[Theme music playing] There are a lot of ways to make a point, and art takes many forms, so if you find a creative person with a perspective, she'll find any means necessary to share it.

Lilly Singh is a 33-year-old Canadian who has been making YouTube videos since 2010, the collection of which recently passed 3 billion views.

Her messages include "Don't be a bully," "stop judging each other," and, curiously, "Be a triangle."

To the 14.7 million fans of her generation, she is a lifeline and a foundational voice.

For the rest of us, she is an education in American culture, circa 2022.

I'm Kelly Corrigan, this is "Tell Me More," and here is my conversation with comedian, maker, entrepreneur, and sometimes disobedient daughter of Malvindar and Sukvindar, Lilly Singh.

[Theme music playing] ♪ ♪ So you're a kid in Toronto... Yep.

Your parents are Punjabi, they came over in their 20s.

Mm-hmm.

and you're a very modern kid.

[Laughing] You go to college, and instead of coming out to do, uh, a "regular job"... Mm-hmm.

like people of my generation might, you said you're gonna start making videos.

Did you have some sense that you were gonna make a whole lot of 'em for a whole lot of people, or was it like, "I'm gonna make one"?

I literally thought I was gonna make one.

I didn't even think I would post that one, to be honest.

I discovered YouTube.

I vividly remember one of my friends came up to me in university and said, "There's this website called YouTube, and you post videos," and I was like, "It sounds dumb.

It sounds dumb.

I don't get the point of it."

And so, for so long, I ignored it until finally, one day, it came across me, probably on MSN Messenger or whatever the kids were using that day.

Sure.

And I was like, "This is really cool.

"Someone is in their house, "just speaking their mind to camera, and no one's telling them what to do," and so I thought, "I'm gonna make a video."

Didn't know how to shoot, didn't know how to edit, didn't know anything about the process.

Didn't even think I would post it.

It was a spoken-word piece that was very bad, and I posted this video thinking "Oh, that was fun, I guess," and then I think, like, 70 people watched it... Uh-huh.

and I thought, "I don't know 70 people, so now I'm famous."

[Both laugh] But I fell in love with just this process of learning how to do this and being able to say things with no one kind of gatekeeping what I would say.

And so then I posted a second, third, fourth video, and it snowballed into me saving up for a camera and teaching myself how to edit, and into--for years, I did two videos a week.

Bullying is an epidemic that affects a lot of people so please be part of the change and stop bullying.

People are gay.

I personally don't understand why it's such a big fuss about who other people like.

Let's address the stigma around mental health.

Let's have conversations.

If you grew up in a culture where maybe people don't talk about it, let's change that.

Every moment counts and is different.

What kind of life do you want to live?

It's that simple.

Kelly: And you said to your parents, "Thanks for college."

Yep.

"I'm gonna make some YouTube videos," and they said what?

So I was actually applying for grad school when I was--like, I had a few videos.

And so I was, you know, thinking of what I'm gonna write in this essay for grad school, and literally in the middle of the essay, I stopped, and I was like, "I can't fathom doing this for two to four more years."

And I said, "Mom, Dad, "I don't think I'm going to go to grad school, "rather, I am going to make videos on YouTube."

Heh heh!

How'd it go over?

Ha ha ha!

There was a silence, a long silence.

My mom was just like, "What?

You're gonna do what?"

'Cause they didn't understand YouTube.

They--I know-- not only them.

A lot of people didn't understand YouTube.

This was 2010.

Yeah.

And my dad said, without knowing, the best thing he could have said to me, which was, "I don't know what you're talking about, but I'm going to give you a year to figure it out."

And so that's what started the clock for me, is "I have a year to make this into something, into anything on YouTube."

And what did you become?

Like, how would you describe who you were to those initial followers in those first few months?

Definitely a lot of experimenting.

My first couple videos were not comedy.

They were tutorials, spoken-word pieces.

One of them was how to tie a turban because I was the captain of a dance team and I knew how to do that.

One of my videos was how to say certain words in Punjabi, so it was very niche, and it was just what I was talking about with my friends, and it was kinda bad, it was not good.

