Payal Kadakia | How to Drop Your Limits and Rise to Your Potential

Payal, Welcome to the Unmistakable Creative. Thanks so much for taking the time to join us.

Payal Kadakia_

Let's go.

Payal Kadakia_

Thanks. Thank you for having me. Excited to be here.

Srini Rao

It is my pleasure to have you here. So you have a new book out called Life Pass, all of which we will get into. But before we get into the book, given some of what I know about your story, I wanted to start by asking you what social group were you a part of in high school and what impact did that end up having on the choices that you've made with your life and your career and where you've ended up.

Payal Kadakia_

Ooh, that's a tough one. Social group, let's see. I was a mix, I think, because I was smart, because I had to be, because I had Indian parents who made sure I got straight As. So I was obviously in all the AP nerdy classes. I'm not sure if that was a social group or an academic group, but I felt I was a part of that. But then I was also captain of my varsity cheerleading squad and a part of that crew as well. So I think I really always dovetailed.

Srini Rao

Ha ha ha!

Payal Kadakia_

a little bit of this nerdy side and then also this cheerleader football group that I was also a part of, which was strange because they both were very different. But I think this actually goes back to so much of what I think has always been a part of my life where I just feel like I never fit in and I never really was one or the other. I was always multiple things.

Srini Rao

Well, I mean, I think it's kind of funny, right? We go through, you know, adolescents trying to fit in, and then you get into the real world where people reward you for standing out. And part of the reason that I wanted to start with that question in particular is because of the fact that I knew that you were a cheerleader. And one of the things that really struck me was the story that you tell about being at a high school football game and then changing into Indian gear clothing, making sure nobody saw you. And...

Payal Kadakia_

haha

Srini Rao

This line in particular struck me. You said, back then I didn't know that each of these identities could bolster the other. If I allowed them to coexist, I didn't realize that one side didn't take away from the other. I was afraid to let the strands overlap, but with time and experience, I've learned that my strength lies in the unique combination of strands that make up no one but me. Everyone's identity is like a rope that's braided together. When our separate strands are woven into one, we become far more beautifully complex and stronger, with strands reinforcing one another's strength and unity.

Why do you think that most of us don't have that realization at a young age? Because I can tell you there were moments when I was definitely ashamed of the fact that I was Indian and one in particular comes to mind. And I've talked about this before on the show. I grew up in Texas for most of junior high up until ninth grade from like third through ninth grade. And there was a year I didn't tell my parents about open house. And it was mainly because I was embarrassed by my dad's accent.

Payal Kadakia_

Right.

Payal Kadakia_

Right, right. I understand that. I can totally relate to the feeling. And I think that's really the answer is that we are scared, right? And I think as much as obviously I've learned to embrace it, it started actually by feeling like I was embarrassed and I was getting made fun of for being Indian, whether it was people telling me I smelled or that my dancing was funny and booing me off the stage. I think it made me feel that I had to hide these things to be accepted.

because I didn't have the confidence to be myself. And I think that is really the key, is to find ways to embrace an environment where you could truly be all the colors of who you are, and you can really build that confidence. And for me, I found that place in dance, right? And I think for everyone, you need to find whatever environment that allows you to be all the threads, right, that you are. So the beauty of who you are really gets to shine.

But I think when we were younger, we're really impressionable. And I think we have to be careful. Obviously, I have a child now too, which is what we say around them and how we box people into different categories. Because as you just said, I think the most exceptional things and exceptional people in the world are the ones who truly do stand out.

Srini Rao

Yeah, yeah, absolutely. Well, yeah, I mean, it's funny you about having kids because I think that, to your point, I think that it's so much more challenging when we're young and we're trying to figure out who we are and we're so impressionable. And I think that if there's one period of my life that I'll happily never go back to it to being a teenager because, you know, your parents are the most horrible people in the world and you think you know everything. And at the same time, you're completely insecure.

Payal Kadakia_

Yeah.

Srini Rao

Which I guess, you know, kind of strange to ask somebody who has a two year old, how do they think about this? But you know, when you think about the fact that, you know, at some point, your son is going to be a teenager and go through all of this. Do you think it's one of those things that kids just have to figure out on their own and go through? Is there any way to avoid the sort of damage that gets done by adolescents?

Payal Kadakia_

Yeah.

Payal Kadakia_

I mean, I don't know, you can maybe ask me in 15 years and hopefully I have some better answers, but I really just want him to be confident. I think that's really the basis to so much of our happiness and fulfillment and our joy is allowing him, allowing our kids to be who they are versus telling them who to be. And I do think a lot of us.

Srini Rao

Hahaha

Payal Kadakia_

went through many periods of our life, whether it was our parents, whether it was external forces of society, of people just telling us who to be and how to be.

Srini Rao

Yeah, well, I mean, I think that's particularly prevalent in, you know, the culture that you and I grew up in, right? Yeah, I mean, you say so in the book, you say when I graduated from MIT in 2005, all my friends are going to bank or consulting. So I followed suit and applied to those types of jobs as well. When I landed a coveted position that would make my parents proud and look good on my resume, I didn't give it much thought beyond that. The only reason I didn't end up in one of those positions is because my grades were shit. But I

Payal Kadakia_

Yes, yes, 100%.

Payal Kadakia_

Right.

