life recently and be like, "What is the common thread here?" And the common thread between everything, especially during this time period we're talking about, can be summarized in one word, and that is disruptor. I think my purpose is to disrupt, and I think I have done it continuously in my life from being a tomboy as a kid, to being outspoken in a room full of uncles, to getting into the entertainment industry not through an agent, not through moving to LA but through YouTube where there are no gatekeepers, from the first late night host, wherever that historic moment was. Like, I continuously feel the need to disrupt, not because I am actively trying to disrupt, because it is just who I am as a person. And I know this even on the personal side-... um, the first openly queer person to host a late night show, the first woman of color, the first... I have just been associated with so many firsts and I used to hate it. Like I used to... I remember thinking and telling my therapist, "I don't wanna be the first. I don't want to be the first anymore. I hate being the first. I don't want the pressure of all this. I just wanna do what I love doing." And my therapist joked and said, "Yeah, you need to pick a cause. (laughs) You got a lot of things going. You have to pick an issue." But I have since embraced that. Instead of looking at it as a thing that I hate about myself and I wanna change about myself and that causes me stress, I have now accepted that it is my purpose to disrupt. It is just how I am built. I am built to break systems and molds. Again, not because I'm actively trying to stir the pot, but because it is just how my brain and my being operates. I have to break molds. So when you ask me that question between that time period, what was it about Lilly? It's that Lilly always would ask the question of, "How else can this be done? And why isn't this being done this way? And maybe there's a different way of doing it." And when she gets told that this is the way things usually are done, I just simply do not accept that. I... Everyone on my team knows that's the worst thing you can say to somebody. "This is how things are traditionally done." I just don't accept that with anything.

6. 19:58 – 26:03

   Why are you wired to be disrupted?

   1. LSLilly Singh19:58

   2. SBSteven Bartlett20:00

      Clearly, you're someone who's built a lot of evidence that d-

   3. LSLilly Singh20:02

      The look you just gave me is the look my parents give me, (laughs) just like-

   4. SBSteven Bartlett20:04

      No. Yeah. Do you know there was so much-

   5. LSLilly Singh20:06

      Yeah. (laughs)

   6. SBSteven Bartlett20:06

      ... going on in my head. And then I was thinking about different ways to take that-

   7. LSLilly Singh20:08

      (laughs) Yeah.

   8. SBSteven Bartlett20:09

      ... and different feelings I got from that.

   9. LSLilly Singh20:10

      Yeah.

   10. SBSteven Bartlett20:10

       One of them honestly was like, especially hearing the obsessive thing. Listen, when I ask these questions-

   11. LSLilly Singh20:15

       Mm-hmm.

   12. SBSteven Bartlett20:16

       ... I'm not... 'Cause I think, 'cause I relate to so much of what you're saying.

   13. LSLilly Singh20:18

       Yeah.

   14. SBSteven Bartlett20:18

       I'm asking the questions to, to pick, d- dig deeper, not because I-

   15. LSLilly Singh20:22

       No. I love it.

   16. SBSteven Bartlett20:23

       ... like disagree. So-

   17. LSLilly Singh20:23

       I love it. But it's just-

   18. SBSteven Bartlett20:24

       Yeah.

   19. LSLilly Singh20:24

       ... the look is like my parents looking at me like-

   20. SBSteven Bartlett20:26

       Yeah.

   21. LSLilly Singh20:26

       ... "Great. She likes to disrupt." (laughs)

   22. SBSteven Bartlett20:28

       Yeah. No. 'Cause m- my brain went, my brain went... Almo- i- she, she's so... Even when you were delivering it-

   23. LSLilly Singh20:33

       Yeah.

   24. SBSteven Bartlett20:33

       ... so passionate that I felt, felt as if she must have... That's exhausting.

   25. LSLilly Singh20:36

       Mm-hmm.

   26. SBSteven Bartlett20:36

       To be obsessive-

   27. LSLilly Singh20:37

       Yes.