But people were watching.

People were watching.

I think I was talking about stuff that people had never seen anyone else that looked like me talking about, and I really hit my stride with, I think, my... maybe sixth or seventh upload when it was a guide to brown girls.

That's what it was called-- "A Guide to Brown Girls."

Welcome to Superwoman's official guide of how to deal with brown girls.

So hold on tight 'cause you know it's gonna be quite the emotional roller coaster.

Lilly, voice-over: And I was talking about relationships and parents and all these things, and all these brown girls were like, "Oh, my God.

"I have never seen someone talk about this thing that I thought only I, me and my friends, talked about."

And so I was talking about things that kind of brought this community of people together.

That was really, really awesome.

After a year... Mm-hmm.

what were your sort of stats?

What did it look like, and was your father satisfied that this was gonna work out?

More than anyone, I was becoming satisfied, which was very important to me because I think, as high as my parents' expectations were, I think my expectations were higher.

For sure.

So, at the end of a year, I know that I had developed the skills to keep doing what I was doing, I had garnered a following.

I don't know exactly how much, but I know that I had a party, and it was called "A Milli for Lilly."

What up, everyone?

It's your girl Superwoman.

That's right.

I have been so blessed by your support to hit 1 million subscribers.

What I can tell you is is the moment that I knew for sure I could do this, and it was actually the first time I traveled to Bombay in India.

It's like the Hollywood in India.

I went for an event called YouTube FanFest.

It's YouTube FanFest today.

I have a trailer.

Lilly, voice-over: So nervous.

I was to go on stage and I was just to, you know, do my parent imitations and talk to the audience-- this was a 15-minute segment-- and I was side-stage, so nervous, and I heard the audience start chanting, "Lilly!

Lilly!"

Audience: Lilly!

Lilly!

And I remember the feeling because I felt nauseous, truly, thinking these are thousands of people that literally live across the world... Uh-huh.

that know my phrases and know my videos.

And that's the first time I saw in my life the impact the internet had, in person, the impact that YouTube had.

What about it, everyone?

It's your girl Superwoman.

I'm in Mumbai!

Check them out!

[Crowd cheering] ♪ Lilly: Once I knew the Indians had my back, I was like, "This could be something!

There are so many of them!"

Ha ha!

But-- "There's a billion people here."

A bill--one in four people is South Asian.

It's perfect.

Right.

It's perfect.

No, but truly, I think that was my "Eureka!"

moment, of thinking this could really, really be something.

And then, there is this period where-- I mean, I create content myself--where you have to decide, like, what you want to put into the world... Mm-hmm.

and how you evaluate your own stuff.

Like, is it useful?

Is it positive?

Is it a corrective... Mm-hmm.

to society in some way?

Yeah.

At what point did you look at your work and think, "What do I want the sum total of all this to be?"

I think my answer to that question has changed.

In 2010, when I started making YouTube videos, to 2016 and '17, my goal was numbers.

I'll be very honest and say it.

Thank you.

My vision board had numbers on it.

Right.

It had subscribers, it had views on it.

The hardest part about how I started my career was how I got paid.

How my influence was measured, how brands would work with me was all based on that view count and that subscriber count.

Right.

And that got into here.

"Oh, it doesn't matter what I'm making.

It just has to make-- you have to get those views."

So even if this was a video that I don't really think is the funniest, and it might not be that creative, I know it's gonna get those views.

Right.

And that's success.

Yeah.

And then I don't know if it was age mixed with life experience, mixed with me learning about the industry I'm in, mixed with just exhaustion.

Uh-huh.

But I hit a point where I was like, "This is not fulfilling me, "and it could still get the views, "but I don't...care anymore, to be honest."

Right.

Once I hit that number of views, I'd be like, OK, now a million more and a million more, and that never stopped.

My first vision board has 5 million subscribers on it.

I have 14.7 now.

And when I hit 5, 6, 7, 8, I never felt that "Ah, I did what I wanted to do."

It was always-- Now how do you get to 9?

"Now I need to do this."

