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Get Unstuck with Goal-Setting

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Whether you want to launch a business or adopt a new workout routine, setting a goal can mean the difference between dreaming about it and doing it.

In this episode, which is a replay from the 2022 California Conference for Women, ClassPass founder Payal Kadakia will share her unique goal-setting method.

Learn to push through limits, focus, screen out unnecessary distractions, and find the momentum to achieve your goals — both professionally and personally.

Payal Kadakia

Payal Kadakia is the founder of revolutionary fitness and wellness platform, ClassPass, which provides people access to the best boutique fitness classes, gyms, and wellness experiences around the world. Payal is also the founder and artistic director of the Sa Dance Company, dedicated to expressing Indian American identity. Payal is frequently featured in major news outlets and has been listed among Fast Company‘s 100 Most Creative People, and was named to Fortune‘s 40 under 40 list. She holds a bachelor of science from MIT. LifePass: Drop Your Limits, Rise Your Potential – A Groundbreaking Approach to Goal Setting is her first book. @payalkadakia

Celeste Headlee

Celeste Headlee

Celeste Headlee is a communication and human nature expert, and an award-winning journalist. She is a professional speaker, and also the author of Speaking of Race: Why Everybody Needs to Talk About Racism—and How to Do It, Do Nothing, Heard Mentality, and We Need to Talk. In her twenty-year career in public radio, she has been the executive producer of On Second Thought at Georgia Public Radio, and anchored programs including Tell Me More, Talk of the Nation, All Things Considered, and Weekend Edition. She also served as cohost of the national morning news show The Takeaway from PRI and WNYC, and anchored presidential coverage in 2012 for PBS World Channel. Headlee’s TEDx talk sharing ten ways to have a better conversation has over twenty million total views to date. @CelesteHeadlee

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Photo credit: iStock/Rudzhan Nagiev

Episode Transcript

Erica Williams Simon:
Payal, it is so good to meet you and see you and be able to talk with you today.

Payal Kadakia:
Thanks for having me. It’s so exciting to be here.

Erica Williams Simon:
It is. I’ve got a confession to make. When I was invited to be in conversation with you, I did my Googles and I was like, oh my gosh, of course, the ClassPass founder. For those who don’t know, Payal founded ClassPass, it has been valued at a billion dollars, which in the business world is considered a unicorn, and everything I saw was highlighting that. In my mind, having had so many of these conversations, I was like, oh, okay, I kind of know what this conversation is going to be. This is the girl boss thing, which I will say I’m kind of grateful that that phrase is on its way out a little bit, for many reasons. I think it was really limiting, but I was like, that’s what this is going to be. It’s going to be a conversation about ambition and drive and building something.
And then, I went to look at your Instagram and I was so happy and so like delighted because what I saw was glimpses of a full well-rounded life, and someone who was showing not just themselves as this driven, ambitious business woman, but I saw a dancer, a passionate dancer. I saw someone who was constantly celebrating and talking about her culture. I saw someone who is a mother and always talking about that, and I just find that to be so rewarding to see. I think we’re in this moment now where people want to see what it looks like to be a complete human being. I believe and I know you believe, too, that to be a complete human being, you have to acknowledge and own and tap in to your passions and your purpose. I guess my first question to you is going to be a big one, but let’s start there. How have you crafted that kind of life? How have you made sure that in addition to meeting these benchmarks that society says are successful, that you’ve also created a fulfilling life driven by passion and purpose?

