Bobbi Brown (3:25)

Hi. So, so nice to meet you and thanks for having me on.

Emily Hickey (3:29)

Oh, it's so great to meet you. I've been looking super, super forward to this and I want to say so first of all, Bobby, congrats. You've built two really successful businesses. The first, of course, being Bobbi Brown, which you sold to Estee Lauder and single handedly created the no makeup makeup movement. And all of us women, I think are very indebted. So thank you. And now you're building Jones Road, of course, which is also just off to an incredible start. And then you, you're late. You've written a lot of books, but this is a really special one because it's your personal memoir and it's. I burned through it and I have a million notes and underlying things. It really meant a lot to me, actually. And so I'm so excited to talk to you about exploring the pursuit of your fullest self and of your most productive and meaningful life. To me is what your book was all about was kind of personal. Why and finding and accepting yourself so truly. Welcome. I can't wait to talk to you about all this. Okay, so the first thing I wanted to ask you, like I've been like sort of obsessing over this lately, is just the concept of contentment. And when I got to the end of your book, it made me feel the same way as when I got to the end of that Ralph Lauren documentary where he says, as you get older, you don't need all the things you thought you needed. Sometimes you have to fulfill your dreams to know what your real dream is all about. And it's about family and children and peace. And I was wondering, you know, I felt like when I got to the end of your book, I was like, she's done it. She's actually content. And so I'd love to hear your thoughts on that, if that is where you've reached and kind of your kind of Ralph Lauren conclusion about all this.

Bobbi Brown (5:04)

No, I'm not there yet. I am not there yet. Should I be? Yes. Do I. Do I constantly question myself. Like, you know, I'm. I'm right now in Florida, one of our, you know, one of our homes. I'm. This is my second podcast of the day. I've got meetings all afternoon. I couldn't be happier. I couldn't be happier. But then I'm like, why is my husband and my son playing golf for five hours and having lunch with their friends? And I'm so happy that I'm doing all these work things, but I'm like, what is wrong with me? I mean, I should be walking at the beach. I should be out, you know, by myself, sitting there reading a book. I am not that person. And so I struggle with what I think I should be and what I actually am. Right. I'm not someone that plays cards or, you know, gardens. I just. I'm curious and I like action. So Am I happy? 100%. Am I content? Yeah. But do I have that itch and that angst that I want to do more or want to do other things? 100%.

Emily Hickey (6:06)

Just so interesting. It really is. Like, I. I've been. This is really. I've been thinking about this really acutely lately, actually. Like, is there some second life that you're supposed to live? And if you put a shot clock on your life, what would you regret not having cut over to doing, you know, But. And I keep thinking, I don't know, like, I'm a real worker, too. This is what you want to be. You could do anything.

Bobbi Brown (6:29)

I could do anything, and this is what I want to do. And the only good thing I'm going to tell you about getting older and being able to look back, especially when you write a book, because it's very cathartic. You realize, okay, I still have the same angst and struggles, but I'm okay with that. It's like I'm less upset that I have those angst and struggles. And now I have two grandkids. And I find myself when Lily, my oldest one, who's three, leaves my house. And, you know, she's my first girl, so she's got a whole kitchen, wooden kitchen. It's so beautiful. I find myself sitting there for 40 minutes organizing all her food and all her things the same way I did with her father. Who's Cody? And I'm like, but you know what? It makes me feel good when it's organized so I don't make myself crazy anymore. Right? Like, do you get it? Like, okay, it's fine.

Emily Hickey (7:24)

Yeah. No, but I. I mean, it's interesting because you. Something very unique happened to you as a woman, which is that you presumably hit your financial goals in your 30s, you know, and your life changed very drastically in your 30s when you sold your company. And I feel like so many of us have this terrible trick. We plan ourselves of this receding horizon of milestones and that we'll let ourselves actually live in a present version of our lives once we make X amount of money or lose X amount of weight or whatever the milestone is. And you actually hit that milestone in your 30s, you know, I just like, what did you see that as a positive or negative?

