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Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements

Episode 2022-04-212022-04-21English

Guests: Lilly

Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements
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§01Transcript — part 1

00:00The thing I think about most, especially when I'm on the go, but also when I'm sat here in the Diary of a CEO studio, is the Wi-Fi and internet that we have to work with.

00:08In fact, any time I'm filming away from the studio, one of the first things I do is when I arrive, I open up an app and do a speed test to see how strong the signal is.

00:16And the number of screenshots I've sent to my team about Wi-Fi signals at different locations is actually pretty crazy.

00:21It matters that much to me because it's such a competitive advantage to have fast Wi-Fi.

00:26Because on any given day, if I'm recording, let's say, hours and hours of footage with a podcast guest, I then often have to have my team send that across to our London team who then do the edit.

00:35So fast Wi-Fi and internet is not a nice to have.

00:37It is absolutely business mission critical.

00:39So when it came to finding the best provider who could supply internet and Wi-Fi to our new LA studio, which I'm sat in right now, we looked at every single option.

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01:15I wanted to be powerful and have influence because I wanted to prove people wrong.

01:21You can't surf the internet for very long without stumbling upon Lilly Singh.

01:24Lilly Singh!

01:25Lilly Singh!

01:26I was born into the reality of being...

01:30a disappointment right away.

01:31There were rules about being a woman.

01:34My mom did not grow up with queer culture.

01:36So for me to expect her to operate from a place of my lived experience, how is that math ever going to add up?

01:43Welcome to the first episode of A Little Late with Lilly Singh.

01:47You got given a late night show.

01:48When I said that, you said, I'm so sorry.

01:49Tell me why you said that.

01:51Because I don't think the thing was good.

01:54The 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.

02:02Did you have anxiety at the time?

02:03I developed it during season one of the show.

02:06Is the struggle worth it?

02:08For me, yes, it is.

02:09I believe in what I believe so much more than the hurt that I feel.

02:14So without further ado, I'm Stephen Bartlett, and this is the Diary of a CEO USA edition.

02:19I hope nobody's listening, but if you are, then please keep this to yourself.

02:31Lilly, thank you for being here.

02:33It's a real honour.

02:34And we've got a mutual friend in Jay Shelley who's really spoken so incredibly highly of you.

02:37And then when I got a chance to delve into your story, I became pretty fascinated by many things.

02:43I want to start because I always believe that the foundation of everybody that I sit here with, and also myself, having studied some childhood psychology, is their childhood.

02:53So I guess the question I had for you is...

02:56When you think about 10-year-old Lilly and the lessons she had learned by that age about the world and life, what were those lessons and where did she learn them from?

03:06The lessons at the age of 10, I don't think were necessarily beneficial ones.

03:12I was...

03:14Born into the reality of being a disappointment right away, being the second daughter in an Indian family.

03:20I was told in my 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.

03:31So that really colored in a lot of my childhood because whether it was ridiculous things like...

03:37Oh, you know, girls aren't supposed to talk that much.

03:39Ridiculous things like girls aren't supposed to whistle.

03:42Whatever girls weren't supposed to do was very apparent to me from a really young age.

03:46So the lessons I was taught that there were rules about being a woman.

03:50There was expectations about being a woman.

03:53And I had to.

03:54Fit that mold if I wanted to be

03:58Not even accepted, but if I want to make people proud, I think more than anything.

04:02I 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.

04:10And so a lot of my upbringing was a little bit of this.

04:14simultaneous, I need to fit the mold, but then this rebellious side of me being like, but I don't want to, and kind of negotiating that balance.

04:23What you said about your grandparents wanting a boy, and generally in an Indian culture, there being a desire to have a boy, how did that impact you?

04:30I read that you were a tomboy growing up.

04:32Yes.

04:32Yes, yes, yes.

04:33I was obsessed with Dwayne The Rock Johnson.

04:35I loved wrestling.

04:36I wore baggy clothes.

04:37I rebelled in every such way because of this expectation that was set upon me.

04:42I think in my adult life, I have learned, and I don't think I knew this growing up.

04:45I don't think I even knew this years ago.

04:47I think this is a quite recent revelation.

04:50And that experience has put a very heavy chip on my shoulder that I carry in my adult life.

04:55And 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.

05:02But now I fully embrace it.

05:03And that chip on the shoulder is for 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.

05:16In every instant, 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.

05:26And that has followed me.

05:27into my adult life.

05:28And 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.

05:34And so even when I started making YouTube videos in 2010, a lot of people asked me, why did you do that?

05:39And I can give you the answer that I think people want to hear, which was, I wanted to create a path and no one else was doing what I was doing.

05:45And 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.

05:55I think that has always been that chip on my shoulder.

05:58I wanted to prove that being a girl was worthy of celebration.

06:02And so that has been a thing that has followed me.

06:03So that is truly the chip on my shoulder that now I'm just fully transparent about.

06:08When I think about my own insecurities 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.

06:16So when I was a kid, only black kid in an all white school, parents with a broke family in a perfect white picket neighborhood.

06:24And so my pursuit in life was like, if I had the things that I'd missed as a child, if I had money and if I was, I don't know, famous or whatever, then it would be filling some kind of childhood void.

06:35I wonder 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

06:42I think it's more so that the people who are the most powerful in my upbringing were men.

06:48They were the men in my family, the men at a family party that were in the corner.

06:52They got to control the conversation, what they said goes.

06:55Men notoriously in Indian culture.

06:57are the decision makers, the powerful people.

07:00And I know one thing that the men in it, and I don't want to paint all Indian culture men, but I'm just saying as a kid, it was evident to me that the uncles made the decisions.

07:09They got to decide what was acceptable, not acceptable.

07:12And so I knew one thing that

07:15the men would understand was power, money, and influence.

07:19And so I think I strived for a career that would give me those things so I could kind of prove a point to them.

07:25Being like, you may not understand my value in any other way aside from money, power, and influence.

07:29And to some extent, I was not wrong.

07:31I've done a lot of cool things in my life, but the things that...

07:35Really made my dad and my uncles go wide-eyed were things like the Forbes list, were things like, oh, she's in a headline.

07:42She has her own show.

07:42Those are the things that they understand to be a value.

07:45And I'm not saying that's right or wrong, and I'm not trying to dissect if it's right or wrong.

07:48I just knew they would understand that.

07:50And so for me to have an impact,

07:53Of course, I want to help people.

07:54Of course, I want to pave the path.

07:55That's all true.

07:57But those are not the things that the people that had power as a kid for me would understand.

08:01They understand power, money and influence.

08:02So I would be lying to say that that wasn't a driving factor.

08:06And so you moved to LA, your YouTube career starts really gaining traction.

08:09You said a second ago that you...

08:11Pursued YouTube because of, you're very honest, power and influence, right?

08:15But when you start on YouTube, there's no guarantee of power and influence, right?

08:18I know your first video did like 70 views or something crazy.

08:20Yeah, yeah, yeah.

08:21So when you started YouTube, a very strange thing to be doing back then, recording yourself, especially doing...

08:27Like funny stuff in your room or whatever.

08:29For sure.

08:30What were you thinking?

08:31Like, what was the...

08:32Yeah, I was thinking a few things.

08:34One was that I was always a very creative kid.

08:37I was the kid that wanted to be the center of the dance circle at a family party.

08:41I watched Ace of Cakes.

08:42I wanted to bake cakes.

08:43I wanted to be creative through any means necessary.

08:45But I think I was convinced that creativity was a phase, that it's something you do as a pastime, as a kid.

08:52Your career shouldn't be creative.

08:53You let go of that.

08:54You get a real job, et cetera, et cetera.

08:56When I was in university and I discovered YouTube, it was a glimpse of...

08:59I could be creative as an adult.

09:02I could express myself in a way that's like on my own terms.

09:07There is no gatekeeper.

09:08There's no rules.

09:09This was something that I got to make the rules about.

09:12I got to decide.

09:13I built a little community of people that also were in a little bit of a dark place.

09:17So I got this sense of connection that I wasn't getting in real life.

09:20And the real, real talk of it is that I'm an obsessive person.

09:24Once I started making YouTube videos, I was obsessed with it.

09:28I was obsessed with learning how to do it well.

09:32Exploring how else I could be creative, learning how to get more views, learning how to market myself.

09:37I, with everything I do, I'm a very all or nothing person, which has been a great pro, but also very detrimental in my life.

09:45This type of obsessive personality.

09:47Especially if you become obsessed about something that isn't fully aligned, right?

09:51Which is possible, right?

09:52Because there can be two conflicting forces.

09:53The force can be, I want to be really successful.

09:56And then the other force can be saying,

09:57Well, this isn't my purpose.

09:58Right.

09:59They can surely come into conflict.

10:00It's also very problematic when you're obsessive over something that is governed by numbers.

10:07That is a very dangerous combination.

10:09When you're obsessive and your success is measured by views and subscribers and stats, that is a bad recipe right there.

10:16Because I would actually, and this is 2010, before YouTube had very complex analytics.

10:22Now you can see, and now you can know how many people with dogs on their laps are watching your videos.

10:26Like it's intense how many analytics you can get.

10:29Now, back in the day, that wasn't the case.

10:30So 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.

10:40And 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.

10:50Before that YouTube phase with the spreadsheets and stuff like that, did people consider you to be a lazy person?

10:57Did they, like, count you out?

10:59One thing I can say is I've been called a lot of things in my life.

11:02I have never been called lazy.

11:04So when you look, because that phase before the YouTube and the spreadsheets, right?

11:09What were you doing in your life at that phase?

11:11So I was applying to grad school.

11:14I had just finished graduating and I was applying to grad school.

11:18And let me put an asterisk to my last comment.

11:21I'm sure my parents could call me lazy from time to time.

11:24It wasn't lazy as much as it was.

11:27My heart is not in this thing.

11:29So I do not think it is worthy for me to put my energy into it.

11:33That's what I was getting at.

11:34Yes.

11:34Which is how someone can go from being perceived by their parents, or in my case, by school, as being, I got kicked out of school for the same thing.

11:42And then just years later, they can see that I'm obsessed when something is in line with, something has caught me like a fish on a hook.

11:48Right, exactly.

11:49For better or for worse.

11:50Maybe it's caught one of my insecurities and dragged me off into the future or whatever.

11:53But 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.

11:58Because 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.

12:09And it was bad.

12:10And I was like, I'm not, this makes no sense.

12:11I don't even care about the outcome of this.

12:13I closed my laptop right then and there.

12:14And I said, if I don't care about this, I'm not going to do well in this.

12:17And so I really had to shift my focus somewhere else.

12:20And that literally five minutes later, I went to my parents'room and I said, I can't do this.

12:24I want to try making videos on the internet.

12:26And they were like,

12:28Say what now?

§02Transcript — part 2

12:29This was in 2010.

12:30And they gave me the best advice ever and the best blessing ever, which was you have a year.

