What If and Why Not? A Mantra for Living with Curiosity and Courage with Bobbi Brown

In this episode, Bobbi Brown explores the questions “What if?” and “Why not?”—her mantra for living with curiosity and courage. Renowned makeup artist, entrepreneur, and founder of Jones Road, Bobbi shares how choosing decency over drama and normalcy over fabulosity shaped both her career and her life. She talks about the power of kindness, the myth of “always-on” authenticity, and how the outside—our clothes, lighting, and even a touch of makeup—can support the inside without replacing it. The conversation also delves into bio-individuality in health, the art of reinvention, and why making small choices, day by day, adds up to resilience and joy.

Key Takeaways:

• Bobbi’s life and career journey as a makeup artist and entrepreneur.
• The importance of kindness and authenticity in personal and professional life.
• The concept of normalcy versus fabulosity and its impact on self-acceptance.
• Bobbi’s approach to makeup, focusing on enhancing natural beauty rather than drastic changes.
• Transition from the beauty industry to becoming a functional health coach and the idea of bio-individuality in health and diet.
• The significance of flexibility and self-compassion in health and lifestyle choices.
• The role of naivety in fostering creativity and resilience in pursuing new ideas.
• The emotional complexities of leaving a successful business and navigating new beginnings.
• The influence of family dynamics and personal history on self-identity and growth.
• The pursuit of joy and authenticity in life, including personal interests and passions.

Bobbi Brown is a beauty industry titan, world-renowned makeup artist, bestselling author, sought-after speaker, serial entrepreneur, and the founder of her eponymous beauty brand and Jones Road Beauty. Born in Chicago and a graduate of Emerson College, Bobbi was named one of Fortune’s Most Powerful Women in 2021 and in 2022, was named one of Forbes “50 Over 50” Most Influential Women. Brown has received the Glamour Woman of the Year Award, the Fashion Group International Night of Stars Beauty Award, and the Jackie Robinson Foundation’s ROBIE Humanitarian Award. She was appointed by President Obama to serve on the Advisory Committee for Trade Policy and Negotiation and was inducted into the New Jersey Hall of Fame. She holds honorary doctorates from Montclair State University, Fashion Institute of Technology, Monmouth University, and Emerson College.

Connect with Bobbi Brown: Website | Instagram 

If you enjoyed this conversation with Bobbi Brown, check out these other episodes:

From Toxic Perfection to Honest Care: Boundaries, Healing, and Wholeness with Sophia Bush

Living Skillfully with Gretchen Rubin

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Episode Transcript:

Eric Zimmer 00:01:14  Some people chase the spotlight. Others carry a quiet light wherever they go. Bobbi Brown, the renowned makeup artist and entrepreneur, built an empire by choosing decency over drama and normalcy over fabulosity. And it turns out that’s not just branding, it’s a way of moving through the world. Today we talk about the power of kindness, the myth of always on authenticity, and how the outside our clothes are lighting. A touch of makeup can support the inside without replacing it. We also get into food, bio individuality, and why there’s no single right plan for everyone. And woven through it all is Bobbie’s deceptively simple mantra. Ask what if and why not? I’m Eric Zimmer and this is the one you feed. Hi, Bobby, welcome to the show.

Bobbi Brown 00:02:08  Hi, Eric. Nice to meet you.

Eric Zimmer 00:02:09  It’s nice to meet you. I appreciate you coming on. We’re going to be discussing your, I guess.

Eric Zimmer 00:02:14  Do we call it a memoir, still, Bobby, about your life and your your business and all the lessons that you’ve learned from that. So I’m excited to get into that. But we’ll start like we always do with the parable. In the parable, there’s a grandparents talking with their grandchild, and they say, in life there are two wolves inside of us that are always at battle. One is a good wolf, which represents things like kindness and bravery and love, and the other is a bad wolf, which represents things like greed and hatred and fear. And the grandchild stops. Think about it for a second. They look up at their grandparent and they say, well, which one wins? And the grandparent says, the one you feed. So I’d like to start off by asking you what that parable means to you in your life and in the work that you do.

