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

Steven Bartlett 0:00 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.

Lilly Singh 0:08 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.

Steven Bartlett 0:39 You got given a, a late night sh- when I said that, you said, "I'm so sorry." Tell me why you said that.

Lilly Singh 0:43 '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.

Steven Bartlett 0:55 Did you have anxiety at the time?

Lilly Singh 0:56 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.

Steven Bartlett 1:06 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

Steven Bartlett 1:27 honor, and, um, we've got a mutual friend in Jay Shetty-

Lilly Singh 1:29 Yes.

Steven Bartlett 1:29 ... 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-

Lilly Singh 1:51 Mm-hmm.

Steven Bartlett 1:52 ... 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?

Lilly Singh 1:58 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!"

Steven Bartlett 3:13 Mm.

Lilly Singh 3:13 And kind of negotiating that balance.

Steven Bartlett 3:16 What you said about your grandparents-

Lilly Singh 3:17 Mm-hmm.

Steven Bartlett 3:17 ... wanting a boy, and generally in an Indian culture-

Lilly Singh 3:19 Yeah.

Steven Bartlett 3:19 ... there being a desire to have a boy, how did that impact you? I, I read that you were a tomboy growing up.

Lilly Singh 3:25 Yes.

Steven Bartlett 3:25 Yeah.

Lilly Singh 3:25 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.

Steven Bartlett 5:01 Mm-hmm. When I think about my own insecurities-

Lilly Singh 5:02 Mm-hmm.

Steven Bartlett 5:03 ... 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-

Lilly Singh 5:13 Mm-hmm.

Steven Bartlett 5:13 ... parents with a broke family in a perfect white picket-

Lilly Singh 5:16 Right.

Steven Bartlett 5:16 ... 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-

Lilly Singh 5:22 Mm-hmm.

Steven Bartlett 5:22 ... 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?

Lilly Singh 5:35 I think it's more so that the people who were the most powerful in my upbringing were men.

Steven Bartlett 5:41 Right.

Lilly Singh 5:41 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.

Steven Bartlett 6:41 Mm-hmm.

Lilly Singh 6:41 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.

Steven Bartlett 6:59 And you, so you moved to

Steven Bartlett 7:00 LA.

Lilly Singh 7:00 Mm-hmm.

Steven Bartlett 7:00 Your YouTube career starts really gaining traction.

Lilly Singh 7:02 Yeah.

Steven Bartlett 7:02 You said a, a second ago that you pursued YouTube because of, you're very honest, power and influence, right?

Lilly Singh 7:07 Mm-hmm.

Steven Bartlett 7:07 But when you're starting YouTube, there's no guarantee of power and influence, right?

Lilly Singh 7:10 Mm-hmm.

Steven Bartlett 7:11 I know your first video did like 70 views or something crazy.

Lilly Singh 7:13 Yeah. Yeah, yeah, yeah.

Steven Bartlett 7:14 Um, so when you started YouTube, a very strange thing to be doing back then, recording yourself-

Lilly Singh 7:19 Yeah.

Steven Bartlett 7:19 ... especially doing, like, funny stuff in your room or whatever.

Lilly Singh 7:22 Yeah, for sure.

Steven Bartlett 7:23 What wa- what were you thinking? Like what was the... (laughs)

Lilly Singh 7:25 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.

Steven Bartlett 8:40 Especially if you, you become obsessed about something that isn't fully aligned, right?

Lilly Singh 8:44 Yes.

Steven Bartlett 8:44 Which is possible, right? Because there can be-

Lilly Singh 8:45 Right.

Steven Bartlett 8:45 ... two conflicting forces. The force can be, "I wanna be really successful."

Lilly Singh 8:48 Mm-hmm.

Steven Bartlett 8:49 And then the other force can be saying, "Well, this isn't my purpose." And-

Lilly Singh 8:51 Right.

Steven Bartlett 8:52 ... they can surely come into conflict.

Lilly Singh 8:53 It's also very problematic when you're obsessive over something that is governed by numbers.

Steven Bartlett 8:59 Ugh.

Lilly Singh 9:00 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.

Steven Bartlett 9:09 Mm-hmm.

Lilly Singh 9:09 Because I would actually be, th- and this is 2010, before YouTube had a, had very complex analytics. Now you can see and-

Steven Bartlett 9:16 (laughs)

Lilly Singh 9:16 Now you can, you can know how many people with dogs on their laps are watching your videos.

Steven Bartlett 9:19 (laughs)

Lilly Singh 9:19 Like it's intense-

Steven Bartlett 9:20 True.

Lilly Singh 9:21 ... how, how many analytics you can get. Now, back in the day, that wasn't the case, so I would actually have my own spreadsheets, like a crazy person, just on my wall, every day tracking, "Okay, how many views? This video did this, this many subscribers, this people..." Like, an obsessive degree. And I don't regret that because it, it got me great success, but I've had to slowly unlearn a little bit of that to not go completely crazy in my adult life.

Steven Bartlett 9:43 Before that YouTube phase-

Lilly Singh 9:45 Mm-hmm.

Steven Bartlett 9:45 ... with the spreadsheets and stuff like that, did people consider you to be a, a lazy person? Did they, did they, like, count you out?

Lilly Singh 9:52 One thing I can say is I've been called a lot of things in my life.

Steven Bartlett 9:55 Yeah.

Lilly Singh 9:55 I have never been called lazy. (laughs)

Steven Bartlett 9:57 So w- when you were... 'Cause th- that phase before the YouTube-

Lilly Singh 10:00 Right.

Steven Bartlett 10:00 ... and the spreadsheets, right? What were you doing with your l- in your life at that phase?

Lilly Singh 10:04 So I was applying to grad school.

Steven Bartlett 10:07 Okay.

Lilly Singh 10:07 I had just finished graduating, and I was applying to grad school. And let me, let me put an asterisk to my last comment. I'm sure my parents would call me lazy-

Steven Bartlett 10:15 Right.

Lilly Singh 10:15 ... from time to time. It wasn't lazy as much it wa- as it was, "My heart is not in this thing."

Steven Bartlett 10:21 That's-

Lilly Singh 10:22 "So I do not, I do not think it is worthy for me to put my energy into it."

Steven Bartlett 10:26 That's what I was getting at.

Lilly Singh 10:27 Yes.

Steven Bartlett 10:27 Which is how someone can go from being perceived by their parents-

Lilly Singh 10:31 Mm-hmm.

Steven Bartlett 10:31 ... or in my case, by school, as being, "I got kicked out of school for the same thing."

Lilly Singh 10:35 Mm-hmm.

Steven Bartlett 10:35 And then just years later, they can see that I'm obsessed when something is in line with-

Lilly Singh 10:39 Right.

Steven Bartlett 10:39 ... something has caught me like a fish on a hook.

Lilly Singh 10:41 Right, exactly.

Steven Bartlett 10:42 For better or for worse. Maybe it's caught one of my insecurities-

Lilly Singh 10:44 Mm-hmm.

Steven Bartlett 10:44 ... and dragged me off into the future or whatever. But I just thought that was interesting that, like, maybe in that phase of your life, others would look at you and go, "Oh, she's lost or-"

Lilly Singh 10:51 Because you could... Well, the, the moment I walked into my parents' room and I said, "I wanna make YouTube videos," um, what I actually was doing five minutes before that is I was writ- trying to write an essay to get into grad school. And it was bad. And I was like, "I'm not... This makes no sense. I don't even care about the outcome of this." I closed my laptop right then and there, and I said, "If I don't care about this, I'm not gonna do well in this." And so I really had to shift my focus somewhere else. And that, literally five minutes later, I went into my parents' room and I said, "I can't do this. I wanna try making videos on the internet." And they were like, "Say what now?" Um, this was in 2010. And they gave me the best advice ever and the best blessing ever, which was, "You have a year." So they also gave me a bit of a ticking time bomb. They said, "You have a year to try whatever you wanna try, whatever this YouTube thing is. You have a year, and if it doesn't work out, you will go to grad school, and you will do exactly what you were doing five minutes ago." And so I ha- also had a bit of a, a time period that I had to (laughs) figure things out, and which was a huge blessing, because it made me, every moment for that year, work on making this pop off.

Steven Bartlett 11:49 When you had that conversation with your parents, how big were you on YouTube, if at all?

Lilly Singh 11:53 Not that big. Not that big at all. I think I had, like... My views were in the thousands probably.

Steven Bartlett 11:58 Okay.