12:34So they also gave me a bit of a ticking time bomb.

12:35They said, you have a year to try whatever you want to try, whatever this YouTube thing is, you have a year.

12:39And if it doesn't work out, you will go to grad school and you will do exactly what you were doing five minutes ago.

12:44And 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 work on making this pop off.

12:57That conversation with your parents, how big were you on YouTube, if at all?

13:00Not that big.

13:01Not that big at all.

13:02I think I had like, my views were in the thousands probably.

13:06Okay.

13:07And this was 2010, like I said.

13:08So I vividly remember when I hit 1,000 subscribers.

13:12Now your cat can meow and you will have like 10,000 subscribers.

13:17But this was a...

13:19A lot of hustle to get to even a thousand.

13:21I know this because I made a Justin Bieber never say never parody when I had a thousand subscribers.

13:26I was like, I made it, baby.

13:29When you reflect now on the role that your parents were playing in your life, like even then, like having to go to them and them like granting you this year, it all sounds incredibly like imprisoned.

13:39You know what I mean?

13:40Yes, I think for a lot of my teenage years, my young adult years, I probably viewed it like that.

13:47I no longer do.

13:48I'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.

13:58So I actually think a lot of what they did, although at the moment didn't seem right.

14:03And even now, a little questionable sometimes, it actually really helped me.

14:06Like 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.

14:13You 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.

14:19So I actually don't hold that against them at all.

14:21It's really interesting.

14:22Mo Gowda, a guy that came on this podcast, said that when he used to work at Google, when they interviewed people and said,

14:27you erase the most traumatic or difficult moments of your life, knowing that it would erase all the lessons it taught you as well and everything that came with it, would people do it?

14:3799% of people said they wouldn't.

14:38No.

14:38And there's an interesting thing about how we look back on our trauma because we also don't know the other outcome.

14:43Because it's interesting.

14:44It's...

14:45And I agree.

14:46When people ask me in interviews, what would you say to your younger self and what would you change?

14:49I 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.

14:57That's the exchange of the universe.

14:58And that's just how things work magically.

15:02And 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

15:11I will still sit here today and think that the pain I'm experiencing today is intolerable and not acknowledge that 10 years from now, I will probably say the same thing about the pain I'm experiencing today.

15:20Something to always keep in mind.

15:22We 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.

15:29It always does.

15:31And we always think that it's still the worst pain.

15:33When you were a kid, you thought, I remember when I was a kid, my mom, I said I couldn't get this shirt.

15:37It said Backstreet Girls on it.

15:39And I remember thinking this is the worst day of my life.

15:41And my life is never going to get worse than this.

15:43I remember thinking that I'm going to run away.

15:45My mom hates me.

15:45She won't let me be a Backstreet Girl.

15:47How dare her?

15:47And then years, years later, something else happened.

15:50I thought that was the worst.

15:51And we keep doing that as humans, don't we?

15:53We keep thinking that whatever this is today, this is the worst.

15:56That perspective.

15:57Completely true.

15:58Completely true.

15:59Been through it myself a million times.

16:00I always say, you know, this is, the current crisis always feels like the fatal one until hindsight tells you that the current one is the fatal.

16:07Right.

16:08But what does, even knowing that, it still doesn't seem, in my case, to stop the current crisis feeling fatal.

16:16It helps a little bit, takes the edge off.

16:19But when we're in the heart of the storm for whatever reason, what else helps you to gain perspective on the situation?

16:25I mean, like, really, I don't mean like the advice that we give in our books and stuff.

16:29I mean, what actually helps?

16:31What actually helps me when I'm going through pain and I can't see myself coming out the other side is...

16:38Truly, 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.

16:48I just have this brain that likes processing things.

16:51And so I think about, okay, what is my success rate of getting through things?

16:58it's actually 100% right now.

17:00I sit here at 100, but we all sit here, everyone watching actually, you sit at 100% right now.

17:04A couple of degrees.

17:05Yeah, 100% is where you sit at.

17:07So I think about things through that lens, but I also think about just, is the struggle worth it?

17:12And...

17:14For me, yes, it is.

17:15I believe in what I believe so much more than the hurt that I feel.

17:19And that's the balance I think we need to keep in check is, is it worth it?

17:22Is your struggle worth it?

17:23And I think you really need to do the work to make that answer yes.

17:26And I didn't.

17:27always operate from a yes, but I think now I do.

17:30I believe I found my purpose.

17:32And 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.

17:38So for me, I think my struggles are worth it.

17:42I think the pain is worth it to get out on the end.

17:45You became a hugely, I'm going to loop back to that topic in a section, but to give the listeners a context, you became a hugely, hugely successful social media star, creator, whatever you want to call it.

17:58Built one of the biggest YouTube channels still to this day.

18:01Some millions and millions of subscribers.

18:03That makes you in the 0.0 whatever percent anomalies in the world.

18:08So I hear the obsessive thing.

18:10You said about the spreadsheets.

18:11I guessed that.

18:12I thought for her to get there, she must be pretty obsessive.

18:14I walked in here and you were like, oh, she has Google Doc written all over her.

18:18Well, there's like, but we all, I think at times in our lives, probably look back and think, I was also probably toxic obsessive.

18:25You know, because the things that I was, you know, especially when you're in the numbers business and the metrics business.

18:29So what else about you when you think about that phase of your life from 2000 and, you know, maybe 13 when you hit a million subs to where you hit 14 point whatever, 7 million subs.

18:41What was it about Lilly outside of the obsessive part that made you?

18:47Such an anomaly through that phase of like career success on YouTube?

18:53This has required a lot of reflection because, um,

18:57I was trying to think recently what my purpose is, going back to our previous conversation.

19:01What is my purpose?

19:02Because I thought my purpose was specific projects I would work on, specific things in the industry.

19:07And I kept thinking, that's too small.

19:09That's such an in-the-moment purpose.

19:11What is your greater purpose?

19:12So I had to go look back through my life recently and be like, what is the common thread here?

19:17And the common thread between everything, especially during this time period you're talking about, can be summarized in one word, and that is disruptor.

19:24I think my purpose is to disrupt.

19:26And 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 L.A., but through YouTube, where there are no gatekeepers from

19:40the first late night host, wherever that historic moment was.

19:43I continuously feel the need to disrupt, not because I am actively trying to disrupt, because it is just who I am as a person.

19:51And I know this even on the personal side.

19:54The first openly queer person to host a late night show, the first woman of color.

19:59I've just been associated with so many firsts and I used to hate it.

20:02I remember thinking and telling my therapist, I don't want to be the first.

20:06I don't want to be the first anymore.

20:08I hate being the first.

20:09I don't want the pressure of all this.

20:10I just want to do what I love doing.

20:13And my therapist joked and said, yeah, you need to pick a cause.

20:15You got a lot of things going.

20:16You have to pick an issue.

20:18But I have since embraced that.

20:20Instead 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.

20:27To disrupt.

20:27It is just how I am built.

20:29I am built to break systems and molds.

20:31Again, not because I'm actively trying to stir the pot, but because it is just how my brain and my being operates.

20:38I have to break molds.

20:41So when you asked me that question between that time period, what was it about Lilly?

20:45It's that Lilly always would ask the question of how else can this be done and why isn't this being done this way?

20:51And maybe there's a different way of doing it.

20:53And when she gets told that this is the way things usually are done, I just simply do not accept that.

20:58Everyone on my team knows that's the worst thing you can say to Lilly.

21:01This is how things are traditionally done.

21:02I just don't accept that with anything.

21:07Clearly you're someone who's built a lot of evidence that...

21:09The look you just gave me is the look my parents give me.

21:11Just like...

21:11No, yeah.

21:12Do you know what?

21:12There was so much going on in my head.

21:14I was thinking about different ways to take that and different feelings I got from that.

21:17One of them, honestly, was like...

21:20Especially hearing the obsessive thing.

21:21Listen, when I ask these questions, I'm not, because I think, because I relate to so much of what you're saying.

21:25I'm asking the questions to dig deeper, not because I disagree.

21:29No, I love it.

21:30I love it.

21:30But it's just, the look is like my parents looking at me like, yeah, great.

21:34She likes to disrupt.

21:35Yeah, because my brain went, my brain went, oh my God.

21:38she's so, even when you were delivering it, so passionate that I felt, I was like, she must have, that's exhausting.

21:43To be obsessed, it's exhausting.

21:44On the other hand, I was thinking, why is your brain wired to disrupt things?

21:49Like, why?

21:49So I understand from an innovation perspective, it's going to be fruitful.

21:53You're going to create new things.

21:55But why is that your predisposition?

21:57Going back to your childhood and saying, I think so.

21:59You didn't like the system?

22:00I have asked that question to myself as well.

22:02Why is 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.

22:12Maybe there's a different way to throw a party.

22:14Maybe there's a different way to have a friendship.

22:15Maybe there's a different way to decorate my house.

22:17And every aspect I have to disrupt, and it is exhausting.

22:20It's absolutely exhausting.

22:22And I've tried to figure out why, what is it in me?

22:25I'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.

22:33I was already that.

22:34And I think that's just me stepping into my power, fully embracing that's who I am and being like, fine, I'm not going to reject that.

22:41I am going to fully embrace that's my purpose in life.

22:44Because another thing is.

22:46You 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.

22:53So in my adult life, when I announced my first world tour, after becoming a YouTube success, I very purposely announced it in India.

23:01I was like, I want to announce the tour in India.

23:03I want the first stops to be in India.

23:05I know that's where, you know, my great grandparents are.

23:07I know that's where my parents are from.

23:08I know it'll mean the most.

23:09It'll have the biggest impact.

23:10So 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.

23:16I had never met him as an adult before.

23:19And.

23:20This 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.

23:27about a daughter who didn't believe a daughter in the family would be worthwhile.

23:32He was standing outside of his house and greeted me with a flower garland.

23:36And he said the words to me.

23:37This is like an 80-year-old Indian man said the words to me.

23:41I was wrong.

23:42You have made this family more proud than anyone else could have ever done.

23:45And he showed me all these newspaper clippings he had saved with me.

§03Transcript — part 3

23:48So that moment for me.

23:50Also validated what disruption can do.

23:53It can make progress.

23:55Progress comes from disruption and breaking systems.

23:58And so I think that for me was a very, and I remember it so vividly because it did leave such an impact on me.

24:05But that for me was like, look, this is what disruption can do.

24:07This is what the uncomfortable.

24:09Process results in.

24:12And am I right in therefore concluding that the fuel of the disruption was that chip on your shoulder?

24:18And it creates almost a bit of an injustice and a sense of anger in people that I've seen so many times in myself and thinking about my friend Umar, who comes from a somewhat similar background, an Indian guy, went on to create a billion dollar company.

24:31He grew up with this internal, just almost frustration, anger, this sense of trying to correct an injustice and that manifests as this chip on its shoulder.