Bobbi Brown (8:02)

I didn't have a milestone to hit because I never thought about it that way. You know, I just. I'm the most naive person you've ever met. So I just kept working and doing things and, you know, met someone that I knew I wanted to marry. I knew I didn't want to live in the city, I wanted to live in the suburbs. You know, I wanted to have this normal life in addition to being the fabulous Bobby in New York and doing all those, you know, high heel moments that, you know, were not always my favorite, but they were fun. I never thought, wow, I've got to make certain kind of money. Like, I, you know, I thought when I was young, if I only could make $100,000 a year, I would be fine. And I'm like, all right, well, you know, I did that. So, you know, now. Now it's like, what am I in pursuit of? You know, I'm in pursuit of, you know, scratching the itch. I'm in pursuit of the unknown. I'm in. I'm in pursuit of learning more.

Emily Hickey (9:03)

Do you think that's the point, the point of life?

Bobbi Brown (9:06)

For me it is. You know, for me it is. I have people that say to me all the time, why are you doing this? You don't have to do this. I'm like, no, I don't have to, but I want to. You know, why did you say yes to this thing that you're going to. You're not getting paid. I said, because it sounds really interesting. And, you know, what's the worst that happens? It's not, you know, I'm like, no big deal.

Emily Hickey (9:28)

Yep, yep. One of the things I wanted to try to do with you, even though I think I have a good sense of it from your book. But I do these brand exercises of trying to figure out the why of a brand and how that would map out to product strategy and everything else. And I think you can put it on a person too, you know, you know your why, you know, it's clear you operate with a high degree of self awareness. But I wanted to try asking you a series of questions to try to ladder out to that, to a guess on you. But I mean, the first one I think is, is just your parents and your childhood. And when I read about your mom, my heart really sank because it seemed like you went from having this great relationship to all of a sudden she was deeply mentally ill and you really like kind of lost her, you know. And so I was curious, like your childhood and your parents, how do you think that that shaped this itch or whatever you're after here?

Bobbi Brown (10:18)

Well, I'm really lucky because my mom really was amazing until, you know, college. So I, you know, the most important years, I was the oldest kid, I got this incredibly, you know, present mom who just thought I was the greatest thing and said you could do anything. And you know, she was the most like, encouraging person. When she had her first nervous breakdown, she recovered and then she didn't, you know, it didn't kind of become like she didn't really recover. After I was in college, like, you know, I got married, she was there, she wasn't the same person. She, you know, I had kids, she kind of was there, but not really. So I didn't have her. But you know, I was really lucky because I had my mother in law. So, you know, I didn't feel bad that I don't have something. I felt really grateful that I had her. And my father at the time kind of became. My parents were divorced by then. He kind of took the role of my mom. Like he would come once a month and we would have the best time and he'd be the most involved grandpa. And so I, you know, I got to fill that hole of not having my mom there. And I think I've always been that person, you know, that I've, I understand. Like, okay, so I didn't get that, but I have this. So, you know, I mean, look, I wasn't a smart kid. I felt really insecure that I was not, you know, as smart as anyone. And then I discovered how frigging smart I am in a different way when I was older. So I got to kind of fill, you know, fill that up.

Emily Hickey (11:56)

That's interesting. So. Because I guess I thought it happened when you were younger. And then you also talk a lot about your mom being pretty hard on you.

Bobbi Brown (12:05)

Yeah, she was. I mean, you know, look, I still have self esteem things. And it's ironic because what I do in life is I help women with confidence, being comfortable in their skin. And a lot of that comes from my childhood where I was never quite pretty enough, at least in my mind, for my parents. And I never dressed the right way. And I, I've always been a little bit of a. Of a dork, you know, even when I get all dressed up, I just, you know, I'm most comfortable in my bathrobe, by the way, and my tights. Like, you know, I, you know, and look, and what I do, I'm in the public eye, so I always have to put on whatever the right face is, you know, And I've learned that I can only do what I'm comfortable being. So I am my most comfortable, you know, when I'm wearing jeans, when I'm wearing plain navy pants, when I'm, you know, I just, I. When I get invited to these parties in the Hamptons and I know everyone's wearing flower dresses and they're going to be twirling around, I'm like, oh my God, like, do I really want to go? And that's when I just find white jeans and a white shirt and I tie it, you know, And I've met other women that kind of dress like me and I'm like, shoo. You know, So I don't feel that out of place now.

Emily Hickey (13:20)

That was one of my favorite parts of your book. I mean, it seems like a big part of your journey was these little rebellions of self, you know, self defense and self esteem, where you just were gonna kind of zag against what you were supposed to be doing and do what you wanted to do, only because.