Srini Rao

was pretty much in the same situation. As a Berkeley undergrad, all of my friends were either headed to banking consulting, medicine or Google or law school, and they didn't just go to those places, they basically went to the best ones. And so how do you overcome that sort of parental conditioning? Because I think it's changing with our generation, but you know, our parents' generation, it was very, very dominant. And at the same time, I realized at a certain point that advice made sense given the context in which our parents grew up.

Payal Kadakia_

Yes, that's exactly right. I mean, that's part of what I think is so important for us to realize is in any expectations that other people have for us, we need to understand where they are coming from, right? And they grew up in really horrible conditions, if you really think about it, in the sense of how much they had to sacrifice to come here, right? They came here with no one, they didn't have money, they had to really fend for every dollar, right? And they...

would never want us to ever feel like that, right? So I think it came from a sense of protection. And I think one of the ways I really had to overcome that was one, by sharing all my successes with them, right? So of course I had checked every box for them that they had told me to, and I was going down that path. And obviously that made them feel more confident in my ability to succeed in life. But I also had to do that in terms of my own things, right? So as I was...

you know, building my dance company on the side of my other job, like letting them come and witness the success of that, the joy of that, the fact that I was able to get people like Mira Nair, who I'm sure you know, who is, you know, an unbelievable, incredible film director, to come and say, wow, like the work you guys do is exquisite, you know, and have that be said to my parents, was something that made them start questioning.

wait, like you are really good at what you do. And they always knew I was a good dancer too, but it was always that side hobby thing. It was never something that I was going to pursue. They kind of just started, I think, believing in me more to the point where when I finally got to the point where I wanted to quit my job, it became an easier discussion. But it was six years after I had graduated college.

Srini Rao

Yeah, well, I think for me, it was for me getting a book deal was kind of that moment when my parents like, oh, you're not just screwing around on the Internet. You're actually doing something that's leading somewhere. But, you know, at the same time, I honestly couldn't help but just feel this tremendous sense of insecurity that entire time. Like I would go to my.

Payal Kadakia_

Right.

Srini Rao

parents, friends, parties, and I'm just like, I don't want to talk about what I do because this just doesn't sound like a real job. And I'm going to have to answer very uncomfortable questions because there's no external marker of success. So I wonder, you know, prior to sort of class pass becoming the success that it is and your parents starting to actually see traction, how did you maintain your sanity during that period?

Payal Kadakia_

Hmm. Right.

Payal Kadakia_

I think it was hard. I think it was, you know, two things I would say. One, like my parents didn't know, obviously, at this time, too, startups were not something that was talked about, right? It was not a profession that I think more people did, right? It was definitely, I was one of the only people they probably knew who was building a startup. And that was probably shocking to them, and especially because it took me three years to even get

you know, my product working, I think there were times they were like, what are you doing? Is everything okay? Um, and they were also, like I said, pressuring me to get married because that's really what they thought was progress in life, right? And they didn't know if, okay, well, if your company doesn't work, then maybe at least if you're married, you'll have like a way to move forward in life, right? Like that was sort of their, their safety net, right? They always wanted me to have a safety net. Um, and I think that was a really tough thing, but you know, the other thing I really did and, um,

Srini Rao

Ah! Yeah!

Payal Kadakia_

this is sort of like a mentality I've had to train my mind into is how do I wake up with a positive thought every day? So I had this practice that I'd wake up every morning and I would go and find a quote and then I would post it on Facebook. Um, at the time, I mean, Instagram wasn't even a thing at that time. And I remember like I would post that quote and it would sort of come back to me every day through people commenting on it or liking it. And I just remember having this practice of trying to stay positive, being a really

important thing for my mind, right? Obviously you can meditate, you can do whatever you need to, but to me that just like having this moment where I could stop thinking about everyone else's thoughts and sort of go into, I'm gonna go change the world today, meant a lot to me and I think I just hung on to that. And I knew that I was meant to do something great. I really did, I really felt it. I knew I was solving something big and I didn't want these distractions to really hold me back. So I just didn't.

I stopped listening at some point and started going with really where the universe was taking me, where my purpose was taking me. And a lot of other stuff just really fell off the plate, you know, and it just fell off and I just didn't care.

Srini Rao

Yeah, yeah. Well, I mean, I think for me, it was basically looking at the people that I surrounded myself with and I realized there were certain times when like, wow, if I go hang out with people like the literary agent, my editors, all these people's like, oh, these people see me as normal to my family. I'm just the weirdo who spends time on the internet basically doing nothing but writing and recording conversations with strangers.

Payal Kadakia_

Yeah, I think that's very telling. I talk about this too in the book, how when I was at Bain and I had all my business friends, and I loved them too and I got along with them as well. But then I had this whole other world in my dance world where people were editors and artists and full-time dancers. And I remember when I was with them, I felt so alive. I didn't feel, they just saw the magic in me too. And I think it's so important that we...

Like you said, find those communities. And also if certain communities aren't serving you, it is okay to not spend time with them, right? It is on us to sort of make those decisions. And I know we feel obliged to doing it, but our life is our own to live, right? We don't need to be, we don't need to be spending time with people who truly like make us feel worse every day. What is the point of that?

Srini Rao

Yeah, I think I finally came to the realization. I was like, OK, yeah, these people are going to criticize. They're going to judge. But none of them are going to live with the consequences and have any of the decisions I make. It's like this auntie once told me, she's like, you need to get married on time. I was like, on time for who? I'm like, you'll be dead at some point. I'm like, I'm the one who's going to have to live with this person. So speaking of which, I think that makes a perfect segue to a part of this conversation. There's no way we're going to get out of this talk without having. And that is Indian parental expectations for marriage, which I think are.