24:39And I guess life, if you start with that predisposition and you go through life with that idea of like disrupting the status quo.

24:47You will win and that will reinforce that.

24:49Yes.

24:50So 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.

24:57Of the disruptive, you know, what we call first principle thinking, when you go to the extra effort of thinking about something from fresh.

25:04Right.

25:04And that's...

25:05It's that.

25:06I also will be really honest.

25:09I 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.

25:17It didn't.

25:18I don't think it will ever actually go away.

25:20Why?

25:21I'm still trying to figure that out.

25:23I think it's because that same chip is still reinforced in so many other places in the world.

25:28It's still that I was the only female late night host.

25:32And so when I was at that seat in that table surrounded by men, that chip was just reinforced.

25:36It's like a new trauma.

25:37Exactly.

25:38So I think it keeps getting reinforced.

25:40It was never just about my grandfather.

25:41It was just about the system.

25:42But that is also, I will just say, I have to get really honest and say that mixed with ego.

25:47Once you get a bit of success, I think Jay-Z says, success is the most addictive drug.

25:51It is.

25:52Once you disrupt and it comes out the other end and you see how amazing it is, you're like, I need to keep doing this.

25:56I need to keep doing this.

25:56I need to keep disrupting.

25:57I need to.

25:58That's been something I've had to.

26:00Really meditate on in my adult life is that when does that stop?

26:04When does that desire to just more, more, more, more, disrupt, disrupt, win, win, win, when does that stop?

26:10That can be the real enemy of happiness, right?

26:11Absolutely.

26:12In your life.

26:13Yes.

26:13Happiness is often right here, but we can't see it because we're still trying to chase it that way.

26:18We're still trying to, it's always the, it's in the future mentality.

26:23You know, happiness will come, success will come, these things will come.

26:26Maybe it's like,

26:27Right now.

26:28Right.

26:29Even saying that there is not enough.

26:31It's not.

26:31Yeah, because I say that to a lot of people, but I still struggle with it myself.

26:34Yeah, you have to do a lot of work.

26:35It's a lot of work.

26:36It's not just words.

26:36It's a lot of work in how you assign value to yourself, how you assign value to other things.

26:40For most of my life, I have hustled.

26:43So I built an entire brand out of hustling.

26:45Anyone that knows anything about me, it's the hustle harder, hustle.

26:47She wrote How to Be a Boss, her first book.

26:50Now, over the past two years, I've done the work to not hustle less.

26:54I still work very, very hard, but it's what does all this stuff actually mean?

26:57What is the value you tie to this stuff?

27:00Is what you thought it was going to be?

27:01I 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.

27:06And it probably never will because of this value we've assigned to all this stuff.

27:11Have you gotten to the point where you know that you are enough?

27:15This is turning into therapy.

27:17What did you think it was going to be?

27:18Clearly never listened to the podcast.

27:19I can't.

27:20I'm going to cancel my therapy appointment.

27:22I saved myself $300.

27:25We charge.

27:26Oh, nice, nice.

27:29I am just now actively right now in the process of believing that through writing my latest book.

27:36My latest book was a lot about that.

27:37It was about, am I enough right now?

27:38Because I think I'll be honest, it's a buzzword.

27:40Oh, you are enough.

27:41Like, for example, kids are born these days.

27:43And in the first words, we tell them, are you enough?

27:45You're enough.

27:45You're great just the way you are.

27:47I think we need to find the balance of hard work and spirituality, of business and spirituality.

27:53There's an intersection of these things where, yes, I think now I'm a full, complete human being.

27:57Does that mean I don't have goals and aspirations and I don't want things?

27:59I still have all of those things.

28:01But 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.

28:09See, a lot of my life, I've defined myself as YouTube sensation, late night host, actress who has this role.

28:18I am doing the work to realize that I'm actually a complete human being that has value aside from that.

28:23And those things are just cool things and experiences I get to do.

28:26And I can strive to be great at them.

28:28I can perfect my craft, but I'm not lesser if I don't have those things.

28:31And I'm not more if I do have those things.

28:33This is an active thing I'm working on.

28:36And when you get to that place, if we are lucky enough in our lives to get to the place where we realize we're enough, that's, you know, I had this really interesting conflict in my life, which I'm sure the 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 ready enough.

28:49I remember thinking, what a load of bullshit.

28:51I'm not going to get out of bed if I have that viewpoint.

28:53I don't need to strive for anything.

28:54Bullshit, get out of my office, right?

28:56And then upon reflecting on that, writing my book, whatever, I realized that my thought that knowing you're enough inhibits ambition is actually false.

29:04What it does, knowing you're enough kills fake ambition.

29:07The minute I knew I started to get closer to realizing that I was enough, my ambitions were all things that I actually wanted, that were actually in line with my...

29:14So it's this weird paradox of when you know you're enough, it doesn't inhibit ambition.

29:17It's the foundation of real ambition.

29:19It gives you a lot of clarity, I think, and you're absolutely correct.

29:23Because...

29:25When you don't feel like you're enough, everything's enough.

29:27Feels important.

29:28Everything feels like something you have to obtain.

29:30Everything feels like a challenge.

29:32You 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.

29:37If anyone asks me who I was, I would never answer as...

29:42I'm a patient friend.

29:43I'm a nice, I would be like, I'm in this show.

29:46I mean, that's how I would, or I would define myself by my struggles, which is another whole thing.

29:50Not by ever my potential.

29:52I would never say I'm someone who's going to change the world because of X, Y, Z.

29:55I would say I'm someone who had a really tough childhood.

29:57We either define ourselves by our struggles or by these other external validations and accolades that we think are important.

30:04When I did that, I would care so much.

30:06For me, what was so important was I need to prove this troll wrong on the internet.

30:10I need to, that's my priority.

30:11I need to prove this troll wrong.

30:12I need to get this rating.

30:14I need to do.

30:15And then the second I was like, you know what?

30:17My purpose is to disrupt.

30:19I know what my values, I'm a complete person already.

30:22Suddenly that stuff became way less important to me.

30:24Suddenly I was like, oh, actually my priority is going to be...

30:29I want to tell stories that I think are really meaningful.

30:33I'm not saying that it has to be a box office breaker in that I'm saying I just want to tell stories that are important.

30:40Things 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.

30:47So I totally agree.

30:48That is something I struggled with where I thought,

30:50And I think that was my resistance against it.

30:52When people would tell me, you're enough.

30:54And when they just tell kids, I'm like, no, that kid's going to grow up and they're not going to, they're not going to.

30:57They're not going to become anything if you just tell them they're enough.

31:00Again, I still think that there's an intersection between hustling and spirituality.

31:04I don't think we have to pick one or the other.

31:06I really don't.

31:06I think there's a way for both of those things to coexist.

31:09But it has become apparent to me that being mindful, feeling like you're enough,

31:16When your cat is acting weirder, or your dog is being louder, your turtle moves slower.

31:26Hello, Ted.

31:27Your cat seems thirstier.

31:30Whoa, slow down, buddy.

31:32Or your puppy is acting clumsier.

31:36Day or night, if you don't know what's wrong, know where to go.

31:40Veg ER for Pets.

31:41This is Kate.

31:42Veg.

31:43The better, kinder ER for pets.

31:46When your cat is acting weirder, or your dog is being louder, your turtle moves slower.

31:56Hello, Ted.

31:57Your cat seems thirsty-er.

32:00Whoa, slow down, buddy.

32:02Or your puppy is acting clumsy-er.

32:06Day or night, if you don't know what's wrong, know where to go.

32:10Veg ER for Pets, this is Kate.

32:12Veg, the better, kinder ER for pets.

32:16Actually allows you to hustle with more clarity.

32:19You know, when people are saying, oh, she needs to get this rating and you're thinking, well, I'm going to prove them wrong and whatever.

32:23And you're getting dragged by external measurements or validation.

32:27And then you get to the point where you say, do you know what?

32:28I actually just want to tell stories.

32:30People 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 by doing something.

32:38And then, you know, in other people's cases, it could be they're working in as a lawyer.

32:42And then they catch sight of what their purpose might be.

32:45And at that crossroads, life says to you, if you go down that route, you're going to lose a lot of this stuff that you've built.

32:53I know it's not aligned with you, but you're going to lose friends, a network, an identity.

32:59Don't go down that road.

33:00Right?

33:01And you face that so clearly in your life, that crossroads.

33:04And even leaving YouTube, you know, when you have 14 million, you're out of your damn mind.

33:11Yeah, totally.

33:12But 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 want to say a lot to lose because that's a presumption, right?

33:22So it's like...

33:23The public would think that you had a lot to lose by taking a different route.

33:27Right.

33:28You're absolutely correct.

33:28I 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.

33:35I want to do other stuff, but I'm still going to make these videos.

33:37I'm still going to dress up as my parents, was that.

33:39It 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 at my fingertips.

33:47I also, to be honest, I was scared of this.

33:51Term relevancy.

33:52I think relevancy is used as currency these days.

33:55Like you're not relevant, so you're worth less now.

33:57And we have

33:57This way to measure people based on relevancy.

34:00This can be summarized in one easy sentence, which is you cannot expect to grow and also stay the same.

34:07It just cannot happen.

§04Transcript — part 4

34:08You have to make room for growth.

34:10And so in order for me to fulfill my ambitions of 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.

34:24You have to make space for that.

34:26You know, 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.

34:35No more energy is coming.

34:36You have 100.

34:37So where are you going to put that energy?

34:39It can be to old habits.

34:41It can be to holding on to the relevancy.

34:44But then that limits how much energy is left for growth.

34:47So it really is just a decision you have to make of making room for growth.

34:51And when you did make that decision back in 2019, was it 2019 you left YouTube?

34:57I still make, yeah.

35:00But yeah, I think around 2009 to where I stopped consistently uploading videos, yes.

35:03So when I read about why you left YouTube, there was clearly some symptoms of life saying to you, you're fucking up here in some way.

35:12What were those symptoms?

35:14I 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.

35:26And how did...

35:27Emotionally feel.

35:28Um.

35:30Stagnant.

35:31I felt like I was trapped.

35:33I felt like I owed people this version of myself that was stuck in space and that was not allowed to grow.

35:39I felt not creative.

35:41I felt not free.

35:44And I felt like...

35:47Even though what I loved about YouTube was freedom, I can post whatever I want, whenever I want, there's no gatekeepers.

35:53I felt trapped in that system.

35:55It became the exact opposite of what I loved about YouTube, which is you have to serve every Monday and Thursday.

35:59You have to post a video.

36:00You have to appease these fans.

36:01It has to be like this.

36:02It has to be this long.

36:03You have to appease the algorithm.

36:04It became the exact same thing I never wanted in the first place, which is to be trapped in something like that.

36:08And so...

36:10It just stopped feeling right to me.

