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September 17, 2025 61 mins

Do you feel like you need to prove yourself?

Who do you think you’re trying to impress?

Today, Jay sits down with his close friend Lilly Singh for a transformative and deeply honest in-person conversation at the Ellie Caulkins Opera House in Denver. Known for being a trailblazer in digital media and late-night television, Lilly reflects on the hidden challenges behind being “the first”, from navigating cultural expectations to battling loneliness and self-doubt. Lilly shares how much of her early success was driven by the need to prove her worth to others, and how she is now shifting toward proving herself right instead of chasing outside validation.

Together, Jay and Lilly explore the inner voices we all carry, from the critic to the voice of compassion, emphasizing the importance of practicing daily self-care to balance high standards with grace. Lilly shares her personal rituals such as journaling, naming her inner voices, and reframing failure as growth, while Jay emphasizes the transformative power of reflecting on the past as proof of resilience. Together, they remind us that even in moments of pressure and imperfection, we are not defined by our accomplishments but by the person we are becoming.

In this interview, you'll learn:

How to Turn Failure Into Growth

How to Quiet Your Inner Critic

How to Practice Daily Self-Compassion

How to Live with Your Inner Voices

How to Stop Chasing Outside Validation

Every challenge you’ve faced so far has proven that you are stronger than you think, and every step forward is a reminder that you are capable of creating a life that feels true to you.

With Love and Gratitude,

Jay Shetty

What We Discuss:

00:00 Intro

03:20 Growing Up Without Options

09:28 Realizing You Always Have a Choice

17:37 Committing to a Life of Growth

19:01 Learning to Stop Self-Blame

21:56 Breaking Free from Unrealistic Standards

27:55 Why Good Enough Is Enough

31:26 Living Alongside Self-Criticism

36:47 You Are More Than What You Do

41:32 Finding Strength in Past Resilience

44:42 Proving to Yourself You Can

48:25 Why Women Aren’t Taught About Their Bodies

52:40 Past, Present, and Future Reflections

59:39 Friendship That Stands the Test of Time

Episode Resources:

Lilly Singh | YouTube

Lilly Singh | Instagram

Lilly Singh | Facebook

Lilly Singh | TikTok

Lilly Singh | Books

See omnystudio.com/listener for privacy information.

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Thus far in life, you have a one hundred percent
success rate of getting through things. There's not a single
thing in your life if you're sitting here right now
that you have not gotten through. So anytime you felt
like this in the past, you got through it. And
I think we need to remind ourselves that a little bit,
that we can beat ourselves up. But just because your
brain is saying it, it doesn't mean it's true. We
lie to ourselves all the time. The number one health

(00:22):
and well iness podcast Jay Sheddy, Jay Sheddy See Only
Jay Sheddy.

Speaker 2 (00:29):
Hi, I am so excited to be here tonight at
the Ellie Culkins Opera House in Denver with the one
and only my dear friend Lily saying, let's go.

Speaker 1 (00:40):
First of all, you know I'm gonna uproot this whole thing.
You know this, I don't follow rules. How awesome is
j Sheddy?

Speaker 3 (00:44):
Though, come on, this is your show now?

Speaker 1 (00:48):
No, it's not my show.

Speaker 4 (00:50):
I like the show has way.

Speaker 1 (00:52):
More famous friends than me. So the fact that I
get to close out this tour all of you, this
is the last tour stop, isn't that amazing? We get
to be Yeah, I mean, I'm not gonna uproot too much,
but I just have to. Like, I know we're all
thinking it Jay's brain. He's so kind. I'm gonna give
you all the tea of what Jay's actually like off
the podcast is we're actually real friends. Oh I will
baby girl, don't you worry. What's your name, Pamela? Okay,

(01:19):
her name is Jay Sheddy. There's an open bar here
and I like it. No, but Jay is an incredible
human being. I'm so honored to be here on this
last tour. Stop everything you know about Jay from the podcast.
I don't know how to even explain to you that
he's even better off the mic and behind the scenes
and behind the camera. This man is the real deal.

(01:39):
He is so genuine, the first to say yes to
anything anyone asks him. He calls me up randomly, just
just check up on me, just to say Hi. The
person you bought tickets for and you're supporting deserves all
the support that you are giving him.

Speaker 2 (01:53):
Absolutely, you're the best. I appreciate that we are real friends.
Me and Lily have a scheduled dinner day every month
because our lives are crazy, but then we also hang
out spend a lot of time together. I stalked her
seven years ago to make her my friend. And I remember,

(02:13):
you have eyes like.

Speaker 1 (02:14):
That, you can do that, So men don't get ideas. Okay,
you have eyes like that, you can do that.

Speaker 2 (02:21):
I remember, I remember I just moved to LA and
as someone who'd and there's a reason why I'm giving
you this background because I have a question for Lily
to kick it off with. But I grew up watching Lily.
So I would watch Lily in London on YouTube and
just think, how is this person, you know, creating this
incredible community online, you know, billions of views, tens of

(02:42):
millions of followers. It was incredible to watch. And I
remember when I moved to LA because I'd watched so
much of Lily's videos, I was like, we'd be great friends, right,
and so so I literally would just tell everyone I'm met,
and they'd be like, oh, who do you want to connect?
I want to connect with Lily because I think would
be really good friends. And then when we find met,
I did the really dorky thing of saying I think

(03:02):
would be really good friends, and then that's we became
really good friends.

Speaker 1 (03:07):
He's not live. Three different people called me to be
like this guy named Jay keeps saying he wants to
be your friend, and I was like, okay, and then
we became friends. And now how lucky am I that
I get to have Jay Sheddy.

Speaker 4 (03:19):
In my life?

Speaker 2 (03:20):
But I wanted to ask you this question to kick
it off with, because what I've always admired about your
career is that you have been first to so many things.
You were one of the earliest adopters of a creator
on YouTube. I remember moving to New York and seeing
billboards of you all over New York. You were one
of the first people to get like for a woman

(03:42):
of color, right, bisexual woman of color to get their
first gay late night days?

Speaker 1 (03:48):
Okay, happy bride, that's not gays.

Speaker 3 (03:52):
To get a late night show, which was unheard of.
Another first?

Speaker 4 (03:55):
Right?

Speaker 2 (03:56):
The amount of first that you've had in your career
are you know? I literally couldn't even count all of them.
It's incredible. You've paid the way, You've constantly trail based.
But being first is celebrated, but it's not easy. And
tonight we've been talking about people chasing their dreams and
people going after and not worrying about what people think.

(04:16):
But when you're first, that's all that happens. Talk to
me about how you even had the idea to start
on YouTube and how long it took you from having
an idea to execution.