Payal Kadakia_

Right.

Srini Rao

far worse for girls than they are for guys. But you say something in the book about this. You say, my mother's focus on my dating life stemmed from a place of love and concern, but she was inadvertently putting the idea in my head that I was incomplete and failing to move forward in life if I wasn't on the path to getting married. And I remember right when we sent the exchange emails the first time, I was like, hey, I just got to that part. It's like, I think I have this conversation with my parents at least once a week. But I think that is so much worse for women. And you know, I wonder

Payal Kadakia_

Ugh.

Payal Kadakia_

Hahaha.

Srini Rao

To mothers in particular listening to this, what would you say to them about the fact that they're reinforcing this message of making their daughters feel incomplete? Because I just can't help but think what kind of choices would people make if they feel they're incomplete if this part of their life isn't checked off?

Payal Kadakia_

Yeah, I mean, the number one thing I would say is that, you know, your daughter is 100% as equal as your son, right? And there is no difference, right? And I think that is something that has sadly been drilled into our society in the wrong way for way too long. I mean, it is something that obviously is still an issue. But I think we really need to understand how in this day and age, especially with the potential and opportunities, you have to almost...

help your daughter really truly break through society's expectations. And I think for me, I've had incredible, you know, people in my life, whether it was my dance teacher and my mom, like, of course, my mom was definitely someone who was forcing me, but she also, you know, showed me a path in when I was younger. She worked, you know, she, she did everything she could. She took care of us, but she still worked, you know? And I think having that.

that sense of having ambitious women and surrounding our daughters with ambitious women is really the key because, and I say this in my book and I really feel it, my biggest regret in my 20s, and yeah, like I did some incredible things. It's even hard for me sometimes to say that because when I went through it, I was drilled in my head that I was doing the wrong thing because I was single.

Right? And how terrible is that, that my company was sitting here, you know, hitting records and setting milestones as a female founder. And in the back of my head, I felt like I was somehow still doing something wrong. Right. And it's funny because I think a lot of times, you know, you, you question things in your life, but to have to question something so, you know, personal and let that define you, it is something that as a rhetoric, I think, you know,

Obviously mothers need to change. I think a lot of times, even mothers need to raise their sons to have more respect also for the women in their lives.

Srini Rao

Mm hmm. Yeah. Well, you know, it's funny because I remember right after my sister's wedding, I did all these interviews with my family members just to document them and to hear their stories and hear, you know, kind of how people had met, you know, why they'd marry each other. And my mom's was somehow delayed. And I ended up doing it after the wedding. And I remember sitting with her and I knew because I was recording this conversation, it might be like a one chance I'd get into this conversation without her, you know, blowing up her, both of us getting mad. And I asked her straight up, I was like, are you unhappy that I'm not married? And she said no.

she was like, my concern is that I'm worried about what's going to happen to you when we're not around anymore. And I'm like, wow, okay, so this was basically coming from the best of intentions just horribly expressed.

Payal Kadakia_

Mmm.

Payal Kadakia_

Exactly. I think that's exactly right. It comes from a sense of them not wanting us to be alone, right, or not or being in a place where we don't have money or something like that. And like you said, it comes from a really great place. They only know how to express it this way because that's how they were also raised. Right. And I think it's about recognizing that and.

Srini Rao

Yeah.

Payal Kadakia_

allowing them to have their place to say it, but also not take it to heart, right? That's what we really need to do is say, okay mom. Thank you. Great. I'm gonna go and that's what I did, right? I literally would be like, thanks mom for the advice. I love you. Peace You know because I didn't want to get into it, you know

Srini Rao

Yeah

Srini Rao

Yeah, well, you know, so I knew if I were the single older brother at my sister's wedding, there's no way I was going to get out of this entire wedding without this conversation. I was like, you know what? I'm like, I'm going to put an end to this right during the speech. So I literally opened my speech by putting up a picture of my phone number on the screen. I was like, for all of you want to know when I'm getting married, you can text profiles, pictures and all other relevant information to this number. Now let's get to actually why we're here. And so I got to avoid any conversations. Anytime some auntie came up to me, I was like, you've been given your marching orders, get to work, and then we can talk.

Payal Kadakia_

Right, right. I mean, it's funny. I mean, everyone faces it, right? And it is one of those things where I think for my parents too, and I talk about this too, my mom was like, I'm going to retire the day you and your sister are married. Like, what is that? What, like, I actually in my head, I mean, going back to what you just said about, it was almost like my marriage would be her freedom. And I don't even know where we built that construct in either of our, you know, agreements in life.

Srini Rao

Yes, I remember that.

Payal Kadakia_

But it's weird that she had that and obviously at some point she was like, I'm going to quit because you're like, now we're getting married. Um, and so she did, you know, but it was funny because I'm like, I love that in a way it was like, so are you really working so you can pay for a wedding? Cause come on, like that's ridiculous. Like why are you even torturing yourself with that?

Srini Rao

Mm-hmm, yeah. Well, speaking of weddings, so I, you know, just from having done my research, I know that you're a Gujarati and your husband is Punjabi, if I remember correctly. And so my sister, so we're South Indian and my brother-in-law is Bengali. And so I've always wondered when people, you know, even who come together from different parts of India, how do you integrate and retain the aspects of each other's culture when you're, particularly when you're raising kids? Because I keep wondering, you know, about my sister.