36:12It stopped feeling like a place that I could grow and learn and thrive.

36:15The Lilly that I would see on camera at that point in the lead up to you deciding to depart versus the Lilly that would be there right after you stopped recording.

36:23Tell me the difference between those two people.

36:24Yeah, she's just as weird in both instances.

36:26I can tell you that.

36:27She's just as weird.

36:27She's just as quirky.

36:28But one of them was definitely a bit more performative.

36:32Pretending 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.

36:39I think after I turned off the camera, I was like, oh, God, I've got to edit this thing, and I've got to do this thing, and I've got to go through these.

36:45There was no growth.

36:46It was just such a repetitive pattern.

36:48And as a creative, I didn't want that.

36:51If I wanted that, I would have just done the grad school thing, right?

36:55And then obviously you get this big...

36:57Opportunity, which is well written about.

36:59And I've watched the episodes.

37:00I've watched season one and season two.

37:02I'm so sorry.

37:03No, no.

37:04Why did you say I'm so sorry?

37:06So first of all, the context for people that don't know.

37:08So you got given a late night show.

37:10You were the first woman of colour to be led.

37:12In over 30 years, yep.

37:13In over 30 years to be led into that boys club.

37:16Yep.

37:17On a major network.

37:18When I said that, you said, I'm so sorry.

37:20Tell me why you said that.

37:21Because I don't think the thing was good.

37:23And I'm not necessarily proud of it.

37:26You know, when I got the show, again, me being the disruptor, the whole first season, the advertising was, we're going to break the mold.

37:35We're knocking down the doors of late night.

37:37We're going to do things differently.

37:38And then I proceeded to do things pretty much exactly how they've always been done.

37:41Why?

37:43Because for the first time in my life, I was in a situation where I could not call the shots.

37:50I couldn't make the decisions.

37:52I didn't have the resources to do things differently.

37:54The system is not built to do.

37:56The issue is the system is not built to do things differently.

37:59It's hard to do things differently when you're told, okay, so the episode has to be exactly 22 minutes and 23 seconds.

38:04It has to be that amount of time.

38:05It cannot be a second over.

38:06It cannot be under.

38:07The acts have to be broken down like this because our commercials have to go in these time things.

38:11So you had a joke that went there.

38:12It can't go there anymore.

38:13You have to do it like this.

38:15Oh, you're following Jimmy and Seth and the audience is kind of used to their formats.

38:19You can do things differently, but it has to start with a monologue.

38:21So you're going to have to come out.

38:22You're going to have to hit the mark.

38:23You have to do the monologue.

38:25So many times when I did that monologue, which was a was a

38:27The worst part of the show was like a 10 minute monologue of mediocre jokes because I had a tiny writer's room and very few resources.

38:37This is to no discredit to the writers.

38:38I just had such few writers that were too overworked.

38:42There 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.

38:48To get it right.

38:49And I would always think, why can't we just put the mess up on air?

38:52The 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 talk some jokes.

39:00And it would be so just natural and funny.

39:03And you would never see that in the show.

39:06Why?

39:07We didn't have enough cameras to shoot the audience.

39:09So we couldn't put it in the show.

39:11So the system was not built for...

39:14Breaking the mold.

39:16At that time, did your gut tell you something was wrong?

39:19Absolutely.

39:19From day one, I thought, this is going to be very hard.

39:25It's going to be very hard to make something that I'm proud of here.

39:29And what I hated about it was the proudness and the pride was of something superficial.

39:33I was proud of the headline.

39:34I was proud of the historic nature of it.

39:36I was proud that I got to make history.

39:38But none of the work could back it up.

39:41And 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.

39:47There was episodes.

39:48I vividly remember this.

39:49There was several episodes where I would be with my.

39:53We didn't even have a showrunner.

39:54It was my head of development for my production company who acted as the showrunner.

39:57For the show.

39:58And I would be walking and the show would be starting in five minutes and we would be going over the monologue.

40:02And I looked at her one and I said, this is not funny.

40:06And this is not good.

40:07And I don't want to go out there and I don't want to have to pretend it is.

40:12And she looked at me and she said, it's a quantity game.

40:15It's not a quality game.

40:16And that broke my heart because late night is a quantity game.

40:20I shot 96 episodes in three months.

40:22And I don't want to come across as if I'm complaining and all this, but I'm trying to highlight that.

40:28It 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.

40:35And it's just too rock solid to be disrupted.

40:38I ask these questions in part because I've just joined a show called Dragon's Den, which is like Shark Tank.

40:43Yeah, yeah, yeah.

40:44Five of us, the investor walks in.

40:46And since then, I've been offered a lot more shows, right?

40:49And I mean, you've been there, right?

40:51Loads of briefs coming in for shows, big promises, whatever.

40:55And some of them are really tempting because it's like, oh, you're going to be on Netflix.

40:59But then my gut says to me, that's a shit show, though.

41:02That is a piece of shit show.

41:03So I'm asking from a perspective of advice, when you find yourself in the...

41:08In the shadow of a great temptation.

41:09I'm, you know, Steve Butler might be the first, whatever, whatever, whatever.

41:13But I look at what's going on, the system in which I'd be operating, as you did.

41:20What advice would you give to me based on the lesson you've learned in hindsight?

41:23I will answer this question by telling you exactly that, the lesson I learned, which is,

41:27Is 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?

41:34You see, when I was offered the show, the first time it was brought to me, I actually said no.

41:38People don't know this.

41:39I said no.

41:40And it disappeared for like a month and it came back to me again.

41:44And I thought, okay, the universe is sending this back to me again.

41:46Let me, let me evaluate this.

41:49The reason I said no first was because I never grew up with the dream of being a late night host.

41:53I know some people have that experience where they're like, I grew up with late night television, watched every night.

41:58I don't think my mom could tell you what Jimmy's last name is.

42:01Like she, they never watched late night.

42:03They, I never grew up with that experience.

42:05So it wasn't my desire.

42:06It wasn't my passion to be a host.

42:08So that's why I said no.

42:09But when it came back around and it was explained to me the historic nature of this, three things came into play.

42:14One, my sense of responsibility and duty and two, my ego.

42:17Those things together, I was like, I want to be part of this historic moment.

42:20That would be really cool.

42:21Also, I have a responsibility for this because what if I say no and it goes to someone else?

42:25Then this history is never even made and we never even got this shot.

42:28So all of these reasons that I thought were so valuable and valid is why I said yes.

42:33I was naive to think that that would be enough to get me through those long shoot days.

42:37It wasn't because I would come home at the end of.

42:4196 episodes in three months, broken.

42:44And I would think that was not fun.

42:48And I didn't enjoy that.

42:49And I have no memory or no positive thought to even show for that hard work.

42:54I learned the value of having fun.

42:57and doing things you're passionate about.

42:59I believe more than anything else, those are the things that actually contribute to longevity.

43:04More than anything else, even money.

43:06Ask any person with a lot of money.

43:08You'll go tired of money.

43:09You'll go tired of buying things.

43:11You will never grow tired of having fun and being passionate about something.

43:16And so since I wrapped that show, any project that comes to my desk now,

43:21my agents will be on the phone and we'll talk about the money for a while.

43:24We'll talk about the schedule for a while.

43:25And then I'll dedicate an amount of time.

43:27I'll say, okay, now we're going to talk about if I'm going to have fun.

43:30And if these people are actually nice to work with.

43:31And do I even care about this?

43:33Do I care about this?

43:34And what is this?

43:35Do I even care about the message here?

43:36What this is saying?

43:37And if my answers are no, my definition of success right now is that I will not say yes to it.

43:42I have to have fun right now where I am, or I'm not successful.

43:46So that's my advice to you is don't undervalue fun and passion because those, you will never go tired of those things.

43:54It makes it even more difficult in that situation where you're coming home after filming those, by the way, which is a ridiculous number of anything to film.

§05Transcript — part 5

44:02This should do the math for everyone.

44:03That's two to three episodes a day.

44:05And traditionally, late night hosts do one a day.

44:08So you're coming home exhausted after doing something that you didn't find fun.

44:12Right.

44:12And then the exacerbating factor of all of that, which I reflect on and I say to myself, Steve, would you have been able to deal with this part as well?

44:20Is the show was by some people well-received, but by others heavily criticized.

44:24Specifically the community, which is the YouTube community you'd come from.

44:28People made very hurtful, very shallow criticisms, sometimes personal criticisms about you and the show.

44:37Yeah.

44:38Unless you're the superwoman.

44:41Which is the pseudonym I think you used to go under.

44:44That has got to doing something you don't enjoy that is not aligned with you and then being criticized for it.

44:51It's like the holy trinity of a bad place to be, right?

44:54100%.

44:54Even you saying this has given me a fourth pimple on my cheek.

44:58And I'm sweating because it does evoke an emotional response out of me.

45:02And it's not just the YouTube community.

45:03It was the South Asian community that I got critics from.

45:05It was a queer community that Chris says.

45:07Every and every community, there was people, not all, but there were some people that were criticizing me.

45:12That's a really hard pill to swallow.

45:14When I just finished telling you that part of the reason I said yes to the show was to help pave a path.

45:18I felt a responsibility to communities.

45:21The tough part about being a minority.

45:23anything is that so many people are counting on you to reflect their experience.

45:30The best you can do is reflect your own.

45:32The best I could have ever done is talk about my experience and my lived circumstances.

45:38That's never going to satisfy over a billion South Asian people, queer people, women.

45:43That's half of the population right there.

45:44There's no way.

45:46And that's a hard pill to swallow to know that you can go out there, try your best.

45:49And still, because you're the only one, people are going to criticize you.

45:53I think that is not discussed enough about why it's so hard to break through.

45:57It's because...

45:59So many people are counting on you and it's an unrealistic expectation.

46:02I also had to, and this is way easier said than done, and I'm still working on it.

46:07I had to learn not, 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.

46:17The 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.

46:32As a logical person, I have to shut that down.

46:36Because that's the equivalent of me watching basketball and being like, you missed that three-point shot?

46:40Oh, my God.

46:41I could never make that shot.

46:43So I really had to retrain my brain to...

46:47Take away value from certain people and add value.

46:49If Jimmy Fallon wanted to give me critique on my show, I would have been all ears.

46:53taken notes and been like, thank you so much.

46:55But if some person on the internet has never done this, I simply cannot take their critique seriously.

47:00And I know some people hear that and they think that's a really perhaps snobby way of looking at things, but not really.

47:07No, practically speaking, you cannot take advice from people.

47:11Who are doing it from inside their comfort zone because they actually don't know what they're talking about.

47:15In that period, and especially in the sort of the cloud of that criticism, was there a particular day where you go, that was my hardest day?

47:22Emotionally, how I felt, where it all just got...

47:25Because I've had those moments in my life where all the factors just line up on one particular day and I think, fucking hell.

47:30Yeah, yeah.