Payal Kadakia:
Such a beautiful question and thank you for even starting and introducing me in that way. I think it’s easy to be introduced with our credentials, but I love that you are able to describe a more full human being that I really am because that is who I try and be and who I really strive to really perfect in the sense of being my full self all the time, and a lot of that for me, to be honest, starts because when I was younger and I think even in my career, I didn’t actually always feel like I fit in. I think there were many times in my life where I felt like I had to be boxed in or I was living two different lives or trying to be somebody I wasn’t, and that happened by being Indian and American, growing up here. It happened by being a woman in tech. It happened because I’m a creative person and also a business person and I just didn’t know how to always be all threads of who I was.
And my initial way of dealing with that, and I think this is what a lot of us do is, I compartmentalized it. I was this one person with this community. I was this person in this community and I lived many different lives, and some of them were really fulfilling and other ones were what society wanted me to be, and I was trying to do it all, all the time. Eventually in my life, I really started charting my own journey, and the anchor of that was something that was a passion as you mentioned, which was dance. I started doing Indian dance when I was really young, and for me, it was more than obviously, just having a hobby and activity. It became a place for me where I belonged and a place where I felt centered and I had confidence, and I think because I felt like I didn’t fit in many other places, it was nice having an environment where I could thrive and be all parts in all colors of who I was. Therefore, when I got older, I really kept this side of me alive.
When I was at MIT, I danced on the side. When I was working as a consultant at Bain, I danced on the side and invited people to my dance shows, and at the same time afterwards, I really built a dance company on top of my corporate job because I was always fighting for this time and place in my life to exist. I knew if it disappeared, a part of me was going to be lost, too, and I would say that, my fight in ClassPass, honestly, was to give that same thing that I had in dance to everyone else in the world. That was why I started the company is because when I hit that problem of not finding the technology to find a class, I realized that this wasn’t just about a tech problem. This was about people not knowing how to prioritize their passions, and here I was, somebody who truly had been working on being more of who she was, not just trying to be one part that society wanted me to be and thriving. As I kept seeing that, I wanted everyone else to have the same thing.

Erica Williams Simon:
I love it, I love it, and I know that so many women can identify with that. I wrote a book literally about that moment of saying, “I’m too many people. I want to be one person. How do I walk away from this career that I’ve been boxed into?” And now you have also written an amazing book called, LifePass, that has just come out-

Payal Kadakia:
Thank you.

Erica Williams Simon:
… where you’re talking about that second half of what you just spoke about, the idea of prioritization being a critical part of being able to create this well-rounded life that has passion and purpose and a little bit of ambition sprinkled in there, too. Talk to me about, how did you go about, once you had this aha moment, that you wanted to be driven by these things in a way that, I think society maybe hadn’t set you up to be driven by, because again, and I can identify certainly as a black woman, you’re talking about trying to fit into all these different worlds. When you made that decision, I got to do something different. I have to change and I have to prioritize me and my true self, what did that goal setting process look like because that’s what you talk about in your book?

Payal Kadakia:
I have a method that I do. It’s called the LifePass Method, which I talk all about in the book, which is about setting priorities. I actually didn’t start that process in my life until a little bit after ClassPass started working, and the reason I actually set that method in my life was because I realized I knew how to be successful in my professional career and I was making a lot of choices that had put me on the right path there to be successful, but my personal life was in shambles, and I think I have learned to realize that to be happy and to be fulfilled, I need everything that’s important to me to be making progress towards where I want it to go, not just one area, and I was very good because the world had taught me to do great things in my career, and professionally, I was very focused on that and I knew I had a system, had to check every mark that anyone ever told me to do, how to reach for the top.
I knew I had a system in there, but why didn’t I set goals in the other aspects of my life to have that full life? And that’s really where it started from, but we can go into that a little bit, but I would say even earlier to answer more of the professional side of things and how I shifted careers and got to a place where I felt confident enough to even start my own company, what I really had to do was start putting a plan in place to be able to chart my own journey. A lot of this, and I do talk about this in my book, how do you set up a financial plan to really be able to take that leap in your life? I love telling people to go after their dreams, but it comes with some pre-planning.
And I worked for six years making money, saving every dollar I could, so when that day came to take that leap and quit my job, I was able to do it. I think that’s a really important part of the process. I worked really hard to get my parents’ support through the journey, and being someone who was in her twenties who decided to start a company and quit her job, it was important for me… My parents immigrated here in the 70s. I wanted their blessing in the path I was going to take, and having them be the people who literally said, “Why you quit your job?” was so important to me and to be able to get them there, and everyone’s always like, “How did you do that?”

Erica Williams Simon:
That’s a big deal.

