Alli Webb ON: How to Embrace Imposter Syndrome & Ways to Take Small Steps Towards Big Success

podcast On Purpose with Jay Shetty. Hey, everyone, welcome back to On Purpose, the number one health podcast in the world. Thanks to each and every one of you that come back every week to listen, learn and grow. Now you know that our community is all about becoming happier, healthier, and more healed. And whether it's your career, whether it's your relationships, whether it's your personal life, we try and

focus on all aspects on on purpose. Today's guest is someone who's excited to share with us what I believe is the truth, and it's called The Messy Truth. Ali Webb, who I'm going to tell you about in a second. This book is all about how she sold her business for millions but almost lost herself. The Messy Truth is available right now. We're going to put the link in the caption so you can order it while you're listening

to this conversation. And for those of you that don't know, Ali Webb is the founder of dry Bar, New York Times best selling author Can It Be, President, co founder of Squeeze, bright Side, and Beckett and Quill. In twenty ten, dry Bar exploded into an nationally recognized and highly sought after brand, growing to over one hundred and fifty locations and highly successful product line which sold for two hundred

and fifty five million dollars in twenty twenty. Staying true to Ali's signature approach to beauty and self care, Squeeze follows suit as an innovative massage concept. Ali joined forces with La based jewelry designer Meredith Quill to build yet another new company, now known as Beckett and Quill. Most recently, Ali joined the Canopy team as president. And I'm excited to talk to Ali because we bumped into each other recently at a soccer game football game for Angel CITYFC.

Please welcome to the show, Ali Webb. Ali, thank you for being here.

I'm really glad that you're sharing this. So I have lots of things I want to ask you from the book today. I highly recommend everyone goes and buys the book, especially if you're on your entrepreneurial journey. Maybe you want to be an entrepreneur, you're thinking about it, and you think about how do I figure out all of this stuff? So let's start with this idea, ALI that a lot of our audience, a lot of our community, wants to

be entrepreneurs. Yeah, they may already be entrepreneurs. Some of them are struggling, some of them are winning, some of them are still figuring out what they're even going to do. What is the messy truth about starting that no one tells you about starting specifically?

I'm super grateful for. Like I said, thirteen years ago, when we started Drybar, that didn't exist, Like nobody was talking about anything, you know, you didn't have access to founders or CEOs the way you do now.

everybody wants to like show their best side. And for me, it's like I I've always just been drawn to the like, you know, the realness, and maybe it's because I've always been a bit of an underdog, you know. I mean starting from the time I was like a kid. My older brother Michael, who's my business partner in Drybar, you know, he was like the overachiever in our family, like very you know, kind of more BookSmart and just you know, it was kind of either always in trouble or always

doing something really amazing. There wasn't really a lot of in between, and I was kind of a bit of a wallflower, which if you know me now, that is not my personality at all, But back then I was just kind of observing my brother in trouble or doing

something great. I grew up in this with this like I was just in the background, and I think that as as I've gotten older, I have felt like more wanting to you know, talk about, you know, my story and like how I was like like a bit of an I think I have a chapter in the book called like the Unlikely Entrepreneur something like that. I should probably know all the chapters of my but but I've always considered myself like kind of this underdog and like

not who you'd expect to succeed. And I think I've guessed I have felt called to shine light on that because there are a lot of us out there, you know, and I don't have a traditional path. And I think that at one point it was like there was the societal like you have to go to college, you have to have a business degree if you want to start

a business. And now you know, there's so many I've spoken at so many colleges that have entrepreneurial programs, which I'm like, I always get a chuckle out of because I'm like, I didn't even go to college, Like do you want me to not mention that, you know, but I think it's just good to show that, like you can find success and have success no matter who you are, whether you went to college, didn't go to college, just like graduate high school, didn't graduate or whatever. You know.

So I've I've just felt really drawn to that kind of like underdog, like the person that you just wouldn't expect, you know, to be successful. And so I try to, you know, highlight that. And there's good there too, and there's a lot of things that I am, you know, I am really good at, but showing like a peak behind the curtain to people that it's not I mean, I think any entrepreneur who's listening to this knows it's

not easy. Of course, it's not easy. I feel like I just want to talk about and highlight more of the hard stuff than just the good stuff, you know, because it's it's completely.

I think that's good that you don't know that, you know. I'm a little bit of like the ignorance is bliss mentality because I feel like the less you know about what you're getting yourself into. And I think just that whole mindset of like, if you can accept you don't know what you don't know, you go into things a little like not as freaked down.

or wrong right, it just wasn't for me. And I've always really trusted my gut and my feeling, and I stay very close into what feels right and I and after staying home with my kids, it was about they

were about two and four when I started Drybar. And about a year before we started Drybar, I got that kind of itch to do something, and I started a mobile blowout business, which was again just like a way to get out of the house for a few hours, get away from my kids, who I loved, love, loved the whole thing, but just wanted to do something for myself. And I knew, having done hair for so many years,

that I could do that pretty easily. I also, you know, had this like intuition on that that if I were to only charge forty dollars, which was like, oh, two twenties, super easy, I'll come over while you're baby sleeping.