47:32This one's hard to talk about, but for the sake of having honest conversation, in my first season...

47:37The first season was by far way tougher than the second.

47:40The second, I tried to make it more fun.

47:42I put more of my team into the staff.

47:44But the first season was really tough.

47:46This was the 96 episodes in three months I talk of.

47:48This was, we didn't even have a showrunner.

47:51We had half a dozen writers, which is half of what usually late night shows have.

47:56I was just worked.

47:59To such an extreme.

48:00Like my from morning to night was just at that studio.

48:03I was a writer.

48:04I was trying to produce.

48:05I was trying to host.

48:06I was just in such a bad state.

48:08And 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.

48:17So at the end of a shoot day at like 10 p.m.,

48:20I would sit alone in that studio and I'd watch the episode to be like,

48:24Is this good?

48:24And then one of the EPs said, you don't need to do this.

48:28We can watch the show for you.

48:30Take this off your plate.

48:31And after much convincing, I was like, you know what?

48:34Today, I'm so tired.

48:35I'm not going to watch this episode.

48:38This episode was my interview with Jessica Alba.

48:42And even though it was not the first episode to air, it was the first one we shot because we shot out of order.

48:47It was the very first episode we shot.

48:48I'm obviously so nervous.

48:50I'm so new to this.

48:50I'm trying to be funny.

48:52Jessica Alba had made a comment about her kids and how they tied towels on their head with turby twists.

48:59In an effort to try to be funny and try to sound personable and make her kids not embarrassed.

49:05I said, oh, I have lots of friends that tie turbans.

49:07And in my head, when I said it, I was like, it's the coolest thing ever.

49:10There's nothing to be embarrassed about.

49:11Like, I'm so familiar.

49:13Of course, not hearing the sentence of towels on heads and turbans in the same sentence and how that could be really problematic historically.

49:20That was the one and only episode I did not watch before it aired.

49:24The one out of 96 episodes.

49:27And the very next day, I was getting dragged on Twitter.

49:30The Sikh community was so upset at me.

49:33I apologize profusely.

49:35And I remember that day, I was just the lowest I've ever been where I thought,

49:41The community that I did this show for is pissed at me because I nervously made a joke out of context.

49:48I didn't watch that one episode.

49:50So I beat myself up about that.

49:51And then I watched every single episode after that.

49:53again and tortured myself all over again.

49:55But 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.

50:05And to also 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.

50:14So that was a very unhealthy moment for me.

50:17And that was a really tough day.

50:18If I was a fly on the wall that day in your room, in your bedroom, what would I have seen?

50:23A lot of crying.

50:24I think I cried in my green room that day.

50:28I remember my friend actually came to visit me because he was like, oh, I know you're in bad state.

50:31I didn't even realize he was there.

50:33I was just staring into space the whole day just...

50:36I just felt like crap the whole day for weeks.

50:39I still do.

50:40Talking about it, I still feel like crap.

50:42Did you have anxiety at the time?

50:43I developed it during season one of the show, for sure.

50:46You developed it?

50:47I never was an anxious person.

50:50I think 2019, the show, maybe even leading up to the show, I definitely developed anxiety.

50:57For sure.

50:58Where I would like be in my green room, not being able to control my body's responses, not being able to control my thoughts.

51:05Like that definitely was something that developed during that first season of Late Night.

51:09And then the second season, you enjoyed it much more.

51:11I enjoyed it much more because...

51:14I was able to make some changes.

51:16I thought we're not going to shoot in a studio.

51:17We're going to shoot in a house.

51:18I'm not going to do a monologue.

51:19I'm going to do a rant.

51:20These things alleviated some of the pressure.

51:23From me.

51:24Did I still think it was the most amazing thing we ever made?

51:27No, I thought it was better.

51:28But the thing is, people had already made up their mind after the first season.

51:31After that first season, because it wasn't instantly, which is another tough thing about any new voice trying to do anything.

51:38If you don't impress people right away, they're giving up on you.

51:42Like the second season of the show, I truly believe if that was the first season of the show, people would have been like, oh, she actually broke the mold.

51:51She's doing something different.

51:51But you can't get there.

51:52You got to go through the process, trial and error.

51:54You got to, every show in history has taken many seasons to find its voice and find its footing.

52:00But it's the, when you are a minority, you're just not given the benefit of the doubt, you know?

52:06There's something that I really take away from this as well, which kind of goes back to the first question I asked on the topic, which is that even in the face of like temptation, I need to make sure that I hold on to my values, my professional, you know, my personal values.

52:18And, you know, people offering me a Netflix show, whatever, if it compromises my like creative and personal values, then I have to say no,

52:26regardless of temptation, until they are going to allow me to do it in line with who I am, like the creativity that you have that made you successful.

52:35May I offer you a devil's advocate perspective here?

52:38Because I've also had this conversation in my brain lots and lots of times.

52:43I wish that...

52:47I'm going to speak from the South Asian experience specifically as well, because that's my lived experience.

52:50But I wish we could hold out for when we're allowed to do things exactly how we want to for them to get done.

52:57I truly believe if we were to all do that, nothing would get made.

53:01And I think that everything is progress.

53:04And so I think it's balancing the line of like, I want to be true to my passion, my vision.

53:08But there is a little bit of compromise I have found has to happen.

53:12And as painful as it is, that's why I don't regret the late night show.

53:15I think that compromise had to happen.

53:17Because 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.

53:29They still do not.

53:31So the option I have is to mold the show into a way that is slightly palatable for them.

53:37So it gets made.

53:38So that another show like this could potentially get made.

53:41And I use Never Have I Ever as an example.

53:42The historic show on Netflix is number one in 30 countries.

53:46Because of that show, other shows like that will get greenlit.

53:48Other South Asian stories will get greenlit because of that show.

53:51So that show has proved to be a great path paver for sure.

53:57Do I believe in my heart that that's the exact show the creators wanted to make and that they didn't have to?

54:02No, I think they had to understand that progress has to be made.

54:07So often when I'm in these rooms, I get irked and I think you're not understanding the cultural nuance.

54:13I don't want to cave on this.

54:14I don't want to explain to you what Diwali is.

54:15I don't want to have to phrase this like this.

54:17I have to ask myself the question, is it better to hold my ground and have the show not be made?

54:23Or 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% and then 90% and then 100%.

54:33That is the reality of minority storytelling right now.

54:36And I wish it wasn't, but that's what it is.

54:39So it's negotiating that reality a little bit as well.

54:42And that's not just a minority storytelling thing.

54:45That's like I was thinking about various facets of life and business and negotiation when there are multiple factors at play.

54:51There are stakeholders who have a say.

54:53There are investors.

54:54There is a timeline that constrains you.

54:55There's a limitation on resources, as you described.

54:58All of these factors cause an unavoidable compromise where you have to go.

55:03But I guess it's that balancing act of like, what are my non-negotiables then?

55:06What am I completely not willing to negotiate on?

55:08Um,

55:09After the second season of the call, you get a call saying that the show's not going to be continued.

55:14Tell me about that day.

55:15So I'm going to describe it as mutual.

55:19Although, yes, the network does control like what's what they're going to put money towards or not.

55:24I was secretly hoping two things and they're both completely contradictory.

55:28Half of me was like, I know this show is a win for the community.

55:32It has to keep going.

55:33It has to keep going or else it's going to be a fail for the community.

55:36So I wanted it to keep going.

55:37The second part of me was.

§06Transcript — part 6

55:39I really hope this show doesn't keep going because I'm going to literally collapse and die if this keeps going.

55:45Going.

55:47And I always judge things by what my gut reaction is to them.

55:51So when I got that call, my gut reaction was actually relief.

55:55That's how I knew that it was the universe doing me a favor I would never do for myself.

55:58Because if they let me, I would have tortured myself for 10 more seasons.

56:01Honestly, I would have.

56:02The universe gave me something I would have never got myself.

56:04I got that call.

56:06I felt a wave of relief knowing I would never have to torture myself in that exact situation again.

56:12But it also, going back to what our purpose is and getting clarity, it made things a lot more clear in my mind.

56:17And in that moment, I was able to see, oh, this has been a huge distraction from what I actually care about and I actually want to do.

56:25This was an obligation.

56:26This was something I thought I had to do.

56:28This is not my passion.

56:29It was never your passion.

56:31Never once did I say I wanted to be a late night host.

56:34I did say I wanted to act.

56:35I did say I wanted to tell stories.

56:36I wanted to produce.

56:37All of those ambitions paused during the late night show.

56:39I couldn't audition.

56:40I couldn't do anything else.

56:41I literally sacrificed two years of my life for something that I didn't even want to do.

56:46That's a sad, sad thing.

56:47That's a sad realization.

56:48So I think I was rewarded with a lot of clarity in that moment.

56:51But what did your ego say in that moment?

56:53Oh, obviously my ego was bruised.

56:54Of course my ego was bruised.

56:56I didn't do good enough.

56:57If I had done better, I've let people down.

57:02I should have gotten more seasons.

57:05This is a bad look.

57:06How do I make myself seem like a winner?

57:08All of that stuff.

57:10Yeah, very honest.

57:11Yeah, super honest.

57:12I would have gone through the same thing.

57:13Yeah.

57:13I have things in my life at the moment where I'm in the exact same situation.

57:15position where I'm like, I don't know if I love doing this, but if I was fired from doing it, or if they said they don't want to continue, I would be in the same conflict.

57:25Like, I think there's certain things in my life that aren't aligned with me completely, but at the same time, you kind of want to make sure it's done on your own terms.

57:31And that's the ego, right?

57:32No one wants to be rejected.

57:33No one wants to be canceled.

57:34No one wants to feel like they could not do something, especially publicly.

57:40Right.

57:41It's not a private rejection.

57:42It's a public, it's a very public type of rejection.

57:44So definitely my ego was bruised.

57:48And I think more than anything, I learned from that experience that part of the problem is that I easily put labels on myself.

57:58And I think we do this to ourselves and we do it with other people as well.

58:01I just kept calling myself first late night host, first this, first late night host has to do this and I have to do this.

58:07And that pressure, like I'm not just that.

58:09I'm someone who tried really hard at this new thing and had to learn a new, like all that context is worthwhile context.

58:16So now when I think about myself through that context, I have more compassion for myself.

58:20And it pains me that other people also didn't give me that context, but I can't control other people.

58:24I can control myself.

58:24I did that to myself.

58:26As harsh as other people were to me, I was way more harsh.

58:29I had to put way more pressure on myself.

58:30And since that experience, I have also learned to not label myself.

58:35So I just got this new show, this Muppet show that I was like wanted so badly.

58:40And I was like, oh my God, I have to get this.

58:42I have to get this.

58:43It's going to be a life changing thing.

58:44And the day I got it.

58:46I had to have a talk with myself to be like, you are not now the lead of the Muppet Show.

58:51That's not now your label.