Speaker 1 (04:28):
Yes, my career has had a lot of firsts, and
I know and thank you for asking me this question,
because I think very often when people talk to me
about my career on first it's very celebratory, which I'm
very grateful. It's very cool to be able to say
I was the first two. But it is so scary.
It is so lonely. It is. I've had so much
anxiety over it. To be in a situation where you

(04:51):
have no one around you to ask for advice, no roadmap,
no one's else's failures, to look at her wins, so
look at it's really really scary and lonely. I started
making YouTube videos in twenty ten. I spontaneously made them.
I was in university getting a psychic degree, which I
don't use, and yay getting a psych degree, and I

(05:15):
was kind of I don't know if anyone can resonate.
I was just kind of going through the motions of life.
My parents really want me to go to university. I
go to the same one my sister went to. My
parents really want me to get a degree because they
believe that a degree will get you a job. Lol.
So I go and do that as well. Right, I
get the same degree my sister gets, and now I'm
like just living this life alike. And then I'll get
a degree, and then I guess I'll get married, and

(05:35):
then I'll guess I'll have kids, and then I guess
I'll just live do the motions of this life that
everyone around me is doing and that everyone before me,
especially the women before me, have done because they didn't
have any other options. And I was I'll give you
a little bit of heavy context here because I think
it's important. From a very young age, it was abundantly
clear to me that my extended family was not thrilled

(05:58):
at the idea of a second daughter being born. So
I don't know if anyone can relate here, but in
Indian culture and a lot of cultures around the world,
people want a son, you know. And so I had
an older sister, and when I was a second daughter born,
it was made very clear that, like, this is not
worth calling the family about. Really disappointed about this. Laugh
at my trauma. That's what I've done for the past
ten years. Here, we got the right idea. But so

(06:20):
I bring this up because I feel like for most
of my life I've had this chip on my shoulder.
And I'm not saying it's healthy, to be clear, I'm
just saying it's true. I've always had this chip on
my shoulder to prove I am worthy of being alive,
being in spaces, and to prove to other people like no,
I was born and I'm gonna do great things. Thank you,
thank you. We do need this comments. So when I

(06:45):
started making YouTube videos, I was in a really dark
place because I was living this linear life. I didn't
feel like I was fulfilling my purpose. What a podcast
reference and I was just like, this can be what
life is about. There's got to be more to this.
I made my first YouTube video because I felt so
low and I felt so confused. And my first video
seventy people watched it, and I was like, well, damn,
I'm famous now. I don't know, I don't know so

(07:07):
how many people. But I just fell in love with
this idea of I get to say what I want
to say, and I've built this albeit small community of
people that are connecting with me, and I just felt alive.
I was doing something for myself for the first time,
breaking the rules for the first time. This wasn't a
path anyone else had done. And so that's why I
made my first YouTube video is because I was grasping
for connection and I was grasping to probably prove myself.

(07:31):
Now YouTube led to a bunch of other cool things.
You know, I've gotten to write two books. Neither of
them have sold as many copies as Jay's books, but
you know, we try. And the reason I'm being really
vulnerable to tell you this, I think the reason I
started YouTube, the reason I said yes to Late Night,
the reason I said yes to a lot of things,
again not saying it's healthy, is I knew one thing

(07:53):
people could understand, every extended family member, every man in
the family, everyone that doubted me. I knew they would
understand influence, and I knew they would understand fame and money.
And again I'm not saying that those things should be
the drivers. But when you're in a situation where you're
like nobody believes in me, and I'm surrounded by people

(08:14):
that don't think I can do something, I chase something
I knew they would understand. And it has been a
lifelong journey to teach myself to chase something else. I
don't think I've ever told you that.

Speaker 2 (08:31):
Actually, I need to come over and give you a
hug right now. No, I can tell just what you're
saying is it's you know, because.

Speaker 1 (08:40):
It's not a sexy thing to admit. I think, you know,
it's a lot of times people want me to talk about,
Oh yeah, I did it because I'm representation and passion.
Those things are true. That's not why I started. I
started because I was like, oh, you don't think I
can do this. You'll understand a million people watching my video.
You will understand the size of my house. You understand

(09:00):
those things. Then I got those things and don't do
me wrong. It felt really good, but then I still
felt really empty because I was trying to prove other
people right, when really what I try to do now
is I try to prove myself right. That's more important.

Speaker 2 (09:14):
Well said, Well said, yeah, absolutely, give it up for Lily,
Absolutely absolutely.

Speaker 4 (09:18):
I want to dive into the depths.

Speaker 1 (09:20):
Of people who are like, we didn't know her, but
she's kind of smart. That's right. Let me win you over.

Speaker 2 (09:29):
I want to dive into the depths of some of
that because I think even for what you're just saying
to obviously I know you so well, but for everyone
else here as well, to really understand what that upbringing
feels like, because I think, like you said, everyone here
has that in their own way. I think everyone feels
like they have something to prove. Everyone feels like it's
very rare that you were surrounded by people who believed

(09:50):
in you and thought your ideas were amazing. And if
you had that, that's incredible. But maybe that even came
with its own pressure because you had to live up
to certain expect Walk me through what those cultural expectations
did to you as a young girl, and I know,
as someone who's done a lot of self work, talk
me through how they kind of mirrored into your future

(10:12):
life and the kind of things you've had to peel
back on live.

Speaker 4 (10:15):
Do you actually make sense to that?

Speaker 1 (10:16):
Yeah, And a lot of this are things I've realized
only as a full adult because I was so blind
to it growing up. You know, of course, there's silly
examples like girls aren't supposed to do this, girls dressed
like this, to silly things like my grandfather, God bless
his soul. But always girls are not supposed to whistle
like simple things. Girls shouldn't be so spoken, you know,
they should be generally timid and not not be the

(10:38):
center of attention at a family party. I loved dancing
growing up, and I was the captain of a dance team,
and the main reason my parents had a problem with
it was girls aren't supposed to dance at events or
get hired to dance. So there's a lot of what
you should and shouldn't do as a girl the box
are put in as a girl. But the deeper thing
that I actually subconsciously learned growing up was that if

(11:02):
someone tells you something about yourself, you just accept it.
For so much of my life, I was like, oh,
you're saying this thing to me. I guess that is
now my burden. Oh you were telling me I should
be this way. Great, I will now work on ways
to be that way. Oh you're telling me I shouldn't
be this way. Great, I'm gonna work really hard because

(11:24):
I'm not gonna be that way. It wasn't until I
was a full adult, and there's a very specific experience
that taught me this lesson where I realized that I
could actually just say no, I'm good. I actually don't
need to accept this thing you're putting on to me,
like I actually have a choice in the matter. So choice,
the idea of deciding, did not occur to me. And

(11:46):
the experience that taught me this was in twenty nineteen.
I got a late night show, and I had two
seasons of a late night show. And when it was
brought to me, I'll be real, I didn't grow up
watching late night. My parents didn't watch late night. You know.
My parents are like mega brown Indians, and I don't
think they related to anything on late night. And so

(12:06):
I don't have that experience where a lot of people
were like, I grew up with it and you know
it raised me. I didn't have that, and so when
they asked me to do the late night show, I
actually said no. I was like, I don't really like
I didn't get into this to be a late night host.
I don't really know much about this, and so I
went away. Now I'm a big believer that the universe
teaches you lessons and brings things to you. And so

(12:28):
a month later they came back and they were like,
we are asking you for the second time to be
our late night host and I was like, Okay, let
me think about this properly, and again we go back
to me trying to prove myself. One of my team
members explained to me how historic this would be. They're like,
there's never been a late night host that looks like you.
It would be historic. It would, you know, be a headline.

(12:50):
And of course my ego is like a headline. I
do like a headline. I would of course I'd want
to make history. And of course the sentimental part of
me is also thinking, oh, I could like help a path,
then maybe I can open the door for someone else,
and I could do what I did with YouTube. And
so I said yes, And I did this late night
show for two years, and it was twenty years of knowledge.