yesterday because I was like, oh, it's great. I love this, Like I'm getting out into the world. It was a great way for me to meet other women, and I would It also informed a lot of the things that we would eventually instill in Drybar, like not doing someone's hair in front of a mirror, because I was doing their hair in their living room and so it was

just perfect. At the time, I wasn't really making any money, but I didn't I've never been like driven by money, so I was like, I'm just happy to do this. I make a little extra cash, I go and do this thing that I really love doing. I get to talk to these amazing women and it was kind of like wildfire. I you know, women would tell their friends and then their friend group and so it would just grow and grow, which which is eventually why Drybar came

to be. Because I was getting so busy operating this mobile business by myself that I was like, I think I need to start having them come to me instead of me come to them, And that's really how Drybar was born. But I was just this like one woman show driving my Knie Sonic Sierra around LA with like a duffel bag full of tools and hairspray, and you know it's funny because it's like I remember it so while like could have never guessed it would turn into the life that I have now. I mean, not in

a million years. I was just happy to be out of the house for a couple hours.

I don't know what it quite is yet or by the way, I'm doing something on the side and my friends all tell each other that I'm good at it, and yeah, I think I could build something, but I'm not sure. Like, what was it that made you feel this is real and it could be bigger versus actually this is great and it fulfills my needs of getting out the house and giving me a little bit of extra cash. Because you could argue that already felt like success totally and it can be successful a lot of people.

What was it for you that said no, this should be bigger. I can be bigger, and I want it to be bigger. Yeah.

I was saying yes. And I was like, you know, scratching my head, going like I'm getting so many calls, and I was pretty good at what I was doing, and so I was like, there's got to be something else here. And at the time, my kids were really little and my mom, who passed away eight years ago now, but she was We used to move her everywhere. We moved, like in an apartment down the street, and she loved being near my kids, and so that was really helpful,

and she was, you know, in our lives. And I remember being like, I wonder what would happen if we had a location one location, you know, I'm like, my mom could help. I could get my kids after you know, preschool, like around three or four, I think I could still make this work. And again still thinking pretty small, you know that, like let me just go from like the next step from going to people's home to like opening a store.

just loved it, you know. And and when you you know this, when you love your passion and like the thing that you it's and you get to do it every day, you know, it was like I just felt

like this is the coolest thing ever. And I couldn't believe, like, you know, when we first opened Drybar and so many people were coming, and and you know, again it was like it just felt so meant to be because this mobile business that I had built and these women that I had come to know in La, and some of them were like, I mean it's La, you know, it's like producers and actors and celebrities, and like, you know, I was a little thrust into that world, and you know,

beyond like the celebrity just you know, there was just so many women who were really connected. And when I started talking to my clients, which by the way, were the first people I talked to about Driver, I was like, what do you think of this idea? And they're like, oh my god, it's the best idea ever. But how do you make it work? And there was like certainly naysayers, but it was such a cool, exciting opportunity and to have women like being like, you should totally do this.

And then we opened that first store and it was so busy and crazy and I and I just I loved every second of it.

are happy, let's get a store. And I think sometimes we kind of go from well, I have a really good idea, it should be a million dollar business, a billion dollar business, or whatever it may be, and we don't get that next step right. So that's one thing I want to share. The second thing that really stood out in what you said is you asked the people you were serving your clients for what they thought of

the idea. A lot of us ask our friends, we ask our family, we ask people around us who don't actually know how skilled we are at this thing, and we're not asking the people who are actually going to be our potential clients. And so the fact that you were asking them and they were saying, oh, I'd turn up there, Oh I'd recommend all my friends we're in, that's a much better person to talk to when you're

sharing a new idea. What's the difference, Sally, Because you've talked about now and in the book you talk about this idea that you've always been pretty decisive, but more deeply when you go into it, and I know you have a deeper side to you and when you're thinking about things like intention and intuition and instinct, and you said I always knew, like I was always listening for that inner voice. What is the difference between intuition and delusion?

If you had to think about how you notice the difference, what would that be for you?

but not early like in a year in, I was like, I think we're going to sell the business for two hundred and fifty million, and that crazy. I mean, I feel like I manifested that. I think it kind of goes back to what you're saying about baby steps. It's like we're doing ourselves a disservice of you know, moving in this like, you know, in a delusional path, I think I would say you know, versus like saying close in and you know. And I have gotten very into

spirituality in the last few years. And one of my very best friends and I talk about her in the book. Her name is pat Paige, and I always say I'm writing her spiritual cot Tails because she's always in Tellis and some retreat and you know, I'm just kind of like trying.

way I can now. And I think we get older, we're wiser, we go through more things, we read more books, we do all the things. I meditate a lot more now. I do all that stuff now, and I pay really close attention. I don't think I did the way I do now back then, but I think I had it instinctually in me. I just didn't know how to pick up on it, you know. Where it's like now I can.

I can almost like I can read something or have a thought and like immediately get a ping in my body of like no, this doesn't not feel good, or get a like oh yeah, this feels really good and it's fascinating. And the thing is, and I'm sure you have, being who you are, would agree with this. It's like if you get really quiet and you pay attention to that stuff, it's pretty clear.