Payal Kadakia:
Yeah, exactly, and I think a lot of it was, I overshared. I think our tendency is to minimize the things that we think people are going to say no to or be scared of us doing, and I showed them every dance thing I did. I showed them everything about the company I was building. I overshared anytime someone would be like, “Hey, I think this is a great idea. Can I write you a check?” or anything positive that was going on because I wanted them to have that faith in me and know that they had done right.
They got me and my sister a great education. They had raised us so well at this point in our lives and I really wanted them to know, let me be free and I will do a good job, and they really believed that, and I think that’s really part of the equation for me that, those were sort of steps in the journey. I didn’t really quit my job right away. I went and took a half step, made sure I was paying the bills, and I started being an entrepreneur really honestly, first by starting my dance company, and that taught me-

Erica Williams Simon:
That’s amazing.

Payal Kadakia:
… everything I needed to be an entrepreneur, and I just got riskier and riskier.

Erica Williams Simon:
I love it. I love it, and what I love about that story, because you said you were so fortunate and privileged and blessed that your parents actually were able to give you that support, I know not everyone has that.

Payal Kadakia:
Of course.

Erica Williams Simon:
But I think the universal lesson there is this idea of, you need someone. You need some people who will see you in a way that you want to be seen, and part of getting that is sharing and being honest and open and saying, “This is who I am. This is what I’ve done,” and I love that you said, especially as women, I think we are taught to shrink those parts of ourselves, and the idea of just saying, “I’m going to open up and I’m going to be vulnerable and I’m going to be myself, even before my job reflects that, even before all the pieces are in place.” That’s a really, really helpful lesson that I think all of us can take.
I guess my next question though is, so we’ve kind of talked about, you figured out that this is something that you wanted, you set up all the pieces. I love that you said, “We know how to make plans and goal lists for work and for doing all these things for other people, but rarely do we know how to do that for those parts of ourselves,” and I think that’s really what people here today are going to want to hear more about. How do you actually go about setting up those goals or those comparable checklists for those parts of yourself that are driven by passion and purpose?

Payal Kadakia:
Absolutely.

Erica Williams Simon:
What is the method that you recommend?

Payal Kadakia:
Here’s the thing. We all have responsibilities. I never want to say, we can do our passions without thinking about the real things in our life, but what we can do is put a plan together to make those responsibilities as efficient as possible and as enjoyable as possible, too, and then have all the time in the world to dedicate towards our passions in our life. Ever since I was young, I literally would come home, I would do my homework really quickly. I would try and get done with all the things I was responsible for doing, so I had every extra minute of my day to do what I loved, which was dance. I literally have set up my adulthood life in a very, very similar way, so when people always ask me, “How do you make time for your family?” and I have a son now, and how do you dance, and how do you still have a professional career and be ambitious?
And it comes down to priorities. Now, the first step of priorities though is about reflection and being self-aware, because it’s easy to list down a bunch of things that you have on your to-do list, but you need to actually know what you want, and most people do not ever tell you how to set expectations and goals for your own life. We are told constantly by other people what their expectations are of us, but you need to find a way and have a practice where you sit down and write those expectations. Something I do, which has always helped me, honestly probably for the last eight, nine years since my life has been busy, is every Sunday night, I have a Google Doc. It’s called Payal’s Weekly Priorities, and by the way, this goes across my professional life and personal life, from things I need to get this person a gift to I want to see this friend for dinner, I need to choreograph this dance piece, and I need to have these three meetings.
These are obviously, they’re critical to my job, but at the same time, they are more things that I know I want and I want to fit in if I can, and I always write those things down. By the way, sometimes I’m like, there’s no way this is going to happen this week. I’m going to move it to next week in this calendar for me in this weekly checklist. It has it for the next few weeks. Sometimes it goes on for the rest of the year because I’m like, I’m going to slate this for May because it’s never going to fit in February and I’m okay with that, but I like that if something is important to me, it goes on this list, and then only after I have that list, do I go and check my calendar.
Usually we let our calendars dictate our lives, especially if people are putting stuff on there, and I have learned to do the opposite way. And then, I go to my calendar and sometimes those things are serving my priorities and sometimes they are not, and I have become very comfortable with saying, “I’m going to cancel that. I’m going to say no. I am not going to feel obliged to doing things that don’t serve me and my priorities.” To add on that a little bit, I know that sometimes can sound selfish. A lot of times people get really into their head about, wait, but I’m being selfless and I’m not really thinking about other people, and I really think, at the end of the day, when you are protecting your mission and your priorities and where you’re going in your life, you’re going to be a better version of you that’s going to be able to give more to other people.