Bobbi Brown (13:36)

It wasn't working the other way. Like, I didn't like to feel bad, right? I felt bad because other, you know, I couldn't do a cartwheel. Like, I felt bad. And then I'm like, I'll be fine without doing a cartwheel, okay? I mean, I'm not a cheerleader. And then when I would, you know, what, what do I do? I go to New York City and I jump into this, you know, high end fashion industry where, you know, Linda, Cindy, Naomi, Christy. And I remember one day there was a fashion show and I was probably eight months pregnant and I was 30 years old and I felt so, you know, much older than these 21 year old, you know, glamazons. And I remember looking up at them right before the show started and said to myself, all right, don't go there, don't compare yourself to them because you're going to lose first of all. And you're, you know, it's okay. You're five foot and married and pregnant and 30, right? You, I can't be that anyway, so I'm not going to waste my, my energy on, on, you know, feeling insecure because they look like that.

Emily Hickey (14:39)

Yeah, self esteem is a hard one. But your mom and dad, you know, you can always mirror image the parents fears with the adults complexes, you know, so I just. Am your mom being critical? You know, your dad, were there aspects of his life that were unlived that, I mean, what, what do you think you, you carried as complexes from how you were raised?

Bobbi Brown (15:02)

I mean, really it was just about my looks, you know, and my parents stopped punishing me for getting D's in, you know, subjects I didn't care about because they had punished me a couple times and I, you know, I got a D in spelling. They punished me. I couldn't go take cooking classes with my friends. Well, you know, I apologize to my husband. I still can't cook. You know, I didn't take the class. And then I somehow managed to get a B plus the next semester. So, you know, I'm like, all right, well, I just got to put a little more energy into it. And so I never got good grades in algebra or, you know, biology or chemistry, but who cares, right? In retrospect, so what, you know, but I felt bad because I didn't understand concepts. And to this day, I mean, like if, if someone hands me, you know, an instruction guide how to do something, I can't do it. I can only do it like when someone shows me because I'm a visual learner. And it took me a while to kind of, you know, know that.

Emily Hickey (16:02)

Yeah, it's so great to get out of school and realize what. Yeah, yeah. Who you actually are. So there was nothing. I mean, as a parent, do you think that you tried to break the chain of that criticism from your mom or how did you translate that to being a parent?

Bobbi Brown (16:22)

You know, I 100%, I was always very aware. And the good news about becoming a parent and having, you know, my husband and I have always been incredibly aligned and tight and he's got the most wonderful family that I got to almost recreate the family dynamic that I wanted. So I'VE been very lucky with that. And, you know, God was great to me. I have three boys and no girls, because, honestly, I don't know if I would have been a good girl. Mom. Because my mom didn't mean to make me feel bad. You know, both my parents were chubby kids, and so when they lost their weight, they realized they were very attractive. And, you know, here they raised. I mean, I wasn't fat, but I was chubby. So here they were, like, you know, probably looking at their selves, you know, in me. So they tried to help me. I mean, they really wanted me to be better. And when I finally kind of broke out of the ugly duckling thing, you know, my dad, you know, he didn't mean it, but he said, wow, I'm so proud to say you're my daughter. For a few years, I'm not sure I. You know, I don't remember. I'm not sure I would have been so proud to introduce. He said something like that. And I remember being like, what the. Who says that? Like, you know, it didn't really trigger me, but, you know, my mother told me I was really pretty, but I'd be gorgeous if I had my nose fixed. And I remember the same reaction. I'm like, who says things like that, Right? And it didn't. Like, honestly, it could have made me in a. You know, but I just didn't let it. And I think that's the one of the things I'm most proud of in my book, that all the things that I kind of was up against, both that part of my life and also working in a corporation with a bunch of men that thought they were smarter than me. I'm like, who says these things? Who. You know? And I just realized I don't need to waste my time and energy and angst on people that are putting such negativity out there.

Emily Hickey (18:21)

But you just naturally were able to do that, or you worked on that?

Bobbi Brown (18:25)

No, I think I was just naturally. I never worked on it. I guess I just realized this is stupid. I've always been someone. Like, my mother used to insist that my room was clean every Monday morning. And she would fight with my brother, like, bloody murder, and he'd be punished. And I just realized it is so much easier to keep the room clean. And she would leave me alone. Like, to me, it's common sense. I mean, why would I, you know, and even, you know, working with corporate, yes, I. I took a lot of those skills. And working with my son now, you know, and. And being happily married 37 years. I use a lot of those things. It's like it's not worth my time and energy, you know, to fight about certain things even if I know I'm right.