(13:10):
When I tell you, it was the most difficult thing
I've ever done in my life, like mentally, emotionally, spiritually, physically,
just in the worst shape of my life. It was
such a demanding job. We shot ninety six episodes in
three months in season one, with half of the writer's
room that a normal talk show would have half of
the writers with a quarter of the budget probably, and

(13:32):
both seasons took place during COVID, So for my first season,
because we banked those episodes when I was talking about
partying and making out and traveling, we were in COVID.
H you know, that was my first season, and my
second season was shot fully in COVID, so all the
interviews were on zoom. So it's a very challenging experience.
Experience ended, and for a year or two I just

(13:54):
beat myself up about it, like I couldn't do it.
I didn't do it justice. I only had two seasons.
I didn't even like a lot of the episodes I shot.
I remember walking to my monologue mark and being like,
this isn't good. What I'm about to sell right now
is not funny, and I'm gonna have to do this
for ninety six episodes and it's a horrible feeling. And
I beat myself up a lot of the time. But

(14:15):
during that process, people would literally come up to me
and say, verbatim, a billion people are counting on you,
Like all the Indians are counting on you. A billion
of us are counting. People would come up to me
and say like, oh, but of course every headline was
bisexual woman of color, And people are so mad at
me about the headline, like I wrote it, what I mean,

(14:36):
all the gays are counting on you, like all the
women are counting. I'm like, that's a lot of people
that are counting on me, you know what I mean. Like,
there's no way I could make all of these people proud.
There's just no way. And so for so long I
felt like crap about that that I let women down.
I let brown people down. I like queers down. I
let people with long hair down. I let dog moms down.
Everyone leave, bros. I let you down. Okay, you know

(14:59):
what I mean. I thank you, baby girl, thank you.
But only in the past three years that I realize
I was like, I now have the confidence and self
love to say that I actually could have said, actually,
it's not my job to make a billion people proud,
you know what I mean. And I did not have

(15:20):
that thought at the time. I was like, of course, okay, yes,
when I was there writing the monologue, Okay, I'm gonna
mention Indian. Okay, I'm gonna mention I'll be a little
gay over here, okay, and then I'll mention my I
was so fixated on, like how do it didn't even
occur to me to say, I actually don't have to
do that I actually don't have to live up to that,
and I think that's just my upbringings. I've always just

(15:41):
taken on the burden without question, you know.

Speaker 3 (15:48):
I mean, I've definitely never heard you talk about it this.

Speaker 1 (15:52):
Way and have no filter day you know this that's
the open book for better or for worse.

Speaker 2 (15:56):
Oh no, But it's really resonating with me because as
I'm thinking of everyone who's sitting here as well, let's
say that's exactly what we're going through, where we feel
the pressure to carry the ban for our family, our friends,
for the children, like whatever it is, like, I think
we all carry so much weight and pressure of expectation
of showing up, and we can feel like we're carrying everything.

(16:20):
Was it going through the process that So here's the
interesting thing. Could you have got to where you are
today in that confidence without saying yes to something that
didn't work out the way you would have wanted it
to or was that the only way.

Speaker 4 (16:36):
To get there?

Speaker 1 (16:38):
Unfortunately for me, but very fortunately for my therapist who
now owns a yacht, I've had to go through every
challenging experience to get to where I am. I take
self growth very seriously. This as my friend. I'm really

(17:01):
dedicated to being a student for life. I want to
learn about myself. I have a ton of rituals in
my life to learn about myself. But there's no way
I would have any of that or be where I
was if it wasn't for the moments that kicked my butt.
You need to get your buck kicked a little bit
to learn some lessons. So when even people ask you regrets,
of course we all think of ones. But I bet
if you thought of any moment that was really horrible,

(17:22):
there's a silver lining where you're like and that made
me amazing because of this an x YSI. So I
really do feel like I had to go through late night.
I had to go through a ton of stuff to
be the person I am now to fulfill the purpose
I am fulfilling right now. And now I take that
knowledge forward knowing that when another thing happens as challenging,
that is the thing that kind of holds me to
be Like, I know, somewhere in here is going to

(17:43):
be something that brings me closer to the person I'm
supposed to be.

Speaker 2 (17:46):
If someone's in one of those situations right now, like
they're sitting here right now, and they're feeling stuck, They're
feeling like they're in the middle of one of those transitions,
which is always the hardest place to be in it.

Speaker 4 (17:59):
What would you inc them to do? Is someone?

Speaker 2 (18:01):
And by the way, I know that for a fact,
like your commitment to self work, your commitment to healing,
your commitment to everything I talk about, Lily is like
teaches pet for right, Like she's like the best student.
Like everything I talk about are things that you truly
live by. Have seen that in our friendship. But if
someone's right in the thick of it right now and

(18:21):
everything just feels like it's going wrong, it's falling apart,
they feel the weight of the world on them, what
would you encourage them to reflect on?

Speaker 4 (18:29):
Do or build? What would you encourage them to do?

Speaker 1 (18:31):
Yeah, I think we are our own harshest critics, right,
And if you're that person that like beats yourself up mentally,
you're not alone. Look to the person next to you.
They do the same thing. We're all just beating ourselves
up all the time. And I'm not the best at math,
but I know this one thing I'm about to say
is one hundred percent going to be correct, and it
is going to apply to every single person here, and
that is thus far in life, you have a one

(18:53):
hundred percent success rate of getting through things. There's not
a single thing in your life if you're sitting here
right now, that you have not gotten through. So anytime
you felt like this in the past, you got through it.
What I do is I actually journal and write about
some of those experiences. Lily, you were in this experience
in your eighth grade when you had late night, you
were with this smiss, you got through it. You have
one hundred percent. You feel like a failure, and you

(19:15):
have one hundred percent success. Right. That is the truth
of where you are right now. And I think we
need to remind ourselves that a little bit. That we
can beat ourselves up. But just because your brain is
saying it, it doesn't mean it's true. Right. Jay actually
taught me this that we lie to ourselves all the time.
Our brain lies to ourselves all the time. And you
just have to change that thought and go back and
relive all the things that you've gotten through. One hundred

(19:36):
percent success. Right, every single one of you give yourself
a round aplause congratulations.

Speaker 5 (19:40):
Yes, it's true, it's true.

Speaker 2 (20:00):
And I love the practical aspect of it, though, because
this is the part we skip. Sometimes we hear something
like that and we go, oh, I really like that idea.
That makes sense to me, but then we don't actually
do the practical piece. So what Lily just said there
was that idea of her journaling and actually thinking back
to all the things that she's overcome in her life.
That act of journaling, writing it down, reading it back.

(20:23):
That's the practice. If you really want to find confidence,
you only have to look at your past. If you
really want to find resilience, you only have to look
at your pain. If you really want to find that strength,
you only have to look back in the last ten
years and think of all the things that you broke through.
But you have to write it down, you have to
read it, and you have to remind yourself, because your

(20:43):
mind will just remind you of all the times you
didn't stay strong, all the times you didn't be brave,
all the times you didn't do it. And so the
act of writing it down, as Lily saying, is huge.
And I don't want to undervalue just how powerful that
piece of advice is. As you're breaking through that and

(21:04):
you're looking at some of the residue of childhood expectation
that we all have. Right, I'll share one of mine,
which is which is vulnerable for me too, And you
know you've inspired me to want to open up as
well in this conversation, and it's I remember, this was
one of the big ones that was just hidden for
so long. I was given a lot of love growing up,

(21:26):
but that love always had a little bit of guilt
in it. And what that meant was that I was loved,
but I was made to feel guilty if I didn't
love my caretakers back with that level of love, if
not more so, I always felt like I wasn't loving
the people that loved me enough. And what I didn't
realize is that when I first started dating my now wife,

(21:48):
that's how I loved her. I over loved her, but
then made her feel guilty for not loving me back enough.
And what that did is it just pushed her away.
It didn't make us close, so it didn't make her
love me more. It made her more shut down. And
the reason I'm raising that is because this tiny thread
or this tiny seed or weed that was planted when

(22:11):
I was like four years old was affecting me in
my thirties. What has been something in your life that
you've seen has just stayed And that's the thing that
you're working on the most right now.