Lilly Singh 11:59 Um, and this was 2010, like I said, so I vividly remember when I hit 1,000 subscribers. Now, your cat can meow, and you will have, like, 10,000 subscribers.

Steven Bartlett 12:10 (laughs)

Lilly Singh 12:10 But this was a w- a lot of hustle to get to even 1,000. I know this because I made a, a Justin Bieber Never Say Never parody when I hit 1,000 subscribers.

Steven Bartlett 12:19 (laughs)

Lilly Singh 12:19 I was like, "I made it, baby!" (laughs)

Steven Bartlett 12:22 When you reflect now on the role that your parents were playing-

Lilly Singh 12:25 Mm-hmm.

Steven Bartlett 12:25 ... in your life, like even then, like, having to go to them and them, like, granting you this year-

Lilly Singh 12:29 Mm-hmm. Mm-hmm.

Steven Bartlett 12:29 ... it all sounds incredibly, like, imprisoned.

Lilly Singh 12:31 Mm-hmm.

Steven Bartlett 12:32 You know what I mean?

Lilly Singh 12:33 Yes. I think for lots, for a lot of my teenage years and my young adult years, I probably viewed it like that. I no longer do. I've done a lot of work to try to figure out and respect, um, my parents' context, which has really, really helped me in those circumstances and really put value to it, not just dismiss it. So, I actually think a lot of what they did, although at the moment didn't seem right, and even now a little questionable sometimes, it actually really helped me. Like this one year, if they w- were so liberal to me and let me do whatever, I might have not worked as hard in that one year, to be honest. You know? And if they did not teach me the value of a lot of the things that they value, I probably wouldn't be the person I am today so I actually don't hold that against them at

Lilly Singh 13:14 all.

Steven Bartlett 13:14 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-

Lilly Singh 13:28 Mm-hmm.

Steven Bartlett 13:28 ... and everything that came with it, would people do it? 99% of people said they wouldn't.

Lilly Singh 13:31 No.

Steven Bartlett 13:31 And there's an interesting thing about how we look back-

Lilly Singh 13:33 Yeah.

Steven Bartlett 13:33 ... on our trauma w- because we also don't know the other outcome.

Lilly Singh 13:36 Because it's interesting.

Steven Bartlett 13:37 You know what I mean?

Lilly Singh 13:38 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.

Steven Bartlett 14:07 Hmm.

Lilly Singh 14:08 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.

Steven Bartlett 14:49 That perspective, completely true.

Lilly Singh 14:51 Mm-hmm.

Steven Bartlett 14:51 Completely true. Been through it myself a million times.

Lilly Singh 14:53 Yeah.

Steven Bartlett 14:53 I always say, you know, this is... i- the current crisis always feels like the fatal one until hindsight tells you that the-

Lilly Singh 14:59 Right.

Steven Bartlett 14:59 ... current one is the fatal. (laughs)

Lilly Singh 15:00 Right.

Steven Bartlett 15:01 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.

Lilly Singh 15:11 Mm-hmm.

Steven Bartlett 15:12 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-

Lilly Singh 15:22 Right.

Steven Bartlett 15:22 ... what actually helps?

Lilly Singh 15:24 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.

Steven Bartlett 15:57 A couple of days is, but-

Lilly Singh 15:57 No matter what. Yeah, 100% is where you sit at.

Steven Bartlett 15:59 Mm-hmm.

Lilly Singh 16:00 So, I think about things through that lens, but I also think about just, is the struggle worth it? And for me, yes, it is. I believe in what I believe so much more than I, the hurt that I feel. And that's the balance I think we need to keep in check, is, is it worth it? Is your struggle worth it? And I think you really need to do the work to make that answer yes. And I didn't always operate from a yes, but I think now I do. I believe, uh, I found my purpose, and I know Jay talks about this a lot, but finding your purpose and what your purpose is on this planet helps you get to that yes. So for me, I think my, uh, my struggles are worth it. I think the pain is worth it to get on the other end.

Steven Bartlett 16:38 You became a, a hugely... I'm gonna leap back to that-

Lilly Singh 16:42 Mm-hmm.

Steven Bartlett 16:42 ... sub-topic in a second-

Lilly Singh 16:42 Yeah.

Steven Bartlett 16:42 ... but to give the listeners a context, you became a hugely, hugely successful social media star, creator, whatever you wanna call it.

Lilly Singh 16:50 Mm-hmm.

Steven Bartlett 16:51 Um, c- built one of the biggest YouTube channels still to, to this day.

Lilly Singh 16:54 Ah, sure. (laughs)

Steven Bartlett 16:55 Some millions and millions of subscribers.

Lilly Singh 16:56 Yeah.

Steven Bartlett 16:56 That is a, that makes you in the 0.0 whatever percent-

Lilly Singh 17:00 Mm-hmm.

Steven Bartlett 17:00 ... anomalies in the world. So, I, I hear the obsessive thing-

Lilly Singh 17:03 Mm-hmm.

Steven Bartlett 17:03 You said about the spreadsheets, I guessed that. I thought, "For her to get there, she must be pretty obsessive."

Lilly Singh 17:07 I walked in here and you were like, "Ooh, she has Google Doc written all over her." (laughs)

Steven Bartlett 17:11 (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."

Lilly Singh 17:17 Mm-hmm.

Steven Bartlett 17:18 You know, 'cause the things that I was ex-... you know, especially when you're in the numbers business-

Lilly Singh 17:21 Right.

Steven Bartlett 17:21 ... 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-

Lilly Singh 17:30 Mm-hmm.

Steven Bartlett 17:30 ... to where you hit f- fourteen point whatever seven million subs, what was it about Lilly, outside of the obsessive part-

Lilly Singh 17:38 Mm-hmm.

Steven Bartlett 17:38 ... that made you such an anomaly through that phase of, like, career success on YouTube?

Lilly Singh 17:45 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.

Steven Bartlett 20:00 Clearly, you're someone who's built a lot of evidence that d-

Lilly Singh 20:02 The look you just gave me is the look my parents give me, (laughs) just like-

Steven Bartlett 20:04 No. Yeah. Do you know there was so much-

Lilly Singh 20:06 Yeah. (laughs)

Steven Bartlett 20:06 ... going on in my head. And then I was thinking about different ways to take that-

Lilly Singh 20:08 (laughs) Yeah.

Steven Bartlett 20:09 ... and different feelings I got from that.

Lilly Singh 20:10 Yeah.

Steven Bartlett 20:10 One of them honestly was like, especially hearing the obsessive thing. Listen, when I ask these questions-

Lilly Singh 20:15 Mm-hmm.

Steven Bartlett 20:16 ... I'm not... 'Cause I think, 'cause I relate to so much of what you're saying.

Lilly Singh 20:18 Yeah.

Steven Bartlett 20:18 I'm asking the questions to, to pick, d- dig deeper, not because I-

Lilly Singh 20:22 No. I love it.

Steven Bartlett 20:23 ... like disagree. So-

Lilly Singh 20:23 I love it. But it's just-

Steven Bartlett 20:24 Yeah.

Lilly Singh 20:24 ... the look is like my parents looking at me like-

Steven Bartlett 20:26 Yeah.

Lilly Singh 20:26 ... "Great. She likes to disrupt." (laughs)

Steven Bartlett 20:28 Yeah. No. 'Cause m- my brain went, my brain went... Almo- i- she, she's so... Even when you were delivering it-

Lilly Singh 20:33 Yeah.

Steven Bartlett 20:33 ... so passionate that I felt, felt as if she must have... That's exhausting.

Lilly Singh 20:36 Mm-hmm.

Steven Bartlett 20:36 To be obsessive-

Lilly Singh 20:37 Yes.

Steven Bartlett 20:37 ... 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.

Lilly Singh 20:47 Mm-hmm.

Steven Bartlett 20:48 But why is that your predisposition? Are... Is it going back to your childhood and saying-

Lilly Singh 20:52 I think so.

