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Lilly Singh

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108
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2022-04-21
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2022-04-21
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  1. A lot of crying. I think I cried 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 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  2. Have this idea validated in my brain that oh, if you don't do 300%, if you don't watch every episode, if you don't do every job, it's going to come back to bite you. So that was a very unhealthy moment for me. And that was a really tough day.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  3. Was the one and only episode I did not watch before it aired the one out of 96 episodes and the very next day I was getting dragged on Twitter the sick 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 myself all over again but that was really tough for me 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 to also

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  4. I was like, you know what? Today, I'm so tired. I'm not going to 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 because we shot out of Orange. It 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, chirby twists. 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  5. 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. But the first season was really tough. This was the 96 episodes in three months I talk of. This was, 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 p.m., I would sit alone in that studio and I'd watch that episode to be like, is this good? And then 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  6. Take away value from certain people and add value. If Jimmy Fallon wanted to give me critique on my show, I would have been all ears and taken notes and been like, thank you so much. But some person on the internet has never done this. 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, practically speaking, you cannot take advice from people who are doing it from inside their comfort zone because they actually don't know what they're talking about.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  7. 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. 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. Is a logical person, I have to shut that down. Because that's the equivalent of me watching basketball and being like, you missed that three point shot. Oh my god. I could never make that shot. So I really had to

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  8. 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 have ever done is talk about my experience and my lived circumstances. That's never going to satisfy over a billion South Asian people, queer people, women, that's half of the population right there. There's no way, and that's 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 going to 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  9. 100%. Even you saying this has given me a fourth pimple on my cheek. And I'm sweating because it does evoke an emotional response out of me. And it's not just the YouTube community, it was the South Asian community that I got critics from. It was a queer community that Chris says. 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 that part of the reason I said yes to the show was to help pave a path. I felt a responsibility to communities.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  10. Longevity more than anything else. Even money, ask any person with a lot of money. You'll go tired of money. You'll go 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 going to 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? What is this? 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 because you will never go tired of those things.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  11. 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 want to 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 this 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  12. 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 going to 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. 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 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 every night. I don't think my mom could tell you what Jimmy's last name is. Like they never watched late night. I never grew up with that experience. So it wasn't my desire. It wasn't my passion to be a host.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  13. I'm trying to highlight that. It was very difficult for me to go into the system being the control freak guy and being the disruptor and just try everything to disrupt it. And it's just too rock solid to be disrupted.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  14. Absolutely. From day one, I thought this is going to be very hard. Gonna be very hard to make something that I'm proud of here. 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 going to be able to deliver on this. There were episodes. I vividly remember this. There was 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 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 and I said, this is not funny. And this is not good. And I don't want to go out there and I don't want to 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  15. 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 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  16. 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 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 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 formats you can do things differently but it has to start with a monologue So you're gonna have to come out, you're gonna have to hit the mark, you 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 is to no discredit to the writers. I just had such few writers that were too overworked. There were 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  17. Because I don't think the thing was good, and I'm not necessarily proud of it, you know, when I got the show, again, me being disruptor the whole first season, 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. 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 issue is the system is not built to do things differently.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  18. She's just as weird in both instances. I can tell you that she's just as weird. She's just as quirky, but one of them was a definitely a bit more performative, 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 she was doing. I think after I turned off the camera, it was like, oh God, I gotta edit this thing. I gotta do this thing. I got to go through these. There was no growth. It was just such a repetitive pattern. As a creative, I didn't want that. If I wanted that, I would have just done the grad school thing, right?

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  19. 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 I'm not creative. I felt not free. And I felt like... Even though 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 is 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 same I never wanted in the first place, which is to be trapped in something like that. And so it stopped feeling right to me. It stopped feeling like the place that I could grow and learn and thrive.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  20. 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, and feeling like you haven't given yourself permission to grow.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  21. In order for me to fulfill my ambitions, I want to do stuff with movies and TVs and I want to just do all this other stuff that is me growing in my craft, I cannot stay the same. You have to make space for that. I also always think about if I have, again, 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. You have 100. So where are you going to put that energy? It can be to old habits. It can be to holding on to relevancy. But then that limits how much energy is left for growth. So it really is just a decision you have to make of making room for growth.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  22. You're absolutely correct. I think one of the reasons I, for so long, kept holding on to the strings of YouTube to be like, no, I want to do other stuff, but I'm still going to do this. I want to do other stuff, but I'm still going to make these videos. I'm still going to dress up as my parents was that. It was that I didn't want to lose this traction I had, this audience I had, this instant gratification I had of having this massive audience that 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 way to measure people based on relevancy. This 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  23. That I'm saying, I just want to tell stories that are important. 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 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 just tell kids, I'm like, no, that kid's gonna grow up and they're not gonna become anything if you just tell them they're enough. Again, I still think that there's an 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 it has become apparent to me that being mindful, feeling like you're enough,

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  24. 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 my priority. I need to prove this troll wrong. I need to get this rating. And then the second I was like, you know what? My purpose is to disrupt. I know what my values. I'm a complete person already. Suddenly that stuff became way less important to me. Suddenly I was like, oh, actually my priority is going to be. I want to tell stories that I think are really meaningful. I'm not saying that it has to be a box office breaker.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  25. 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 am my job. This is what defines me. If anyone asks me who I was, I would never answer as. Patient friend, I'm a nice, I would be like, I'm in this show, I mean, that's how I would, or I would define myself by my struggles, which is another whole thing, not by ever my potential. I would never say, I'm someone who's gonna change the world because of X, Y, Z. 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

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  26. 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  27. 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 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  28. 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 in how you assign value to yourself, how you assign value to other things. For most of my life, I've hustled so I built an entire brand out of hustling. Anyone that knows anything about me is a hustle harder, hustle. She wrote how to be a boss or first book. 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 what you thought it was going to be. 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 going to give me. And it probably never will because of this value we've assigned to all this stuff.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  29. Yes, a happiness is often right here. We can't see it because we're still trying to chase it that way. We're still trying to, it's always the. It's in the future mentality. Happiness will come, success will come, these things will come. Maybe it's like right now.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  30. 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, win, win, win, when does that stop?