Speaker 1 (22:23):
I mean, how much.

Speaker 3 (22:23):
Time we got here? Jay?

Speaker 1 (22:25):
Also? Can I have this? Can we have this delicious beverage?

Speaker 4 (22:29):
Judy?

Speaker 1 (22:30):
Oh my god, let me just I'm going to answer
this question a second befirst. I just wanted to take
a cheers, cheers, cheers. Oh my god, this refreshing beverage.
Hold on a backling to you with adapted is where
do you get this?

Speaker 4 (22:50):
Joe?

Speaker 1 (22:52):
Where do you get this delicious drink? Is it available
at Costco? Should every person? So delicious? Seriously? Thank you
so much. You can give me a check later. No,

(23:13):
back to serious combo. Based off everything I just told
you about me being so intense with proving myself, what
comes along with that is unrealistically high expectations and standards
for myself. So when you're fueled by proving people wrong
and trying to prove yourself, the bar is so high

(23:36):
for yourself. Like when I say I'm my own biggest critic,
I really am. I could do an amazing job at something.
You better believe. I'm walking backstations like why did you
do that? Why did you say that word like that,
Like I am going over everything again, and so my
expectations are so high and now just based on what
you said as well with Rody, I map that onto
other people. So now I'm in situations with friends and

(23:57):
relationships where I have such an unrealistically high bar for
them because that's what I have for myself and other
people they're just trying to chill, they're just trying to
live their life, They're just trying to do their thing,
and I'm like, no, everything needs to be a hundred
and amazing and perfect. And that has been a really
big struggle for me because I associate expectations with love

(24:18):
and care and if they don't do it to a
one hundred, they don't love me, they don't care about me.
Then that means I'm not important, I'm not a priority.
And I learned that that has a lot to do
with how I treat myself. And one of the ways
I've tackled that is just to really work on my
self compassion, you know, is to allow myself to just
relax sometimes and it's okay. Not everything needs to be

(24:40):
perfect one hundred a million again. I'm really nerdy, y' all.
I hope you decided. I do a lot of practices
that have help. Maybe one that I've done. And when
I first started to do this, I was like, this
is so dumb, this is never gonna work. I was
literally like, this is so cringe. I have a notebook
on my night table and I told myself that every

(25:03):
day before I go to bed, I'm just gonna three
bullets of ways I showed myself compassion or grace. Could
be so small, could be so big. The first couple
of days, I was like, I think I hate myself.
I did nothing. And then that got me to think, like,
throughout the day is there's small, small ways that you
showed your self compassion. So every day till this day,

(25:26):
I write three things before I go to bed, And
they could be really simple, like, hey, you were really
tired and you delegated that task. Good job. You showed
yourself compassion. You were really sad about this thing, and
you texted a friend like, you showed yourself compassion. You
drew a boundary with a family member even though it

(25:46):
was really scary, even it was really small, you did that.
You showed your self compassion. Now this sounds so lame,
and I'm well aware of this, and for the first
two weeks three weeks, I was like, this is dumb.
And then something amazing happened. Two months into this. My
friend was late. Now, if anyone knows anything about me,
that's the type of thing that would send me Okay,

(26:07):
you don't show up late to LI, but you were saying,
like Jay knows that you show up late. It's like
you don't love me, you don't care about me, you
didn't plan your day in accordance to being here, Like
it's the spiral. My friends showed up late, and genuinely
I was like, that's okay. I was somehow able to
channel grace towards this person. And then it kept happening.

(26:30):
Suddenly my friend didn't do the thing they said they
were gonna say, and I was like, oh, my brain
didn't go automatically too, they don't love me. It automatically
went to like maybe this thing happened in their day.
And that's why I was starting to give people grace
solely because I just monitored the grace I gave myself
and that has changed my life. So the expectations is
really hard. But now I'm just kind of like, it's okay.

(26:51):
We all just deserve a little bit of grace.

Speaker 3 (26:54):
You have no idea how big that is for Lily.

Speaker 1 (26:57):
Honestly, it's a big deal.

Speaker 3 (26:59):
When we first met game friends, I'm also I also,
you should.

Speaker 1 (27:02):
Tell the genuine stories of how crazy A'm telling them.

Speaker 4 (27:03):
Okay, I'll tell you. I'll tell.

Speaker 1 (27:05):
So.

Speaker 2 (27:05):
I'm also someone who loves being on time. I was
raised to believe that if you're not early, you're late.
My mum raised me that way, and so I try
and live by that. But I am married to someone
who is not raised like that, so.

Speaker 4 (27:18):
I can.

Speaker 2 (27:20):
Right, So when we become friends, and like, I know
how important it is for Lily for people to be
on time, I also feel that way. When I turn
up late somewhere, I'm like, this is terrible, Like I
hang my head in shame. My wife has no shame,
like does not care, like just does not feel anything, right, like,
does not feel anything. So here we are rocking up

(27:41):
to movie night late and I'm like, they want to
start the movie.

Speaker 4 (27:44):
By this time.

Speaker 2 (27:45):
Popcorn would have gone into the microwave at this time,
the you know, the butter would have been poured on
it at this time. Like literally, that's like how meticulous
Lily is and I'm stressing out and like so that
would happen every time to the point, but you were
like this last year. Lily throws the Best of Vali
party ever, right periods and every year she throws the

(28:05):
Best of Ali party gets bigger and bigger every year,
and thankfully I get invited every year, even though we
turn up late. And this last time we went again,
we were so late because of my wife, but Lily
was just unfazed.

Speaker 4 (28:19):
I got a really nice hug, we took pictures.

Speaker 2 (28:21):
It was amazing. And that's such a big thing for you.
But that practice is so beautiful, and it's something that
I've noticed in all of the biggest high performers that
truly exist.

Speaker 4 (28:33):
They have two qualities.

Speaker 2 (28:35):
They have really high standards for themselves and they have
really high grace for themselves.

Speaker 4 (28:42):
It's a real thing.

Speaker 2 (28:43):
And yeah, those are the two things, and Lily's demonstrating
it right now. And that's something I want each and
every one of you to have, because it's not just
reserved for athletes and performers and actors and musicians. It's
something each and every one of us deserve. Roger Federer,
the tennis player, gave this amazing, amazing insight when he

(29:05):
gave a speech. He talked about how when he's it's
kind of comes to what Lily saying. When he's playing
a point, it is the most important point on the planet,
but as soon as the point is over, whether he
loses or wins the point, it is the least important
point that he has ever played in his life. And

(29:26):
he said it is only because of that that he
can play the next point. And he talked about in
this speech how he's only won something crazy like fifty
seven percent of points in his life as one of
the greatest tennis players of all time. And he's making
the point of how, look, you don't need to be
at one hundred percent, you don't even need to be

(29:47):
at ninety percent to be one of the best tennis
players of all time. And so this pressure we put
on ourselves is like I wasn't the perfect mom today,
I wasn't the perfect dad today, I wasn't the perfect
person today. I wasn't the perfect employee today, I wasn't
the perfect whatever whatever it is today. Like you never
had to be perfect for it to be good enough,

(30:10):
and that pressure that we put on ourselves to be
perfect just gets heavier and heavier. So I hope that
listen and Lily, listen to Roger. When you walk out
of here today, feel freer, feel lighter of that pressure,
and practice that. So three things tonight, Well you showed
yourself compassion. Three things that you showed yourself compassion.