58:52You will not now describe yourself as this thing because then that's just going to be the late night host again.

58:57It's going to be the YouTube sensation again.

58:58You are Lilly.

58:59You are a complete human being.

59:01This is a cool thing you get to do.

59:02That's one of your goals.

59:03Great.

59:03You get to do it.

59:04You get to experience it.

59:04But this is not now your definition.

59:06I think part of that struggle with late night was it just became every part of who I was.

59:10And so people weren't criticizing the show.

59:11They were criticizing me.

59:13They were criticizing every part of me and who I was.

59:15And that's just a really unhealthy boundary.

59:18Amen.

59:19You know?

59:19And people do that.

59:20I noticed I've done that more in my life when I didn't think I was enough.

59:24So my identity or the label would make me make sense to the world.

59:28It would make me, you know, put me in a community.

59:30I would become social media CEO.

59:32And then the problem is social media CEO or any of these labels you described comes with a set of implicit instructions.

59:39On how to behave and how to be and how to act.

59:41And that can be really imprisoning.

59:42Generally, I wrote this chapter in my book called Resisting Your Labels because of how imprisoning they've been in my whole life.

59:46And also, you know, as we're going to get on to with you now, when I left my label, so when I was no longer a social media CEO, I had a bit of an existential crisis and life goes, well, just go be another one again, because that's what you are.

59:57And I think that's when people have these like midlife crises where they realize they spent the last 10 years or whatever, being the label and not the person.

60:04You leave the late night show.

60:07How was life like for the next year?

60:09Well, exactly.

60:11That was right around the time of the pandemic.

60:13So I think that was a very...

60:15strange time because I couldn't bounce back into anything else, really.

60:19Everything was shut down.

60:21And my plate was pretty empty because my gigs were canceled.

60:24My travels were canceled.

60:26Projects were canceled.

60:26Everything was paused.

60:28So it was a very hard time to let go of something that was keeping you busy.

60:32And that was how you defined yourself.

60:35Through 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.

60:41And it's when I wrote this second book, Be a Triangle.

60:44Because the thing about the pandemic was it wasn't just that I didn't know what to do with my time.

60:48It was that it was the first time I was faced with the reality of...

60:53Me not believing I had any value because I didn't have work.

60:57And that was a sad, scary realization for me.

60:59It was the first time my schedule allowed me to sit there and be like, now I am alone and I'm with my thoughts.

61:05And I feel like I'm ceasing to exist as a person because I don't have a purpose and I don't have value.

61:09And that's really sad because that means every time work goes away, I will feel this way.

61:15And that's not what I want.

61:18That's not setting me up for success.

61:19That's not setting me up for a spiritually happy life.

61:22And so I did the work to really dive deep into my soul and be like,

61:27you're going to figure this out.

61:28And 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.

61:37Everything I've operated on has been what people have told me, whether it's school, whether it's my parents, whether it's society.

61:44I have never...

61:45given thought into what it is I actually want.

61:48I never thought that was an option.

61:49It sounds ridiculous to say, but I guarantee you people that are listening to this will actually also think and be like, wait, have I ever done that?

61:56Have 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 I'm ever going to work on.

62:04And so I vow during the pandemic to create a strong foundation for my life.

62:09Well, what does that mean?

62:10Because that's a fluff word.

62:11And you know, I hate fluff words.

62:12You have already expressed, I hate fluff words.

62:14And 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.

62:28Because my biggest fear was that the pandemic would be over and then I would have work stuff happening again.

62:32And then again, I would just teeter to happy, sad, success, fail, whatever was happening in my life, I would change to my core.

62:38And I didn't like that.

62:39I wanted to create something that was true to me.

62:41And no matter if I won 15 Oscars tomorrow or I fail tomorrow, that safe place in my mind would still exist.

62:46And so that's what I did in this book.

62:48I came up with four things that I don't think will ever change in my life to make up the foundation.

62:53Of that safe place in my mind.

62:56And that's why you call it.

62:58Well, good, good, good, good question.

62:59He's like, so the Illuminati?

63:01No, no, no.

63:02Be a triangle.

63:02Yeah.

63:03So 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 foundation, foundation.

63:09And Google spit back the triangle because structurally speaking, the triangle is the strongest shape.

63:15It has the strongest foundation out of any shape.

63:18And then I started to think about triangles a lot.

63:19And I was like, oh, my brain is very visual, like I expressed.

63:22And I think of things in diagrams.

63:24And I started to visualize a triangle.

63:25And I thought, the shape is actually really interesting because when you add to any other shape, you change the shape.

63:32It turns into something else.

63:33You add to a square, it becomes a rectangle.

63:35You add to a circle, it becomes an oval.

63:36You add to a triangle.

63:38It stays a triangle.

63:39It just becomes a bigger triangle.

63:41And I thought, that's really interesting.

63:43I want to 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.

63:50Because especially in this industry, and all industries, actually, you could really easily lose yourself, but what's happening in your life.

63:56But the goal is to create something that doesn't allow that to happen.

63:59And the triangle is the perfect shape for that.

64:01And what is the, what constitutes your foundation?

64:03What are the ingredients of your foundation?

64:05If it was a recipe?

64:06Yeah.

64:07So I talk about four things that make up the foundation of my triangle.

64:11I know the hardest part of this book was figuring out what those four things are.

64:15And how I did it was I looked for several months.

64:17I looked at every struggle and issue or conflict in my life.

64:21And I looked at it through the lens of four things.

64:24That was one way I determined them.

64:25The second way was what are four things that will never, ever change no matter what's happening in my life?

64:29So I came up with four pillars, which are relationship to yourself, relationship to the universe, understanding distraction, and implementing design.

64:38I 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.

64:45And it is the lens through which you can look at everything in your life through.

64:49On the point of distraction, which I was going to talk about, because it was a big part of your book, and you referenced there that the pandemic was the only time in your life where you'd really been forced to, all the distraction fell away and you were left with yourself.

65:01So many people that I know, and I'm sure you can relate to this,

65:05fill their lives with distraction and noise and things and busyness to avoid stillness, to avoid meditation or taking time for their own mind.

65:13You've picked up meditation and breath work and things like that.

65:16Can you speak to me a little bit about the impact that's had on you, specifically breath work?

65:22Because I'm getting a little bit more into this at the moment.

65:24And when I read that you'd started doing it, I thought, ooh.

65:26And I'm still, let me preface this by saying I'm still a novice and there's much to learn.

65:30I'm just starting my journey with really getting into meditation and breath work.

65:33But I, over the past year, started to have...

65:38So this is from a scientific point of view before I even hit the spiritual point of view.

65:42I started to have panic attacks, which I thought I knew what they were.

65:46I think most people who have not had a panic attack, they think it's the same as an anxiety attack.

65:50They think it's like, oh, you're really stressed and you don't know how to deal with what's happening in your life.

65:54That's what I thought a panic attack was until I had a panic attack.

§07Transcript — part 7

65:57And I'm like, oh, it's very different.

65:58The first time it happened, I dismissed it because I was like, I don't know what that was.

66:01The second time it happened, I was like, this is a reoccurring thing.

66:04I was talking to my friend and we were talking about something so unrelated.

66:07It was like he was telling me a funny story about work.

66:10And suddenly in my brain, I started to get outside my body.

66:14Like I was watching myself.

66:16And I started to have these really strange thoughts like, I think I'm going to take my head and slam it against the table for no apparent reason.

66:25And I'm not going to be able to stop myself.

66:27And then I started spiraling up like, and then I have to call the ambulance and I'm going to be bleeding and everyone's going to be.

66:31And then it's just like you progressively are just spiraling to being sure that you're going to smack your head against the table and nothing you say can change your mind.

66:39This is a minute of just completely irrational, dangerous thought.

66:44And then.

66:45Suddenly I was like, oh, wait, no, no, I can stop myself from hitting my head on the table.

66:51Of course I can stop myself.

66:52That is a panic attack.

66:53It's happened once before to me when I was driving and I was like, I'm going to drive off this cliff and there's nothing I can do that's going to stop me.

66:59I won't be able to control myself.

67:00It's going to happen.

67:02When that sort of happened, I talked to my therapist about it.

67:04And she explained to me that as someone who always operates on 10, because I'm always just working really hard and I'm always thinking about the next thing.

67:12I'm an all or nothing type person.

67:13I have an obsessive personality that some things can trigger my nervous system, just go a little bit into overdrive.

67:20And that's the body's response.

67:21It's going into overdrive.

67:22Your nervous system doesn't know what to do.

67:25Breath work really helps with that.

67:26It's just bringing your nervous system back down to a state that's not an 11.

67:30You're bringing it back down.

67:31So from a scientific point of view, breath work has been my saving grace to just health.

67:36Having said that, from spirituality, it's just my belief of, you know, I talk about these pillars and I talk about a connection with yourself.

67:44Meditation is...

67:46You making time for the partnership with yourself.

67:48You know, I believe we're all in a relationship to ourself, whether we want to acknowledge it or not.

67:52Most of us are bad partners to ourselves.

67:53We don't make time for ourselves.

67:54We don't listen to ourselves.

67:57If anyone treated us how we treat ourselves, we would not be in a relationship with that person, probably.

68:02So meditation is more than anything else.

68:04It's not about religion.

68:05It's not about doing something so specifically.

68:07It's about making time to be in a relationship with yourself.

68:10And that's something I really, really value.

68:12And I think that's a huge form of self-love.

68:14So from a spiritual point of view also, meditation is my everything.

68:18Some people are really avoidant of like that time with themselves though.

68:21I think it is because sometimes when I talk about meditation, a common response I get is,

68:26Oh, I'm not good at that.

68:27That doesn't work for me.

68:28And I ask why.

68:29And they say, well, I can't turn my brain off.

68:31I have all these thoughts that go in my brain.

68:33And then, so I'm not doing it right.

68:34And my response to them is, who says that's not right?

68:37Maybe what you need is to hear those thoughts.

68:39Maybe you've not given your brain a chance to get those thoughts out.

68:42And what you need during meditation is to hear those thoughts.

68:44Who says that's wrong?

68:45The only thing meditation, the only, I'd say there's one rule of meditation is just spending time with yourself.

68:51Whether that's you hearing these thoughts that are uncomfortable.

68:54It's not about problem solving.

68:55It's not about solving everything.

68:56It's just about giving time to yourself, allowing yourself the space and energy to be like, I care about myself.

69:01I dedicated these 15, 20 minutes to hearing myself out.

69:04That is the only thing.

69:08In the book as well, I think chapter six, you talked a little bit about your difficulties with making friends as an adult.

69:13Yes.

69:14Yes.

69:15So one of the things that I have come to terms with is that I, like I've been mentioning, I'm a very all or nothing type person across the board.

69:24And it has been good in some instances because it has allowed me success in my career, but it's bad in some instances because when human things don't live up to my expectation, I write them off in situations where I don't have to.