Why are you're not listening? I heard something Renee Brown said, I'm sure she's been on the show. Oh you have to have her on. She's amazing and she was really there for me in my first divorce, which is crazy, but she I just saw something recently where she was like, every once in a while, the universe taps you or not everyone's while when you get to mid age, the universe like taps you on the shoulder and it's like you can't run anymore. And I was like, is she

talking to me? You know? But it's a fascinating thing because I think at some point in our lives and it seems to me like it's more midlife, you get that tap and you're like, yeah, I gotta be really like I got to pay attention to what's happening, Like you can't get away with it anymore, you know. And I think as we're when we're younger, we can. I don't know why that is, and I think maybe we're just ignoring the red flags and thinking it can just

all work out. And I'm such a like it all works out kind of galt anyways, which I think is true. And now I've come to realize that those mistakes and those red flags and the things that we don't pay attention to when we should actually are really great gifts, not in the moment. In the moment you're like, why is this happening to me? But then afterwards you're like, Oh, I needed to learn this.

more noise, more competition, et cetera. It still always starts with you, your idea, your skill set, your purpose, and your gut instinct. And you say, what is the thing that you just can't stop thinking about? Which which I

love that. I love that language to it but you talk a lot about this finding your skill set as an entrepreneur, and I think there could be nothing more true about than that, Like, I'm so aligned with you, and I think often we're doing things we're passionate about that we're not skilled at, or if we are passionate, we haven't thought that we need to be skilled at it. And obviously you could be doing the opposite, where you do something that you're not passionate about. Sure, and that's

what a job is pretty much. Yeah, but how do people discover what they're skilled out? Because what I've found is that most of us, when we're skilled at something, we devalue it as a skill because it's so easy to us. And we see someone else with another skill. And you talk about this a lot in the book about don't become someone else's story, don't chase another entrepreneur,

don't try and imitate. But we look at someone So for example, people will look at me and be like, oh, Jay, like you're really good at X, y Z. But then if I'm not aware of that skill set, I'll be like no, no, no, but you're really good at ABC. And then we play this kind of tag of like no, I don't have your skills, but we rarely sit and go, no, I'm actually really good at that because we devalue what we find easy.

the experience. And everybody always asks us like, is it really hard to work with your brother and now ex husband and that's not why we got divorced and whatever, But I was like, no, it was great because we were all very clear on what we did and what we did well and what our highest and best use was. I had that conversation so many times. I still go back to that what's my highest and best use always in life because I think it's like really like think about it, you know.

of my or who I became. But they had this like old Lady clothing store and it was right next to this like old Lady hair salon, and they and they think in their mind, they were like, you want to work there? And I was like, no, I'm going to move to New York City. I'm gonna do editorial and like fashion shows. And I had these like grand ideas. I didn't have dry bar at the time, you know,

but it was like that's what I'd loved. Like I grew up in South Florida, I have naturally curly hair, and my hair was just massive and frizzy all the time. And I was just fast by hair. I loved hair. It's just what I loved, you know. And so it took me a lot. It would take me many years to finally like get the courage to say, Like when my friends were going to college and they were studying whatever, and I was always like, how do you guys know what you want to do? Very confused by that whole

notion of college and majors and all that. And I just loved hair and that was the thing that I really loved. And it would, you know, and I talked about it in the book that it took me a while to figure out again. It comes back to like being close in like I always loved hair. I would spend hours in the bathroom in high school and I was just so. I worked at a hair salon as a receptionist when I was in high school because I wanted to get free blowouts and because I loved being around hairstylists.

for me. But I was just like, stay really focused. And I talk about that a lot to entrepreneurs that I'm mentoring. It's like, don't you know, shut all that out, you know, listen to what really feels like is good for you, not what everybody else around you wants.

you know, but I think we can do it. And like, I literally not not great at math, but I was like, I think if we can do like, you know, ten blowouts an hour and we're open, you know, ten hours to day, like I think it'll work, you know. And I remember my brother started like putting an actual spreadsheet together and running the numbers. It was like, yeah, if we do thirty or forty blowouts today, we'll have a

nice business, you know. And of course we never did that little We always did like seventy eighty one hundred blow out, say, which was just bananas. But it was like people were the ones who put it in my

head that like, maybe maybe this idea doesn't work. I mean, so many people and then we started raising money, and you know, that's a whole other conversation of like raising money with like walking into these rooms with men in suits who like did not understand the concept of drybar, and we're like what, you know, like how does this work? And just didn't believe in it. So many people didn't believe in it, and it did seem like a tough

you know, how do you make this work? Like on a large scale, is there enough women who want to do this? Is the price the price points really low? Like margins are really thin? How does it work, and you know, and I just I'm like, I'm just telling you. I really, you know, from a gut level, know that this is going to work. And then you're like, oh shit, this better work, you know. But it did. And I always felt like there was money on the line for sure,

and that's not a small thing. But you know, I remember when I started cutting hair, and I mean when you're starting to cut hair and you have really sharp scissors in your hand, it is very scary and like and you know, it's so funny. It's like the very first hair.

lose money. In my case, it was going to really be my brother's money and my you know, my my husband at the time, and I put in our life savings, which wasn't really that much but a lot to us at the time, and you know, I was like, it's gonna really suck and we're going to lose money, but we're like, we're really smart, capable people, and if this idea doesn't work, like we'll figure something else out. And I think that that mindset of like you got to just like put it on the line is like it

is really why I think I've been successful. It's like not holding anything too tightly of like, yeah, I really hope this works, and I really think this is going to work. But if it doesn't, like we're all going to be okay, you know. And I think that's like, you know, I think a lot a lot of entrepreneurs I talk to are like, I have to have this much money, stave, and I have to do this, and I have to do this, and I have this. I was like, yeah, prepare for sure, but like.