   28. SBSteven Bartlett20:37

       ... is exhausting. On the other hand, I was thinking, "Why is your brain wired to disrupt things? Like why?" So I understand the... from an innovation perspective, it's gonna be fruitful. You're gonna create new things.

   29. LSLilly Singh20:47

       Mm-hmm.

   30. SBSteven Bartlett20:48

       But why is that your predisposition? Are... Is it going back to your childhood and saying-
7. 26:03 – 31:15

   Do you think you are enough?

   1. LSLilly Singh26:04

   2. SBSteven Bartlett26:04

      Have you gotten to the point where you, you know that you are enough?

   3. LSLilly Singh26:08

      Oh, this is turning into therapy. Damn!

   4. SBSteven Bartlett26:09

      What did you think it was gonna be?

   5. LSLilly Singh26:11

      Damn!

   6. SBSteven Bartlett26:11

      Clearly nobody's

   7. NANarrator26:12

      (laughs)

   8. LSLilly Singh26:12

      I'm gonna, I'm gonna cancel my therapy appointments.

   9. SBSteven Bartlett26:15

      (laughs)

   10. LSLilly Singh26:15

       Save myself $300. Um...

   11. SBSteven Bartlett26:18

       We charge. (laughs)

   12. LSLilly Singh26:19

       Oh, nice, nice. Um, I am just now actively right now in the process of believing that through writing my latest book. My latest book was a lot about that. It was about, am I enough right now? Because I think, I'll be honest, it's a buzzword. "Oh, you are enough." Like, for example, kids are born these days and we, and it's the first words we tell them are, "You're enough. You're enough. You're great just the way you are." I think we need to find the balance of hard work and spirituality, of business and spirituality. There's an intersection of these things where, yes, I think now I'm a full, complete human being. Does that mean I don't have goals and aspirations and I want things? I still have all of those things, but I'm at the point right now where those things, whether I have them or don't have them, will not impact the way I define myself. See, a lot of my life I've defined myself as YouTube sensation, late night host, actress who has this role. I am doing the work to realize that I'm actually a complete human being that has value aside from that, and those things are just cool things and experiences I get to do and I can strive to be great at them, I can perfect my craft, but I'm not lesser if I don't have those things and I'm not more if I do have those things. This is an active thing I'm working on.

   13. SBSteven Bartlett27:28

       And when you get to that place-

   14. LSLilly Singh27:30

       Mm-hmm.

   15. SBSteven Bartlett27:30

       ... if we are lucky enough in our lives to get to the place-

   16. LSLilly Singh27:32

       Yeah.

   17. SBSteven Bartlett27:32

       ... where we realize we're enough, that's re- I, you know, I had this really interesting conflict in my life which I'm sure that listeners have heard about before, where when someone said to me one day, maybe seven years ago, they said, "You need to realize that you're already enough."

   18. LSLilly Singh27:42

       Mm-hmm.

   19. SBSteven Bartlett27:42

       I remember thinking, "What a load of bullshit."

   20. LSLilly Singh27:43

       Yep.

   21. SBSteven Bartlett27:44

       "I'm not gonna get out of bed if I have that viewpoint."

   22. LSLilly Singh27:46

       Exactly, yes.

   23. SBSteven Bartlett27:46

       "I don't need to strive for anything. Bullshit. Get out my office." Right? And then upon reflecting on that, writing my book, whatever, I realized that my thought that knowing you're enough inhibits ambition is actually false. What it does, knowing you're enough kills fake ambition.

   24. LSLilly Singh28:00

       Mm-hmm.

   25. SBSteven Bartlett28:00

       The minute I knew, I started to get closer to realizing that I was enough, my ambitions were all things that I actually wanted-

   26. LSLilly Singh28:05

       Mm-hmm.

   27. SBSteven Bartlett28:05

       ... that were actually in line with my... So it's this weird paradox of when you know you're enough, it doesn't inhibit ambition; it's the foundation of real ambition.

   28. LSLilly Singh28:12

       Correct. It gives you a lot of clarity, I think, and you're absolutely correct.