Emily Hickey (19:12)

So. See, it's so interesting. You're just a very high functioning person. Like. But you say in the book, I thought you said in the book that you'd worked on a lot in therapy.

Bobbi Brown (19:22)

No, I've. My, I was in therapy when I was a kid. My mother put all of us kids in therapy so I never did it as a, you know, a grown up. When I first met my husband, he was into alternative therapy. So we saw these two people and I just remember like you know, hitting pillows and I just remember it was like very odd. But you know, I was with my, a new, a new guy. So we did that a couple sessions and I'm like, I don't need to hit this friggin pillow, you know, to get whatever happened to me when I was a kid. So I'm more into working with life coaches because life coaches kind of help you deal with, you know, some of the things that I'm struggling with, with like action plans. Like I am someone, if I have an action plan, I'm fine, I can move forward. If I, if I'm like stuck in the weeds or, you know, whatever, I don't do really well, you know, I need to go forward. I am high functioning. That is correct.

Emily Hickey (20:17)

It's so interesting because you haven't really, it sounds like you don't really have any glass ceilings that you've set for yourself in terms of bad self narrative. And once you got through the appearance stuff, that was kind of the. Your gotcha. Yeah.

Bobbi Brown (20:30)

And it's, I mean, it's still something I deal with every day. I'm, you know, I'm not gonna lie, it doesn't get easier as you get older because I can't just throw on my little skirt anymore. Am I sleeveless? Because you get to be a certain age and I'm like, I don't want to be, I don't want my arms photograph there's nothing wrong with my thin arms, but I just don't like, you know, I'm such a visual person. I'm like, no, no, no, no, not happening. So I, you know, I've never seen a glass ceiling. I just don't get it, you know, I mean, yes, I don't have an mba, you know, I don't have the intellect that other people have, but it doesn't have anything to do with Me being successful, you know, I'm completely like, ADD and a little ocd. Those are just my gifts. Instead of seeing them, that they're a curse, you know, I'm like, I'm so curious. I'm so open. Everyone's like, well, now what are you going to do? I'm like, I don't know, but I know I'm going to be doing it, you know, And I think that's kind of interesting and cool.

Emily Hickey (21:31)

I agree.

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Emily Hickey (22:51)

So I asked Cody, your middle son, a few things, and among them, I said, what do you think motivates your mom? And that's basically what you just. He said, you know, I think she has a chip on her shoulder from her mom being hard on her, but that she. It's. It's. It's a. It's not a curse for her. It's a blessing because it motivates her. And that's really clear from everything you're saying, that you're just. When you have a. An obstacle, that's a blessing for you.

Bobbi Brown (23:17)

I love obstacles, and I love when people call me, you know, with problems, because it's such common sense. Like, I use my Chicago common sense in my business life, in my personal life, you know, with my friends. And I think that has been my superpower. Like, I'm really into. People have superpowers, what they have, and once you realize what yours are and the things that you don't feel, you have superpowers, you got to. I always bring people around me that have those superpowers that makes me a better person. I'm not. I don't feel less of a person because I have someone that's more capable than me.

Emily Hickey (23:53)

So what, what do you think you're trying to resolve outside of the ongoing, you know, self esteem and appearance? But what about things like vulnerability and letting go of control and being unstructured in ways? I mean, is that hard for you?

Bobbi Brown (24:11)

Well, let's see. One at a time. I don't like structure, but I like process. And I come from a lot of structure and a lot of process. And Jones Road, the startup, doesn't have as much process as I think we should, you know, and doesn't have the structure, which I think we maybe could use a little bit of. But, you know, we're working, we're working on that. You know, it's been such meteoric growth for five years that now is the time. Like, okay, hold on. How do we kind of recalibrate to make sure the team is, you know, really has what they need and has and it's the right team. So that's what we're kind of in right now. So, you know, I like organization. I just, I have mastered it because now I hire organizers to come in and help me because, you know, by the end of a, you know, a summer at the beach or the end of, you know, my season in Florida, my OCD is out the window, my ADD has taken over. So I need someone to kind of. There's nothing that makes me feel better than to open a drawer or a cabinet or a garage when someone else visually organized it. So, you know, so that was one point. And what was the other vulnerable thing you asked?