Payal Kadakia_

Yeah, yep.

Srini Rao

And her husband was like, is this kid gonna speak Bengali or is this kid gonna speak Telugu? Or are they gonna speak neither? Because I feel like for me, if I don't marry an Indian girl, the first thing to go is gonna be language.

Payal Kadakia_

Yeah, I think, you know, for all of us, we need to be very, very thoughtful on what our culture, religion, whatever it is means to us individually, before we can even think about putting it onto our children, right? And one of the things me and my husband are very cognizant of is, you know, my mom's super religious, his dad's super, my husband's also Sikh and he wears a turban, and so does my, so does everyone in my husband's family. So.

you know, there's even like, there's even another structure to that. And I think, you know, his dad's also super into Sikhism, which is beautiful. And I want to take part to that and put them onto my child. But I also have to be careful on how much I do that without making them feel like one is good and one is bad. Right? You have to be very thoughtful in making sure it's really about what makes Nick happy, who's my husband and me happy. Right? Like I love the volley, right? My husband didn't really celebrate that growing up so much, but...

Srini Rao

Hmm.

Payal Kadakia_

I'm like, hey, like I really love it. So every year we're gonna have to do a big thing for the valley and he's like, great, you know? And then at the same time he's like, I wanna raise Zayn Aserdar and I'm like, great, like that's important to you, we're going to do it, right? So I think it's really about agreeing on what it is and then also I think it's like I said, keeping the grandparents in check at times.

Srini Rao

Mm-hmm. Yeah. Well, yeah, I'm sure that's a whole other battle in and of itself. But what about language? I guess I've always wondered this. So I have a my best friend from college is Bengali and her husband is Yudharathi. And I'm like, what language do you speak to your kids? And, you know, do you just end up with these very like trilingual kids as a result? Because you just basically speak to them in both languages. Because my sister's Bengali is apparently really bad. My brother in Laos, Telugu is shit too. So.

Payal Kadakia_

Um, so I would say, like, we speak Gujarati to him. My husband doesn't really speak that much Punjabi, so I don't think he's gonna... It's really about what they're around. And my parents are here a lot at the house, so he's exposed to Gujarati more. He also has, like, you know, he's got caretakers who speak Spanish and stuff, too. So he's kind of just, like, he's right now just learning everything. I think as he gets older, like, we're gonna expose him.

to both and I think it's really gonna be about like what we speak, but we speak majority English in the house, so I think the only reason we all learned Gujarati in the house is because my parents' most familiar tongue was Gujarati, right?

Srini Rao

Yeah, I mean, I think the same with us. And the funny thing is now parents basically speak to us in Telugu and we just reply in English, even though we understand everything they're saying.

Payal Kadakia_

Yeah, exactly. Exactly. Only when I go to India do I like really speaking Gujarati. Exactly.

Srini Rao

Yeah, totally, totally. Well, let's get into, you know, what you talk about as, you know, false signals of success, because I think that really struck me as one of the most important parts of the book and something that I think is really hard to wrap your head around, because you say that as a society, we tend to conflate the idea of success with achievement when somebody accomplishes a specific goal.

or reaches a new milestone in their life or career, we view that as success. You get a raise a success, a new job a success, launch a company, marriage, kids, a new house. And I think that what I wonder is for somebody who's not in your position to understand that, I think any one of us can understand that intellectually, but to actually internalize that when people are not in the same position that you're in, how do they do that?

Payal Kadakia_

Yeah.

Payal Kadakia_

So I think for me, when I started on this journey, I truly wanted to make an impact in the world. I was not looking for fame. I was not looking for money. I was not looking for power, you know? And I think what happens, and by the way, all those things can be received by doing what we love. I think when we go towards those things versus the actual heart of...

you know, the joy of doing something, right? And people always say, like, if you really love what you do, you aren't working a day in your life. I really truly believe that. And I think I got, you know, not, I'm not gonna say lucky. I think I just really, since I was younger, I followed my heart and my passion. And honestly, that is really what I want other people to do because I think the more you are enlightened in that way and can sense a feeling that is almost greater than any of these things of like money and fame and all of that, you just...

you beat to a different drum beat, right? And here's what I will say, is that when you have something like that, that gives you so much joy and centers you and feels so connected to your purpose, when you get a raise or get a house, those things feel good, but the worth of them doesn't compare to the feeling of feeling fulfilled, right? Because most of those things like, okay, yeah, like I got a raise, like those things kind of last for a day and like, and disappear, right?

Srini Rao

Mm-hmm.

Payal Kadakia_

they don't sustain, right? And the journey of fulfillment to me, and like for me, you know, once again, I really found that in dance, is this feeling of giving to others, being in service of other people. That's when you truly can't compare your life to a lot of these other milestones, right? And then, you know, I talk about it more specifically when it came to starting ClassPass.