   29. SBSteven Bartlett28:16

       Clarity. (laughs)

   30. LSLilly Singh28:16

       Because when you don't feel like you're enough, everything feels important. Everything feels like something you have to obtain. Everything feels like a challenge. You know, when I didn't feel like I was enough and I felt like I am the late night host, I am this actor, I, I am my job, this is what defines me, if anyone asks me who I was, I would never answer as, "I'm a patient friend. I'm a nice..." I would be like, "I'm a, uh... In this show, I'm this..." That's how I would def- Or I would define myself by struggles, which is another-
8. 31:15 – 35:50

   Advice when stuck at a crossroads

   1. SBSteven Bartlett31:15

      the one. You know, when people are saying, "Oh, she needs to get this rating," and you're thinking-

   2. LSLilly Singh31:18

      Mm-hmm.

   3. SBSteven Bartlett31:18

      ... "Well, I'm gonna prove them wrong." And whatever.

   4. LSLilly Singh31:20

      Mm-hmm.

   5. SBSteven Bartlett31:20

      And you're getting dragged by external, you know, measurements or validation, and then you get to the point where you say, "Do you know what? I actually just wanna tell stories."

   6. LSLilly Singh31:26

      Mm-hmm.

   7. SBSteven Bartlett31:27

      People r- reach that crossroads a lot in their life, where they've kind of, like, built an identity, in your case, tens of millions of followers-

   8. LSLilly Singh31:33

      Mm-hmm.

   9. SBSteven Bartlett31:33

      ... by doing something. And then, uh, uh, well, you know, in other people's cases, it could be they're working in, as a lawyer.

   10. LSLilly Singh31:38

       Mm-hmm.

   11. SBSteven Bartlett31:39

       And then they, they, they catch sight of what their purpose might be.

   12. LSLilly Singh31:42

       Mm-hmm.

   13. SBSteven Bartlett31:42

       And at that crossroads, life says to you, "If you go down that route, you're gonna lose a lot-

   14. LSLilly Singh31:48

       Mm-hmm.

   15. SBSteven Bartlett31:48

       ... of this stuff that you've built. I know it's not aligned with you, but you're gonna lose friends-

   16. LSLilly Singh31:53

       Mm-hmm.

   17. SBSteven Bartlett31:53

       ... a network-

   18. LSLilly Singh31:54

       Mm-hmm.

   19. SBSteven Bartlett31:54

       ... an identity. Don't go down that road." Right? And you've faced that-

   20. LSLilly Singh31:58

       Mm-hmm.

   21. SBSteven Bartlett31:58

       ... so clearly in your life, that crossroads.

   22. LSLilly Singh32:00

       Right.

   23. SBSteven Bartlett32:01

       And e- even leaving YouTube-

   24. LSLilly Singh32:02

       Mm-hmm.

   25. SBSteven Bartlett32:03

       ... f- you know, when you have 14 million f-

   26. LSLilly Singh32:05

       Mm-hmm.

   27. SBSteven Bartlett32:06

       What, are you out of your damn mind? (laughs)

   28. LSLilly Singh32:07

       Yeah.

   29. SBSteven Bartlett32:08

       But you-

   30. LSLilly Singh32:08

       Yeah, totally.
9. 35:50 – 42:50

   Your late-night talk show

   1. LSLilly Singh35:50

      right?

   2. SBSteven Bartlett35:50

      Mm-hmm. And then obviously you get this big, um, opportunity-

   3. LSLilly Singh35:54

      Mm-hmm.

   4. SBSteven Bartlett35:54

      ... which, which is well-written about. And I've watched the episodes.

   5. LSLilly Singh35:57

      Mm-hmm.

   6. SBSteven Bartlett35:57

      I've watched season one and season two, various clips.

   7. LSLilly Singh35:59

      I'm so sorry. Yep. (laughs)

   8. SBSteven Bartlett35:59

      No, no. (laughs) Why did you say, "I'm so sorry"?

   9. LSLilly Singh36:02

      Um-

   10. SBSteven Bartlett36:03

       So first of all, the context-

   11. LSLilly Singh36:03

       Yeah.