Emily Hickey (25:31)

Well, vulnerability. So I looked at your, your birth chart for two seconds before we jumped on the screen. And I don't even know if I believe in astrology, but there are a couple things I think are always really metaphorically interesting in someone's chart. One is where is Saturn? Because that's where, where the fears and insecurities are. And then the other one is this north, south axis. That's sort of the hero's journey of someone's life and goes from structure and control and personal success. It goes to things that aren't as defined and controlled and that it would say that your growth would be to let go. So I'm just curious if.

Bobbi Brown (26:03)

Yeah. So you know when you're a freelance artist and you're so angst that no one's calling you, you know, you're busy, busy, busy, and all of a sudden like the phone stops ringing, you're like, oh, how Am I going to pay my bills? It's over. I learned to let go because as soon it seemed like as soon as I was able to let go, the phone started ringing again. It was just one of those weird things. And then I'm like, busy again. And I'm like, darn, I could have been doing all these fun things. And I was so busy worrying so that I've been able to let go when it comes to working with my team. I let go when I have confidence that the person could make the right decisions if I'm not around. But as a manager, I like to be involved in the decision making of what we're doing, and then I like to know how we're doing. And, you know, and look, I'm happy for people to do things without me. As long as they don't mind. If they do something I don't like, I can call them and tell them.

Emily Hickey (27:07)

You were born to be in charge.

Bobbi Brown (27:09)

Yes, but I'm also born to have other people doing things because, you know, like, it took us 15 minutes to get on this podcast. I only use my iPad. I couldn't figure out my son's, you know, my youngest son's computer. It's brand new. He already warned me to get. Don't get fingerprints anywhere, you know, so I'm like, all right, so I don't know how to use a computer, but I figured out the answer. I have my two amazing assistants, and they FaceTime me. So we figure it out, and I don't. I don't get stressed or panic because I know we'll figure it out. So, you know, yeah, I like to be in charge, but I like to let go because I have. I want to have confidence that it's all going to work out fine.

Emily Hickey (27:51)

Yeah, letting go is a real trick.

Bobbi Brown (27:53)

Yeah.

Emily Hickey (27:53)

Yeah. So you've kind of. I mean, a big theme of your life has been helping women. And I'm curious with your experiences with women, you know, what advice would you give women trying to build meaning into the second half of their lives if they don't work for one thing or if they work. Like, what if your life hadn't been successful? You know, like, what if you had tried to build Bobby Brown and it didn't work and you had to. You wasted 10 years on it and you didn't get anywhere financially and you had to start over and rethink? You know, do you think you could have reached this level of happiness and resolve? Or what advice would you give women who haven't had your path?

Bobbi Brown (28:36)

Well, you pat yourself on the back because you at least did it right. I think, I think it's really sad when people always wanted to do something and they never did. So I think a lot of it has to be like, okay, that didn't work. You know, I wasted all this time and then you got to talk to yourself and say, no, I didn't waste it. I put my best effort in. Not everything is perfect. You know, I enjoyed this, I learned this. And so, you know, that's fine. But I think what happens, it's in people's lives when their kids go to go to college and all of a sudden they're home by themselves or they get divorced, you know, which happens a lot. Like, whatever it is, then it's like, okay, this all sucks, but like, let's stop for a second. What makes you happy? Right? Like, what makes you happy? And look, I have friends that are so happy. They play pickleball, they play tennis, they've started doing whatever, they play kaluki. And I don't even know what these people play card games, but they're really happy and they love this. And they go to plays with their girlfriends and some of them never worked and others used to work. And that's okay because you find what makes you happy. I don't have any hobbies and I was feeling bad about it until I realized if I'm not actually working, I'm either thinking about work or I'm exercising. I love exercising. I love, you know, I love meeting up with people, especially people that, you know, I, I, they're not necessarily my, my day to day friends, but they have businesses and you know, their founders. I love, you know, catching up and getting like, you know, it's like fuel, hearing what they're, what they're doing. And you know, I love, I love those things, you know, and so I stopped feeling bad that I don't have a hobby.

Emily Hickey (30:29)

Well, I, I know. I, I really noted that reading your book because I'm a big hobbyist and that's a really interesting thing to me that, like, And I'll get to that when I'm going to try to interpret your personal. Why? Because I think that's actually a meaningful thing. But I, I do think, you know, like, can there be meaning in something without success attached to it? You know, whether you're trying to be an artist and. Yeah, yeah.