69:37I'm throwing a party.

69:39This party has to be the best.

69:40Everyone that RSVP'd has to show up.

69:43And so I'll throw this amazing party that everyone has fun at.

69:46But if one person didn't show up that said they were going to show up,

69:49In my brain, I go, well, it was nothing.

69:52It wasn't good.

69:53It wasn't exactly what I thought.

69:55If it's all or nothing, there's no middle.

69:57I have learned that that is not healthy and that it, that also hinders me because there will be no joy and there'll be no celebration.

70:04There'll be no progress if you're all or nothing.

70:06I did that with friendships.

70:07I told this to Jay.

70:09Jay is my friend in LA, but for a long time I struggled because my definition of friendship was all, which meant you have to know me since I was a kid.

70:17You have to know me before I was famous.

70:18You have to know me before all of these things.

70:20So that's a true friend.

70:21And so my definition of friendship was very rigid.

70:24And so when I met Jay later on in my life, I struggled with that because I was like, he's such a good friend.

70:28He's so supportive.

70:29But he didn't know me like how my other friends know me from back in Toronto.

70:33So I don't really know if this is a real friend.

70:35No, you got to let go of these definitions and these labels we put on things and be a little more organic with things because that's where humans lie in that compromised.

70:45organic space.

70:47When I heard the thing, the analogy you gave about the party, one person not showing up and you being like, well, then it's not perfect.

70:53That sounded probably like also the underlying reason why you were so successful.

70:58Yeah, that's what I'm saying.

70:59So that's why it's been so hard to challenge that belief because it has served me so well.

71:04So I think now what I'm learning is when that serves me and when it doesn't.

71:09That's actually been a lot of my work in this book.

71:11It's not being mad at myself for having certain thought patterns and not trying to completely do a 180 and be like, now I'm not that person anymore.

71:18It is learning which ideas serve me well in certain circumstances and which ones do not.

71:24It's unlearning this idea that I have to be one thing all the time.

71:28For example,

71:29Speaking of labels, I call myself a hustler.

71:31I hustle really hard as my whole brand.

71:33And I found that on days when I was lazy and I felt like just so tired, there would be a lot of resistance in my brain because I wasn't living up to my own label.

71:40I was doing the opposite of this label I put on myself.

71:44But I've learned you cannot be everything all the time.

71:47We exist on various places, on various spectrums.

71:50And so it's not about changing who you are as a person.

71:52It's about learning what ideas serve you well in certain circumstances and which ones do not.

71:56And then on and off, on and off, on and off.

72:00Have you got a lot of friends?

72:03People might think I have a lot of friends.

72:05I wouldn't say I have a lot of friends.

72:06I think I have a good number of friends.

72:09And it depends how I define friend.

72:10People that I can call just to call and ask how they are without an agenda for the phone call.

72:17Like friends.

72:18Five?

72:19Four or five?

72:21I think that's a good number.

72:22I'm not mad at that number.

72:24Yeah, I mean, it's a good number, I think, especially as we get older.

72:27Me and Jay, we're talking about Jay Shetty, by the way.

72:30Me and Jay were talking about this the other day about how when you get older in life as well, the amount of friends you have, it becomes increasingly harder.

72:35You don't have the work thing.

72:36You don't have the university, school, whatever.

72:39So really, it's more about depth and quantity as opposed to what your producer told you.

72:42It's also a little bit about, at least in my experience,

72:47watching the adults in my life as a kid, they never prioritized friendship and they never placed value in friendship.

72:53And so I believe for a long time that as you grow up, you need to value the companion you have as a partner.

73:00And that takes the place of friendship.

73:01And you don't have time for friendship because you have a job.

73:03I have since unsubscribed to that idea.

73:06Um,

73:07I never saw anyone value friendship.

73:08That doesn't mean I can't value friendship as an adult.

73:10And I've actually learned this from Jay.

73:11Jay is very good at maintaining friendships.

73:13Jay is the type of person that will message you with no agenda.

73:15You're like, hey, just checking in, just saying hi.

73:17So I've started to reciprocate that to him and call him and FaceTime him just to be what's up.

73:21But that's something I had to actively learn.

73:23Because growing up, I don't think I could name one adult that was like, I'm going to go out with my friends.

73:28Were you comfortable with friendship?

73:31both platonic and romantic.

73:34Were you comfortable with it?

73:35Because I remember, because I grew up in a similar way, I genuinely would cringe and feel deeply uncomfortable when someone said the word best friend.

73:40Oh, I don't use the term best friend even today.

73:42Even today, I don't use the term.

73:44Steve is my best friend and my body would like shut up.

73:45Oh my God, I'm so glad you said this because everyone knows I do not use, unless we're talking about my dog, who can do no wrong, I do not use the term best friend because I do have this little bit of like,

73:56cringiness where I'm like that means I rely on you and we're kind of pedantic I don't know if I want that so there is a little bit of work to be done there still um

74:03but yeah that's interesting I thought that was only me no yeah I think I've said this to a couple of guests and you're the first one to buy it no 100% 100% people that are so like oh they're my best friend I'm like oh sounds dangerous but that

74:14I've learned that with that comes a commitment issue romantically so I also would run from any prospect of sort of romantic commitment because that also it felt like a bird trapped in a cage it felt like prison to me so in the same way that friendship was just like yeah

74:27I think it's because my parents weren't affectionate.

74:29They weren't affectionate at all, to be honest.

74:31We didn't have that very close relationship that a lot of my white friends did.

74:35I don't even call my mum and dad, mum and dad.

74:36I call them by their names.

74:37I mean, you probably can't do that.

74:38No, I could never do that.

74:39I'd get slapped up in the face if I did that.

74:41It was just a distance.

74:42I think also what it is, is...

74:44You know, I talk a lot in the book about unsubscribing to ideas that do not serve us.

74:48But I encourage people to look at everything in their life as an idea.

74:53A lot of things we think are fact and are rules are just ideas.

74:56They're still just ideas.

74:58So what we even think of friendship is supposed to look like, what we think a relationship is supposed to look like,

75:01supposed to look like, how we think a romantic relationship is supposed to be, those are all just ideas.

75:05And I think because I thought they were facts, like it has to look one way, I resisted that a lot.

75:10Just like I did with friendship, I just told you.

75:11With a romantic relationship, I did the same thing.

75:13That means that you have to sacrifice a lot.

75:15There's a lot of compromise.

75:16You can design any relationship the way you want as long as two people are on the same page.

75:20So I encourage everyone to think about that.

75:22I think what has really helped me get over some of the anxiety with commitment and relationships is it doesn't have to be this idea of what I think.

75:29It doesn't need to be this one way.

75:30I can design one that works for me and someone else as long as we're on the same page.

75:35I'm trying to figure out where to go with this because I want to go down the relationship route, but I'm also, there's a point, you're talking about unsubscribing from ideas.

75:41One of the ideas you talk about unsubscribing from in the book in chapter three is about the idea of success and what that is and the definition of it.

75:47If Lilly at 60 years old told me she was successful, what would that mean?

75:55See, if you asked me this years ago, I would have answered this question in relation to accolades.

76:02I would have said.

76:03And numbers.

76:04I would have said, oh, that means she's had made several movies that are box office hits.

76:09Now my answer, and it's been a hard journey to get here, but genuinely my answer is.

76:15That at 60 years old, I still fully understand and believe I'm a complete human being.

76:21And everything that has happened is just extra cool stuff.

76:24My goal is to never write another book.

76:26Truly.

76:27I know I said that after my first book and I'm saying it again right now.

76:30My goal is that this book can be the blueprint for that safe place in my life forever.

76:36That I never have to make another blueprint.

76:39That is true.

76:40If I never write another book again, that means that I was successful in this suite.

§08Transcript — part 8

76:44So truly 60 years from now, I want to know that I'm fully complete and anything that would have happened or didn't happen was just life experiences, goals, cool stuff, but I'm not lesser or more because of it.

76:56Relationships then.

76:56Mm-hmm.

76:57Romantic ones.

76:58Yes.

76:59Have you been at a difficult to date?

77:03Difficult to find romantic love?

77:06Probably.

77:07Absolutely.

77:07I'm sure.

77:08All of my exes right now are like, do you have to think about that?

77:12Absolutely.

77:13If I asked your exes.

77:14Mm-hmm.

77:14Why it was you were, you know, in their point of view, why you were difficult.

77:20What would be the common response, the most common response?

77:26That a few things.

77:28One would be that I have an inability to forgive.

77:32Ooh.

77:33I do.

77:35That I am very transparent about.

77:38This might scare people off, but as soon as I know I'm going to get into a relationship with someone, I very honestly tell them, I say, one of my weaknesses is that if you lie to me or wrong me and betray my trust, it is very difficult for me to trust you again.

77:50Even if every part of me wants to, I will not be able to.

77:54And I tell people this very, very honestly.

77:56Where does that come from?

77:57I'll tell you right now.

77:59I didn't know.

78:00First, I thought it was like, oh, from my childhood, from this.

78:02But no, I think that's all a lie.

78:04I think my inability to forgive people stems from my inability to forgive myself.

78:10I think that because I expect perfection from myself and I, for so long, didn't give myself grace to be human, I didn't give people grace to be human either.

78:19And as I've done the work to treat myself like more of a human and to have the inner dialogue of like, it's okay.

78:26It's okay.

78:26You don't always have to be performing.

78:27You don't always have to be perfect.

78:28You're allowed to be a human.

78:29You're allowed to be lazy.

78:30You're allowed to be flawed.

78:31The more I've done that work, I have given people permission to do that as well in my relationships.

78:36I've noticed since writing this book, one of the biggest changes I've seen in my relationships is that I can actually forgive people now.

78:44And I think it's because I've learned to forgive myself.

78:47I've learned to embrace humans for being humans.

78:50And that started with myself.

78:51So that is something an ex would definitely say.

78:54Also with the fact that I have very high expectations.

78:56All of my exes will say I have absurdly high expectations.

79:00Ouch.

79:01Yeah.

79:02That's a tough one.

79:03The expectation one.

79:05Are you in love now?

79:08I'm in love with myself, which is the most important love, I think.

79:14And I think that's perhaps why I was never a good partner before.

79:17I don't think I was ever...

79:20Unconditionally in love with myself.

79:22My love for myself was always very conditional.

79:25Always based on my performance.

79:27Always based on my ability to accomplish.

79:31Never just for like the things that were me.

79:35You know, you had such a high standard for yourself.

79:37You talked about that obsessiveness and even that the party, if one person's not there, it's not perfect.

79:42Are you saying that that same level of expectation would sometimes be mirrored onto the person?

79:47You would expect them to be wildly ambitious?

79:50Because I had this problem for sure.

79:51I'm like, why aren't you changing the world?

79:52Why aren't you an entrepreneur?

79:53In some of my past relationships, definitely it would irk me if I was working.

