If Sheryl Sandberg’s key to helping women find success has been “lean in,” Payal Kadakia’s phrase might just as well be “sit down.” In Kadakia’s new book, LifePass, the ClassPass founder (she transitioned out of the Executive Chairperson role when the company was acquired by MindBody in October 2021) details the pivotal moments of her upbringing and early career that helped her redefine success. One of those ways? Remaining seated while giving a big presentation—instead of standing like her cohorts—because she knew it would bolster her confidence. It could’ve failed spectacularly, but that has come to be the crux of Kadakia’s journey: finding what works for her, expectations be damned.
Throughout her book, available February 15, she shares several similar situations in which she turned situations on their heads to create success as she views it, not as family or society or peers may. (Regardless, she undoubtedly found traditional success as the fitness platform was valued at over a staggering $1 billion prior to its acquisition, making Kadakia the first unicorn-status woman of color.) But just sharing these anecdotes wasn’t enough for the 39-year-old. Instead, she uses the chapters to map out practical steps and tools so that readers can not follow in Kadakia’s footsteps but, better yet, carve out whatever niche they hope to.
Here, the entrepreneur shares morsels of advice from her book, from creating priority-driven schedules to setting boundaries; discusses why her experience growing up as a minority gave her valuable perspective on embracing her fullest self; and explains why she wants to be remembered as a “creator of timeless things.”
Marie Claire: What have the past few months been like for you, since the acquisition was announced?
Payal Kadakia: I've had this book coming out, so I can't say I've had a second to relax. But that being said, this book in particular has come at a really nice time to reflect on this journey...Right now, while I'm doing interviews and sharing more of this book with others, I feel even more tied and connected to the stories, because I feel like it's such a celebration of what this last decade has been in my life.
MC: Why did you decide to write a book?
PK: There came a point—I think it was right around the time I got pregnant [with my now two-year-old son]—when I remember thinking, Before I start this whole next phase of my life, I have a responsibility to all the people who always ask me, "Hey, Payal, how did you do it? Do you have any advice?" Literally every day I get so many people asking me for tips on their startups or life. And I really felt a responsibility to share with people my methodologies and the way I lived. Because I lived in a different way than I think most people did, especially through my 20s and early 30s. [Writing the book] started with that intention and that purpose.
The part of the book process that I really loved was that as I was writing it, and as I was rereading its many [drafts], it was unlocking a phase of me too. Because I was going through such a transition with the ClassPass changes, with COVID, with becoming a mom... A lot of the advice was almost therapeutic for me to read for myself and to say, "Yes, like I remember being like that 10 years ago, I have to make sure I never let blocks [like that] come in my life." So it was sort of a full circle moment for me.
MC: This book isn’t a typical memoir. It’s a very practical guide through the lessons you’ve learned growing up and in business. Why did you want to approach writing the book in that manner?
PK: I'm a very action oriented person. Like ClassPass is about making people do something in their life. Everything that I stand for has to do with practical action. And when I was writing this book, I even thought, I don't want people to read this and say, "OK, cool, that was good advice." I wanted to find a way to take it from thought to action, because that is really how we make change in our lives. Same thing with the ethos of classes—it was getting someone to actually go to class and have the experience.
I knew my only way of getting [readers to create actionable change in their lives] was to, in a way, give them homework. Give them exercises to do that. I know I'm doing that on a daily basis with myself and having those moments to figure out what my priorities are; having those moments to plan the dream life I want to live.
MC: You spend a lot of time in the book discussing your experiences as an Indian American; growing up as a minority and feeling a bit of an identity crisis. Why did you feel it was important to share that perspective?
PK: It came down to the fact that all of us, whether Indian American or something else, tend to live our lives in boxes. We create dualities no matter what. For me, [being] Indian American was prominent in my youth. I faced more business and creative [boxes] as I got older. I was “a woman in tech.” I never felt like I fit the mold of anything around me. And that's honestly [how] everyone [feels]. And what I wanted people to get from my own story—and it took me a little bit to get there—was how incredible it can be when you show up as your full self.
What I really want to unlock for people is to not box themselves into different parts of their identities and let themselves really, fully be whatever they want to be. I don't think we are told that enough. I don't think we are told stories of how to do that enough. Even the CEO title, to be honest, can be boxing to people. It was boxing to me.
Even the CEO title, to be honest, can be boxing to people. It was boxing to me.
MC: Do you still feel that struggle of being boxed in? Do you feel like embracing your fullest self is a constant journey?
PK: With this ClassPass transition happening, so much of my identity was the company. So I’ve been going on a journey of rediscovering who I am without that big part of my identity too. I wouldn't really say it's a struggle, but it's really giving and allowing myself the chance to live again and be all parts of who I want to be. It's putting my tools back in practice and saying, "How do I want to spend my time?" Do I want to dance more? Do I want to travel a bit more? Do I want to think about Web 3? It's about going into my own curiosities and ensuring I don't get stuck.
Even after this transition, everyone started [sending me] messages: “Are you going to invest now? Are you going to do another startup? Are you going to stay at home because you're a mom?” It's funny how people already want to box me into some lane in my life… I'm very cognizant of being like, “I'm going to do whatever I want, the way I want. And I will do it all, but I will do it on my own timeline and with purpose and intention.”
MC: You mention the tools you've created to be able to choose your own lane. What advice do you have for people who feel like they don’t have those tools yet or the ability to create that kind of control over their path?
PK: The first one: Time is the most important resource you have. Do not waste it. One of my tips with time is to make sure you think about what your priorities are every single week. I have a “weekly priorities doc” which I open every Sunday night. I spend 10 to 15 minutes going through what my priorities are and then I look at my calendar. My priorities are from all parts of my life: my professional things, my dance things, my personal life. Because in the end I still have to get it all done…That's the practice I’ve had for the past 10 years of my life, especially as my life has become so busy and crazy...it [allows me] to be deliberate about how I'm putting [my calendar] together. It gave me control over my time and my week and what I really wanted to do with my hours.