Bobbi Brown (30:52)

I mean, look, I, I don't paint. I can't draw, you know, a picture of a bird, but I have this desire to go into a, an empty Room with canvases and these bright neon colors and some whites and blacks and paint. Not for any reason. I just have this urge. I haven't done it yet. I want to learn graphic design. That's something that, you know, I always have to ask people to do things, so I've figured out ways how to show them what I want to do by, you know, taping things together and doing screenshots. I want to learn that. So those are things that, you know, would be my hobbies. Like, if I could ever, you know, find a graphic design tutor, you know, to come to my house. I love to dance, you know, so I was doing a lot of hip hop, and I haven't really been doing that, and I need to find another hip hop instructor because it just makes me happy. So those are. Those are things. I mean, they're not work, you know, I mean, graphic design would help my work, but, you know, that's not why I want to do it.

Emily Hickey (31:57)

No, that's. So. Yeah, that's. That's a perfect example. But no, I think I keep. I'm on this whole David McCullough deep dive right now, and he's like. He was such a happy camper, you know, in the way that he wrote about American history and people, you know, had, like, really had kind of a twinkle in his eye. Really. Like, it's been a lot of fun to kind of deep dive on him. But I keep looking at this picture of him writing in this little, you know, the tiniest little shingled box in the back of his house in Martha's Vineyard on a typewriter. That's how he wrote all those books on a typewriter.

Bobbi Brown (32:29)

Wow.

Emily Hickey (32:29)

Past the advent of computers, but he just liked a typewriter. But. And I get really jealous, actually, when I see that picture. I think that it really pulls on me of, like, this whole contemplative life that I could have lived, you know, and here I am working five zillion hours a week and running around, and that's the thing I would do if I were. If I had a minute left to live, you know.

Bobbi Brown (32:50)

Yeah. But you know what? Like, you need to put yourself on a budget, meaning you have your time. How you choose the time. There's always, like, area. So you need. If there's something that you're not able to do, just look at your schedule and just start booking out some personal time. And maybe it's just sitting in your box in back of your house thinking about what you can do that you're not leaving and getting on a subway and going to an office. And even if you were, you could probably carve out some personal time. So I think anything is possible. I.

Emily Hickey (33:34)

That is such good advice. And I've never thought about in terms of a budget, but that is. My goal for 2026 is to create a budget against my time and insist on the things that I want to.

Bobbi Brown (33:44)

Get done right and schedule it right. I mean, because you schedule your meetings.

Emily Hickey (33:49)

That stuff is really important, like the, the. It's like the archaic sides of our minds, you know, that need to be fed and isn't work and work and work and work. It's other stuff. So.

Bobbi Brown (34:00)

And you're so young, really, you're so young that you have your whole, like, life ahead of you. You could. There's nothing you can't do.

Emily Hickey (34:10)

I know. Well, I mean, I'm almost 52 and I, I don't feel young.

Bobbi Brown (34:15)

Okay. I'm 68. Does that make you feel better? I am 68. I mean, you know, and I started Jones Road at 62, you know, so it's like, you know, 63. I guess I'm not good at math. It's been five years.

Emily Hickey (34:31)

Well, no, I think it's important to keep that in mind, you know.

Bobbi Brown (34:34)

Yeah. And I'm young. I am. I mean, you know, if I ever think, oh, my God, I'm so old, I'm like, stop. I am. I'm the youngest I'm going to be. And I still have it in me to do all these things. I'm going to act young and I'm going to make sure I walk young and I, you know, I talk young and I listen young, you know, and that's, that's a lot of work, by the way, keeping yourself, you know, with strength and conditioning and, you know, eating the right foods and, you know, whatever, you know, I'm like all obsessed with Peptides. I haven't. That's my new thing I'm going to do some research on.

Emily Hickey (35:08)

So first of all, I wanted to ask you, like, why do you think women are. Why is appearance so important to women?