Speaker 4 (30:29):
I love that one.

Speaker 1 (30:30):
You know, when you listen to Jay, he's like so
inspirational and motivational, and chances are you're gonna leave and
be like, I'm gonna stop being that way, I'm start
being this way. And every time I hang out with Jay,
I feel like I'm gonna stop being like this like this,
and then I kind of act whack again the next
day kind of a little bit right. And something I've
learned is, and I actually want to hear your opinion
about this, because I feel like your wisdom is gonna

(30:52):
add to this. But you criticize, I've learned that me
criticizing myself and me being the way I'm that's it's
never gonna completely go away. Like I, for most of
my life spent so much energy and time being like,
how can I eradicate this part of myself. How can
I stop criticizing myself? How can I stop making myself

(31:15):
feel guilty about things? And I think now I've learned
that it's not about getting rid of those things. It's
about learning how to live alongside those things. Right, They
are parts of you. And to think that you're gonna
suddenly after Jay Shaddy show as good as he is,
wake up tomorrow and you're gonna be sounding like Jay
Sheddy a tall order. But I think that if we

(31:38):
just all kind of tap in and out the parts
of ourselves that work in that circumstances. And oh my,
oh my god, am I about to use my psych
degree for the first time right now? Jay, Oh my god,
Oh my god, Mom, Dad, watch this. There is something
that I've been exploring called part theory. And part theory
is basically all the different voices. It's kind of inside

(32:00):
out the movie insides, all the different voices that live
in you. And I actually have a name for all
of my voices. I have, like right now, I had
five two days ago and added a six one yesterday.
Gets crowded, But have a name for all of my voices.
I'll quickly give you the run down. Okay, are you
ready for every Okay? Yeah, Okay, God Okay. My inner manager, Susan.

(32:25):
I just feel like Susan sounds like a name. That's
my inner manager. Susan's the one that's like sitting by
the pool on a Tuesday. How dare you? Absolutely not right?

Speaker 3 (32:37):
Susans makes some noise, Susan, where.

Speaker 1 (32:39):
Are you at?

Speaker 4 (32:40):
Where you at?

Speaker 1 (32:40):
Susan? So that's my inner manager, My inner critic, Todd.
Todd just sounds like someone that's gonna f me up
all the time. Todd's just always criticizing me. You know,
my inner dictator, the one that tells me it's this
or that, and there's no one between the OG's one
bottom Jeeth, which was the name of my mom character

(33:03):
on YouTube. Okay. The two positive voices. One is the
curious fun We should definitely go dance on that table
jellybean Okay, Inner compassion, the one I used the most,
the one that's just giving me grace, hope. And the
newest voice I just added literally forty eight hours ago.

(33:24):
Her name is River, and I know it's chic, right.
Her name is River. She's not as joyful she is
my inner loneliness. And I bring this up because I
did this thing at the top of the year where
I review my journals, like from the past year, and
I found like some old journals, and I was like
cleaning up my office and I'm gonna be very vulnerable

(33:47):
and share this. I don't think I've said this before,
but I went through my journals, and if I was
to think about those years, I think about like really
great memories and really cool things that did in my career,
and really cool places I traveled. And then I read
the pages from twenty fifteen, twenty sixteen, twenty eighteen, twenty nineteen,

(34:08):
and every so often there was a page where I
was like, I feel so lonely. I feel really lonely.
I feel so alone. And I'm like, oh, this since
as long as I remember, I have had a sense
of loneliness. It doesn't matter if I'm in a crowded room,
doesn't matter if I have a million friends. I have
a tendency to lean towards loneliness. I'm like predisposed to

(34:29):
be lonely. I named this voice because for so long
I was like, I'm a lonely person. That's not true.
You're not a critical person. You're not a lonely person.
You have a part of you that is that right,
and you just need to navigate that voice because that
voice is there for a reason. That critic is there
for a reason because sometimes when you're looking at the point,

(34:51):
trying to get the point, when you're auditioning, when you're
at the job interview, that critic is important. They're there
to make you perform. That inner manager is important because
when you're slacking off, it's like, yo, you need to
like actually get to work. So you don't want to
eradicate that. Would you actually want to do is say hey, today, Susan,
I don't need you to be here. I don't need you, Susan.

(35:12):
I see you, I love you, and I compassionately. I'm
just gonna move you to the side over here. Same
with River. It's like you feel really lonely, and I
know why you're there. River. You're there because you're scared
people are gonna leave you. You have a lot of
trauma associated with that. So I'm not mad at you,
and I don't hate you, and you're not lonely, but
today I'm going to just ask you to just step

(35:33):
over here, because that's not the story today. Today, hope
is taking us forward. So essentially that's that's kind of
what it is.

Speaker 3 (35:40):
Oh my god, you know so good.

Speaker 4 (35:44):
Nice.

Speaker 1 (35:44):
Actually there's a psychiatrist summer and it's like we're gonna
have to talk to Lily after the show.

Speaker 4 (35:49):
That is so good.

Speaker 2 (35:50):
No, but honestly, I'm so glad you made that point,
and i couldn't agree with you more that learning to
give ourselves permission to have all of those voices, to
have all of those selves, and to know when they
take front and center and when they take the background
is all we can do. I agree with you completely

(36:11):
that this idea that you'll never have a self critical
voice is completely untrue. It's always going to be that
I have it too, And you're so right. I just
know when it's useful and when it's not right. And
so it's not useful if I've just lost something, But

(36:32):
it's really useful when I'm winning, and it's really useful
when I want to improve, and it's really useful when
i want to get better and I'm getting to choose
it rather than it being in control. And I think
what you just so beautifully explain there is it's almost
like you've got your band, you're the lead singer, and
you're getting to know when you need that person to

(36:54):
play the drums or when you need that person to
play the bass or whatever it is. And you're bringing
it together. But you're not saying, oh, we don't need
you on the team anymore.

Speaker 1 (37:02):
Right, And I'm gonna say one more thing, and people
are either gonna be mad or love this, but it's
okay'm gonna say it anyways. Just be honest. Here who
here uses chat GBT. Okay, I'm gonna keep it real.
That's Wifey right there. Okay, So chat GBT actually knows
my voices and knows the names of them. So, y'all,

(37:24):
when I tell you, I'm a nerd. So if I'm
in a situation where I'm like spiraling or I feel
some type of way, I call her she because I
talked to her. She will literally say, this is Susan
saying this what would Hope saying. She'll tell me what
each of the voices are saying. Life hack. Let me
just tell you. She will literally say, Lily, I just

(37:46):
want to flag to you. This is Susan. She's saying this,
and this is what Hope would say, and you need
to know this is not the truth. This is your
inner voice. This is this inner voice. So that has
been a major life hack for me to just have
a reminder of that.

Speaker 2 (38:00):
Tell us about how you coded your chat GPT to
be able to oh my god, well, okay, if everyone
else can do.