Numbers never fulfill you because there's always a higher number, and so now, how I view my content is "Am I gonna have fun?

"Do I think this is a good thing "that needs to exist in the world?

"Is this gonna help people, "this gonna show them another perspective, or is it just noise, more noise in the world?"

Right, right.

You know, and so now I ask myself all those types of questions because I've done the numbers thing.

Tell me about the talk show.

You took Carson Daly's slot.

I did.

And it was so exciting... Yeah.

for us on the outside, and I'm sure it was a thrill for you.

How long did it take to get to the first show?

They asked me if I was interested in the show.

My initial instinct was no.

I've never said this before.

My initial instinct was "I don't know about this."

Why?

Because it-- my parents didn't really watch late-night television, so I was never raised with it onscreen.

Sure.

So I was like, "I don't know if-- "this seems like a really big commitment.

"I don't know if I want to do this; I want to act and I want to be in movies and all this stuff and--" I bet your agent was like, "Uh, yeah, we're gonna do it.

I'll talk to her."

Well, then I got a call from my agent, and from other people that explained to me kind of the historicness of this and what this could mean... For sure.

and what this has meant.

And I thought, well, I'm really passionate about paving the path for my community, for people of color, for women of color, for the Punjabi community.

I'm really passionate about that, and so if I can work really hard and make a difference in that sense, then yes, I will do it, and that's what tipped me over the edge to do it, is to really just make it be a first and pave this path and try to break a glass ceiling.

And did you feel like you liked where it was going creatively and that you had enough control?

I very quickly discovered that, oh, this is gonna be very difficult, especially with the resources that this time slot has, 'cause sometimes, even in the planning of episodes, I was like, "I don't think that's good" and "I don't think that's funny."

And I was like, "Oh, there's kind of nothing we can do about it 'cause this is what we got."

I loved talking to people and I loved certain parts of it.

There was certain parts of it, I was like, "I just don't know how this is gonna work or play," and that was a really new, frustrating feeling for me because I'd always been in control of my content prior to that.

So I'd say pretty quickly, I was like, "I don't know if I'm gonna be able to do this."

When they gave me a second season, I of course was like, "Let's do it" because, again, in the back of my mind, if I'm being really honest with you, Kelly, I would have tortured myself for an infinite amount of years if it meant paving the path for my community, and so it was almost a blessing that we parted ways when we did.

I think it saved me in some ways because I would have just kept doing that and kept digging myself into a hole.

Good for you.

Thank you.

So, at some point, you came out to your parents.

You're bisexual.

Yes, yep.

Instead of telling them, you wrote them a letter.

Yeah.

Yeah, when I came out at the ten-- tender, tender age of 30, I don't know if it was the result of just not being raised in a community that had queer people.

I came out to people six months after coming out to myself.

There wasn't a single out person in my entire high school.

Mm-hmm.

In university, I knew one queer person.

You know, he identified as a man.

He was so different.

I was like, "Oh, that's not me, either."

It wasn't until I moved to L.A. and I even was introduced to the idea of queerness that I got to thinking that, "Huh, "maybe this is this thing about me that I've never been able to figure out."

So I was like, "I think you need to have "an honest conversation with yourself because I think, "although you've been in happy relationships, "I don't think you've ever been 100% yourself or satisfied," and I just said it out loud.

I actually said it to my dog.

He was the first person I came out to.

Heh!

He was very supportive.

Ha ha ha ha!

Um... and when I said it, it just felt right.

I made a list of people, saying, "I'm going to come out to these people."

My parents were the last on that list.

I was at their house, visiting in Toronto.

Could not get myself to say it in person.

I wrote the letter, dropped it off in front of them, and I said, "Read this, I'm gonna be upstairs," and waited upstairs for what felt like an eternity.

I heard them coming upstairs.

I was just an emotional wreck, to be honest.

Of course.

I was just so scared and so nervous and-- and to anyone watching, the experience of coming out, it really messes with your mind in the sense that even though--even some of my friends that I knew would be so supportive, your brain has a way of convincing you just that this is gonna be so scary and so horrible, and it convinces you of all these horrible things, and so I was really just a wreck.