And I did a lot of these things wrong. So I think, you know, you're absolutely correct in saying it's obviously easier said in hindsight. I'm obviously giving this, giving this advice because if there are entrepreneurs who are doing sort of the traditional thing out there, which is, you know, okay, let me go get as many followers as I can, raise as much money, get as much press. And by the way, these are, these things aren't great or are wrong. They're just not exactly the only thing that matters. And for me, those ended up being sort of false signals that I was succeeding and I forgot to actually work on.

the most important thing, which was getting people to class, right? Which was the mission. And and I say that wholeheartedly because I think a lot of times, especially because entrepreneurship is a bit glorified now, people just want to be entrepreneurs. They want to start companies because they think they'll get rich and all of that. And and yes, like all of that intention is so good. Just make sure you are.

Srini Rao

Right

Payal Kadakia_

solving something for other people in the world and let that be your guiding light. And I had that guiding light and I forgot it at times and I had to be reminded. And so my advice to everyone is make sure you anchor yourself there. And when you get lost by all this society stuff, just go back to that because I'm telling you the answer is in that guiding light.

Srini Rao

Yeah, well, I very distinctly remember Y Combinator did this free class at Stanford that they made available as a podcast. And at the very end, Sam Altman talks about press and he was like, press is basically just a distraction. And he said, be careful that you don't get distracted by your press. And so I'm always very cognizant of that because I remember somebody wrote an article about us and Forbes as one of the best podcasts of 2021.

I shared it on Facebook, people were like, congratulations, my dad is like, oh, this is huge. I was like, dad, this is meaningless. I'm like, it's just a mention in a media outlet. I'm like, it doesn't actually make any difference. You know, it basically is what you would call a false signal of success.

Payal Kadakia_

Right. It's a perception. But look, like sometimes those things are great. And like, I think if you have a product that's working, which you obviously do, and people enjoy your podcast, um, I think that's what's great. I think people forget that that's the important thing is to keep working on the product, not keep working on the press, right? At the end of the day. So, so back to whatever, you know, he was saying, he's absolutely right. Is don't get caught up in getting more press, get, get caught up on having an awesome product that's going to garner the press.

Srini Rao

Mm hmm. Yeah, absolutely. Yeah. I mean, even, you know, when I think about something like writing a book, I always think that the moment you hold the book in your hand, it almost feels empty because you know what it represents is so much bigger than what it actually is like the finished product and every writer I've ever talked to says this like, yeah, compared to the blood, sweat and tears that went into writing this thing, holding it in your hand almost feels empty.

Payal Kadakia_

Yeah, I could see that. I definitely can see that. I mean, it's your whole life in one. It is. It's been, I mean, this whole process of writing this book has been, you know, an up and down journey. But I, you know, I'm proud of this book. Like, I'm really proud of where it's come to and I feel like people will really be able to grow from it. And I think it's also helped me, especially with where I am in my life right now. Reading my own book has almost been...

therapeutic for myself because I think so much change has happened in my life in the last few years.

Srini Rao

Well, I want to ask you about one more thing related to sort of press and external measures and sort of, you know, the world of attention all around us, you know, Instagram followers, social media. How have you managed not to get influenced or distracted by this? Because I feel like this is just a big issue for so many people in the world we live in today. They confuse attention with accomplishment, and they pursue attention often at the cost of accomplishment as a result.

Payal Kadakia_

Yeah, yeah, it's a really interesting cycle we are in today. I mean, it always really comes down to product. And I have this sort of, I guess, my own vision for myself, which is to create timeless things. And something that's timeless is not about attention, right? It's about lasting. And I think about that with my dance work. I think about that with my tech products, with this book.

And I think people really need to think about things that last instead of thinking about things that will be a part of a 24 hour news cycle. Um, right. And I think the way you go back to that is by once again, going back to what everything I've been talking about in this is what is at the heart of you and your why, and you're the deep part of what's guiding you. And if you don't have that, yeah, you are going to crave these once again, false signals of success, and you're going to think that all those things make you happy.

Srini Rao

Mm-hmm.

Payal Kadakia_

And let me tell you something, they are very fleeting, right? That is not a rich life by any means. They will come and they will disappear and you will be left feeling empty, right? And I think, you know, I always go back with ClassPass, like I had a chance to affect millions of people's lives, like I know, and the thing I am most grateful for more than any press or evaluation or anything for the company is we've helped people book over a hundred million reservations and that's a hundred million hours.

of people's lives. Like nothing, no post on Instagram, right? Like can compare to the way that makes me feel. And the fact that people will come up to me on a daily basis and say, Oh my God, I went and worked out today and I felt so good. That is given, right? And that comes back to you so much more than someone just liking a pose. So I think people really have to think about building stuff that's timeless because like

Who knows like Instagram is even not timeless, right? Like Snapchat's not timeless, TikTok's not timeless. Like we used to all be on Facebook and it's not there anymore, right? Or I guess it is, but you know, we're like kind of over it or I guess it's like our parents are on it now. And so it's one of those things where you have to remember timeless things are our products, right, and are things that truly add value through to human society at any point.

Srini Rao

Mm-hmm.

Srini Rao

Yeah, I mean, this is why I will often choose no-name guests at the cost of our metrics, because they have good stories.

Payal Kadakia_

Exactly, right. Care about what the intention is because that will always go further than, of course, like getting just, like you said, the likes and the metrics.

Srini Rao

Hmm. So one thing I'm very curious to ask you about, you know, both of us grew up, you know, in relatively privileged circumstances. I mean, we both were pretty much guaranteed to be able to go to college. You know, and both of us were pretty much conditioned to go to the best damn school we got into. In the position that you're in now, how do you think about making sure that you raise kids who are aware of the fact that they are growing up with a tremendous amount of privilege and that is not normal?