Erica Williams Simon:
So true. So true. First of all, I love that you said it starts with reflection because so often we don’t really know what we want or who we want to be, and I think we do two things. One is we see what the world has told us we should be, and two, we spend a lot of time whether that be through social media or however we consume other people’s images and kind of what we think their life looks like, and maybe we should model ours after theirs, and so it’s really good to just be with yourself by yourself, take a moment, dig deep and kind of figure that out that, and then go through the process you just talked about. That’s so helpful.
Here’s one thing I want to say though. We’re having this conversation, which again, I think is a timeless one for women because we all, no matter the time or place, have a lot of things we want to do, want to accomplish, have responsibilities, but this conversation is happening in a very unique time. In this era, post 2020, I don’t even know what to call it. Is it during COVID, post-COVID, whatever.

Payal Kadakia:
BC?

Erica Williams Simon:
But we’re in a crazy time. I don’t know if this is what our future’s going to look like forever. Who knows? But it’s a unique time where women are feeling, really all of us are feeling a level of, I think burnout, that I don’t know that we’ve experienced before because it’s cultural. It’s not just individual and personal. It is societal. There’s so much happening. It’s a heavy time. Obviously, the women who are here at this conference are here because they want to reignite some passion in them. They want to actually reconnect, they want to reenergize, and do all those things, but have you ever experienced burnout? If you’re the kind of woman who makes a Google Doc for her personal life, I know that you are driven, I know that you are ambitious, and always on the go, but if you ever just felt a sense of burnout and if so, how did you overcome that or address that, especially within this context of goal setting?

Payal Kadakia:
I love that. By the way, I think burnout can be misconstrued in the sense of, working hard for something you don’t want to do is going to result in burn out. Working hard for something you have a purpose towards, you won’t ever feel burnt out, and usually that’s the key.

Erica Williams Simon:
That’s interesting.

Payal Kadakia:
I have been beyond busy in my life working towards a dance show or when ClassPass was going through the iteration, but I saw people going to class and I never once felt burnt out even though I was clocking the craziest hours. Then there are other times where I’ve worked half of that on things that haven’t really lit my soul on fire and I have felt burnt out. It really to me, is actually about the why behind the work. It is not about the work and having too much to do, and I think that’s really why, once again, what we were just talking about is so important because it’s not about being a slave to the grind. It’s about infusing all of it with some sort of purpose and some sort of fire in it, and I really believe that even in stuff that we have to do in certain jobs that we feel like we have to, find a way to inject that purpose into it. What are you extracting from that lesson? What mentors could you be meeting in that?
I talk a lot about this in my journey when I was at Bain. Maybe it wasn’t my dream to be a consultant, but the foundation I got from being there, the experience I got from being there, the network I got from being there, set me up to flourish in my future. Going back to the burnout question, it really to me, comes down to, your to-do list is wrong. Your priority list is wrong. It’s not serving something that’s burning inside of you. I have definitely been there at points in my life. I’ve been there when I was sometimes even in my own company, I knew I was in the wrong role.
In 2017, I no longer wanted to be the CEO of my company, which to most people was crazy, but that role and the work I have to do is not serving me. It is not what I’m excited to do and I started feeling burnt out because as much as I loved my company, the work I was doing wasn’t lighting me on fire anymore and I needed to switch that so I could go back to say, “I love my company. I want to do the work that fires me up,” and that is, by the way, on us. No one’s ever going to make you shift that.”

Erica Williams Simon:
No one will come for you.

Payal Kadakia:
Especially in your career, people are just, especially if you work hard, which most people here I’m sure do. You can get taken advantage of. Actually, I just remembered that, it was one of my first jobs and I remember getting, it was a feedback review and he said to me, he goes, “My fear with you is people are going to take advantage of you because you work so hard.” And I’m like, “What? What do you mean?” He was like, “You have to enjoy what you do because you know have such grit and you care so much about your work and doing everything at 150%,” and I will always do things like that, and at that level, and that reputation has followed me, but it’s been so much nicer doing it towards something I truly love. I never feel burnt out.