had to figure out a lot of things. And that's that's also the beauty of this book is that I feel like I got an education in this. I got like a you know, a business degree while I was running a business, because I was having to figure all these things out, and I made tons of wrong.

wasn't always right. It was just like me havy. And I used to think that that was like, oh, you're just the boss, and you just you your book stops with you and you have to And now I feel like and how I approach that question now is like, well what do you think? Which is not something I

would have said. And that's like I think that was all ego because I was like, oh, I feel this pressure, like I'm supposed to know the answer because I'm sitting where I'm sitting in this company, and now I'm like, well, what do you think about that? And then people are like what you know? And I'm like, well I don't. I actually don't know the answer, but I'd love to

hear what you think. But I didn't have enough, like you know, I was too focused on like feeling like I had to be And maybe that does go back to imposter syndrome. I felt like I needed to know all the answers because I was the boss and this was my company and blah blah blah. Where now I'm like, there's so much freedom in saying I don't know, you know, like let's.

And that's something that took me a long time to get comfortable with.

what someone else is feeling. And I wanted to ask you what's been the best or most memorable piece of feedback that you gained on your professional journey that's kind of stuck with you where maybe even in the moment it was so painful to hear Yeah, but you now look back and go, I believe that. Well.

talking about? What do you mean people are scared of me?

You could see it all over my face because I was like, why are the floorboards dirty?

tell me the good things. And I did start to perpetuate this reputation of like Alice's come and watch out, and you know, part of me was like, I think, maybe that's a good thing, but then I was like, no, it's not. And I would learn eventually to you know, like I would take notes and I would then like, you know, not like ruin everybody's day when I would come in the store, you know. And I had to

learn that the hard way. But it really did take my brother probably one of the only few people in our company who felt comfortable enough to say to me because he wasn't scared of me.

It's like you don't want to be surrounded by yes people, like please no, tell me, tell me the truth, tell me what people are saying. I want to know what people are thinking if I if I can't ascertain that on my own, you know, so if you have people around you who are willing to give you like the feedback, it's like you're only going to be better for it, you know it. It stings in the moment, and it

still does. Like you know, sometimes someone will tell me something and I'll be like, oh gosh, like I can't believe that. And then if you're open to it, and then you you then now you have the awareness about it, and I'll tell you. I'm like, I don't think you have children, right, you know? For me, I have a sixteen and eighteen year old, two boys, and like talk about honesty. I mean, I'm really really close to my kids.

But they will tell me things like that are very hard here, and it is a real practice, a mental exercise for me to not you know.

in Ohio. He's playing football, and I went out to see him and this, you know, he like came off the field, you know, he was like didn't really want to talk about some of the stuff that we want to talk about. And my younger son said to me, like, just give him a minute, mom, And I was like what he's like, just give him a minute. And I was like, oh right. You know, because as a mom and anybody listening to this, who's a mom, You're like when your kid isn't like perfect and happy, You're like,

what's wrong? What's wrong? What's wrong?

you talking about? You know, and he's like, you know, and I was like, you're right, you know, and I was like okay, and I thanked him, you know, and I backed up and I was like, when he's ready to talk to me about it, he'll talk to me about it, and sure enough, he did a couple hours later talk he opened up and it was like such a great lesson and reminder of like, so you know, you need to give people space and you can't just have what you want when you want it. And that's

been a really hard lesson for me. And I think it's also like being at the helm of a company and having this like mentality of like I can do and say whatever I want because I'm the boss and blah blah blah, you can just do whatever. That bleeds over into your real life, which you know, my kids are kind of a living example of that of like you know. And I used to say things to my kids like I've been around longer than you guys, and I just know. And they're like, you don't always know, mom,

you know. And it's like, you know, so your kids are like talk about mirrors, you know, and they they've all of that awareness. I think has been such a gift to me, and that you can get that anywhere in your life, from your best friend, from your spouse, from someone who works for you or with you. It's like, if you ask genuinely, they're going to tell you. And like, what a gift to like get that awareness, and you know, and it does sting for a second, and then you're like, oh, okay,

I'm going to take that and be better. My best friend tells me stuff too, you know. It's like thank you, you know.

and it's perfect at it because that's its job. Yeah, but it's not protection. It's actually your resilience is getting thinner and thinner and thinner and getting weaker and weak and weaker. I wanted to ask you because you're shifting into that, you know that. I love how honest you were about the kind of feedback you get from kids. I think people often talk about, oh, you know, my kids said I'm not cool anymore, whatever, that kind of

stuff that is insting. But hearing this kind of stuff, do you think it's because you definitely have a take on this in your book, Like do you think it's possible to be really materially successful and have a happy marriage. I got those two things possible.

first place. Like we met when we were twenty six, and I'm pretty sure I put this in the book, that he tried to call the wedding off a month before the wedding and I was like, oh no, we are not doing that, like and he had some real good reasons for that, Like, you know, the relationship was really hot and heavy in the beginning, it had faded quite a bit, like the intimacy wasn't really there, but

we were best friends. And I would later learned that, like my parents had that marriage, which they ended up getting divorced too, And I think I definitely emulated my parents' marriage, which is just wild when you read all that about how we do that, because I didn't see it at all. But you know, we we had kids very quickly, which I really wanted. I was very like, I'm very driven, and I was like, I want children, and so we

had kids a year after we got married. And then you know, like I said, we started the business drive Bar when my kids were three and five. So it was like boom boom boom, and Drive Bar felt like a third baby, and then you know, Cam was doing all the creative and I was doing all the other stuff, and so you know, we're on this path.