Payal Kadakia_

Um, so look, I think yes, like we grew up with privilege. That being said, I also grew up in times where I didn't know I could shop, right? Or I couldn't buy new clothes. Like I think I've had, I know the value of a dollar. And I think that's really the most important thing to teach your kids is the value of that dollar, right? Of what it takes and

I mean, obviously I haven't crossed that bridge with my son yet, but that being said, like I think it really comes down to exposing him to all the different experiences in the world. I think someone once told me like, you know, there was a son they had and they would send him every summer to like helping others, right, in other countries and exposing them to new experiences that make them really worldly knowledgeable, right? Like I think back to my childhood and why I think people didn't understand me.

And it's because people just weren't knowledgeable, right? And I think it really comes down to having the knowledge of it and then the empathy towards all of it.

Srini Rao

Well, let's talk specifically about, you know, sort of taking the leap to take a risk. There was something that really struck me that you said, and the reason this struck me in particular is because I've seen this, you know, come back in our survey data over and over and over again. We've asked our readers. They always say, I don't know what to do next. And you say no one pursues their calling already knowing everything they need to know or possessing all the necessary skills. But by taking action and hitting dead ends, by learning from failures and trying again, we learn what skills and knowledge we're missing. And we can close that gap.

Payal Kadakia_

Mmm.

Srini Rao

And I always described it as basically standing in two different spots in the same room. When you stand in a different spot, you see things you can't see before. But what is it that keeps people trapped there? And how do they get out of that trap?

Payal Kadakia_

Right.

Payal Kadakia_

They get comfortable and they're scared of failing, right? The fear of failure holds people back so much. It's, oh, if I move and I fail, but we don't really think about what that means. Okay, it's fine, you go and fail. So what is the worst that's going to happen? I almost feel like when you fail, and actually for me, I think about this all the time, I became an entrepreneur the day I really failed because up until then I had really nothing to lose, right? And I didn't even think about it.

And once I failed, I was like, oh, I really need to go and work on this. And I almost think the feeling of failing is so important for us to wake up and start seeing the world, like you just said, in a different way. And we should be running towards it, not against it. And we should be trying as many things as possible, making hard decisions, iterating, pivoting on ourselves until we feel we are more in line with the course we're supposed to be taking.

Srini Rao

Now, speaking of failures, what have been sort of the rock bottom, you know, all his lost moments for you in this journey? Have there been any?

Payal Kadakia_

Yeah, of course. I mean, I think earlier on, things felt more rocky. I think as your company scales, and I think as you know, ClassOS was moving so fast, the peaks and valleys started to smooth out if that makes sense, even though they were bigger peaks and valleys, if that makes sense. To me, they felt more

Srini Rao

Mm-hmm.

Payal Kadakia_

they just felt more milder because I had been used to it at that point. So whenever people ask me this question, I always do go back to more of like earliest days because that's when I wasn't, I wasn't used to it. Right. So the roller coaster was sort of just beginning. And I think that's a really important way to think about it is I've almost, you know, and I say this to my friends, like even when like the pandemic hit, like I just think our company was like, okay, like, let's go do this, because we had been here before, you know, and I think you, you stay resilient because you are used to that. Right. And so,

Srini Rao

Yeah.

Payal Kadakia_

I think going back to the earliest days, I mean, I talk about some of these stories in the book, like when the product wasn't working, it was so hard, right? Because I had this vision and this mission and I had people working and I had money and I wasn't figuring anything out. Like I was literally like living and dreaming on a bunch of ideas, right? And dreams that weren't necessarily coming to fruition. And that was just a really hard time to keep everyone motivated to keep.

you know, myself motivated and you know, I think I, I talk about this moment where I got maced and mugged sitting at a coffee shop and you know, I lived, like you said, a pretty like protected life and nothing bad had ever really happened to me in my life. And I remember that happened in the midst of like our first product getting close to fail, failing. And I shut down inside and that was totally the wrong move, but I just really shut down. And I remember I stopped like feeling anything. I just kind of was going through.

Srini Rao

Mm-hmm.

Payal Kadakia_

the day-to-day motion. And I remember it took like a big, it took some, a few things, like I had to start working out. It took me talking to certain advisors and sort of coming to terms with how I felt, right? Because we tend to run away from our emotion to really get out of that. And then I started really embracing my emotion and being like, no, I really wanna build this. I truly believe in what I'm doing. I really wanna motivate my team. And once I came back to that emotion and that...

feeling and motivation, I was able to re-motivate the team around me. And that's when we started actually building the second product, which was our passport product for ClassPass, which then helped us build the actual product, which was ClassPass. But I think we forget sometimes that we need to feel. And I think I almost did the wrong thing by trying to shut it all off, because that's sort of what I was told to do, and I felt like was the professional thing to do, but that was the wrong move.

Srini Rao

Mm-hmm. I can relate. I think that it's kind of interesting. You talk about vulnerability in the book, and this is something that I've always wrestled with, is when you're in the public eye, your actions have serious implications. Like everything that you say and do is so much more magnified. And I learned that firsthand from the reality show situation. I was like, OK, I remember calling a cousin who was a media attorney. He was like, look. He was like,

Payal Kadakia_

Yeah.

Srini Rao

Anybody can make you look like a jackass in editing, your job is to give them no ammo to do that with.