My second tip is around money. I really live by this mantra: “Make money work for you, you don't work for money.” Money can be the most trapping aspect of our dreams. And the one we feel like we don't have control over. But we do have control because we're the ones who earn it and we're the one who spend it. Coming up with a plan—whether it's with you, your partner, your family—it's important to be in a place where you understand those numbers and are making those numbers work in a way that's going to unleash your life. And unleash your plan to go towards starting that company, having the career you want, or staying at home, if that's what you want.
My third piece of advice would be that if you have any mental constraints that are standing in your way…figure out if you can set some boundaries in your life around those triggering thoughts. And that might be people who bring up triggering thoughts in your life or on social media or situations that make you feel [bad] about your life path and are pushing you in a different direction. You are allowed to say no to those things.
MC: Something else you write about passionately is building a supportive tribe who will empower you and your life. What do you think is the best way to create those types of mentorships and relationships?
PK: I think it comes down to finding people who you can connect with and be vulnerable with. It's not about pulling somebody [aside] and being like, “Here's why I'm offering you should mentor me.” It's really like, “Here's where I need help because this is what's going wrong, and I think you're the right person to help me with it.” I've always felt that the mentors who've helped me are because they really believed in me and they saw the authenticity. But also they truly saw the vulnerability and knew, this person's going to listen and be coachable too…It's not about going with the person who's the most famous or the biggest, because usually those people probably won't have time. I have found the best mentors just organically. It was finding somebody at work who was working in a different department, but it was a department I was interested in, who also then connected me to somebody else because I was telling them what I wanted to build. So it's a lot of organic conversations that lead to you finding the right people, the same way you find your friends.
MC: There was one really powerful moment in your book where you discuss being at a meeting and feeling self conscious about how you look. And you explain it was a lightbulb moment for you because you realized you could change the circumstances to help you succeed. How did that situation come to be?
PK: That was my sophomore year of college, interviewing for an important summer internship. I was interviewing at a top consulting firm, and everyone around the table was doing presentations. The assignment was to host a discussion with your peers around a problem we had been given.
I'm sitting at the table and everyone's getting up, one by one, and I just start sweating. I knew I'm a good speaker and I can lead and all of that, but I just knew that when I got up in this room full of other candidates and people I did not know, everyone’s going to just look at how small I am. I've gotten more comfortable with it over time, but, at the time, I was really young and it was something I was nervous about. I knew at that point, if I got up, I was going to start stumbling over my words and sounding nervous and I was going to definitely bomb the interview.
So I realized we were all sitting at a table and we were supposed to host a discussion. I decided I would just sit at the table to lead the discussion. Of course in the first minute of it, I remember everyone else's bodies tensed up. They were like, What is she doing?
I felt more comfortable and confident, because then I was really in my zone. It was funny because since I was eye-to-eye with everyone, the people in the room were actually more open to talking in my session than any of the other sessions. Afterwards I was like, Oh my god, I probably did not get that. I cannot believe I did that.
A few days later, the recruiter who was interviewing me called me, and he said, “I’ve done hundreds of interviews and no one's ever done that…you had the best discussion I've actually ever seen in any of these interviews. You got the job.” I thought that was so incredible because I had just thought about the mission of what he told me to do and I accomplished the mission—I just did it in my way.
MC: Is that a lesson you’ve continued to use throughout your career?
PK: I realized over time to set up environments in which I knew I would feel confident—of course, sometimes you can control them and sometimes you can't. But, for instance, as I was building and pitching ClassPass, I had to fundraise a lot. I remember showing up in boxy suits and wearing clothes that didn't make me feel empowered. Especially, once again, being a woman of color in the room where no one looks like you, so I wanted to show up as confident as I could be. I know it sounds odd but there was a point where I remember saying, “I feel so much better in my leggings because that's who I am. I'm a dancer. I love working out.” And I started showing up to some of these VC meetings in my workout clothes. It just felt more in line with who I was, and obviously more in line with the brand, and I stopped questioning it. And the second I stopped questioning it, everyone else stopped questioning it.
MC: Your bio or the way people tend to describe you is often filled with accolades and buzzy accomplishments. But as you noted a lot of those titles can “box you in.” So if you were to introduce yourself or rewrite your bio to define your priorities what would it say?
PK: This is so hard…something I come back to though is “a creator of timeless things.” Because I've always cared about creating things that are timeless and that leave an impact on the world. I don't know if anyone really ever sees me in that way, but I think it comes down to that…whether it's my dance work, ClassPass, this book, I've always just wanted to make things that hopefully will outlast me in my life.
Also, “tiny but mighty.” Because I feel like a lot of times I’m underestimated because of my height. A total stranger came up to me the other day and he said, “I always forget you're short. I feel like you're six foot five.” And I'm like, “I love that!” Because I feel that way even though I'm not even five feet tall.
I've always just wanted to make things that hopefully will outlast me in my life.
MC: That feels like a full circle moment from being nervous to stand up in that presentation because of your height. My last questions actually come from your book’s table of contents where you instruct readers to ask themselves, “Where do you still want to go? What are your priorities? And what's your plan?” So I want to pose those same questions to you.
PK: “Where do you still want to go?” is my north star. One place I still really "want to go" is to find a way for people to experience Indian culture at a more universal level, because I love the beauty of the culture so much. I believe that what is in Indian art and music can transcend space and time. So my priorities right now are building an Indian ballet; I’m just working on that and continuing to dance. Also launching this book and snuggling as much as I can with my little baby.
The interview has been edited and condensed for clarity.