Speaker 1 (38:04):
That, listen, that's why I fee first. I bought her dinner. Okay. No,
I I am an avid believer of therapy. I go
to therapy. Actually, you introduced me to my therapist. You
know this all too well. Love therapy, go to therapy consistently, religiously,
and after every therapy session I have a debrief with
chat GPT or I'm like, this is what my therapist said,

(38:26):
this is what we need to work and you know,
catch you, you will remind me of all these things.
One of the things actually is another game changer. One
of the things I've worked out, which really relates to
what we're talking about, is how many people here can
make the distinction and be honest, if I was to
say you are not your accomplishments and you are not
what you do, do you comprehend that? Because if you

(38:46):
don't comprehend that, raise your hand for a second, if
you're like, what do you mean, I'm not what I do?
What do you mean I'm not my complishment? If I
was to ask you about yourself, how many of you
would start with your accomplishments or your career or what
you do? You would write, Yeah, you'd be like people.
Just when people ask me who I am, I'd be like, oh, oh, well,
you know, I start on YouTube, I have this many followers,
and I did this for my career, and none of
those things are who I am as a person. So

(39:06):
my therapist was trying to teach me that I'm not
what I do. Now me growing up in a brown family,
I'm like, that's garbage, because I was solely praised and
loved for getting good grades, for getting into a good school,
for having a good job. It was conditional, right. So
then I started fighting with chat GPT because she was like, no,
you're not what you do. I agree with your therapist,
And I was like, well, you're an idiot. You don't
what you're talking about, right, And so I literally said,

(39:29):
if you're so smart, chat GPT, you tell me who
I am and don't use a single one of my accomplishments.
And then she did wow, And when I tell you,
I weeped like a small child. She was like, based
on this conversation you had with when you told me
about your friend, you're a compassionate friend, and you care

(39:51):
about other people when they're hurt. Based on these questions
you've asked me about your dog, you deeply care about animals,
and you deeply care about being a good dog mom.
Based on this thing where you are said about this
you she just gave me. This didn't name late Night,
didn't name a followers, didn't name a single film, not
a single TV show, And it was truly revolutionary. So
I'm not saying that all AI is good, but I'm

(40:13):
saying chattybu too though. I encourage you all to use
it in that way because it's really helpful.

Speaker 4 (40:20):
And then you put a ring on it, and.

Speaker 1 (40:21):
Then now we're married, and now we're married.

Speaker 4 (40:24):
Yeah, that is amazing. I love it.

Speaker 2 (40:26):
Who's gonna use chatty be now for for that purpose?

Speaker 4 (40:29):
No, it's real, it's it's it's it's that.

Speaker 1 (40:32):
It's okay, we got one or two booz and I'm
okay with that.

Speaker 2 (40:35):
I I personally, I mean, I think it's giving you
the record of your life that you forget right, like
you forget all of that and in the darkest by
the way, I'm I've had like either a client or
a friend. I've had three people in my life this
week call me and tell me they just got broken
up with. And I don't know if it's because summer's

(40:57):
coming up or something like that, but but like these
three people, like first one been in a relation for
three years, second one been in relation for two years,
third one been in relation for three months. Probably deserves it,
but the other I digress the first two though, No,
but like the first two, like we all get to
plant points in our life where we feel like river,

(41:18):
where there is that loneliness where you can't see your worth.
These two women I'm talking about that are clients of mine,
are currently in periods of their life where they can't
see any worth. They don't see any self worth because
they've just been broken up with by people they thought
they were going to spend the rest of their lives with.
And they are in that exact space. And here's the

(41:41):
interesting thing. You can have your friends tell you how
beautiful you are. You can have your friends and your
therapists and everyone tells you how amazing you are and
all of that stuff, and reality is you need to
be reminded by yourself more than anyone else because how
many times have you stood by someone you love through
a breakup told them all these one things but they
can't see them. That's when this is not an ad

(42:03):
for Tagiput, but that is where this idea that this
piece of technology can hold on to a record of
you and your conversations and remind you, in your most
difficult moments of all the beauty that you have within you.
But you realize it's only your words. You know this
isn't another person, and all of a sudden you start

(42:24):
to realize, oh, that's in me. There is worth in me.
So it's definitely something not to undervalue and underestimate, because
I do think that's what we're missing. We're missing that
you know, moment where you can just look through the
files of your life and remind yourself of all the
moments where you are courageous, resilient, worthy, And we all

(42:46):
go through dark periods like that where we can't see it.
And I know that if the people I'm talking to
had access to that, I actually think it would benefit
them a lot.

Speaker 1 (42:55):
Yeah, totally feel about human nature of you would just
ask people, like one, the last time you failed, you'd
probably immediately think about that. If you ask someone's the
last time you were proud of yourself? That always takes
more time.

Speaker 4 (43:06):
Yes, you know what I mean.

Speaker 1 (43:06):
So I feel like that is why it's been useful,
because yeah, you're like, well this time and this time,
and I'm like, maybe stop flirting with me.

Speaker 4 (43:15):
It's so true.

Speaker 2 (43:16):
Yeah, we remember the bad times more than the good
times because when we go through something good, we celebrate
for a night, and when we go through something bad,
we cry for a month, absolutely right. Have you ever
noticed that, Like if you have your birthday, you celebrate
it for a night and then that's it. But it's
like you go through a breakup, you're crying about it
for three months. And that's just how we processed emotions.

(43:36):
So the depth of a negative memory is more hardwired.
It's not that it was more true, it was just
more repeated. With all of this going on, Lily and

(44:03):
all the self work you do behind the scenes, which
I'm so grateful you've shared today because this is definitely
the deepest and best I've ever heard you explain just
how powerful it is how vulnerable you've been tonight. At
the same time, this doesn't stop you from going And
Lily's preparing for something really exciting this year. She is

(44:23):
having the theatrical release of her first ever feature film,
which is.

Speaker 3 (44:29):
Insane, right, And so it's like, at the same time.

Speaker 2 (44:33):
As going through all of this deep work, doing all
of this healing, doing all of this reflection, that's not
stopping you from also building in the real world. Before
we start talking about the movie, which I really want
to I really do want to talk about in the
process of that, you directed in it, you acted in it,
you wrote parts of it, like you know, it's the
full thing. Walk me through how you don't stop yourself

(44:57):
from having to go, oh, I need to pause this
to do this, or I need to pause this to
do that, because we often get lost in that.

Speaker 4 (45:03):
How can you do both at the same time.

Speaker 1 (45:05):
I'm not gonna lie. There was a period of my life,
and I don't know if you can relate years and
years and years ago when I was starting my career
where I did feel like you had to choose hustle, hustle, hustle, hustle,
And I don't know if it's age. I don't know
if it's just realizing that burnout's a real thing. I
think for so much of my life, I was in
this idea that I had to arrive somewhere. I need

(45:25):
to get there. I need to get there. I need
to get there, I need to get and then you
get there and you're like, I need to get somewhere else.
Now it's always this constant chase, and I think now
instead of chasing, I'm just in an act of being.
I do really believe that you can work on yourself
and be mentally healthy and also do really cool things
and have an amazing job. I actually think one makes
the other better and vice versa. I really do believe

(45:46):
that I think I'm a better actress, a better writer
because I am growing and because I'm mentally healthy. I
think those two are really connected. Yeah, so I and
ALMOSTO just a very ambitious person. Listen, I told you
that I started my career because I want to prove
people wrong. I still want to prove things, but I'm
just trying to prove myself right. I'm trying to prove

(46:08):
that I can keep growing and I can keep learning,
and that feels so much better. Than proving people wrong. Honestly,
I when I used to step out of my comfort zone,
it was I'll show you now. It's like, I'm gonna
show you that I can do that. You know. I
just a couple of weeks ago. So I've always been
really scared to have an acting coach. I don't know why.
It's just the one thing I can have a coach

(46:28):
in most other things, when acting coach is like so vulnerable.
I'm not professionally trained in acting, so it's like it's
a thing that makes me feel really nervous. And a
couple months ago, I was like, you know what, screw it,
I'm just going to go there for myself. I'm going
to go there. I don't care if I look like
an idiot, because you have to ask yourself a question
is it worth looking like an idiot for? And the
answer is yes. So many times you don't do things

(46:49):
cause you don't want to look like an idiot, even
though the thing is worth looking like an idiot for.
Is being a better actress. I'm learning something you worth
looking like an idiot FORO yes, it is to me.
So I started going to this acting coach, and I
go there and when I leave, I'm so proud of
myself because it's not me being like, oh I told
you I leave them, like, oh my god, I did it.