you know, the material success. I didn't I didn't want to shatter the whole image, you know, and and obviously, like i've you know, come to realize that like you just you have to and that's the message, ruth of it all. And then it was then I made the really hard decision to end the marriage. And then my son, who's now eighteen and doing really well at Dennison. He went into rehab because he started doing drugs and there's a whole chapter about that, and just my life completely unraveled,

you know. And and to your question, it was like, on this hand, I had all this success and I was like doing all this cool stuff, and like anybody who didn't know me, I was like I was a guest on Shark Tank, like the coolest thing ever.

And then I come out of Grant after about two years, like it really worked, all the treatment we put Grant through, and he really came out on top, and he really did the work, and he's such a I mean, he ended up in a couple of different programs. One of them was an outdoor wilderness program in Utah, which I actually think every human should probably have to go through. We went to visit him once and he was like making fire out of like, you know, two sticks, and

he was like learned how to mean the thing. It was amazing and I was like, this is really profound, and he really came out such a better.

the other side of that is just remarkable. And it brought me and my ex back together as friend and like we learned how to co parent because of all that, and even my younger son really bet I mean, it was all like such an amazing blessing. At the time, I wouldn't have ever i mean asked for that, you know. And so it was like the both and and the

odds and the duality of what I was living. And then I came out of that situation, you know, and rushed back into another relationship that was like now I'm looking for like real love because I didn't feel like I had it the way I wanted it in my

first marriage. And then I jump into that, you know, And at that time we were like, you know, it was right before that I met him, like five months before the pandemic, and I was already kind of like transitioning out of dry Bar in a lot of ways because the company was so big, we had so many people running it now, and what I was doing on a day to day basis wasn't really there anymore. And and now I was like, you know, just looking for love and like and then I found it and I.

It's like what I haven't learned yet, which I'm hoping I get now, is that, you know, I have to keep myself intact, like what do I love and what do I want to be doing?

and I'm so it's such a good question. I love that you asked it because I haven't been able to find it yet and I get it now and now I'm like anxious to like try it out, you know, and be like, can I be in love madly in love, have the right kind of love with a person and myself and what I'm doing. I haven't been able to figure that out yet. And I think, you know, I think a lot of us it falls one of those things inevitably fall by the way. I guess. I don't know.

with me? But it's such, which is why I really love and I hope people who are listening to that like feel that too, because and I was telling you before, like I get a lot of people who now reach out to me and they're like, I'm really unhappy in my marriage.

in together after five months. I don't know that we would have done that had COVID not thrust this like very crazy change into all of our lives. And you know, I think it all happened the way it was supposed to you. But it is a like, yeah, we're always growing and changing and how do you do that together?

you can't make something work. All you can actually do is track whether you're getting closer or moving further apart. That's actually all you can do is track and monitor, because like I said, so much is changing all the time, and so all you can do is track change. You can't force a result or a direction. You can only track change and try and move closer together and move apart.

And it's what you said, like I think, when we think about the word balance, if you think about it, we all have a finite number of hours, we have a finite number of resources, and we have a finite number of amount of energy. So if you had one hundred percent and you said you've got yourself, you've got your partner, you got your work, you've got your kids, and then you've got your family, and you put twenty percent into each of those, Now you're going to get

a twenty percent result on each of those. That's a balance life if we look at it in that way. So if it doesn't work, or it may work for someone, but the idea then being okay, well, now you got like a eighty percent return on your career, which means eighty percent of your energy was going into the work part, which means then five percent was going to all the others.

this month or this year. That naturally means I can't focus on these three areas. And I think people who stay together or adapt or whatever in a healthy way are people who found a way of saying, I understand what you're focusing on, and I get that and I respect it. But guess what, when you're back and you have time, I may be focusing on something else. And so I think anyone who's navigating their relationship in a healthier way, there's no better or worse, but in a

way that we would consider healthier. It's only because two people are communicating, as you said, enough when they're just having conversations. It doesn't mean there's a perfect standard, or there's complete intimacy at all times, or they're having the best you know, sexual relationships at all times while everything else is going on like just mathematically impossible.

knew there were things that weren't right. And I think now, and you know, I work with therapists and coach and I have lots of people, you know, because I love getting is I love getting as much? I mean now, I'm like, I love the feedback. Give me all the feedback, Like I really want to hear as many perspectives as I can and from people that like I really trust

and admire. And you know, one of the things that I was talking to my coach about recently was like, because I've I've been trying to like put a bow on this to like make myself feel better about it not working, and I've come to realize like if well, I'm like, if we had had the conversation that we weren't having, you know, the right I mean, you're shaking your head because you know what I'm gonna say, What if we had talked about the thing, maybe it would

have worked. Maybe it wouldn't have worked, Like obviously nobody nobody knows, you know, And and and he and I had that conversation in the aftermath of all of this, like had we called out, you know, one of the big things that wasn't working for us early on that we both did not want to call out because it would have potentially probably meant that the end of the relationship,

and we didn't want that. You know. We were very like wrapped up in like the excitement and the newness and the lust and the chemistry and the passion and all the things that happened when you're brain. I mean, I'm sure, I'm sure there's some science on like what happens to her, Yeah, but you know, and so we weren't.