Erica Williams Simon:
I love connecting the idea of burnout to prioritization, to mission, to purpose, because like you said, society absolutely. I use the term society in a very broad sense because sometimes that means your job, sometimes that means the culture of wherever you are, but will absolutely take advantage of you overworking or of you doing something that doesn’t serve you. It really is up to you to do that, as you said earlier, that reflection, that pausing. It is okay, and I’ll just say it. Is okay to pause, if you are in that moment of feeling that kind of burnout to the best of your ability.
We know that some things just don’t stop. You can’t pause on taking care of your family, but pause what you can enough to be able to do that kind of reflection and possibly re-prioritization because that’s the only way… It sounds like this is also what you’re saying. That is the only way that you’ll be able to set the right goals that then don’t really require you to put those kind of limits on yourself, that you can work hard and you can work passionately because it’s something that you know is serving a deeper purpose for you.

Payal Kadakia:
The LifePass Method, which is the third part of the book, which is a deep goal setting process that I do.

Erica Williams Simon:
Yes.

Payal Kadakia:
Step one is reflection. Step two is similar to the reflection, but we flip it and we dream about the coming year and how we want to feel and what words we want to embody in our year. And then, we actually go to a whole process of focusing. This is all about what am I going to prioritize in my life? And people do a time diagnostic. We rate those areas of our life, and then we choose three to five areas we’re going to focus on for the next three months. This whole goal setting process I also do is a quarterly process. I’m not setting annual resolutions, I’m also not doing things for one week. I’m anchoring myself on things I want to do and improve in my life.
Once again, personally as well, there are times in our life where we need to improve personal things. There are times in our life when it’s professional, but we are the only ones who can say that to ourselves and put that plan together. Usually, we all know how to do that professionally, we don’t know how to do it in other areas. And that’s why I found the system really helpful for me because I remember I moved and I didn’t have time to decorate, and I remember one of my words for the year, my dream words, was home and I wanted a way to feel home, but I just didn’t have time to prioritize it. And I remember writing down, okay, I’m going to make sure these three rooms are done this quarter. And that just felt like an achievable goal in my mind versus feeling like I was just never going to decorate my house and I was just too busy to ever do it.
And I think it’s things like that. It’s also, I talk a lot about this, too. It’s learning how to delegate, and I think for women there’s such a stigma around that. I’ve had that stigma with me, too. I don’t know how to cook. I totally don’t know how to cook and I do not belong in the kitchen whatsoever. It’s taken me a really long time to say that. And I was even talking to my mom the other day and she kind of was pushing me to be like, Why don’t you come in the kitchen? I’m like, Mom, you know me at this point, there’s no point.

Erica Williams Simon:
Not going to happen.

Payal Kadakia:
And maybe one day when I have a goal and I’ve tried it, I’ve tried to put cooking into one of my goals because there are times where I’m like, let me explore this. And you know what I’ve realized, I just don’t enjoy it. So, it’s good for me to actually not set these unrealistic goals that don’t serve me in my life, and I’d rather delegate it to my husband who loves food thankfully.

Erica Williams Simon:
Truth moment. Truth moment. I love it. I love it. It is a safe space. It is okay to admit that and also kind of then delegate accordingly.

Payal Kadakia:
Exactly.

Erica Williams Simon:
Yeah, I love that. Okay, and that’s another reason, what you just talked about that process is one of the reasons why I love this book and I encourage everyone to buy it and read it because it’s very practical. I think we can have these conversations at a theoretical level about mission and values and purpose and I mean those are my favorite conversations to have.

Payal Kadakia:
Totally.

Erica Williams Simon:
But at some point, you get up from having the conversation and you have to go back to your life, and what I appreciate about the book is that it actually does walk you through systems, plans, processes to actually begin to prioritize and goal set.

Payal Kadakia:
Absolutely.

Erica Williams Simon:
But here’s my question for you. I already talked about the fact that we’re living in crazy times, but let’s say you go through this process and you set the goals, you do the reflection and you do the focusing exercises, and you get your three things and you get your calendar. You are just crushing it and then life happens, which again, so many of us have experienced in a myriad of ways, but if at the very least we all experienced it with COVID.

Payal Kadakia:
Totally.

Erica Williams Simon:
Life happens. For you at ClassPass, I think it was in an instant, 90% of your business was impacted because gyms were closed down. How do you build respond to that first of all, but really how do you build flexibility into this plan?