Steven Bartlett 20:52 ... you didn't like the system or-

Lilly Singh 20:53 I have, I have asked that question to myself as well. Why is it that no matter... And this is where it can be d- to a detriment sometimes, 'cause sometimes I'll take simple, simple tasks that are... don't need that much effort, but I will make it so I'm disrupting even those small, small things. Maybe there's a different way to throw a party. Maybe there's a different way to have a friendship. Maybe there's a different way to decorate my house. In every aspect, I have to disrupt. And it is exhausting. (laughs) It's absolutely exhausting. And I've tried to figure out why, why, what is it in me? I'm still trying to figure it out, but I think from my work thus far, I have determined that it's just that from the moment I was born, I was already a disruption. I was already that. And I think that's just me stepping into my power, fully embracing that's who I am and being like, "Fine. I'm not gonna reject that. I am going to fully embrace. That's my purpose in life." Because another thing is, you know, when you ask me about the chip on my shoulder, the part of the story I didn't say is that I actually did come out the other end. So in my adult life, when I announced my first world tour after becoming a YouTube success, I very purposely announced it in India. I was like, "I wanna announce the tour in India. One of the first stops to be in India." I know that's where, you know, my great-grandparents are. I know that's where my parents are from. I know it'll mean the most. It'll have the biggest impact. So after I announced that tour, I went and did the eight-hour drive to visit my grandfather for the first time in my adult life. I had never met him as an, as an adult before. And this was the, the grandfather where... And I hold nothing against him because again, I under- respect people's circumstances, but he was the one that didn't wanna hear about a daughter, who didn't believe a, a, a daughter in the family would be worthwhile. He was standing outside of his house and greeted me with a flo- flower garland.

Steven Bartlett 22:29 Mm-hmm.

Lilly Singh 22:29 And he said the words to me. This is like an 80-year-old Indian man said the words to me. "I was wrong. You have made this family more proud than anyone else could have ever done." And he showed me all these newspaper clippings he had saved with me. So that moment for me also validated-

Steven Bartlett 22:44 Mm.

Lilly Singh 22:45 ... what disruption can do.

Steven Bartlett 22:46 Mm.

Lilly Singh 22:46 It can make progress. Progress comes from disruption and breaking systems. And so I think that for me was a very... And I, and I reme- remember it so vividly because it did leave such an impact on me. But that for me was like a, "Look, this is what disruption can do. This is what the uncomfortable process results in."

Steven Bartlett 23:05 And am I right in therefore concluding that that disrup- the, the, the fuel of the disruption was that chip on your shoulder?

Lilly Singh 23:11 Mm-hmm.

Steven Bartlett 23:11 And it creates almost a bit of a- an injustice and a sense of anger in people-

Lilly Singh 23:14 Yeah.

Steven Bartlett 23:14 ... that I've seen so many times in myself. And thinking about my friend Umar who's, who's come fr- comes from a somewhat similar background.

Lilly Singh 23:20 Mm-hmm.

Steven Bartlett 23:20 An Indian guy, went on to create billion-dollar company. He, he, he grew up with this internal, just almost frustration, anger, this sense of trying to correct an injustice-

Lilly Singh 23:30 Mm-hmm.

Steven Bartlett 23:30 ... and that manifests as this chip on his shoulder and-

Lilly Singh 23:32 Right.

Steven Bartlett 23:32 ... and I guess life w- if you start with that predisposition and you go through life with that i- idea of like disrupting the status quo-

Lilly Singh 23:39 Mm-hmm.

Steven Bartlett 23:40 ... you will win. And that will reinforce that.

Lilly Singh 23:42 Yes.

Steven Bartlett 23:43 So now imagine when I work with you. If I came up with a conventional idea, you know from 33 years of experience that the rewards are on the other side of the disruptive, you know, what we call first principle thinking. When you go to the extra effort of thinking about something from-

Lilly Singh 23:56 Mm-hmm.

Steven Bartlett 23:56 ... fresh.

Lilly Singh 23:56 Right.

Steven Bartlett 23:57 And that's, um-

Lilly Singh 23:58 It's that. I also will b- be really honest. I thought that that moment of-

Steven Bartlett 24:05 (laughs)

Lilly Singh 24:05 ... uh, "My grandfather knows now. He knows what's up. He knows my name," would eliminate the chip on my shoulder. It didn't. I don't think it will ever actually go away.

Steven Bartlett 24:13 Why?

Lilly Singh 24:14 Um, I'm still trying to figure that out. I think it's because that same chip is still reinforced in so many other places in the world.

Steven Bartlett 24:21 Ah.

Lilly Singh 24:21 It's still that I'm... was the only female late night host.

Steven Bartlett 24:25 Mm-hmm.

Lilly Singh 24:25 And so when I was at that seat, in that table surrounded by men, that chip was just reinforced.

Steven Bartlett 24:29 It's like a new trauma.

Lilly Singh 24:30 Exactly. So I think it keeps getting reinforced. It was never just about my grandfather. It was just about the system. But that is also... I will just say, I have to get really honest-

Steven Bartlett 24:38 Mm-hmm.

Lilly Singh 24:38 ... and say that mixed with ego.

Steven Bartlett 24:40 Mm.

Lilly Singh 24:40 Once you get a bit of success, I think Jay-Z says-

Steven Bartlett 24:42 Mm-hmm.

Lilly Singh 24:42 ... su- success is the most addictive drug.

Steven Bartlett 24:44 Mm.

Lilly Singh 24:44 It is. Once you disrupt and it comes out the other end and you see how amazing it is, you're like-

Steven Bartlett 24:48 Everything goes.

Lilly Singh 24:48 "I need to keep doing this. I need to keep doing this."

Steven Bartlett 24:49 Yeah.

Lilly Singh 24:49 "I need to keep disrupting. I need to..." That's been something I've had to...... really meditate on in my adult life is that, when does that stop? When does that desire to just more, more, more, more, disrupt, disrupt, when, when, when, when does that stop? You know.

Steven Bartlett 25:03 That can be the real enemy of happiness, right?

Lilly Singh 25:04 Absolutely.

Steven Bartlett 25:05 In life.

Lilly Singh 25:05 Yes. Happiness is often right here.

Steven Bartlett 25:08 Mm-hmm.

Lilly Singh 25:08 But we can't see it because we're still trying to (laughs) chase it that way.

Steven Bartlett 25:11 Mm-hmm.

Lilly Singh 25:11 We're still trying to... It's always the "it's in the future" mentality. You know, happiness will come, success will come, these things will come. Maybe it's, like, right now.

Steven Bartlett 25:21 Hmm.

Lilly Singh 25:21 Right?

Steven Bartlett 25:22 Even saying that, though, is not enough, right?

Lilly Singh 25:24 It's not. Yeah.

Steven Bartlett 25:24 Yeah, 'cause I say that to a lot of people but-

Lilly Singh 25:26 100%.

Steven Bartlett 25:26 ... still struggle with it myself.

Lilly Singh 25:27 Yeah, you have to do a lot of work. It's a lot of work. It's not just words, it's a lot of work-

Steven Bartlett 25:30 Mm-hmm.

Lilly Singh 25:31 ... in how you assign value to yourself, how you assign value to other things. For most of my life, I've hustled so... I mean, I built an entire brand out of hustling. Anyone that knows anything about me, it's hustle harder, hustle... she wrote How To Be a Boss, her first book. It's... Now, over the past few years, I've done the work to not hustle less, I still work very, very hard, but it's, what does all this stuff actually mean? What is the value you tie to this stuff? Is it what you thought it was gonna be? And I think you can only learn that once you get there and you get it and you're like, "Oh, it's not giving me the feeling I thought it was gonna give me."

Steven Bartlett 25:59 Mm-hmm.

Lilly Singh 25:59 And it probably never will because of this value we've assigned to all this stuff.

Steven Bartlett 26:04 Have you gotten to the point where you, you know that you are enough?

Lilly Singh 26:08 Oh, this is turning into therapy. Damn!

Steven Bartlett 26:09 What did you think it was gonna be?

Lilly Singh 26:11 Damn!

Steven Bartlett 26:11 Clearly nobody's

Narrator 26:12 (laughs)

Lilly Singh 26:12 I'm gonna, I'm gonna cancel my therapy appointments.

Steven Bartlett 26:15 (laughs)

Lilly Singh 26:15 Save myself $300. Um...

Steven Bartlett 26:18 We charge. (laughs)

Lilly Singh 26:19 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.

Steven Bartlett 27:28 And when you get to that place-

Lilly Singh 27:30 Mm-hmm.

Steven Bartlett 27:30 ... if we are lucky enough in our lives to get to the place-

Lilly Singh 27:32 Yeah.

Steven Bartlett 27:32 ... 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."

Lilly Singh 27:42 Mm-hmm.

Steven Bartlett 27:42 I remember thinking, "What a load of bullshit."

Lilly Singh 27:43 Yep.

Steven Bartlett 27:44 "I'm not gonna get out of bed if I have that viewpoint."

Lilly Singh 27:46 Exactly, yes.

Steven Bartlett 27:46 "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.

Lilly Singh 28:00 Mm-hmm.