79:58And the person I was with was not.

80:00And I don't even mean had a job.

80:02I mean, if I'm working at two in the morning, you should be working at two in the morning.

80:05We should both be equally as ambitious.

80:07I know that sounds ridiculous and I'm admitting that I was wrong.

80:10And that's not a good perspective to have.

80:12But that's how I felt.

80:13Like I want someone equally as ambitious.

80:15Since then, what I have learned.

80:17Is that what I thought I wanted, if I was actually dating someone that was just like me, that would be horrific.

80:22Me and Jay talk about this all the time.

80:25Me and Jay talk about how both of us in some part of our life thought that we wanted to be with someone just like us.

80:30Me and Jay are so similar.

80:33We, in any time anyone is having a disagreement, we take the same side.

80:37We always have the same perspective.

80:38We're so similar.

80:40And since meeting Jay, I've learned that, oh, if me and Jay were in a relationship, we would kill each other.

80:45We would actually hate each other because there's no balance there.

80:48You need someone to balance you out and bring something else to the table.

80:53And I have.

80:54fully acknowledge that now and I think I was a little delusional in some of my past relationships thinking I wanted me

81:00but I don't who that no but none of you might think you want that but you would kill that person you're totally right you know my girlfriend now is very much in every way the opposite of me and that is in fact as you've described that is actually the value of our relationship is one plus one will equal three

81:14when we have different perspectives and healthy debates around things like that right um

81:19I've never asked anybody this question before.

81:21Oh my God, I love it.

81:22Hit me.

81:22What is the one question?

81:24Because when I saw that you're on a book tour at the moment, you've got a great book that's just come out, April 14th.

81:30And on that, I was watching you do all of these interviews and you're doing some great shows and things.

81:34And I was thinking to myself, having been in this process over the last week where everyone's asking you questions,

81:41What is the most uncomfortable question you think that I could ask you?

81:48That would make me feel uncomfortable?

81:49Yeah.

81:51It can be a topic.

81:55Or a question.

81:55You kind of already asked it, to be honest.

81:58For me, I get very uncomfortable when we talk about people critiquing things I worked very hard on because those are my babies.

82:08My projects are my babies.

82:10And it...

82:13To be just really blunt, it hurts my feelings.

82:15And I think I thought for a long time I had to put on a facade that it doesn't hurt my feelings, but it does.

82:19I think I am a sensitive artist in a lot of ways.

82:22And so the question you asked about people criticizing the show, I think that is the most uncomfortable question you could probably ask.

82:28Aside from that,

82:32Another really uncomfortable question, I have been asked this though, is in the book I talk about my experience coming out to my parents.

82:42And that is really uncomfortable because I'll just be really honest.

82:46A lot of times when anyone tells a story about their coming out experience, people's instant reaction is, you're right.

82:51Everyone should have been very understanding.

82:53You should have been cared for and nurtured and accepted right away.

82:55That is the default answer.

82:57It was a very difficult thing for me to do, to go against that.

83:02And in the book, talk about how I was wrong in that moment.

83:05Because I didn't do that before.

83:09I came out to my parents.

83:11I was offended by their...

83:15Lack of instant accommodation and celebration.

83:19They were very supportive.

83:20They said everything that they knew how to say at that time, but because of it,

83:23was not instant celebration.

83:25I judge them harshly for that.

83:27And that's a hard thing to admit when you're the one coming out.

83:32Because by default, like I said, everyone thinks you're right.

83:34And everyone thinks you should be celebrating, accepted right away.

83:36And to actually challenge that idea and say, no, actually, that's not where humans operate from.

83:41This place of instant knowledge and accommodation.

83:43It's actually a learning process.

83:44And we should meet in the middle and we should be compassionate.

83:48That's not a popular opinion, I don't think.

83:50And so that was difficult for me to talk about.

83:53It's definitely the most mature, useful position.

83:58And you've expressed at the very start of this conversation when you highlighted your parents'context in regards to potentially the mistakes they made and the lessons they taught you before the age of 10.

84:07And you talk about that in the book as well.

84:08Understanding, having empathy for their context and how that formed their reaction to that situation, I think is just the most...

84:15Amazing place to be in because then you don't, I mean, the first thing that comes to mind is you're not going to walk around with resentment that they weren't, you know, they weren't perfect as you might see in like a fake movie or something.

84:26But also I think you can have better communication when you, when you are able to lean into their world and understand them.

84:32And it tends to be the case, you'll know, because I haven't, my mom's from Nigeria.

84:35I was born in Africa.

84:36Like,

84:37in all facets of like the first generation, second generation immigrant story, you actually tend to both want the same thing.

84:44So your parents would do different ways of going about it.

84:46Yeah, right.

84:47Because as you say, like often, they don't know about YouTube.

84:51So doctor or lawyer was the path to this.

84:53The happy, successful, secure life, right?

84:56And I think immigrants, like I had to with my mom when I said I'm starting a business, I'm never speaking to you ever again.

85:02We didn't speak for two years.

85:03It's not just that I'm going to tell all your family not to speak to you.

85:06So it's having, it took me a long time to get to the place you got to.

85:10Yeah, it took me long too.

85:11I also for two years was like held resentment against my parents.

85:15And I created that drift.

85:16And that was how I learned this lesson.

85:18And I think it's also because...

85:21The world today, the internet today, social media today, it really, really encourages us to label situations, conversations and things very easily.

85:29Right, wrong, cancelled, you made a mistake, you cannot redeem yourself, you are now bad, you are now good.

85:35That is not how humans operate.

85:37It is not a realistic lens through which you should view humans, you know.

85:43To expect people to know everything you know without having your lived experience is a really entitled place to come from.

85:51And I'm even going to challenge people online that cancel people for saying incorrect things and behaving in incorrect ways and the person can apologize over and over again.

85:59We don't accept their apology.

86:00We're creating a culture of expecting other people to operate from our lived experiences.

86:05How is that possible?

86:06How is that remotely possible?

86:08My mom did not grow up with Lady Gaga bops.

86:11She did not grow up with queer culture.

86:13So for me to expect her to operate from a place of my lived experience, how is that math ever going to add up?

86:19It's never going to.

86:21And I know online we like to sit on our high horse.

86:23And think it will, but it will never.

86:25It will never add up.

86:27That's an unpopular opinion, I'm sure, on Twitter, but that's okay.

86:29I will die on this hill.

86:31No, I think it's popular.

86:32It's definitely a popular opinion here.

86:33Okay, good.

86:35So when you look off into your future, you've got a lot going on, movies, Disney+, there's all these other things happening in your life now.

86:41What is the next...

86:43And I'm scared of us sort of falling into accolades and numbers and accomplishments.

86:47No, that's okay.

86:47But what is the next thing?

86:48There's a time and place for those conversations.

86:50I'm happy.

86:50The goals that I have for myself are associated with elevating storytelling.

86:57So I do definitely want to be on screen and behind the camera and produce and write and start in stories that highlight underrepresented voices.

87:05That is something I'm really passionate about because I believe stories make the world go around.

87:09Stories are how I understand myself and other people.

87:12And I think there's not every story has to be about everyone but there should be stories for everyone and so I'm very passionate about that so and I just love being creative in that way so I think

87:22acting, producing.

87:24I have a book club called Lilly's Library that's all about South Asian stories as well.

87:29That's just something, that's just what I'm most passionate about.

87:31So I think most of my goals will align with that.

87:34Lilly, thank you for writing such a great book.

87:36And I think there's going to be so many people that are listening to this now that have heard the context of the journey that led up to you creating this book that might be having questions about their own foundation.

§09Transcript — part 9

87:45And I also will say, I don't know if you can see if anyone's watching this.

87:48It's a short read.

87:50It's a short, concise, and I guarantee you will hear my voice.

87:52You will hear my voice.

87:53voice reading it to you because I've written it in that way.

87:56So how many pages is that?

87:58I don't even know.

87:5893.

87:59There you go.

88:00An hour.

88:01An hour read.

88:02No, it is.

88:02It's really digestible.

88:03It's the type of handbag book that you could travel with and really, if you're one of those people that doesn't like tiny letters and thousands of pages, this is definitely a book for you.

88:11And it's written from such a place of, as you've expressed today, self-awareness, wisdom and vulnerability.

88:17And those are always the best books because they are the truest and the most necessary.

88:20Thank you.

88:21So thank you for creating a wonderful book.

88:23We do have a closing tradition on this podcast.

88:25Let's do it.

88:26Which is the previous guest, right?

88:27The question for the next guest.

88:28Ooh, nice.

88:29Okay.

88:30How many times have you been properly in love?

88:38I'm going to say...

88:43Perhaps including in with myself three times.

88:48And I'm not just thinking about love romantically.

88:51I don't think love is just romantically.

88:54I think one time romantically, I think one time with myself, and I think one time after writing this book, truly, truly, truly,

89:04when I saw my mother for all the glory that she is.

89:07Like I have no problem saying I'm in love with my mom and the person she is.

89:13I was going to answer with a higher number, but for me, what translated, what I, the synonym I used for properly was,

89:21How many times have you been in love where both people in the equation became better versions of themselves?

89:29And that's what eliminated a few of the numbers.

89:33I think in every scenario I'm talking about, both people were better versions of themselves because of the love.

89:39It's a beautiful answer.

89:40Yeah.

89:40Once romantically.

89:42He wants romantically.

89:43Figure out which one of you it is, baby.

89:48You know who you are.

89:50Thank you, Lilly.

89:51Thank you.

89:51Thank you so much.

89:52I appreciate this.

89:52It's such a joy.

89:53Thank you.

90:18The thing I think about most, especially when I'm on the go, but also when I'm sat here in the Diary of a CEO studio, is the Wi-Fi and internet that we have to work with.

90:26In fact, any time I'm filming away from the studio, one of the first things I do is when I arrive, I open up an app and do a speed test to see how strong the signal is.

90:34And the number of screenshots I've sent to my team about Wi-Fi signals at different locations is actually pretty crazy.

90:39It matters that much to me because it's such a competitive advantage to have fast Wi-Fi.

90:44Because on any given day, if I'm recording, let's say, hours and hours of footage with a podcast guest, I then often have to have my team send that across to our London team who then do the edit.

90:53So fast Wi-Fi and internet is not a nice to have.

90:55It is absolutely business mission critical.

90:57So when it came to finding the best provider who could supply internet and Wi-Fi to our new LA studio, which I'm sat in right now, we looked at every single option.

91:05And of all the providers, the one that came back with the steadiest connection, as well as being the cheapest, was today's sponsor, Spectrum Business.

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91:43Hello, Ted.

91:44Your cat seems thirstier.

91:47Whoa, slow down, buddy.

91:49Or your puppy is acting clumsier.

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91:57Veg ER for Pets, this is Kate.

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— A LITTLE MORE TO THINK ABOUT. —