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  31. 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 and say that mixed with ego. Once you get a bit of success, I think Jay-Z says success is the most addictive drug. It is once you distrapped and it comes up the other end and you see how amazing it is. You're like, I just keep doing this, I need to keep doing this. I need to keep disrupting. I need to, that's been something I've had to.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  32. It's that I also will be really honest. I thought that that moment of 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. 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. It's still that I was the only female late night host. And so when I was at that seat in that table surrounded by men, that chip was just reinforced.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  33. 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 what disruption can do. It can make progress. Progress comes from destruction and breaking systems. And so I think that for me was a very, and I remember it so vividly because it did leave such an impact on me. But that for me was like, look, this is what disruption can do. This is what the uncomfortable process results in.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  34. First World Tour after becoming a YouTube success, I very purposely announced it in India. I was like, I want to 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 there to 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 adult before. This was the grandfather where and I hold nothing against him because again, I respect people's circumstances, but he was the one that didn't want to hear about a daughter, who didn't believe a daughter in the family would be worthwhile. He was standing outside of his house and greeted me with a flower garland. And he said the words to me. This is like an 80-year-old Indian man said the words to me.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  35. I have asked that question to myself as well. Why is it that no matter, and this is where it can be to a detriment sometimes, because sometimes I'll take simple, simple tasks that 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, it's absolutely exhausting. And I've tried to figure out 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

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  36. So, when you ask me that question between that time period, what was it about Lily? It's that Lily 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. Everyone on my team knows that's the worst thing you can say to Lily. This is how things are traditionally done. I just don't accept that with anything.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  37. Disrupt because it is just who I am as a person. And I know this even on the personal side. The first openly queer person to host a late night show, the first woman of color, I've just been associated with so many first and I used to hate it. I remember thinking and telling my therapist, I don't want to 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 want to do what I love doing. And my therapist joked and said, yeah, you need to pick a cause. 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 want to 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  38. This is required a lot of reflection because I was trying to think recently what my purpose is, going back to our previous conversation. What is my purpose? Because 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 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 you're talking about, can be summarized in one word and that is disruptor. I think my purpose is to disrupt. And I think I've 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 a continuously feel the need to disrupt, not because I'm actively trying to

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  39. Yeah, 100% is what you said at. 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 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 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 struggles are worth it. I think the pain is worth it to get on the other end.

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  40. What actually helps me when I'm going through pain and I can't see myself coming out the other side is truly 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? Actually, 100% right now. I sit here at 100%, but we all sit here, everyone watching actually you sit at 100% right now, no matter what

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  41. And not acknowledge that 10 years from now, I will probably say the same thing about the pain I'm experiencing today, something to always keep in mind. 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 wife is never going to get worse than this. I remember thinking that I'm going to 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. 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.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  42. Because it's interesting. And I 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. 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.

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  43. Yes, I think for a lot of my teenage years, 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 my parents' context, which has really, really helped me in their 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 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 all.

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  44. Not that big. Not that big at all. I think I had my views were in the thousands probably 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. But this was a... A lot of hustle to get to even a thousand. I know this because I made Justin Bieber never say never parody when I had a thousand subscribers. I was like, I've made it, baby.

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  45. The moment I walked into my parents' room and I said, I want to make YouTube videos, what I actually was doing five minutes before that is I was 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 going to do well in this. And so I really had to shift my focus somewhere else. And that literally five minutes later, I went to my parents' room and I said, I can't do this. I want to try making videos on the internet. And they were like, Say what now? 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 want to 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 also had a bit of a time period that I had to figure things out in, which was a huge blessing because it made me every moment for that year.

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT

  46. I was applying to grad school. I had just finished graduating and I was applying to grad school. And let me put an asterisk to my last comment. I'm sure my parents could call me lazy from time to time. It wasn't lazy as much as it was as it was. My heart is not in this thing. So I do not think it is worthy for me to put my energy into it.

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  47. It's also very problematic when you're obsessive over something that is governed by numbers. 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 because I would actually, and this is 2010 before YouTube had very complex analytics. Now you can see you can know how many people with dogs on their laps are watching your videos like it's intense 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 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.

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  48. Once I started making YouTube videos, I was obsessed with it. I was obsessed with learning how to do it well, 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, this type of obsessive personality.

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  49. 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 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 adult. I could express myself in a way that's like on my own terms. There is 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.

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  50. 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, I just knew they would understand that. And so for me to have an impact. Course, I want to help people, of course, I want to 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

    2022-04-21 · The Diary of a CEO · Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements · IDENTIFIED FROM THE TRANSCRIPT