We didn't have those conversations. And perhaps had we had it, maybe it would have shifted and we could have figured something out that would have changed the directory of our relationship and it maybe it had worked, and maybe it wouldn't have.

or conscious of? Every quarter I ask is this relationship going in the direction you want? Or is it going in the direction? Ife one? If it isn't, what are we both willing to do to put it in the right direction? Are you willing to do something? And am I? And then every year a simple one of like, well, what's your goal this year? Or what are you pursuing this year? And those four questions or checkings don't save

a relationship. They do what I was saying earlier is they help you track whether you're on the same page or you're completely on another page, and if you're even aware and conscious. And the reason you have to do that is those should be four checkings you do with yourself. Coming back to your point, like checking in with every day and going myself, what's my highlight today? Checking with myself every week or every month and going, hey, what do I need help with this month? Who have I

asked for that. Every quarter is my life going in the direction that I wanted to go in? And every year what am I pursuing? Like If I'm not checking in that with myself and I'm not checking in that with my wife, then how can I know myself? And how can I know this human? And I think the assumption that I know someone like i've you know, me and my wife have only been together for ten years, But it's all I know is that she's constantly evolving,

growing human. Sure, just because she's over thirty doesn't mean that she's fully formed and done. God no, and neither am I. And just like your children are growing up, your son's are changing and growing, I think we assume that kids grow and adults stay the same. Yeah, And it's like, well, wait a minute, that's so untrue.

are always changing and growing. And I love that you said about tracking it and and I think there was a phase in our relationship when we were doing more of like check ins and we probably had listened to something like this and we're like, oh, we should be

checking in more. And then eventually we stopped doing this and you're like, oh man, we lost we lost our way you know, and it's just so easy to do that, and you know it and it really does like straddle defence on business and personal because I did it all the time in the dry bar era when I would like, you know, stop paying attention to what was going on people around me and stopped having you know, those conversations like I really needed to be having, and just like

would get all like sulky, and you know, like why wouldn't Why wasn't I having those conversations? I was, I was causing my own suffering, you know. And it's like we just as humans do that, which I you know,

which I think is like the self awareness piece. It's like the things that we use to nurture ourselves, like what we're listening to, what we're watching, what we're reading, you know, if you kind of sometimes I'm like, especially in the last few months, having gone through going through my divorce and being so sad, and I'm like ingesting so many books and so many things, and I'm like, Okay, I've read enough, I'm done. I'm good. But then I'm like, no,

I'm not. I got to keep I mean, I got to do at least a couple of things a day. That like keep me on that spiritual path, you know, And it's like, what's the word I'm looking for. I don't want to say it's like a job or responsibility habit, you know. Yeah, It's like it's so important. It's so easy to lose track of that, especially when like something you get really excited or you meet somebody new and you're like, which is exactly what I do. I'm like, oh,

I'm so happy now. I'm like, I got it. I don't get I only to do with any of that stuff anymore, Like, you know, yeah, I remember and ruled in.

and so they never will. Or I have a couple of friends that have kind of had the courage to get to the other side, but they now experience the judgment or they feel the shame that comes from other people's projection of it. Yeah, what is the hardest thing about getting divorced? Like, what's the toughest part about it?

and now I'm a single mom. And at the time, my ex didn't really want to be talking to me, and so I was like my world spun out of control and I fell into a bit of a depression. And I remember people telling me that like, even though you're not in love with your ex husband anymore, he still held like a space and energy that is no longer there, and it's like a death And I for months and months and months.

a book called Energy Speaks. Don't if you've ever heard of it, and he was talking about energy and whatever. And after the show, I pulled him aside and I like very quickly told him what was going on. And I was and how like I was, you know, coping with my divorce and I was in this depression. And he was like, listen, your husband, even though you don't love like love him like that and want to be with him, he still held an energy that's gone and that is a very big hole, like black hole for

you to fill in your life. And it's just gonna, you know, take some time, which isn't rocket science. And I'm sure other people said it to me, but at that moment I was like, oh my god, HiT's right. And so that change of life of like your whole life being one way and then it becoming another way. And in my case, like my son going through rehab

and that like very hard time. So it was all rolled into like just being hard and I was really sad and I and I was really struggling and you know, and then the identity stuff started to kind of creep into and so that was that was hard. I think from like more of an identity like a personal identity standpoint was hard. And like a rebuilding my life after so long, this divorce was was quite different. It felt

just much more like heartbreak. Like I was heartbroken, like just heartbroken, and I'd never experienced that kind of heartbreak. I recognize now truly that it's it's for the best, and I think for both of us, for all of us, it's for the best, but it just hurts so bad that like to experience heartbreak like that where you're like, oh, someone just put it really well. That like trauma is the intersection of unexpected and overwhelm And I think that's

such a simple way to understand trauma. It's like this thing you didn't see coming really and then the overwhelm of it, like the boom, you.

And it's the perfect analogy to me, is like I was in so much fog around it and like my ego is all like bent out of shape. And I was, you know, and I was worried, like my kids were going to be mad at me, and I was worried what the world was going to think and all this stuff.