Payal Kadakia_

Right.

Srini Rao

But I had a mentor who told me, he said, none of your problems are gonna go away when a company becomes successful. He's like, they magnify. He said, what changes is your capacity to handle them? And I remember thinking, I was like, yeah, I'm guessing Mark Zuckerberg still has plenty of problems. They're probably just a much bigger magnitude now than they were before.

Payal Kadakia_

Uh huh.

Payal Kadakia_

Right. And every step in the process helps you get the skills and experience to do the next step. Right. And I actually think like this is actually a big part of what I talk about in the book with the goal setting process I do is what I really want people to do is break down things into small steps that they can execute on because we learn so much about ourselves by doing the small thing first and building the confidence to do the next bigger thing. Right. And you know, as biggest

Srini Rao

Yeah.

Payal Kadakia_

has gotten in its life. I truly believe I learned everything by putting on a small dance show in New York City in 2008 probably, right? Which was so, it's so small for like 100 people, that's what I was able to do. But that was sort of like this first huge thing in my life that I did, that I was able to succeed at, which then helped me say, okay, let me do a bigger show. Okay, wait, that went well. Let me go and start a company, right? It was this journey.

to do something bigger. And like you said, so as things were magnifying and scaling my capacity to do bigger things in my life expanded. And I think sometimes people want to get to the big thing but they have to actually start with the small steps to be able to get there. Not just because, you know, oh, everyone's saying you need to start small to get there. It's really because it's a part of the learning and growing process to even be able to handle the big things. I think when companies get really big overnight,

a lot of times they cannot handle it, right? And they end up like disappearing or like hitting major catastrophes because like they've lost their Y, right? They don't have the systems in place. They don't know how to actually maneuver themselves. And you know, ClassFest has been around for over a decade and you know, we've been able to maneuver so many different things because we started with so much of those ups and downs and learning through the big, like the big steps, small steps and then, and taking in what we needed to. So our capacity.

kept growing and I feel like that as a human too.

Srini Rao

Well, let's actually talk about this goal-setting method at the end because I remember going through it and looking at it I was like, oh some things in my life are kind of out of whack. This wet day. Oh, I came to the realization I was like, okay, you know what like I don't do anything but work, which is kind of a problem It's like work against snowboarding. I've even remember telling my dad the other day. It's like I have no life I'm like, how can I date anybody right now? I've got to like make sure this thing succeeds. I'm like dating is not a priority He's like seriously man. Like yes but I think that

Payal Kadakia_

Yeah!

Srini Rao

what I appreciated about the methodology that you offered was it was really a tool for awareness more than anything else for me. Because I mean, as you might imagine, after a thousand plus interviews, I've heard every goal setting method imaginable. But I liked the fact that it was something that created so much awareness. Can you just explain it in a bit more detail?

Payal Kadakia_

Yes, yes.

Payal Kadakia_

Right.

Payal Kadakia_

Yeah, so, you know, it's a process that takes from like an hour to hour and a half. So we can't get through the whole thing right now, but I'm happy to talk about what the methodology really is. And the biggest thing, and I love that way you just even set this up, but, you know, the first three steps are all about that awareness for yourself, because I truly believe before you get to the practical side of setting the goals and the big achievements you want, you need to really be able to reflect and think about what you want out of life, right?

And so the first step, we go through a reflection period where we think about, you know, what has this last year really been? What were the words and themes that were prevalent? We need to anchor ourselves in, you know, what we are and who we are. And then I think the next part of it, what we do is we go into dreaming phase and we go into a phase where we're doing the same thing we would have done in the reflection phase, but a year from now. So we really end up anchoring ourselves on the themes that we really want in our coming year. And...

that we really want to strive towards. So these aren't necessarily achievements like we just talked about, right? These are really about words. How do I wanna feel in a year? And then the next big step, which is really, I think sometimes the most revelatory for people who do the exercise is I really help them focus in, right? Because we cannot make, we can't make change in all areas of our lives at the same time. And so this whole process for me is always a quarterly process. So I focus in on

only the next three months and I go through a time diagnostic of, you know, where am I spending all my time and how is that time serving these dream words in my life? And then I go and focus in on, okay, I'm going to set goals in home. I'm going to set goals in, like in dance, and I'm going to set goals in my book, right? And I get very specific about the areas of my life I'm going to work on. And then only do I start setting the goals, right? So we've gone through a process where we've actually gone on to really focus in on

the areas of our life we're going to set goals against because they are really the ones that sort of need the work that we need to do. And so like you said, a lot of that is about intention. And then the goal setting part, and this is all in the book. I mean, I'm really good at setting goals. And the reason I have had to become is because that's been my life. I think it's all about execution, right? Ideas are a dime a dozen. Like dreams are always there, but really what gets...

Payal Kadakia_

get stuff done is writing them down and crossing things off, right? And this doesn't mean you need to have a to-do list. It's about having goals that serve you and your dreams. And for me, like if I write something down and if I tell you I'm gonna do it, you can guarantee I will do it. Like I have like a contract with myself that I will do the things that I say yes to. And I think that's the other important thing you have to really learn with yourself because I think...

Srini Rao

Mm-hmm.

Srini Rao

Hmm.

Payal Kadakia_

It's about you believing in yourself, right? And being able to say, okay, I set out these 10 to 15 goals and I'm gonna do them and I'm excited to do them. And you will feel so great on the other side of them. You just have to really build that discipline with yourself to actually get these things done.