   12. SBSteven Bartlett36:04

       ... of the, for people that don't know.

   13. LSLilly Singh36:05

       Yeah.

   14. SBSteven Bartlett36:05

       So you got given a, a late night show. You were the first woman of color-

   15. LSLilly Singh36:08

       Mm-hmm.

   16. SBSteven Bartlett36:08

       ... to be l-

   17. LSLilly Singh36:09

       In over 30 years, yep.

   18. SBSteven Bartlett36:10

       ... in over 30 years-

   19. LSLilly Singh36:10

       Yep.

   20. SBSteven Bartlett36:10

       ... to be let into that-

   21. LSLilly Singh36:11

       Mm-hmm.

   22. SBSteven Bartlett36:12

       ... boys club-

   23. LSLilly Singh36:13

       Yep.

   24. SBSteven Bartlett36:13

       ... on a major network.

   25. LSLilly Singh36:15

       Mm-hmm.

   26. SBSteven Bartlett36:15

       When I said that, you said, "I'm so sorry."

   27. LSLilly Singh36:16

       Mm-hmm.

   28. SBSteven Bartlett36:16

       Tell me why you said that.

   29. LSLilly Singh36:18

       Because I don't think the thing was good. And I'm not necessarily proud of it, (laughs) you know? When I got the show, again, me being the disruptor, the whole first season, the, the advertising was, "We're gonna break the mold. We're knocking down the doors of late night. We're gonna do things differently." And then I proceeded to do things pretty much exactly how they've always been done.

   30. SBSteven Bartlett36:38

       Why?
10. 42:50 – 53:36

    The impact criticism had on you

    1. LSLilly Singh42:50

    2. SBSteven Bartlett42:51

       It makes it even more difficult in that situation where you're coming home after-

    3. LSLilly Singh42:55

       Mm-hmm.

    4. SBSteven Bartlett42:55

       ... filming those nu-

    5. LSLilly Singh42:55

       Yeah.

    6. SBSteven Bartlett42:56

       ... 'cause by the way, which is a ridiculous number of anything to film.

    7. LSLilly Singh42:58

       This is... It's, that's... Let's just do the math for everyone. That's two, three episodes a day-And, and traditionally-

    8. SBSteven Bartlett43:03

       That's crazy.

    9. LSLilly Singh43:03

       ... late-night hosts do one a day.

    10. SBSteven Bartlett43:05

        So you're coming home exhausted-

    11. LSLilly Singh43:07

        Mm-hmm.

    12. SBSteven Bartlett43:07

        ... after doing something that you didn't find fun.

    13. LSLilly Singh43:08

        Right.

    14. SBSteven Bartlett43:09

        And then the exacerbating factor of all of that, which I, I reflect on and I say to myself, "See if you would you've been able to deal with this part as well-"

    15. LSLilly Singh43:16

        Right.

    16. SBSteven Bartlett43:16

        ... is the show was by some people well-received, but by others-

    17. LSLilly Singh43:20

        Mm-hmm.

    18. SBSteven Bartlett43:20

        ... heavily criticized.

    19. LSLilly Singh43:20

        Mm-hmm.

    20. SBSteven Bartlett43:21

        Specifically the community, which is the YouTube community you'd come from.

    21. LSLilly Singh43:24

        Mm-hmm. Mm-hmm.

    22. SBSteven Bartlett43:24

        People made very hurtful, very-

    23. LSLilly Singh43:27

        Yeah.

    24. SBSteven Bartlett43:28

        ... shallow cri- criticisms-

    25. LSLilly Singh43:30

        Mm-hmm.

    26. SBSteven Bartlett43:30

        ... sometimes personal criticisms-

    27. LSLilly Singh43:32

        Mm-hmm.

    28. SBSteven Bartlett43:32

        ... about you and the show.

    29. LSLilly Singh43:33

        Yeah.

    30. SBSteven Bartlett43:35

        Unless you're the Superwoman, which is the pseudonym I think you used to-
11. 53:36 – 1:01:52

    What happened after the show got cancelled?