Bobbi Brown (35:16)

Okay. I mean, that's like, you know, the hardest question. Because it just is. I mean, you know, it's always been about how you look no matter what. You know, it. It's also, you know, a little important to men. It is, you know, they lose their hair, they're short. Like, you know, that, that is insecurity for them. But, you know, for women, there's, there's. Forget about even, you know, before the. We had social media and saw it, you know, you see the actresses, you see, you know, your friends in high school and you know, it just looks a little nicer. Right. It just looks like they're having more fun and you know, and there's, there's like, society's like treatment of how they treat beautiful people. I, you know, I, I know this for a fact. Being in the fashion industry, you know, I, I get it. So, you know, the, it's not going away, you know, was, it was here when Jackie Kennedy was there. You know, it's just how you deal with it that really matters.

Emily Hickey (36:21)

Yeah, I mean, I, because I feel like with your work, you know, you, you're kind of giving it to women as a lever for self esteem or to getting into some more forward approach to their life, you know. It is a lever.

Bobbi Brown (36:35)

Yeah. And I'm lucky because I have the real women that I'm working with and helping. I also have the history and a lot of, you know, models and celebrities that, you know, they struggle with it too. Right, they struggle with it too. Especially when they get to a certain age and not comfortable with their aging process because of society's, you know, pressures.

Emily Hickey (36:59)

It's such a shame. I know. And I, I do feel that a big theme of your book and your life, you know, have been getting past conditional love, you know, and I think that's a real, that's such a gotcha in life, you know, is conditionalizing your own self esteem.

Bobbi Brown (37:17)

Yeah.

Emily Hickey (37:25)

So the empty nesting, if we get back to that, like how, how filled with dread should I be that in a year and a half my son is going to college and my daughter will be behind that, you know, soon. Behind that.

Bobbi Brown (37:38)

Yeah. Well, it's actually, I wouldn't think of it as dread because there's such, you know, it's an amazing, it's a sad and amazing thing to set your kids out into the world because, you know, you've, I've done too good of a job as a mother. Even if they, you know, say I haven't, I've done a great job teaching them about, you know, independence and how not to over drink and all the things, you know, call me when, text me when you land. Don't do stupid things. I, I really, I've spent my life on that and you know, and it's, and it's natural and they, and they come back, by the way, because they're not just self sufficient as soon as they graduate. And you're going to have all this precious time with your daughter as an only kid, which is great. And by the way, then when she goes to school and they're both out of a house, it's really scary, but it's really fun if you make it right. It's like all of a sudden, you don't have to come home and do this. You can do whatever you want. Like, I love spending time with my husband, you know? What do you want to do for dinner? I don't know. What do you want to do? I don't know. All right, let's go out. Or I'll go to the store, I'll pick up a piece of fish. It's not like a chore anymore, so there's nice things. And by the way, all we do when we're out to dinner, you talk to the kids. What's Dylan up to? What's Cody up to? What's Duke doing? That's all we do is talk about the kids now.

Emily Hickey (39:01)

It's been that way since they were babies. You get date night, and that's all you do, right? Yeah.

Bobbi Brown (39:06)

And you're going to have grandkids one day. I mean, look, you're way, you know, down the road, and there's a whole nother set of joy that comes that you didn't even expect.

Emily Hickey (39:14)

I do look forward to that. I mean, you. But you became an empty nester when you sold your company or when you left Bobby Brown.

Bobbi Brown (39:21)

Right. It was really, really tough time. We always had foreign exchange students. So I had, you know, not just my kids. I had other kids, people's kids. I had my nephews in the house. I just was always like, you know, I was the home that had everyone. I fed them all, you know, I just. They, you know, we had sleepovers, whatever. And then all of a sudden, you know, I leave. Bobbi Brown Cosmetics. Duke's in high school. And Telluride. Cody's in college. Dylan's in college. Foreign exchange. Exchange. Exchange students leave. Nephews, you know, already have jobs. And it's me and my husband. It was a, you know, a quiet, weird silence in the house, you know, that, you know, if I was on your podcast, then it would be probably harder not to cry.

Emily Hickey (40:08)

Oh, that's interesting. I mean, have you ever been at a point of just total misery?

Bobbi Brown (40:14)

Not for long. You know, I get sad. I get, you know, I don't have. I don't have a depressed gene. You know, I. And if. And if things are like, if my husband and I are fighting, I don't like it. I don't like, you know, the silence coming out of Him. So I end up, you know, either saying truths or apologizing in a way like, I don't mean. You know, I didn't mean to upset you, because I just don't like it. And also, like, I'm sorry. Our life is so active. We need to communicate. So whenever I feel blue or sad, I try to figure out what to do about it. And often it means I'm dehydrated, I'm not drinking enough water, I haven't exercised, you know, So I use my lifestyle to kind of help my mental state.