Payal Kadakia:
I love that question and honestly the plan is built to be flexible. I think it’s really more about having the habit of being able to say, “My dream words are still my anchor. What I really want to feel is not going to necessarily change. My true north doesn’t change. A tree just fell in the middle of the road, but I still have to get to the other side, and I think that’s really the mentality to have. Life is going to happen. There’s going to be, not even one tree, there’s going to be multiple trees and lots of bumps along the way, but do you lose sense of your true north? That’s usually what gets people off. It’s that they start wavering and then you don’t know what direction you’re going in and that’s when you start feeling like you’re not making progress, so I always go back. Make sure your dream words are right, which is step two of the process, because if they’re right, they will carry you through.
You can change your goals. You can even change your focus areas if you need to. If all of a sudden, someone might have a fitness goal and they get an injury, that doesn’t mean you can’t go towards some sort of sense of movement or some sort of sense of health. There are ways to improve on those areas. It’s just more of breaking it down in a different way, and that’s really what I want people to know, and I love what you even said earlier. It’s knowing that true north but also, then breaking it down to take steps towards it. How do you overcome a challenge when it’s in front of you? It’s not about getting stagnant. That’s the worst thing you could do is just sit there. The thing you have to do is start gnawing at the tree and being like, “How am I going to get through this?” Little steps will help you get over there.

Erica Williams Simon:
I love that imagery so much. The tree fell in the middle of the road, you still got to get to the other side, and I think even just stating that… Stating it in that way, because so often we either are in denial that the tree fell and we’re trying to pretend it didn’t.

Payal Kadakia:
Acknowledge the tree.

Erica Williams Simon:
We just keep driving. No, there’s a tree there, or we get discouraged and we’re like, I guess I need to figure out an entirely new kind of set of goals, and it’s like, no, you just have to find a new way to get there and it may take you longer and it may take a detour, but the other side is still there waiting for you, and I love that.

Payal Kadakia:
Actually with that point, I talk a lot about this a lot with entrepreneurship and people have always asked me, how did ClassPass last through so many ups and downs, wrong turns all of it, but it was that. It was the fact that I cared so much about that true north and if I, at any point was willing to change the true north, the company probably wouldn’t exist or we’d be something else, and I think that’s what’s so important is, that’s about a company, but we have to remember that personally as well. It’s the same thing. It’s about fighting for what we truly want. And you’re right, a lot of times when you give up on something it’s because you didn’t care enough in the first place. Why even start on something that you might even give up on in the future?
I was adamant I was never going to give up on trying to solve this problem, and I think that’s really what I want people to know is, when you start on these journeys, whether it’s entrepreneurship or whatever it might be, if it’s coming from your true purpose and calling, you are never going to give up even when that tree falls, and that’s how it’s the right thing. If you are willing to say, “Hey, you know what? I’m all right, I’m okay. I’m going to go find another true north over there,” then that first one was never really there.

Erica Williams Simon:
I love it, and it goes back to something else you talk about in your book that really then, when you set that true north and you are committed to it and you are holding onto it, then the challenge or the task for you is just to figure out how. It’s really the how. Once you have set the why, then everything else is just trying to get the right process in place for the, how are you going to achieve it? How are you going to get there?

Payal Kadakia:
Right. Right.

Erica Williams Simon:
And I think your book is so helpful in that. I know we’re almost at a time, let me ask this one question. I want to bring back the theme of this conference. It’s three Rs. I’m going to read them to make sure I got them right because I want to know how you would respond to women who are trying to do these three things, renew, reconnect, and reignite. That is the theme of this conference. Renew your sense of purpose, your sense of passion. Reconnect to who you truly are, and your true north. Reignite all of that. Light that match. What would your final words of inspiration be to women who are trying to do that?

Payal Kadakia:
Reflect inward. I think so much of what we need to realize in the life has to come from inside of us and it’s already inside of us. It’s not from anything outside, so listen to yourself and then put a plan together and go for it.

Erica Williams Simon:
I love it. Thank you so much, Payal. This was amazing because like I said, it was both inspirational and very, very practical. Those are the two words I would also use to describe not just your career and your life and the work that you do in the world, but this book LifePass. Make sure you get it. Thank you again, Payal.

Payal Kadakia:
Thank you.





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