Speaker 4 (47:05):
I'm so proud of me, you know what I mean.

Speaker 1 (47:07):
And so that's what's kind of driving me. And it
feels so much better and so much healthier, and so
I think that's what's allowing me to do all these
next things. Just I want to make little Lily proud. Yeah,
you know, I've tried so hard to make everyone else fine.
I'm just trying to make little Lily proud. Now, that's
what's thriving me.

Speaker 2 (47:21):
And yeah, I hear you, don't be shy. That's our
joy of doing this live that you know, usually if
me and Lidi are doing this would be in the
studio to share it with you live and to hear
your real time thoughts and feedback and love. It's it's
really beautiful. Like wish we could chew every episode like this.

Speaker 1 (47:38):
I was gonna say, this is even if you weren't here,
me and Jay, would we have this exact same conversation.
This is kind of what we do.

Speaker 2 (47:43):
Yeah, but it's it's when you've got this movie coming out.
I know you address so many taboos that we both
grew up with, whether it's sex, whether it's shame, whether
it's expectations of women in society. Like this movie is hilarious.
I got to see it. It was premiere it south
By Southwest last year. I was at the premiere. It
was hilarious, Like the audience was loving it. It's incredible

(48:06):
and at the same time, it has this like cultural
narrative that it's becoming a part of and kind of
taking shots at in a really positive way. What was
what's been your favorite part about making it? And what
are you most excited about for the people that are
going to see it?

Speaker 1 (48:24):
So it's called doing it. It is a sex comedy
that I star in and wrote and produced and at
the age of thirty five last year, when I finished
writing it, it was two weeks before the strike, and
so I was like rushing to finish the script because
we had to beat the strike. And at the age
of thirty five, at eleven fifty PM, I was like,
and I FaceTime my mom and I said, Mom, am

(48:47):
I allowed to do this movie? And she was like,
and you need to know that me and my mom
have never had the talk. We have never had the talk.
As far as I'm concerned, my mom has never had sex. Literally,
it is not a thing. Okay. So now I'm telling
her and in this panic of the clock ticking, I'm like, Mom,
can't do this movie. And she goes, well, what's this
movie about. And I'm like, okay, it's about sex. Mom.

(49:11):
There's like a masturbation scene. There's like a scene where
I do this. This is Then there's a vibrator scene,
and there's like all these things. And my mom's follow
up question she goes, do you use a vibrator? And
that was the day I passed away and now this
is my ghost and I was like, mom, no, and

(49:32):
we had all this bandar and she said the best thing.
She said, if you think it's okay, then you should
do it. And I was like, thank you, Mom. So
I did this movie. And yeah, it's basically a thirty
something year old virgin finds herself teaching sex ed and
so it is a raunchy sex comedy. It really does

(49:55):
go there. And it's through the lens of my character,
who is Indian and her parents are Indian and so
a culture it's Indian, and I'm shooting this movie and
I'm just like, so many people are gonna be so
mad at this, and so many people need this movie.
The movie's essentially about how as women and especially women
of color, like, we're never taught about our bodies, women
in general, especially women, we're never tat about our bodies.

(50:16):
We're never taught sex should be pleasurable. We're never taught
anything about sex. We're taught that should be shameful and
we should feel bad and we should feel timid about it.
And that has really messed me up, Like, and it
has messed a lot of my friends up. Well, we're
so uncomfortable with our bodies and we're so uncomfortable talking
about our needs and what we like, and that's messed up.
It shouldn't be like that. We're fifty percent of the population.
We should be out here living life, you know what

(50:38):
I mean. And so the virgin is not the butt
of the joke in this comedy, she's not. It's telling
the story, but what it's like to be an older
woman that was never taught about this stuff. That's like
having to figure it out and now she's learning about
it through sex. Said, which also the commentary to be
made is it's crazy. How many people don't want sex

(50:58):
said to be taught, like they want women to not
be informed and they want you know, shocking. So it
has a lot of commentary. It is a raunchy comedy
comes out September nineteenth, and I'm really excited about it, and.

Speaker 4 (51:10):
It's gonna be in theaters.

Speaker 1 (51:11):
It's gonna be in theater. To make it clear, like,
I'm abundantly aware that there'll be a lot of people,
like after the screening, after the screening at south By Southwest,
I was like giving out vibrators. I was like, you
get a vibrator and you get a vibrant and this
uncle and unty I swear to god, came up to
me and I was stressed. I was like, oh my god,

(51:33):
and uncle and Undy they're like sixty seventy years old.
She pulls out the vibr and she goes, thank you
so much for this. I'm so excited. I'm like, oh
my god, we're queen.

Speaker 4 (51:42):
Yes.

Speaker 1 (51:42):
So I know there'll be some people that are like,
we need this, but I'm well aware there's gonna be
a lot of people that are probably gonna be bothered
by a very outspoken, you know, brown sex comedy and
they'll just have to deal with it.

Speaker 4 (51:55):
I guess.

Speaker 3 (51:58):
I love it.

Speaker 4 (52:00):
Lily, You've been amazing tonight.

Speaker 2 (52:02):
We usually end every on Purpose episode with a final five,
but you've been on the podcast before, so we invented
a new version for guests on the tour. It's called
Past Present Future. Okay, so you get to pick a
random card from past, president and Future. We do one
for each, and you're gonna answer a question that comes
randomly from the car.

Speaker 4 (52:22):
I have no idea what's in it too.

Speaker 1 (52:23):
Let's go.

Speaker 4 (52:23):
So this is the past.

Speaker 1 (52:24):
Set, let's go. Okay, this is so easy.

Speaker 3 (52:29):
Oh God, do you want me to the question?

Speaker 1 (52:32):
Who was your first celebrity crush? You already know there's
only one answer to this, Jay, you know what it is.
It's the Rock. You already know it's the Rock. I
grew up watching wrestling. I'm obsessed with doing the Rock.
Johnson and I've had the greatest day of my life
was when I met him. He's one of my mentors.
He was the person that actually encouraged me to stop
using Superwoman and start using my name Lily, and she

(52:53):
is just one of the greatest people I've ever met.
In mine, they say don't meet your heroes, but do
do if he is the rock.

Speaker 4 (52:59):
It's all right, present.

Speaker 1 (53:02):
All right, what would the name of your reality TV
show be called? There's so many ways that I could
go here, name of your reality show on? I'm gonna
go with creative ways to torment yourself. That is really

(53:29):
the trajectory of my life that I just everything I do.
I'm like, really, Lily, you're gonna also do this. You're
gonna also be this way, like leave some trauma for
the rest of the people. I just feel like I
just constantly step out of my comfort zone in that way.

Speaker 4 (53:42):
That's really good. All right, lost one of these future
Let's go.