Steven Bartlett 28:00 The minute I knew, I started to get closer to realizing that I was enough, my ambitions were all things that I actually wanted-

Lilly Singh 28:05 Mm-hmm.

Steven Bartlett 28:05 ... 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.

Lilly Singh 28:12 Correct. It gives you a lot of clarity, I think, and you're absolutely correct.

Steven Bartlett 28:16 Clarity. (laughs)

Lilly Singh 28:16 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-

Steven Bartlett 28:43 Hmm.

Lilly Singh 28:43 ... whole thing. Not by ever my potential. I would never say, "I'm someone who's gonna change the world because of XYZ." I would say, "I'm someone who had a really tough childhood." We either define ourselves by our struggles or by these other external validations and accolades that we think are important. When I did that, I would care so much. For me, what was so important was, "I need to prove this troll wrong on the internet. I need to... That's, that's my priority. I need to prove this troll wrong. I need to get this rating. I need to do..." And then the second I was like, "You know what? My purpose is to disrupt. Uh, I know what my values... I'm a complete person already," suddenly that stuff became way less important to me.

Steven Bartlett 29:17 Mm-hmm.

Lilly Singh 29:17 Suddenly I was like, "Oh, actually my priority is going to be, I wanna tell stories that I think are really meaningful." I'm not saying that it has to be a box office breaker-

Steven Bartlett 29:30 Mm-hmm.

Lilly Singh 29:30 ... in that I'm saying I just wanna tell stories that are important. You, things become a little more clear when you accept, you make space for priorities to become clear, when you stop pretending that all this other stuff is important. So I co- totally agree. That is something I struggled with, where I thought... And I think that was my resistance against it, when people would tell me, "You're enough," and when they'd just tell kids, I'd be like, "No, that kid's gonna grow up and they're not gonna, they're not gonna become anything if you just tell them they're enough."

Steven Bartlett 29:52 (laughs) Let the Indian finger.

Lilly Singh 29:52 Again, I still think that there's the, uh, uh, intersection between hustling and spirituality. I don't think we have to pick one or the other. I really don't. I think there's a way for both of those things to coexist. But I do, it has become apparent to me that being mindful, feeling like you're enough, it actually allows you to hustle with more clarity.

Steven Bartlett 30:12 I had a few words to say about one of my sponsors on this podcast. As the seasons have begun to change, so has my diet. And, um, right now, I'm just gonna be completely honest with you, I'm starting to think a lot about slimming down a little bit, because over the last couple of, probably the last four or five months, my diet has been pretty bad. Um, and it's started to show a little bit. Really over the last two months. I go to the gym about 80% of the time, so I track it with 10 of my friends in a WhatsApp group, in this tracker online that we all use together. We call it Fitness Blockchain. And I'm currently at 81%. Um, so 81% of the days I've done a workout in the last 150 days. Right? So I'm going to the gym about six times a week. That's been a little bit impacted by the Diary of a CEO Live tour, but I'm trying to stick to it.And so one of the things I'm doing now to reduce my calorie intake, and trying to get back to being nutritionally complete in all I eat, is I'm having the Huel protein shake. Thank you, Huel, for making a product that I actually like. The salted caramel is my favorite. I've got the banana one here, which is the one my girlfriend likes, but for me, salted caramel is

Steven Bartlett 31:15 the one. You know, when people are saying, "Oh, she needs to get this rating," and you're thinking-

Lilly Singh 31:18 Mm-hmm.

Steven Bartlett 31:18 ... "Well, I'm gonna prove them wrong." And whatever.

Lilly Singh 31:20 Mm-hmm.

Steven Bartlett 31:20 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."

Lilly Singh 31:26 Mm-hmm.

Steven Bartlett 31:27 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-

Lilly Singh 31:33 Mm-hmm.

Steven Bartlett 31:33 ... 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.

Lilly Singh 31:38 Mm-hmm.

Steven Bartlett 31:39 And then they, they, they catch sight of what their purpose might be.

Lilly Singh 31:42 Mm-hmm.

Steven Bartlett 31:42 And at that crossroads, life says to you, "If you go down that route, you're gonna lose a lot-

Lilly Singh 31:48 Mm-hmm.

Steven Bartlett 31:48 ... of this stuff that you've built. I know it's not aligned with you, but you're gonna lose friends-

Lilly Singh 31:53 Mm-hmm.

Steven Bartlett 31:53 ... a network-

Lilly Singh 31:54 Mm-hmm.

Steven Bartlett 31:54 ... an identity. Don't go down that road." Right? And you've faced that-

Lilly Singh 31:58 Mm-hmm.

Steven Bartlett 31:58 ... so clearly in your life, that crossroads.

Lilly Singh 32:00 Right.

Steven Bartlett 32:01 And e- even leaving YouTube-

Lilly Singh 32:02 Mm-hmm.

Steven Bartlett 32:03 ... f- you know, when you have 14 million f-

Lilly Singh 32:05 Mm-hmm.

Steven Bartlett 32:06 What, are you out of your damn mind? (laughs)

Lilly Singh 32:07 Yeah.

Steven Bartlett 32:08 But you-

Lilly Singh 32:08 Yeah, totally.

Steven Bartlett 32:09 But tell me, so like, at that crossroads in life, what advice would you give to people when, in your case, you're one of the ones that really had, you know, I don't wanna say a lot to lose, because that's a presumption, right? So it's like, the public would think that you had a lot to lose by taking a different route.

Lilly Singh 32:23 Right. You're absolutely correct. I think one of the reasons I, for so long, kept holding onto the strings of YouTube to be like, "No, I wanna do other stuff, but I'm still gonna do this. I wanna do other stuff, but I'm still gonna make these videos. I'm still gonna dress up as my parents," was that. It was that I didn't wanna lose this traction I had, this audience I had, this instant gratification I had of having this massive audience at my fingertips. I also, to be honest, I was scared of this term relevancy. I think relevancy is used as currency these days, like, "You're not relevant, so you're worth less now," and we have this, this, this way to measure people based on rele- relevancy. This m- can be summarized in one easy sentence, which is you cannot expect to grow and also stay the same. It just cannot happen. You have to make room for growth. And so in order for me to fulfill my ambitions of, "I wanna do stuff with movies and TVs and I wanna, I wanna just do all this other stuff that is me growing in my craft," I cannot stay the same. I can't, you have to make space for that. You know, I also always think about if I have, again, going, me going back to diagrams and the way my brain thinks, if I have 100% energy at the start of a day, I can only spend 100% energy. No more energy is coming. I- you have 100, so where are you gonna put that energy?

Steven Bartlett 33:35 Mm-hmm.

Lilly Singh 33:36 It, it can be to old habits. It can be to holding onto s- relevancy, but then that limits how much energy is left for growth.

Steven Bartlett 33:43 Mm-hmm.

Lilly Singh 33:44 So it really is just a decision you have to make of making room for growth.

Steven Bartlett 33:48 And when you did make that decision back in 2019-

Lilly Singh 33:51 Mm-hmm.

Steven Bartlett 33:51 ... to, to... Was it 2019 you left YouTube?

Lilly Singh 33:54 I still lo-... I still make-

Steven Bartlett 33:55 I know you still post, but th-

Lilly Singh 33:56 Yeah, yeah, but yeah, I think around 2019 was when I stopped consistently uploading videos, yes.

Steven Bartlett 34:00 Yeah. So, um, when I read about why you, you left YouTube-

Lilly Singh 34:04 Mm-hmm.

Steven Bartlett 34:04 ... there was clearly some symptoms-

Lilly Singh 34:05 Mm-hmm.

Steven Bartlett 34:05 ... of life saying to you, "You're fucking up here-"

Lilly Singh 34:08 Mm-hmm.

Steven Bartlett 34:09 ... "... in some way." What were those symptoms?

Lilly Singh 34:11 I think doing things because you feel like you have to, doing things because you feel like you owe people, doing things that you're not really passionate about, um, and feeling like you don't, you haven't given yourself permission to grow. It's-

Steven Bartlett 34:23 And how did it emotionally feel?

Lilly Singh 34:25 Um, stagnant. I felt like I was trapped. I felt like I owed people this version of myself that was stuck in space and that was not allowed to grow. I felt un- not creative. I felt, um, not free. And I felt like even though I, what I loved about YouTube was freedom, I can post whatever I want whenever I want, there's no gatekeepers, I felt trapped in that system. It became the exact opposite of what I loved about YouTube, which was you have to serve every Monday and Thursday. You have to post a video. You have to appease these fans. It has to be like this. It has to be this long. You have to appease the algorithm. It became the exact thing I never wanted in the first place, which was to be trapped in something like that. And so, um, it just, it, it stopped feeling right to me. It stopped feeling like a place that I could grow and learn and thrive.