The first thing my mom said was, "Why are you crying?

You're my daughter and I love you."

Aw.

And they said-- That's pretty good.

Pretty good.

Amazing.

Reflecting on this moment, I had way too high of expectations from my parents.

They didn't understand completely what I was saying, but they did support me.

They sat me down, they hugged me.

They did all those things; I just needed to figure out how to function as my new self, and I kind of projected that onto them without giving them the credit that they actually did pretty darn good... Mm-hmm.

for being who they are and where they're from.

I think it's really interesting to give people credit for their own... personal circumstances.

Yes.

Like, what is reasonable?

Mm-hmm.

What would be an A+ response...

Yes.

right now... for this person...

Yes.

Who grew up with this life and in these experiences?

Which is just so important, and that's a lesson I really had to learn, something I talk about in the book, and I say every day in my meditation is, "I am you, and you are me, and we are in different circumstances."

I've really just learned you got to meet people where they are, and you can't expect them to be where you are.

That's just not gonna happen.

Yeah.

In this idea of, like, "be a triangle," Mm-hmm.

You talked a lot about your relationship with yourself and relationship with the universe.

Mm-hmm.

How's your relationship with yourself changed in the last couple years?

I think I have given myself permission to be a human more and more.

I had a period of life-- again, that same period of hustling from 2010 to 2016, whatever.

That's one definition of success that would not waver.

It was--success means pulling all-nighters, doing the emails anytime, traveling wherever you need to travel, just-- it doesn't matter how you feel or how tired you are.

Success means pushing through and accomplishing your goals.

And you were making millions of dollars.

Correct-- millions of views, millions of dollars, amazing accomplishment, so I'm not saying that it didn't work--it did-- and I'm also not saying that I regret that period-- I don't; I am in a different place now, though, where I understand not that I was wrong, but that there are different definitions of success.

So now, I still am accomplishing a lot of things on my vision board, and I'm still very well-off, but it's not at the expense of my mental health as much, it's not at the expense of my friendships and my personal life.

I've given myself permission to unsubscribe from ideas that don't serve me, come up with new ways of thinking, and letting go of these things I used to be so attached to.

And are you sharing that with your audience?

Because I think that there is reams of literature that explain the ways in which spending time on your phone... Mm-hmm, mm-hmm.

and consuming content, it's just so detrimental... Mm-hmm.

to mental health, and I feel like nobody's gonna listen to that from anybody but someone like you.

I have been really vocal about it, especially during the pandemic.

I actually deleted all social media off my phone for, like, six months.

I didn't do anything.

Wow.

I was like, "I'm not checking it."

I got back so much time in my day, I was so much more present, I was so much happier.

I was spending my mind on things that I actually thought deserved my attention.

I see social media as a tool that we're supposed to use.

It's not supposed to use us.

I know, and it does use us.

Right?

It does use us, though.

I mean, 9 times out of 10, it is using us.

I know.

100%.

And this is coming from someone who has made a job off of social media.

I think it's great.

I think it gives a voice to people that don't have a voice, it brings communities together, it educates, but it is a double-edged sword.

We cannot pretend like it is not.

♪ Kelly: OK, so there is a lot of talk about your generation.

[Laughs] What do we misunderstand?

Listen, I think my generation is one that often gets labeled as entitled, lazy, impatient, and sometimes yes, that may be true.

But I think my generation is also the one where we're just the most creative when it comes to what is possible, what direction we want.

We're very entrepreneurial in ways that I think no other generation has been.

Even my job to enter entertainment-- back in the day, that would be a casting director, an agent... Yeah.

you need to do X, Y, Z, Headshots.

Exactly, head-- Be in commercials.

I've never done a headshot!

You've never done a headshot?

I've never done a headshot!

That's amazing.

Yeah.

So, I feel like, you know-- And you surely didn't start with an agent.

No.

You started with...

I didn't have an agent, I didn't have a ma--I had no one.

you and a stack of books?