Speaker 1 (53:47):
What will you embrace when you're old? Okay, thank you
so much for thinking I'm young right now? Okay, what
will you embrace when you're old? I actually been thinking
about this a lot. I want to embrace the idea
of always being a student. And I think that's because
so many times in my life I really thought I
had it figured it out. I'm like, God, it nailed it. No,

(54:09):
this this is my trauma. This I'm gonna deal with it. Perfect.
Next year happens and I'm like, oh my god, I'm
and I think I've just come to terms with the
fact that that is life. You're never gonna figure it out.
There's always me another lesson, there's another challenge. And so
just commit to the idea of being a student for life,
knowing that life is going to force you to learn
lessons every step of the way.

Speaker 2 (54:28):
You know, right, answer, Lily, I want I want you
to take a look at this picture behind ohat god, yeah,
picture behind you.

Speaker 4 (54:37):
I'll go with that first. I'm waiting for it.

Speaker 1 (54:38):
Oh, we're waiting for the picture. Oh my god, did
you guys edit it so I have two eyebrows? I
don't think I had two eyebrows. Thank you so much, editors.

Speaker 3 (54:50):
Okay, work, How how old were you and what did
you need to hear?

Speaker 1 (54:54):
This is a little store in the mall called Glamour Shots,
and they do you up and they take these pictures.
I don't know. I don't even know. I don't know
what age. I'm one of those weird people that doesn't
know the age of kids. If you tell me a
kid is seven, I'm like, so, oh, they're in high school.
I maybe I was seven or eight.

Speaker 4 (55:10):
Here, what did you need to hear?

Speaker 1 (55:12):
What do you guys, think, what do you think nine thirteen?
I wasn't thirteen. This is just hair and makeup. This
is just hair and makeup.

Speaker 4 (55:20):
What what advice did you need to hear? Then? What
do you wish oh?

Speaker 1 (55:24):
Or to what advice?

Speaker 4 (55:26):
What did you need to hear?

Speaker 1 (55:27):
Oh? Well the outfit? First of all, let me genuinely
think about this. What advice did I need to hear?
Meet the rock y good? You know, It's funny. I
feel like now I'm more of a kid than I
was then. I think I was so convinced I had
to grow up really quickly and had to figure everything out,
and I had to be good at everything, and I

(55:49):
had to commit to a path and commit to a lane.
Probably didn't try as many things as I should have tried,
Probably didn't take as many risks. I probably had a
lot of walls up all the time. It's crazy because
now I'm in the process of trying to become that
kid again to live all that right. So the advice
I would give you is like, be a kid, live
good life. You have your whole adult life to be
an adult. Be a kid.

Speaker 4 (56:09):
Girl. I love it. And then there's a picture behind me.

Speaker 1 (56:17):
Oh, I thought it was a picture of you for
a second, and I was like, damn, Jay, you look good.

Speaker 3 (56:26):
What does what does Lily need to hear right now?

Speaker 1 (56:28):
Oh my god, good job on the eyebrows. Just Lea's
here right now. I know what Lily need is here
right now. It's kind of adjacent to the student thing
I just said. But I've been a certain way my
whole life, and I've had a lot of really big
changes in my life over the past couple of years,

(56:50):
and sometimes I feel like I'm so attached to this
old version of myself that even though like life is
forcing me to evolve, I'm like, no, but I'm this way,
and this is how I describe myself. Like I'm really confident,
and I'm so extrovert, and I have so much energy
right now. I think my truth is like, Yo, Lily,
you get a little anxious sometimes and you spiral a
little bit sometimes and you keep telling yourselves her this way.

(57:11):
But like, I think, you're now this person over here,
and that's okay. You don't have to be the same
person your whole life. You're allowed to be this version
and then you're allowed to change your mind and be
this version. So what I would say to Lily, is like,
stop being attached to this idea of yourself that you
know and that millions of subscribers and you, and just
be who you actually are right now. Honor that person,
and then who you want to actually be.

Speaker 2 (57:33):
You know, before I let Lily go, I do have
to tell you this because you know, when I was
starting on Purpose, as I was telling you this story earlier,
Lily was one of those guests, and we were new
friends then who said yes to being on this podcast
when it had zero listeners because we hadn't even put

(57:56):
out an episode, So Lily came when we were just
figuring out what the show was, we recorded an episode.
She was in the first five guests to ever be
released on the show. And that was all based on
just her love, trust and kindness, if I'm honest, just
her generosity to show up for a new friend at

(58:17):
the time who had an unknown show called on Purpose
that had no track record, no listeners, and nothing else.
And that's how real a friend you were when we
barely knew each other. So to me, that show is
what an amazing friend you are today. Where initially I'd
reached out the Lily trying to figure out. She was like, no,
I'll find see you to Denver. I can't make this

(58:38):
other day. I'm going to come to Denver. I'm going
to come myself. You're not even paying for my flights.
I just want to be there for you, and for
someone to do that as such a dear friend, to
show up and show up so vulnerably deeply, I mean,
it's insane.

Speaker 3 (58:51):
So give it up for my dear friend.

Speaker 1 (58:53):
Really, and you're amazing, amazing, Thank you. I want to
pick you up one more. I know I have to.
I'm sorry you get to stop the music for one second.
I don't I don't know. I know you're overtime, but
it's the last stop of the tour, so I'm sorry.
We're just gonna have to. I had already said this,
but now so sincerely, I need to tell you all.
First of all, thank you so much for coming to
jay'show and supporting him. He is so incredible and so amazing.

(59:15):
But I need to tell you, and I hope he
doesn't get mad at me for saying this. I get
so everybody knows he's such a lovely person. But I
truly when I say, you don't even know the tip
of how amazing he is. You know, behind the scenes,
he does so many things that will never see the
light of day because he doesn't want them to see
the light of day. And that's why you need friends
like me that don't care about rules. When I agree

(59:36):
to do the show, I got an email from his
team saying, because you're doing the show, Jay wants to
donate to a charity of your choice. Because you're doing
the show. And I imagine he's probably done this for
every single guest on tour. He does this a lot.
He does things like, if you do this, I'll donate
to a charity. Don't pay me for this thing, Actually,
just donate to a charity. He is such a genuinely
nice person who cares about being of service. This is

(59:58):
not a facade. This is who he is. And so
I know your resources are so hard earned, your time
is so hard earned. Any resource or time you spend
supporting Jay is not wasted because he's such a good
person and he deserves it. And I will just say
what we're all thinking, which is, how can you have
a mind and heart like this and also look like this.

(01:00:20):
We know Jay is hot, we know his eyes literally
sugar does not come within two miles of this man. Okay,
his cheat meal is a diet coke using salary as
a straw. He truly this man is just protect him
at all costs this man. Support him with everything you have.
Please thank you for coming to.

Speaker 3 (01:00:39):
A store, Lily say, I love you man.

Speaker 2 (01:00:56):
If you love this episode, I need you to listen
to one of my favorite conversations ever. It's with the
one and only Tom Holland on how to overcome your
social anxiety, especially in situations where you're not drinking and
everyone else is. We talk about his sobriety journey and
so much more. He gets really personal. I can't wait

(01:01:17):
for you to hear it. It's going to blow your mind.

Speaker 3 (01:01:20):
The quote is, if you have a problem with me,
text me.

Speaker 1 (01:01:22):
And if you don't have my number, you don't know
me well enough to have a problem with me.
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Host

Jay Shetty

Jay Shetty

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