Steven Bartlett 35:11 The Lily that I would see on camera at that point-

Lilly Singh 35:13 Mm-hmm.

Steven Bartlett 35:13 ... in the lead-up to you deciding to depart, versus the Lily that would be there right after you stopped recording, tell me the difference between those two people.

Lilly Singh 35:21 Yeah, she's just as weird in both instances. I can tell you that.

Steven Bartlett 35:23 (laughs)

Lilly Singh 35:23 She's just as weird, she's just as quirky, but one of them was definitely a bit more performative, um, pretending to be a little bit more passionate than she was, pretending not to be tired and exhausted, and pretending to be excited about what, what she was doing. I think after I turned off the camera, I was like, "Oh, God, now I gotta edit this thing, and I gotta do this thing, and I gotta go through these..." There was no growth. It was just such a repetitive pattern. And as a creative, I didn't want that. That's, if I wanted that, I would've just (laughs) done the grad school thing,

Lilly Singh 35:50 right?

Steven Bartlett 35:50 Mm-hmm. And then obviously you get this big, um, opportunity-

Lilly Singh 35:54 Mm-hmm.

Steven Bartlett 35:54 ... which, which is well-written about. And I've watched the episodes.

Lilly Singh 35:57 Mm-hmm.

Steven Bartlett 35:57 I've watched season one and season two, various clips.

Lilly Singh 35:59 I'm so sorry. Yep. (laughs)

Steven Bartlett 35:59 No, no. (laughs) Why did you say, "I'm so sorry"?

Lilly Singh 36:02 Um-

Steven Bartlett 36:03 So first of all, the context-

Lilly Singh 36:03 Yeah.

Steven Bartlett 36:04 ... of the, for people that don't know.

Lilly Singh 36:05 Yeah.

Steven Bartlett 36:05 So you got given a, a late night show. You were the first woman of color-

Lilly Singh 36:08 Mm-hmm.

Steven Bartlett 36:08 ... to be l-

Lilly Singh 36:09 In over 30 years, yep.

Steven Bartlett 36:10 ... in over 30 years-

Lilly Singh 36:10 Yep.

Steven Bartlett 36:10 ... to be let into that-

Lilly Singh 36:11 Mm-hmm.

Steven Bartlett 36:12 ... boys club-

Lilly Singh 36:13 Yep.

Steven Bartlett 36:13 ... on a major network.

Lilly Singh 36:15 Mm-hmm.

Steven Bartlett 36:15 When I said that, you said, "I'm so sorry."

Lilly Singh 36:16 Mm-hmm.

Steven Bartlett 36:16 Tell me why you said that.

Lilly Singh 36:18 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.

Steven Bartlett 36:38 Why?

Lilly Singh 36:38 Um, because for the first time in my life, I was in a situation where I could not call the shots. I couldn't make the decisions. I didn't have the resources to do things differently. The system is not built to do... The, the issue is the system is not built to do things differently.It's hard to do things differently when you're told, "Okay, so the episode has to be exactly 22 minutes and 23 seconds." It has to be that amount of time. It cannot be a second over, it cannot be under. "The acts have to be broken down like this because our commercials have to go in these time things. So you had a joke that went there, it can't go there anymore. You have to do it like this. Oh, you're following Jimmy and Seth, and the audience is kind of used to their format, so you can do things differently, but it has to start with a monologue. So you're gonna have to come up, you're gonna have to hit the mark, you're gonna have to do the monologue." So many times when I did that monologue, which was the worst part of the show, it was like a 10-minute monologue of mediocre jokes because I had a tiny writer's room and very few resources. This, this is to no discredit to the writers, I just had such few writers that we're too overworked. There were e- episodes where I would miss the mark and I would mess up and it was the best part of the show, and I would have to do it again to get it right. And I would always think, "Why can't we just put the mess up on air?" The best part of the show even beyond that was before we were even rolling, I would go out and I would warm up the audience, and I would just riff with them and t- talk some jokes, and it would be so just natural and funny, and you would never see that in the show. Why? We didn't have enough cameras to shoot the audience. So we couldn't put it in the show. So the system was not built for breaking the mold.

Steven Bartlett 38:12 At that time-

Lilly Singh 38:13 Mm-hmm.

Steven Bartlett 38:13 ... did your gut tell you something was wrong?

Lilly Singh 38:15 Absolutely. From day one, I thought, "This is going to be very hard. It's going to be very hard to make something that I'm proud of here." And I ha- and what I hated about it was the proudness and the pride was of something superficial. I was proud of the headline, I was proud of the historic nature of it, I was proud that I got to make history, but none of the work could back it up, and that broke my heart every day to know that I'm just riding this headline and I'm not gonna be able to deliver on this. There was episodes, I vividly remember this, there was, uh, several episodes where I would be with my... we didn't even have a showrunner. It was my head of development for my production company who acted as the showrunner (laughs) for the show, and I would be walking, and the show would be starting in five minutes, and we would be going over the monologue, and I looked at her one day and I said, "This is not funny, and this is not good, and I don't wanna go out there, and I don't wanna have to pretend it is." And she looked at me and she said, "It's a quantity game. It's not a quality game," and that broke my heart because Late Night is a quantity game. It's... I shot 96 episodes in three months, and I don't wanna come across as if I'm-

Steven Bartlett 39:20 96 episodes?

Lilly Singh 39:20 ... complaining and all this, but-

Steven Bartlett 39:22 Who the fuck

Lilly Singh 39:22 ... I'm trying to highlight that it was very difficult for me to go into the system being the control freak I am, being the disruptor, and just try everything to disrupt it, and it's just too rock solid to be disrupted.

Steven Bartlett 39:35 I ask these questions in part because-

Lilly Singh 39:37 Mm-hmm.

Steven Bartlett 39:37 ... I've just joined a show called sh- Dragon's Den-

Lilly Singh 39:39 Okay.

Steven Bartlett 39:39 ... which is like Shark Tank.

Lilly Singh 39:40 Yeah, yeah.

Steven Bartlett 39:41 You know?

Lilly Singh 39:41 Yeah, yeah.

Steven Bartlett 39:41 So five of us sit there, investor walks in.

Lilly Singh 39:43 Mm-hmm.

Steven Bartlett 39:43 And since then, I've been offered a lot more shows, right? And y- I mean, you've been there, right? Loads of sh- loads of-

Lilly Singh 39:49 Yeah.

Steven Bartlett 39:49 ... briefs coming in for shows-

Lilly Singh 39:50 Mm-hmm.

Steven Bartlett 39:50 ... big promises, whatever, and some of them are really tempting 'cause it says, "Oh, you're gonna be on Netflix," but then my gut says to me, "That's a shit show though."

Lilly Singh 39:58 Mm-hmm.

Steven Bartlett 39:58 "That is a piece of shit show."

Lilly Singh 39:59 Mm-hmm.

Steven Bartlett 39:59 So I'm asking from a perspective o- of advice. When you find yourself in the, in the shadow, in the shadow of a great temptation, I'm, you know, there are... Steve Bartlett might be the first whatever, whatever, whatever-

Lilly Singh 40:09 Mm-hmm.

Steven Bartlett 40:09 ... but I, but I look at what's going on, the system in which I would, I'd be operating, as you did.

Lilly Singh 40:15 Mm-hmm.

Steven Bartlett 40:16 What advice would you give to me based on the lesson you've learned in hindsight?

Lilly Singh 40:20 I will answer this question by telling you exactly that, the lesson I learned, which is, it wasn't until the show finished that I really had to reflect on that experience and be like, "What am I gonna do differently?" You see, when I was offered the show, the first time it was brought to me, I actually said no. People don't know this. I said no, and it disappeared for like a month, and it came back to me again, and I thought, "Okay, the universe is sending this back to me again. Let me, let me evaluate this." The reason I said no first was because I never grew up with the dream of being a late night host. I know some people have that experience where they're like, "I grew up with late night television, watched it every night." I don't think my mom could tell you what Jimmy's last name is. Like she ne-

Steven Bartlett 40:58 Mm-hmm.