And then I was like, now as the clouds and the fog started to clear, I'm like, oh no, this was not ultimately the right thing, you know, And maybe in some universe like had we have these conversations, we've done this thing, da da, maybe it.

I had. It was a lot of tough lessons I had to learn, and I was looking at myself in this lens that I had not looked at myself through of like why he made that decision and why he didn't want the marriage anymore, which is just I mean, you can imagine, I mean, you put yourself in those

in that for a second. If your wife was like I want to divorce right now, you you would just be like it's devastating if you're you know, in love with somebody, but then when and so I was like trying I've tried to now put myself in the very painful place of like why why didn't he want to be with me? And sure like I not not to go down the rabbit hole of like I'm a terrible

person and I'm not worthy. It's not that. It's more of like, let me see what what the things were that I didn't like about myself that I can now see through his eyes, And this is not a conversation with him. This is a conversation with me and how I perceived a lot of things and the way I acted and the way I showed up a lot that I don't like. You know that I'm like, oh, I don't ever want to show up like that again. And what a gift and what a lesson to like be

this better version of myself now. So to answer your question, those were like the hardest things of it, but it is I'm literally living proof that you can you will get through it. And everybody kept saying that to me, and I would grasp onto that, like when people would say it's you're going to be okay, it's gonna I promise you're going to be okay, and I would like hold on to that, like thank you. I needed other people to say it to me because I couldn't find it in myself.

and go in different directions. And the fact that you had the inner wisdom and the intuition to say, actually, I'm going to turn towards advice and therapy and coaching and insight and learning and reading and hearing this message from a supportive community, Like that's what I want people to take away because I want you to hear that that that's the choice we have to try and make. And something you said, this concept you're talking about, the intersection.

Something sparked for me as you said that, and I was going to complete your sentence, but I didn't want to because you know, I didn't know what you were going to say, and that's why I waited, because I didn't know what you'd read or heard. But I was thinking about it that when I heard the word. When you think about trauma or even like a trigger that eventually leads to trauma, it's actually the intersection between an

unexpected event but a familiar feeling. And so there's what you were talking about earlier as well, like how you repeat your parents' marriage, like the idea that it's an unexpected because you didn't think you would ever do that, but then it's a really familiar feeling and you're like, oh, I feel that, or like I'm going through a divorce.

Someone's asking me for a divorce. It's an unexpected event, but it's a familiar feeling of I don't like myself already, and this is a reminder of something I know deep down, and it's that familiarity with that unexpectedness that completely converges to create such disharmony and misalignment in.

terrible person. No one's ever gonna love me again any any man I'm going to date and be like, oh, you're a marriage twice sorry se yah, you know, which isn't true, you know, but it's it is the things that you know we do, which you know I have spent a lot of time. A lot of the stuff that I read is on like, you know, mindset and the brain and how powerful the brain is and how we can change our thoughts and that stuff's also fascinating to me, you know, like that you can we have control.

I didn't believe that until now, like until very recently. I was like, it is what it is, you know. But now I'm like, oh, we can change our thoughts and we can you know, decide, and it's like there's a to me, there's like a well, you still got to grieve the thing, but I can also because I was like, you know, I was I started listening to Joe Despenza.

it's like, but there's still the grief over there. And I think that's another challenging part of like anything like dying, is that the grief your body physically needs to go through if you change your mindset too fast, and like you know, so it's kind of an interesting I think it's a little of both. I'm really fascinated by the whole thing the brain can do.

no longer existent. And so there's some identity is such a fascinating subject in and of itself, and it's like you weren't complete in the first place either, and so there's just so many layers to it that are so challenging. And all of these things that you're talking about, whether it's your work, your marriage, your kids, they put a

spotlight onto all of this and all the gaps. What would you say was the most important lesson you took away from your first relationship and then your second relationship because you've just you were talking so much about it was all about lessons atill and what would you say was the first one that you took away from the first and then from the second? What have you taken away? What's been the big lesson that stayed with you?

like exactly what I wanted them to be. And again, it's a hard thing to say because it's like nothing's ever exactly what you wanted it to be. With some of the things that were happening with us, I think I actually was pretty open and honest about them. But what we weren't open and honest about was like what I actually needed it to be. And if it wasn't going to be that like, then it probably wasn't going to work. And we both needed to come to terms

with that. So you know, I think the lesson is like really level setting what you need and what that other person needs, not just what you need, Like sometimes you have to be the one that's willing to say like I don't think this is gonna work because blah blah. But like to me, I don't think I've ever been strong enough to be like I'm completely in love with you, but I don't think this relationship is going to work. Like who can do that? That's so hard?

them to be together, you know. And that's how I feel in this second marriage, like I really wanted it to work, and as the viewer watching the movie, you're like, I know, it wasn't right and it wasn't supposed to be and it's like, you know, and that's how I felt like Legends of the Fall, you know, it's like I feel like, oh, yeah, like why we're they together

at the end? You know, you're and you watch that movie and I've watched a couple of times, such a great movie, and you're like, you know, she marries another guy, and you're like, sorry for anybody who hasn't watched a lot of that, it's been a while, yeah, And it's that is really how it's like landed for me in this Like sometimes like what we want to work just doesn't, you know, and you have to just learn to accept it. And I think that's that's been the big lesson for me.