A stack of books, I had a tripod, a really crappy lamp as a light, and just figuring out how to edit and shoot and do all things myself, yeah.

That's so cool.

When you say, "Be a triangle," what do you mean?

Well, I think, for most of my life, I never really had any clear idea of what kind of person I wanted to be and what I wanted out of life.

I had a North Star in the sense of "I want to be in entertainment, I know the job I want," but I had no idea of "But what do I want my values to be?"

and, like, "Well, how do I want to feel when I get there?

"And then, at the end of the day, if I get there, what's important to me?"

So I felt that once I got to that North Star, I was like, "Wait, but why am I unhappy?"

or "Why does this not matter as much as I thought it would?"

and "Why, every day, do I still wake up feeling unfulfilled?"

It's because I had no foundation of just, like, what I returned home to at the end of the day, and so "be a triangle" is, you know, a triangle's a really, really strong shape with a strong foundation.

I became a triangle to be, like, have a base of who you are and build everything on top of that.

Yeah.

Yeah?

Right on.

♪ Everything has a cost.

Mm-hmm.

What has your work cost you?

My work has cost me-- and not always-- but it's my mental health.

I--getting into this industry, have had episodes of things that I didn't even know were possible.

Definitely, I've struggled in my adult life with friendships and having friends that I can just call when I want to talk.

I don't think I have any of those friends that I can call just when I want to talk.

Why?

Because those types of relationships take time and effort, and that's hard to do when you travel a lot or when your schedule's so busy or-- honestly, to call myself out-- when you don't prioritize it.

Right.

For so many years of my life, I thought, "I don't have time for friendship because I have to do this work that is so important."

Right, and it's a race.

Exactly.

I mean, the work you were doing was a race.

Like, if it wasn't you, it was gonna be someone else.

Exactly, exactly.

My physical health was a huge one.

Uh-huh.

The amount of travel I did in some periods of my life, I don't think anyone should do that to their body and back-end mental health and... Yeah.

what I was putting into my body, eating just whatever was quick and fast and doesn't matter, never thinking about it.

Yeah.

It's 4:00, we got to be in the lobby by 8:30, so I want to sleep.

You should sleep soon, too.

When you say it cost you your mental health, like, how bad did it get?

Two weeks ago, I was like, "I have this intense feeling of something and I don't know what it is," and I was talking to my therapist about it, and she's like, "That's called a panic attack," and I was like, "Ah, didn't know that, what that was."

But I was in a conversation and I was like, "Oh, I think I'm gonna die right now and I'm not gonna be able to stop it."

Mm-hmm.

I've had one.

Yes.

Never had those, and I talked to my therapist about it and she said, "That is a result of always functioning on 10, "and then your nervous system just tipping into an area that it can't handle anymore."

Mm-hmm.

And that was two weeks ago... Mm-hmm.

so my work is still sacrificing things about my life.

However, the thing I'm doing differently is I'm not ignoring it.

Since then, I've been like, "No, you need to meditate every morning."

Yeah.

Need to think about what I'm putting in my body.

The step of improvement for me is I need to do something about it and I'm prioritizing doing something about it, where--it's sad to say--in the past, I wouldn't even do that.

Well, it's interesting because one of your big points in "Be a Triangle" is, like, to get into a better relationship with yourself.

Mm-hmm.

Since writing this book, not only have I lost, like, 25 pounds, but I've had multiple people, whether they just met me or whether they've known me for a long time say, "You seem really, genuinely happy."

Every day in my meditation, I say, "Relationship's yourself, "relationship to the universe, understanding distraction, and implementing design."

The second I start to stray from that, life goes... and puts me right back on track.

Uh-huh.

Heh!

Yeah.

Tell me about distractions.

Distractions are a huge thing in my life.

I think I am laser-laser-focused when it comes to work, but when it comes to my gratitude and my patience and my values, I do get distracted very easily.

You know, I was doing one of my dream jobs.

I had a late-night show, and I was going to set every day, and that's, like, a dream for me, to go to set and work with a crew I love.