Lilly Singh 40:58 They never watched Late Night. They n- I never grew up with that experience, so it wasn't my desire, it wasn't my passion to be a host. Um, so that's why I said no. But when it came back around and it was explained to me the historic nature of this, three things came into play. One, my sense of responsibility and duty, and two, my ego. Those things together, I was like, "I wanna be part of this historic moment. That would be really cool. Also, I have a responsibility for this because what if I say no and it goes to someone else? Then this history is never even made, and we never even got the shot." So all of these reasons that I thought were so valuable and valid is why I said yes. I was naive to think that that would be enough to get me through those long shoot days. It wasn't. Because I would come home at the end of 96 episodes in three months broken, and I would think, "That was not fun, and I didn't enjoy that, and I have no memory or no positive thought to even show for that hard work." I learned the value of having fun and doing things you're passionate about. I believe more than anything else, those are the things that actually contribute to longevity, more than anything else. Even money, ask any person with a lot of money, you'll grow tired of money, you'll grow tired of buying things. You will never grow tired of having fun and being passionate about something. And so since I wrapped that show, any project that comes to my desk now, my agents will be on the phone and we'll talk about the money for a while, we'll talk about the schedule for a while, and then I'll dedicate an amount of time, I'll say, "Okay, now we're gonna talk about if I'm going to have fun and if these people are actually nice to work with." And do I even care about this? Do I care about this and... What is this? And do I even care about the message here, what this is saying? And if my answers are no, my definition of success right now is that I will not say yes to it. I have to have fun right now where I am or I'm not successful. So that's my advice to you, is don't undervalue fun and passion 'cause those... you will never grow tired of those things.

Steven Bartlett 42:51 It makes it even more difficult in that situation where you're coming home after-

Lilly Singh 42:55 Mm-hmm.

Steven Bartlett 42:55 ... filming those nu-

Lilly Singh 42:55 Yeah.

Steven Bartlett 42:56 ... 'cause by the way, which is a ridiculous number of anything to film.

Lilly Singh 42:58 This is... It's, that's... Let's just do the math for everyone. That's two, three episodes a day-And, and traditionally-

Steven Bartlett 43:03 That's crazy.

Lilly Singh 43:03 ... late-night hosts do one a day.

Steven Bartlett 43:05 So you're coming home exhausted-

Lilly Singh 43:07 Mm-hmm.

Steven Bartlett 43:07 ... after doing something that you didn't find fun.

Lilly Singh 43:08 Right.

Steven Bartlett 43:09 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-"

Lilly Singh 43:16 Right.

Steven Bartlett 43:16 ... is the show was by some people well-received, but by others-

Lilly Singh 43:20 Mm-hmm.

Steven Bartlett 43:20 ... heavily criticized.

Lilly Singh 43:20 Mm-hmm.

Steven Bartlett 43:21 Specifically the community, which is the YouTube community you'd come from.

Lilly Singh 43:24 Mm-hmm. Mm-hmm.

Steven Bartlett 43:24 People made very hurtful, very-

Lilly Singh 43:27 Yeah.

Steven Bartlett 43:28 ... shallow cri- criticisms-

Lilly Singh 43:30 Mm-hmm.

Steven Bartlett 43:30 ... sometimes personal criticisms-

Lilly Singh 43:32 Mm-hmm.

Steven Bartlett 43:32 ... about you and the show.

Lilly Singh 43:33 Yeah.

Steven Bartlett 43:35 Unless you're the Superwoman, which is the pseudonym I think you used to-

Lilly Singh 43:40 Yeah. (laughs)

Steven Bartlett 43:40 ... go under, that has got to-

Lilly Singh 43:42 Mm-hmm.

Steven Bartlett 43:42 Doing something you don't enjoy that is not aligned with you and then being criticized for it is like the holy trinity of-

Lilly Singh 43:49 Mm-hmm.

Steven Bartlett 43:49 ... a bad place to be, right?

Lilly Singh 43:50 100%. Even you saying this has given me a fourth pimple on my cheek.

Steven Bartlett 43:54 Ugh.

Lilly Singh 43:55 And I'm sweating because it does, it does-

Steven Bartlett 43:57 Yeah.

Lilly Singh 43:57 ... evoke an emotional response out of me. And it's not just the YouTube community.

Steven Bartlett 43:59 Mm-hmm.

Lilly Singh 44:00 It was the South Asian community that I got critics from. It was the queer community that criticized. Every, in every community there was people, not all, but there were some people that were criticizing me. That's a really hard pill to swallow when I just finished telling you about part of the reason I said yes to this show was to help pave a path. I felt a responsibility to communities. The tough part about being a minority anything is that so many people are counting on you to reflect their experience. The best you can do is reflect your own. The best I could've ever done is talk about my experience and my lived circumstances. That's never gonna satisfy over a billion South Asian people-

Steven Bartlett 44:38 Mm-hmm.

Lilly Singh 44:38 ... queer people, women. That's half of the population right there. There's no way that... And, and that's such a hard pill to swallow to know that you can go out there, try your best, and still because you're the only one, people are gonna criticize you. I think that is not discussed enough about why it's so hard to break through. It's because so many people are counting on you, and it's an unrealistic expectation. I also had to... And this is way easier said than done, and I'm still working on it. I had to learn not... And, and I mean this with love, but I mean this very bluntly, not to take advice from people giving it from inside their comfort zone.

Steven Bartlett 45:13 Hmm.

Lilly Singh 45:14 The amount of people, especially on YouTube, that would criticize the jokes on my show, the delivery on my show, the sound quality of my show without ever, never having stepped foot into a late-night studio. L- as a logical person, I have to, I have to shut that down.

Steven Bartlett 45:32 Mm-hmm.

Lilly Singh 45:33 Because that's the equivalent of me watching basketball and being like, "You missed that three-point shot? Oh my god."

Steven Bartlett 45:38 No.

Lilly Singh 45:38 "I could never make that shot."

Steven Bartlett 45:40 No.

Lilly Singh 45:40 So I really had to retrain my brain to take away value from certain people and add value. If Jimmy Fallon wanted to give me critique on my show, I would've been all ears and taken notes and been like, "Thank you so much." But if some person on the internet who's never done this-

Steven Bartlett 45:54 Hmm.

Lilly Singh 45:54 ... I simply cannot take their critique seriously. And I know some people hear that and they think that's a really perhaps snobby way of looking at things, but not really. No.

Steven Bartlett 46:04 (laughs)

Lilly Singh 46:04 Practically speaking, you cannot take advice from people who are doing it from inside their comfort zone, 'cause they actually don't know what they're talking about. (laughs)

Steven Bartlett 46:12 In that period, and especially in, in the sort of the cloud of that criticism-

Lilly Singh 46:16 Mm-hmm.

Steven Bartlett 46:16 ... was there a particular day where you go, "That was my hardest day"? Emotionally how I felt, where it all just got... 'Cause I've had those moments in my life where-

Lilly Singh 46:23 Mm-hmm.

Steven Bartlett 46:23 ... all the factors just line up on one particular day, and I think, "Fucking hell."

Lilly Singh 46:27 Yeah. Yeah. Yeah. This one's hard to talk about, but for the sake of having honest conversation, in my first season, the first season was by far way tougher than the second. The second I tried to make it more fun. I put more of my team into the staff. I tr- but the first season was really tough. This was the 96 episodes in three months I talk of. This was, um, we didn't even have a showrunner. We had half a dozen writers, which is half of what usually late-night shows have. I was just worked to such an extreme. Like, my, from morning to night was just at that studio. I was a writer. I was trying to produce. I was trying to host. I was just in such a bad state. And one of the tasks that was on my plate because of me, I said I had to do this, was I had to watch every single episode before it would air. So at the end of a shoot day, at like 10:00 PM, I would sit alone in that studio, and I would watch the episode to be like, "Is this good?" And then, (laughs) one of the EPs said, "You don't need to do this. We can watch the show for you. Take this off your plate." And after much convincing, I was like, "You know what? Today I'm so tired I am not gonna watch this episode." This episode was my interview with Jessica Alba, and even though it was not the first episode to air, it was the first one we shot 'cause we shot out of order. This was the very first episode we shot. I'm obviously so nervous. I'm so new to this. I'm trying to be funny. Jessica Alba had made a comment about her kids and how they tied towels on their head in turby twists. And in an effort to try to be funny and try to sound personable and make her kids not embarrassed, I said, "Oh, I have lots of friends that tie turbans." And in my head when I said it, I was like, "It's the coolest thing ever. There's nothing to be embarrassed about." Like, I'm so familiar. Of course not hearing the sentence of towels on heads and turbans in the same sentence and how that could be really problematic historically.