    1. LSLilly Singh53:36

       negotiating those- that reality-

    2. SBSteven Bartlett53:37

       Mm-hmm.

    3. LSLilly Singh53:37

       ... a little bit as well.

    4. SBSteven Bartlett53:38

       And that's not just a- just a minority storytelling thing.

    5. LSLilly Singh53:42

       Mm-hmm.

    6. SBSteven Bartlett53:42

       That's like- I was thinking about various facets of life and business and negotiation-

    7. LSLilly Singh53:46

       Mm-hmm, mm-hmm.

    8. SBSteven Bartlett53:46

       ... when there are multiple factors at play.

    9. LSLilly Singh53:48

       Right.

    10. SBSteven Bartlett53:48

        There are stakeholders who have a say. There are investors.

    11. LSLilly Singh53:50

        Mm-hmm.

    12. SBSteven Bartlett53:50

        There is a timeline that constrains you. There's a limitation on resources, as-

    13. LSLilly Singh53:53

        Right.

    14. SBSteven Bartlett53:54

        ... as you described.

    15. LSLilly Singh53:54

        Mm-hmm.

    16. SBSteven Bartlett53:55

        All of these factors cause an unavoidable compromise-

    17. LSLilly Singh53:57

        Mm-hmm.

    18. SBSteven Bartlett53:57

        ... where you have to go a- you know. But I guess it's that balancing act of, like, what are my non-negotiables then?

    19. LSLilly Singh54:03

        Right.

    20. SBSteven Bartlett54:03

        What am I completely not willing to negotiate on?

    21. LSLilly Singh54:04

        Right.

    22. SBSteven Bartlett54:05

        Um, after the second season of the call-

    23. LSLilly Singh54:07

        Mm-hmm.

    24. SBSteven Bartlett54:07

        ... you get a call saying that the show's not gonna be continued.

    25. LSLilly Singh54:09

        Mm-hmm, mm-hmm.

    26. SBSteven Bartlett54:10

        Tell me about that day.

    27. LSLilly Singh54:12

        So I'm gonna describe it as mutual, although, yes, the network does control, like, what's- what they're gonna put money towards or not. I was secretly hoping two things, and they're both completely contradictory. Half of me was like, "I know this show is a win for the community. It has to keep going. It has to keep going, or else it's gonna be a fail for the community." So I wanted it to keep going. The second part of me was, "I really hope this show doesn't keep going 'cause I'm going to literally collapse and die if this keeps going." Um, and I always judge things by what my gut reaction is to them. So when I got that call, my gut reaction was actually relief. That's how I knew that it was the universe doing me a favor I would never do for myself, 'cause if they let me, I would've tortured myself for 10 more seasons. (laughs)

    28. SBSteven Bartlett54:57

        Mm-hmm.

    29. LSLilly Singh54:58

        Honestly, I would've. The universe gave me something I would've never got myself. I got that call. I felt a wave of relief.... knowing I would never have to torture (laughs) myself in that exact situation again. But it also, going back to what our purpose is and getting clarity, it made things a lot more clear in my mind. And in that moment, I was able to see, "Oh, this has been a huge distraction from what I actually care about and I actually wanna do." This was an obligation. This was something I thought I had to do. This is not my passion. It was never your passion. Never once did I say I wanted (laughs) to be a late night host. I did say I wanted to act, I did say I wanted to tell stories, I wanted to produce. All of those ambitions paused during the late night show. I couldn't audition. I couldn't do anything else. I literally sacrificed two years of my life for something that I didn't even wanna do. That's a sad, sad thing. That's a sad realization. So I think I was rewarded with a lot of clarity in that moment.

    30. SBSteven Bartlett55:48

        But what did your ego say in that moment?
12. 1:01:52 – 1:04:25

    What makes up the foundation of your life?

    1. LSLilly Singh1:01:52

    2. SBSteven Bartlett1:01:52

       And that's why you call it-

    3. LSLilly Singh1:01:55

       Well, good, good, good, good question.