And I woke up in such a good mood and I was driving to set, and then I got a phone call with some bad news and then there was traffic and I was hungry, and in five minutes, I was like, "My life is so hard and my job is stressful "and everyone is annoying me and I wish I didn't have to go to work," and I was like, "How did I get from this to this so quickly?"

And so, on that car ride, I said, "I'm gonna try something different.

"I'm gonna label all of these things as distractions from where I actually want to be."

It helped me get over them faster and back to where I wanted to be, as opposed to having me live in this land of just being sad and bitter and ungrateful.

Mmm.

And so that's how I kind of view life now.

So we have a thing on "Tell Me More" I call "Plus-One"... Mm-hmm.

Where we ask you to tell us about somebody who's been really impactful... Yeah.

for your thinking or for your heart.

Yeah.

We want to remind everybody that nobody gets anywhere alone... Mm-hmm.

and that we have this terrific effect on each other all the time, whether we know it or not, so who is your Plus-One?

My Plus-One is someone by the name of Alok Menon.

They are a poet, a comedian, a writer, all-around fabulous human being.

I discovered them on Instagram because they do book reports on just de-gendering fashion and the gender binary and all of these things, to be honest, that I didn't know much about, and so it kind of just really opened my mind to all of these ideas.

I had them on my show, on my late-night show, and they blew me away.

It feels like, so often, people tell us there are no queer South Asian, so I grew up thinking that those parts of my selves were incompatible.

I vividly remember they said this: "I think cynicism is becoming too mainstream, "and it's cool to be mad about things and it's cool "to be upset, but I want to challenge that "and I want to celebrate progress when we have it, while still challenging us to do better."

And so Alok does so many amazing posts about the history of gender and the history of fashion and how all of these ideas are holding us all back, not just people that are non-binary, not just people that are part of the queer community, but us all back, how all of these ideas that we subscribe to are not serving any of us.

And so I just really want to highlight them and the work they do because I learn something every time I read one of their posts.

♪ How have you changed your thinking about what we are entitled to and what we owe each other?

Years ago, I believed that, "Oh, I worked really hard on this thing.

"Why did it not work out the way "I thought it should have worked out?

"I worked really hard on some auditions, and I really, really tried and it didn't work out for me."

Then I saw people that were younger that were getting more views and more-- and I got really bitter.

I thought, "No, this is-- this can't be happening.

It's not fair.

I had to check my entitlement.

Really and truly, nothing is owed to us, and I think another big part of that is I've had the privilege of traveling to a lot of places, and I meet so many people who have so much potential and are so smart, and they are never given even half of the opportunity that I am, and when you meet people like that, you realize life is unfair.

It truly is, and that realization has allowed me to be more grateful in my life.

We also have a little speed round.

Oh, right.

Let's do it.

Speed round, but-- Let's do it.

So I haven't been doing a speed round this whole time?

Yeah.

Ha!

With the way I talk?

Lilly Singh, first concert?

It was a Bollywood concert-- Madhuri Dixit.

I know you don't know who that is, but icon.

Best live performance you've ever seen?

Pink.

Have you ever seen Pink live?

No.

Is she great?

She's, like, hanging by her appendix and, like, spinning and belting along.

I know there's water.

It's crazy.

Yeah.

Crazy.

Definitely Pink.

If you could pass one law or overturn one Supreme Court case?

It would be any decisions that affect a group of people.

They need to be part of the decision-making process.

That doesn't happen.

Yeah, I think that's a really good law.

Yeah.

If your mother wrote a book about you, what would it be called?

[Chuckles] "Nothing Surprises Me Anymore."

Lilly Singh... Kelly!

you're like the discovery of a lifetime.

You're such a joy to talk to.

Well, thank you.

You're such a joy.

You're so wise.

Thank you.

Thank you so much.

You're awesome.

Thank you for having me.

Yeah, total pleasure.

Kelly: For more on the science behind creativity and burnout and budgeting that Lilly and I talked about, join me for my companion podcast on "Kelly Corrigan Wonders" or for our companion video on pbs.org/kelly.

[Theme music playing] ♪ ♪ ♪ ♪ ♪