Srini Rao

Yeah, no, totally. I remember when my editor Penguin said, can you finish a 45,000 word manuscript in six months? And I looked at it, I was like, yeah, I can do that. I write a thousand words a day, not realizing that writing a book is a very different beast. But because I made that commitment, I was like, yeah, hell or high water, I'm gonna deliver this thing in six months.

Payal Kadakia_

Yeah.

Payal Kadakia_

That's amazing and yeah, it's definitely a process.

Srini Rao

So one thing that also struck me, and the reason I wanted to ask about this is because it was a theme that I heard from a lot of our readers, and I did one-on-one interviews with my listeners to find out what was going on in their lives. And this came in particular for parents that I had spoke to. And you say that guilt often keeps us from focusing on our own priorities. This is especially true for women who often feel pressured to nurture and put the goals of others first. Women can often end up living their lives for someone else because they feel guilty prioritizing their own dreams.

I particularly saw this with women and ones who had young children like yourself. When they would work on anything creative or anything that didn't seem like it was going to basically add to the bottom line or add to their economic stability, they felt guilty. It was like I'm prioritizing something that's not as important as my kids. What do you say to them to get them past that feeling of not feeling guilty about the fact that they're prioritizing something that's important to them?

Payal Kadakia_

Right.

Payal Kadakia_

So first, and I think this is something I've had to do, is you really need to get the people in your life on board with your dreams and purpose, right? So, you know, and I've had to sit down with my husband, he'll be like, wait, or even my mom, right? She'll be like, wait, you have another dance class today? Like, why are you not playing with your son? And I'm like, no, like I have rehearsal or whatever it might be. It's about being very, very clear on your own priorities and sharing those with the people around you, right? They can't support your life unless you are very clear about what your own priorities are.

And I think, you know, in that process, I have learned to really be clear about what I want to accomplish every single day and knowing that those things are things I really enjoy. I think when I feel bad, it's usually because I am doing something I feel forced to. And in my head, I'm like, yeah, I would totally rather be with my kid right now than being forced to do, to do this, you know, meeting or this, you know, like social thing that I really don't want to be doing. Right. And so I think it really comes down to if you are doing the things you love,

then you're not going to feel that guilt, right? And you have to obviously find a way to communicate that to the people around you because you need to set yourself up to actually being able to do that in your life. But it really comes down to you knowing what you want to say yes to, right?

Srini Rao

Mm-hmm. Well, I want to finish with two final questions. You've alluded to the fact that dance is this huge part of your life. And if I dance really honestly, it was kind of the underlying motivation for starting ClassPass. And I remember even early on in the book, you described this experience of the feeling you got from dancing that just seems like it just brought you to life and puts you into sort of a flow state almost. And for me, that had always been writing. I played an instrument in high school.

Payal Kadakia_

Yeah.

Srini Rao

And I feel like so many people have these moments when they're young, and then they're just that. They're moments that become an afterthought. Why do you think that is and how do they reconnect with that part of themselves?

Payal Kadakia_

That's such a beautiful question. And honestly, like this is the anchor of the book. It's the sort of the anchor of ClassPass. It is really, we should never stop. We are never too old to have that flow state, that playful set in our lives. I think what happens is as we get older, society gives us responsibilities, which of course are important. I by no means think that we shouldn't be doing the things that are expected of us in the sense of responsibilities. But that being said, I think we need to.

really think about in our lives what we truly, what truly lights us up, right? And why should we stop playing when we get older, right? I never wanted to stop dancing and I felt odd about it. Like I remember being at Bain and inviting my whole office to my dance shows, thinking I was really weird and strange for doing that. But I remember when they would see me light up on stage and see me in my element, they actually had a deeper respect for me the day after, right? Because they were like, wow, like she's really talented.

at what she does. And I think we have to hang on to these things. We need to 100% prioritize these things in our lives because without them, we're gonna just be a part of the grind of society, right? And lose our life. Like you just said, that's what I talked about. I found it when I was really young and I really believe like my entire purpose in life has been how do I make sure other people feel that same life I so lucky, luckily found when I was younger.

Srini Rao

Yeah, amazing. Well, I have one final question for you, which is how we finish all of our interviews with the Unmistakable Creative. What do you think it is that makes somebody or something unmistakable?

Payal Kadakia_

I think when people are truly living their unique calling, it is 100% mistakeable and the universe will guide you through it.

Srini Rao

Hmm. Amazing. Well, I can't thank you enough for taking the time to join us and share your story, your wisdom, and your insights with our listeners. This has been really, really cool. Where can people find out? Yeah, absolutely, my pleasure. Where can people find out more about you, your work, the book, and everything else that you're up to?

Payal Kadakia_

Thank you so much.

Payal Kadakia_

Yep, they can go to lifepassbook.com and I'm usually on Instagram at pile, that's P-A-Y-A-L.

Srini Rao

Wow, you actually got that as an Instagram handle.

Payal Kadakia_

Yeah, I did. Can you believe that? I know I couldn't believe it. I remember I asked them because I had Pile 222, I think, and I was like, I kind of want to switch it to at Pile. And I was surprised that Pile is the most common Indian name, right, for a girl. And I got Pile.

Srini Rao

Amazing. Awesome. Well, thank you again so much. And for everybody listening, we will wrap the show with that.