Steven Bartlett 48:16 (laughs)

Lilly Singh 48:17 That was the one and only episode I did not watch before it aired. The one out of 96 (laughs) episodes. And the very next day, I was getting dragged on Twitter. The Sikh community was so upset at me. I apologized profusely, and I remember that day I was just the lowest I've ever been where I thought, "The community that I did this show for is pissed at me because I nervously made a joke out of context." I didn't watch that one episode, so I beat myself up about that, and then I watched every single episode after that again and tortured (laughs) myself all over again. But that was really tough for me to, to, to feel like I let so many people down, to feel that I didn't get the benefit of the doubt of just being a human being that was nervous and misspoke, and then to also...... have this idea validated in my brain that, "Oh, if you don't do 300%, if you don't watch every episode, or if you don't do every job, it's gonna come back to bite you." So that was a very unhealthy moment (laughs) for me, um, and that was a really tough day.

Steven Bartlett 49:15 If I was a fly on the wall that day-

Lilly Singh 49:16 Mm-hmm.

Steven Bartlett 49:17 ... in your room, in your bedroom, what would I have seen?

Lilly Singh 49:20 A lot of crying. (laughs) I think I cried the- like, in my green room that day, I remember my friend actually came to visit me because he was like, "Oh, I know you're in a bad state." I didn't even realize he was there. I was just staring into space. The whole day just- I just felt like crap the whole day, for weeks. I still do. Talking about it, I still feel like crap. (laughs)

Steven Bartlett 49:38 Did you have anxiety at the time?

Lilly Singh 49:40 I developed-

Steven Bartlett 49:41 Or did that happen?

Lilly Singh 49:41 ... it during season one of the show, for sure.

Steven Bartlett 49:42 You developed it?

Lilly Singh 49:43 I never was an anxious person. Um, I think 2019, the show, maybe even leading up to the show, I definitely developed anxiety, for sure, where I would, like, be in my green room not being able to control my body's responses, not being able to control my thoughts. Like, that definitely was something that developed during that first season of Late Night.

Steven Bartlett 50:06 And then the second season, you enjoyed it much more.

Lilly Singh 50:08 I enjoyed it much more because I was able to make some changes. I thought, "We're not gonna shoot in a studio. We're gonna shoot in a house. I'm not gonna do a monologue. I'm gonna do a rant." These things alleviated some of the pressure from me. Um, did I still think it was the most amazing thing we ever made? No. I thought it was better, but the thing is, people had already made up their mind at- after the first season. After that first season, because it wasn't instantly, which is another tough thing about any new voice trying to do every- anything, if you don't impress people right away, they're giving up on you.

Steven Bartlett 50:39 (laughs)

Lilly Singh 50:39 Like, the second season of the show, I truly believe if that was the first season of the show, people would've been like, "Oh, she actually broke the mold. She's doing something different." But you can't get there. You gotta go through the process, trial and error. You gotta- every show in history has taken many seasons to find its voice and find its footing. But it's the- when you're a minority, you're just not given the benefit of the doubt. (laughs)

Steven Bartlett 51:01 Mm.

Lilly Singh 51:01 You know?

Steven Bartlett 51:02 There's something that I really take away from this as well, which kinda goes back to the first question I asked on the topic, which is, um, that even in the face of, like, temptation, I need to make sure that I hold onto my values.

Lilly Singh 51:12 Mm-hmm.

Steven Bartlett 51:12 My professional, you know, my personal values, and, you know, people offering me a Netflix show or whatever, if it compromises my, like, creative and personal values, then I have to say no regardless of temptation until they are going to allow me to do it in line with who- who I am, like the creativity that you have-

Lilly Singh 51:29 Mm-hmm.

Steven Bartlett 51:29 ... that made you successful and the c-

Lilly Singh 51:31 May I- may I offer you a- a-

Steven Bartlett 51:32 Please. Please.

Lilly Singh 51:33 ... devil's advocate perspective here? Because I've also had this conversation-

Steven Bartlett 51:36 Please.

Lilly Singh 51:36 ... in my brain lots and lots of times. I wish that... I'm gonna s- I'm gonna speak from the South Asian experience specifically as well, because that's my lived experience, but I wish we could hold out for when we're allowed to do things exactly how we want to for them to get done.

Steven Bartlett 51:53 Mm-hmm.

Lilly Singh 51:53 I truly believe if w- we were to all do that, nothing would get made.

Steven Bartlett 51:58 Mm.

Lilly Singh 51:58 And I think that everything is progress. And so I think it's balancing the line of, like, I wanna be true to my passion, my vision, but there is a little bit of compromise I have found has to happen. And as painful as it is, that's why I don't regret the Late Night show. I think that compromise had to happen, because when you- when I'm in rooms right now with my production company and I'm having meetings with Netflix and the Hulus and all these people, the room of people giving me notes do not look like me. They still do not. So the option I have is to mold the show into a way that is slightly palatable for them so it gets made so that another show like this could potentially get made.

Steven Bartlett 52:37 Mm-hmm.

Lilly Singh 52:37 And I use Never Have I Ever as an example. The historic show on Netflix was number one in 30 countries. The- because of that show, other shows like that will get green lit. Other South Asian stories will get green lit because of that show. So that show has proved to be a great pa- path paver, for sure.

Steven Bartlett 52:53 Mm-hmm.

Lilly Singh 52:54 Do I believe in my heart that that's the exact show the creators wanted to make and that they didn't have to... No, I think they had to s- understand that progress has to be made. So often when I'm in these rooms, I get irked, and I think, "You're not understanding the cultural nuance. I don't want to cave on this. I don't want to explain to you what Diwali is. I don't wanna have to phrase this like this." I have to ask myself the question, "Is it better to hold my ground and have the show not be made, or is it better to get it made 70% of the way I want it to be made so that the next iteration of the show can be 80%?"

Steven Bartlett 53:28 Mm-hmm.

Lilly Singh 53:28 "And then 90% and then 100?" That is the reality of minority storytelling-

Steven Bartlett 53:32 Mm-hmm.

Lilly Singh 53:32 ... right now. And I wish it wasn't, but that's what it is. So it's

Lilly Singh 53:36 negotiating those- that reality-

Steven Bartlett 53:37 Mm-hmm.

Lilly Singh 53:37 ... a little bit as well.

Steven Bartlett 53:38 And that's not just a- just a minority storytelling thing.

Lilly Singh 53:42 Mm-hmm.

Steven Bartlett 53:42 That's like- I was thinking about various facets of life and business and negotiation-

Lilly Singh 53:46 Mm-hmm, mm-hmm.

Steven Bartlett 53:46 ... when there are multiple factors at play.

Lilly Singh 53:48 Right.

Steven Bartlett 53:48 There are stakeholders who have a say. There are investors.

Lilly Singh 53:50 Mm-hmm.

Steven Bartlett 53:50 There is a timeline that constrains you. There's a limitation on resources, as-

Lilly Singh 53:53 Right.

Steven Bartlett 53:54 ... as you described.

Lilly Singh 53:54 Mm-hmm.

Steven Bartlett 53:55 All of these factors cause an unavoidable compromise-

Lilly Singh 53:57 Mm-hmm.

Steven Bartlett 53:57 ... where you have to go a- you know. But I guess it's that balancing act of, like, what are my non-negotiables then?

Lilly Singh 54:03 Right.

Steven Bartlett 54:03 What am I completely not willing to negotiate on?

Lilly Singh 54:04 Right.

Steven Bartlett 54:05 Um, after the second season of the call-

Lilly Singh 54:07 Mm-hmm.

Steven Bartlett 54:07 ... you get a call saying that the show's not gonna be continued.

Lilly Singh 54:09 Mm-hmm, mm-hmm.

Steven Bartlett 54:10 Tell me about that day.

Lilly Singh 54:12 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)

Steven Bartlett 54:57 Mm-hmm.

Lilly Singh 54:58 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.

Steven Bartlett 55:48 But what did your ego say in that moment?

Lilly Singh 55:50 Well, obviously my ego was br- bruised. Of course my ego was bruised. I didn't do, I didn't do good enough. If I had done better, um, I've let people down. I should have gotten more seasons. This is a bad look. How do I make myself seem like a winner? All of that stuff.

Steven Bartlett 56:07 Yeah, very honest.

Lilly Singh 56:08 Yeah, super honest, 100%.

Steven Bartlett 56:08 I would have gone through the same thing.

Lilly Singh 56:10 Yeah.

Steven Bartlett 56:10 I have things in my life at the moment where I'm in the exact same position where I'm like, "I don't know if I love doing this, but if I was fired (laughs) from doing it or if they said they don't wanna continue-"

Lilly Singh 56:20 Right.