Emily Hickey (41:05)

I am the exact. We really have this in common. I'm the exact same way. It's a real gift. You know, I think a lot of women are this way where, like, you'll spend about a day, you know, nursing some horrible feeling, then you kind of wake up with a pencil in your hand and.

Bobbi Brown (41:19)

And just say, I'm enough. Yeah. Now what?

Emily Hickey (41:21)

Yeah. And your marriage is awesome, Bobby. It's really like, that's a real accomplishment in life, you know, the marriage you guys have had. It's awesome.

Dermalogica Advertiser (41:31)

Yeah.

Bobbi Brown (41:31)

And by the way, I'm not gonna lie, it's not easy. You know, I don't just piss off my kids. I piss off my husband, too. So, you know, I try really hard not to. I don't mean to, but I do. So, you know, I've learned ways to do it less. And it just has and has worked for me. You know, I feel incredibly lucky that I met Steven, because from the pit of my stomach, the bottom of my heart, I just. I still love him. Like, I feel butterflies when I think about even meeting him, and so that we're really connected, and I'm lucky. That doesn't always happen.

Emily Hickey (42:09)

No, it doesn't. I mean, I remember reading in a book one time how the. It was a Ryan Holiday book talking about. He was saying he realized at one point that everybody he admired had found some way to spend their life with the same person. And it. It. You know, that really resonated with me because I. I've tried to do that too, you know. Yeah. That's one thing I'm really proud of, is my marriage. I don't think that that's always possible. It's not always a person that you can do that with, you know, but it's really a worthy battle, I think.

Bobbi Brown (42:39)

Oh, I agree. And, you know, it's. It's an art keeping people happy. It's really an art. It's not a science. It's an art. And, you know, you know, the main Thing is trust. I mean, no matter what, I trust my husband completely.

Emily Hickey (42:56)

And I think it's also, it's what you were saying before of wanting it to be happy, you know, and not digging into fights and trying to resolve. You have to actually want the outcome. And I don't know that everybody wants that, but. Okay, so I want to take a stab at your personal why, which could be wrong. But again, this is a thing that I, that I do for brand positioning with brands. It's a really fun exercise and I've done it with a couple people in my life who are trying to figure out their own why. And you can just say you've really missed it, which is fine. But I think that you're, you're very driven to be a, an original and to achieve totally autonomous self esteem. And I think you've always found so much success in doubling down on yourself. And I think you do this primarily through mastering a craft. There are a lot of things you could have done with your life. You know, the makeup you've put into your career, what your emotional why is, which is this defense of intrinsic self worth and self esteem. And you've helped women do that. And then your second one, I think clearly is to inspire other people to see their own value and achieve unconditional love of themselves and share the wisdom that you've developed through your own life. And then lastly, I think you really have a deep need to be a builder and a leader and to create structure and success and sort of throughway for people to achieve themselves within. And then I would think that your gotchas are more around the vulnerability and control and just not bringing your own standards that you have for yourself to other people.

Bobbi Brown (44:27)

Yeah, because I expect them to just have it. That's the problem.

Emily Hickey (44:30)

Right, right. To be able to burn through challenges and negativity and to expect that of other people can be hard. So that's my read on you.

Bobbi Brown (44:39)

I like it. No, I spot on. Know what my why is? It's really simple. I live my life by why not. I'm serious, like, why not? I know it makes no sense, but why not? My problem is I don't think a lot. I just do. And you can ask Cody about that. He can't stand that part. We need strategy. We need the. I'm like, Cody, I have a strategy. I just haven't written it down.

Emily Hickey (45:09)

Well, it served you very well. You're truly a role model and you've really put your, your gifts to use in a way that it really benefits other people.

Bobbi Brown (45:18)

So that's so nice.

Emily Hickey (45:20)

You really, you're very inspiring.

Gwyneth Paltrow (45:26)

Thanks for listening to my conversation with Beatrice Dixon. You can learn more about her amazing brand@thehoneypot.co. thanks for tuning in. This has been a presentation of Cadence 13C Studios. I hope you'll listen, follow, rate and review all of our episodes, which are available for free on Apple Podcasts, Spotify, Odyssey, or wherever you get your podcasts.