It's like, you know, a lot of people and people close to me know and have said to me in the aftermath of this, like you've you've had things work out for you pretty well most of your life, you know, And I have, and I'm really blessed and lucky in that way. And this has been like one of the first things that like didn't work out the way I wanted to, and I couldn't control it, you know, no

matter what I did, I couldn't change the outcome. And like, oof, that's rough, you know, and I'm sure and I know a lot of people have dealt with that on a much bigger and harder scale than me. And and so that was a real lesson of like surrender of like you just don't get control. You know. I look at my first marriage and think that, like we were married for so long, and for so long I didn't have

that like electric chemistry love that I wanted. But yet I had these two amazing kids, and I built this great business, and so like that was enough for me. You know, in this stage of my life, I feel like I actually want more of it all now, you know where I was always like, well I have this, I don't have that, but I have this. And now I'm like, I want to do something that I really love and feel passionate about for myself and I want to have a great love too, And now I'm trying to find both.

I can't think of anyone who's listening to this that isn't going to feel comforted, supported, held, and feel connected to your journey in some way. I don't think it's mathemat spiritually, emotionally possible for someone to master every area

of their life perfectly at all times. I just want to throw that out there because we still keep putting it up when we say things like power couple, when we say things like oh my god, the perfect match, when we say things like you know, we don't realize how many ideas we've put into the world that oh

my god, did you know they're both billionaires now? And they're both and it's like, you have no idea, just how many ideas you're we plant seeds in people's minds that these headlines exist in reality and if you're someone who knows anyone. You know that the headline is so untrue about everyone. And that doesn't mean people kin't have healthy relationships. It doesn't mean people can't have happy relationships. But do people have perfect relationships?

And I think that that that's what I'm so appreciative of watching and observing you on this journey, is you're so courageously and bravely doing the hard un learning.

It didn't sink into me until I started thinking about the whole movie thing, which is like he was like, you know, if you're in heartbreak or you're in sadness, He's like he equated it to Again, it only connected for me recently, not when he said it, but this like idea of when you watch a movie and you get sad about something, it's like you ow and you tell all your friends about it and you talk about it.

It's like you almost like the sadness and the emotion that it brings in, but it's just like when it happens to you, you don't like it quite as much. But if you can put yourself in that, like it's just your movie, you know, and you're just watching it and you're not going to feel sad forever, you know, it's such a good perspective of it. And it's funny how it's like come full circle for me of like, oh, this is my sad movie and it's sad and then it's but it's also okay, you know.

I'm like, you just just just go and even if it's not a good one, just go and like learn from it, you know, go on that date.

figure it out. Like I I love using you know, Steve Jobs obviously a brilliant, brilliant man. It's like nobody knew that we didn't know we needed iPhones and maybe we don't need iPhones, but like we sure love them, but but we didn't know we needed them, No, I know what you say. Yeah, Like even the I feel like I saw a preview of the new movie coming out about the founders of Blackberries.

the company was like, only is gonna happen. And obviously we know what happened, and BlackBerry went away, which, by the way, my brother like had the last BlackBerry standing as he loved the little button. A lot of people did, and the BlackBerry was like revolutionary. They were amazing. They were the first thing, you know. But this this the story, as I believe it's set up in the preview, is like that company could have taken the similar paths as

iPhone did, but they didn't. And again I'm loosely remembering the story, but I just think it's really fascinating that you got something. You got to just like try something and see if it's going to work, and see, I people are gonna want it. And I'm I've always been a massive fan of Steve Jobs, and I'm like so many others and the iPhone, and you know, it's like it's just so cool like this, you know, he.

the time. I before I get on my phone and check all my stuff and do all the things like I like keep my phone on sleep mode and get into a meditation while like I'm still in bed, and I think that like quiet time in the morning, and then I'll usually like write for a little while, not even like a page, you know, just something to get

like like the cobwebs out almost, you know. And I think it's I think it's just important as a human, but you know, as a as an entrepreneur, just like you know, like level set yourself and I and I really try to do it before I go to bed at night too.

of those things. And I'm like, I'm so glad. I almost never turned my TV out of my bedroom anymore. And I know that probably a lot of people don't believe even in that. And I'm actually about to move and I'm like, don't want to put a TV in my bedroom because I feel like I almost never watched TV in my room anymore, because by the time I get in bed, I usually want to read, I want to do my meditation, I want to write, and by

the time I do all that, I'm so tired. And I also, I don't know, I pick up so much random information. But I heard somewhere somebody said it. Maybe it was you, who knows because I watched much of your stuff, but like, by ten thirty, you should be off screens.

so much better. I mean, I was also on a mission to like I got to feel better here, like I got to get out of this depression and the sadness, so I better do everything I can do. And now I'm like, oh, I'm not really that sad anymore. I'm not sad anymore. But I think I should still keep doing these things, you know, and so that I think is important to have that kind of practice.

that that's okay and good. And then there's some things I'm just donating my time, but it's all in like in the name of service. It's beautiful for sure, right now?

coming on the show today. This is amazing, genuinely being so open and honest and courageous in your own life and here and I look forward to continuing our new relationship. Yeah, very grateful for it. Thank you so much, Thank you so much for having me. If you love this episode, you will also love my interview with Charles Douhig on how to hack your brain, change any habit effortlessly, and

the secret to making better decisions. Look, am I hesitating on this because I'm scared of making the choice because I'm scared of doing the work, Or am