Steven Bartlett 56:20 ... I would be in the same conflict. Like, I think-

Lilly Singh 56:22 Mm-hmm.

Steven Bartlett 56:22 ... there's certain things in my life that aren't aligned with me completely, but at the same time-

Lilly Singh 56:26 Yeah.

Steven Bartlett 56:26 ... you kinda wanna make sure it's done on your own terms. And that's the ego, right?

Lilly Singh 56:28 No one wants to be rejected.

Steven Bartlett 56:30 Yeah, yeah.

Lilly Singh 56:30 No one wants to be canceled.

Steven Bartlett 56:31 Yeah, amen.

Lilly Singh 56:31 No one wants to feel like they could not do something, especially publicly.

Steven Bartlett 56:36 Mm-hmm.

Lilly Singh 56:37 Right? It's not a private rejection.

Steven Bartlett 56:39 Mm-hmm.

Lilly Singh 56:39 It's a public, it's a very public r- type of rejection. So definitely my ego was bruised. Um, and I think more than anything, I learned from that experience that part of the problem is that I easily put labels on myself, and I think we do this to ourselves and we do it with other people as well. I just kept calling myself first late night host, first this, first late night host has to do this and I have to do this. And that pressure, like, I'm not just that. I'm someone who tried really hard at this new thing and had to learn a new... Like, all that context is, i- i- it's worthwhile context. So now when I think about myself through that context, I have more compassion for myself, and it pains me that other people also didn't give me that context, but I can't control other people. I can control myself. I did that to myself. As harsh as other people were to me, I was way more harsh.

Steven Bartlett 57:25 Mm-hmm.

Lilly Singh 57:25 I had put way more pressure on myself and since that experience, I have also learned to not label myself. So I, I just got this new show, this Muppet show, that I was like wanted so badly.

Steven Bartlett 57:37 Mm-hmm.

Lilly Singh 57:37 And I was like, "Oh my God, I have to get this, I have to get this. This is gonna be a life-changing thing." And the day I got it, I had to have a talk with myself to be like, "You are not now the lead of the Muppet show. That's not now your label. You will not now describe yourself as this thing because then that's just gonna be the late night host again. It's gonna be the YouTube sensation again. You are Lilly. You are a complete human being. This is a cool thing you get to do. That's one of your goals. Great. You get to do it. You get to experience it, but this is not now your definition." I think part of that struggle with late night was it just became every part of who I was.

Steven Bartlett 58:07 Mm-hmm.

Lilly Singh 58:07 And so people weren't criticizing the show, they were criticizing me. They were criticizing every part of me and who I was.

Steven Bartlett 58:12 Mm-hmm.

Lilly Singh 58:12 And that's just a really unhealthy boundary. (laughs)

Steven Bartlett 58:15 Amen.

Lilly Singh 58:15 You know?

Steven Bartlett 58:16 And people do that. I, I've noticed I've done that more in my life when I didn't think I was enough, so my, my identity or the label-

Lilly Singh 58:22 Mm-hmm.

Steven Bartlett 58:22 ... would make me make sense to the world. It would make me, you know, put me in a community. I'd become social media CEO.

Lilly Singh 58:29 Mm-hmm.

Steven Bartlett 58:29 And then the problem is social media CEO or any of these labels you described comes with a set of implicit instructions on how to behave and how to be and how to act.

Lilly Singh 58:37 Mm-hmm.

Steven Bartlett 58:37 And that can be really imprisoning. Generally, I wro- there's a chapter in my book called Resisting Your Labels-

Lilly Singh 58:41 Mm-hmm.

Steven Bartlett 58:41 ... because of how imprisoning they've been in my whole life. And also, you know, as we're gonna go into with you now, when I left my label, so when I was no longer a social media CEO-

Lilly Singh 58:49 Mm-hmm.

Steven Bartlett 58:49 ... I had a bit of an existential crisis-

Lilly Singh 58:50 Mm-hmm.

Steven Bartlett 58:50 ... and life goes, "Well, just go be another one again-"

Lilly Singh 58:52 Mm-hmm.

Steven Bartlett 58:52 "... because that's what you are." And I think that's when people have these, like, midlife crises where they realize they spent the last 10 years or whatever s- b- being the label and not the person.

Lilly Singh 59:00 Mm-hmm.

Steven Bartlett 59:01 You leave, um, the late night show. How was life like for the next year?

Lilly Singh 59:06 Well-

Steven Bartlett 59:06 And the pandemic rolls in.

Lilly Singh 59:07 Th- exactly, that was right around the time of the pandemic. So I think that was a very strange time because I couldn't bounce back into anything else really.

Steven Bartlett 59:15 Mm-hmm.

Lilly Singh 59:16 Everything was shut down. And my plate was pretty empty 'cause my gigs were canceled, my travels were canceled, projects were canceled. Everything was paused. So it was a very t- hard time to let go of something that was keeping you busy-

Steven Bartlett 59:29 Mm-hmm.

Lilly Singh 59:29 ... and that was how you defined yourself. Through the pandemic, and I think a lot of people can agree with this, the biggest silver lining was the work I was forced to do on myself and is when I wrote this second book, Be a Triangle. Because the thing about the pandemic was, it wasn't just that I didn't know what to do with my time. It was that it was the first time I was faced with the reality of me not believing I had any value 'cause I didn't have work. And that was a sad, scary realization for me. It was the first time my schedule allowed me to sit there and be like, "Now I am alone and I'm with my thoughts and I feel like I'm ceasing to exist as a person 'cause I don't have a purpose and I don't have value." And that's really sad because that means every time work goes away, I will feel this way, and that's not set u- that's not what I want. That's not setting me up for success. That's not setting me up for a spiritually happy life. And so I did the work to really dive deep into my soul and be like, "You're gonna figure this out." And what I came to the conclusion of is that I don't have any original thoughts when it comes to who I am as a person and what I want out of life and what I value out of life. Everything I've operated on has been what people have told me, whether it's school, whether it's my parents, whether it's society. I have never given thought into what it is I actually want. I never thought that was an option. It sounds ridiculous to say, but I guarantee you, people that are listening to this will act- actually also think and be like, "Wait, ha- have I ever done that? Have I ever stopped to be like, let me work on myself like a project and let me actually think about life as it's the greatest project ev- I'm ever gonna work on?" And so I vowed during the pand- pandemic to create a strong foundation for my life. Well, what does that mean? 'Cause that's a fluff word, and you know I hate fluff words.

Steven Bartlett 1:01:09 Mm-hmm.

Lilly Singh 1:01:09 You, I've already expressed I hate fluff words. And so how I define a foundation is I wanted to create a safe place in my mind that I could return home to...... that was not connected to anything external and not connected to what was happening in my life. Because my biggest fear was that the pandemic would be over and then I would have work stuff happening again, and then again, I would just teeter to happy, sad, success, fail. Whatever was happening in my life, I would change to my core and I didn't like that. I wanted to create something that was true to me, and no matter if I won 15 Oscars tomorrow or I failed tomorrow, that safe place in my mind would still exist. And so that's what I did in this book. Um, I came up with four things that I don't think will ever change in my life to make up the foundation of that safe place in my mind.

Steven Bartlett 1:01:52 And that's why you call it-

Lilly Singh 1:01:55 Well, good, good, good, good question.

Steven Bartlett 1:01:56 ... The Triangle.

Lilly Singh 1:01:56 He's like, "So the Illuminati?" (laughs)

Steven Bartlett 1:01:58 No, (laughs) th- the, the triangle.

Lilly Singh 1:01:59 Yeah.

Steven Bartlett 1:01:59 Yeah, yeah.

Lilly Singh 1:01:59 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.

Steven Bartlett 1:02:58 And what is the, what constitutes your foundation? What are the ingredients of your foundation, if it was a recipe?

Lilly Singh 1:03:03 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.

Steven Bartlett 1:03:45 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.

Steven Bartlett 1:04:26 On the point of distraction-

Lilly Singh 1:04:27 Mm-hmm.

Steven Bartlett 1:04:27 ... which I was gonna talk about, 'cause it was, it was a big part of your book-

Lilly Singh 1:04:29 Mm-hmm.

Steven Bartlett 1:04:30 ... 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-

Lilly Singh 1:04:35 Mm-hmm.

Steven Bartlett 1:04:35 ... 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-

Lilly Singh 1:04:44 Mm-hmm.

Steven Bartlett 1:04:44 ... and busyness to avoid stillness-

Lilly Singh 1:04:47 Mm-hmm.