    4. SBSteven Bartlett1:01:56

       ... The Triangle.

    5. LSLilly Singh1:01:56

       He's like, "So the Illuminati?" (laughs)

    6. SBSteven Bartlett1:01:58

       No, (laughs) th- the, the triangle.

    7. LSLilly Singh1:01:59

       Yeah.

    8. SBSteven Bartlett1:01:59

       Yeah, yeah.

    9. LSLilly Singh1:01:59

       So when I discovered that a foundation is what I needed to create, I jumped onto Google and I was just like, "How to build a strong f- foundation, foundation," and Google spit back The Triangle. Because structurally speaking, the triangle's the strongest shape. It has the strongest foundation out of any shape. And then I started to think about triangles a lot, and I was like, "Oh, my, my brain is very visual," like I expressed, and I think of things in diagrams. And I started to visualize a triangle and I thought, "The shape is actually really interesting," because when you add to any other shape, you change the shape. It turns into something else. You add to a square, it becomes a rectangle. You add to a circle, it becomes an oval. You add to a triangle, it stays a triangle. It just becomes a bigger triangle. And I thought, "That's really interesting. I wanna build my life like that where no matter what happens, what experiences come my way, I'm still building on this foundation that will not change." Because especially in this industry, and, and all industries actually, you could really easily lose yourself, but what's happening in your life. But the goal is to create something that doesn't allow that to happen, and the triangle is the perfect shape for that.

    10. SBSteven Bartlett1:02:58

        And what is the, what constitutes your foundation? What are the ingredients of your foundation, if it was a recipe?

    11. LSLilly Singh1:03:03

        Yeah. So I talk about four things that make up the, the foundation of my triangle. And w- the hardest part of this book was c- figuring out what those four things are. Um, and how I did it was I looked... For several months, I looked at every struggle and issue or conflict in my life, and I looked at it through the lens of four things. That was one way I determined them. The second way was: What are four things that will never, ever change, no matter what's happening in my life? So I came up with four pillars, which are relationship to yourself, relationship to the universe, understanding distraction, and implementing design. I think no matter where you are in your life, who you are, what job you have, what country you live in, how old you are, those four things are always true in your life, and it is the lens through which you can look at everything in your life through.

    12. SBSteven Bartlett1:03:45

        I had a few words to say about one of my sponsors on this podcast. As you might know, Crafted are one of the sponsors of this podcast, and Crafted are a jewelry brand, and they make really meaningful pieces of jewelry. And this piece by Crafted, when I put it on, for me it represents courage, it represents ambition, it represents being calm and loving and respectful and nurturing, while also being the antithesis of that, seemingly the antithesis of that, which is, um, sometimes a little bit aggressive with my goals and determined and courageous and brave. The really wonderful thing about Crafted jewelry is it's super affordable, it looks amazing, the pieces hold tremendous meaning, and they are really well-made.

13. 1:04:25 – 1:08:41

    Panic attacks, meditation, and breath works

    1. SBSteven Bartlett1:04:26

       On the point of distraction-

    2. LSLilly Singh1:04:27

       Mm-hmm.

    3. SBSteven Bartlett1:04:27

       ... which I was gonna talk about, 'cause it was, it was a big part of your book-

    4. LSLilly Singh1:04:29

       Mm-hmm.

    5. SBSteven Bartlett1:04:30

       ... and you, you referenced there that you'd nev- th- the pandemic was the only time in your life where you'd really been forced to-

    6. LSLilly Singh1:04:35

       Mm-hmm.

    7. SBSteven Bartlett1:04:35

       ... all the distraction fell away and you were left with yourself. Um, so many people that I know, and I'm sure you'll, you can relate to this, um, fill their lives with distraction and noise and things-

    8. LSLilly Singh1:04:44

       Mm-hmm.

    9. SBSteven Bartlett1:04:44

       ... and busyness to avoid stillness-

    10. LSLilly Singh1:04:47

        Mm-hmm.

Episode duration: 1:29:51