Bobbi Brown 00:02:59  Well, it’s not negotiable. Being kind is everything. And I think that even after all of my years of hard work and you know what I view as success, kindness to me is probably the number one thing.

Eric Zimmer 00:03:13  That makes me think of a later chapter in your book, which is called Be Normal, where you talk about you’ve met lots of famous people from all sorts of actors, actresses, makeup models, musicians, the Obamas, all these people. And you. You talk about how some of those people maintain a certain degree of normality and you say to me, being normal has nothing to do with one’s status, income or title. To me, being normal means treating people with decency and respect. It means valuing family and relationships over business and profit 100%.

Bobbi Brown 00:03:48  I mean, you know, I don’t want to be a name dropper, but just a couple weeks ago, I was, you know, invited to a screening of a documentary about Paul McCartney. And Paul was there and honestly, before I left for the evening and thanked him, I just said to him, you are so normal. I mean, he’s a beetle.

Eric Zimmer 00:04:06  Right?

Bobbi Brown 00:04:06  But you know, his kids, his family, his friends and I could I could relate to that.

Bobbi Brown 00:04:12  You know, I’ve been around enough people that, you know, you would expect them to have attitudes or just think they are better than anyone else. And I just, I really like people that are normal, that are nice, that are caring, that are present.

Eric Zimmer 00:04:26  What do you think enables certain people to do that and others not? Do you think it’s something in who they are? Is it something in the way they learn to relate to fame? Like if you had to speculate, you know, why are some people able to do this? And we hear all the horror stories of of poor celebrity behaviour.

Bobbi Brown 00:04:44  Also, you know, I think from my experience, a lot of people I met, you know, who are incredibly nice and, and, you know, beyond beyond the top of their game, whether it’s Yogi Berra or Gloria Steinem. You know, I’m mentioning some of the kindest people I’ve ever worked with. I think they just knew the difference of the person they were when they were at work, or in front of a camera, in front of a crowd on stage.

Bobbi Brown 00:05:10  And what the people in their life when they go home made them feel, you know, their friends. It’s their comfort zone. What is the difference? I think it probably has a lot to do with how we were brought up, and also how we feel about ourselves.

Eric Zimmer 00:05:25  Yeah, I think that how we feel about ourselves is a is obviously a really big one. And you’ve always had from reading your memoir, it’s not like I’ve known you for years. I don’t know you, but from your memoir, it seems to me that you’ve always had a certain amount of confidence in who you are. It’s not to say that you haven’t had you talk about in the book struggles with body image or other things that points, but you’ve also seemed to have a certain I am who I am, you know, Popeye type A type thing. Is that true?

Bobbi Brown 00:05:57  You know what? It’s not true because it’s taken me a long time to realize who I am. Is that is okay. No. I always thought I should be someone different.

Bobbi Brown 00:06:06  Even even in the middle of my success. I should dress a certain way that I thought I should dress like I should act a certain way, because that’s how professionals act like. So I didn’t really figure out, you know, how how to be the best version of myself, but that’s, you know, kind of divided because when I’m either with my quote unquote, my work posse that I could be myself, I was okay. But when I’d walk into situations where, you know, I was all of a sudden, you know, looked at differently, it was more like, all right, how should I be? You know, it’s I keep thinking of Melanie Griffith and Working girl, you know, with her, like, with her shoulder pads and her briefcase. I tried that on for a while. You know, when I became an employee at a big corporation, I’m like, well, that feels uncomfortable, you know? Right. And and I honestly remember a big turning point was when I was honored for I think it was the mother of the year award.

Bobbi Brown 00:07:05  I don’t know how how how they choose that, but I remember I wore blue jeans. I wore really dark blue jeans and a blue blazer, and someone came up to me and they were like, oh my God, you are confident enough to wear blue jeans? No one did that back then. And I just said, yeah, why not?

Eric Zimmer 00:07:23  Right. Because I hear you saying you have a lot of doubt. And yet I also see you throughout the book sticking to certain convictions. So if we go all the way back to you as a, as a budding makeup artist. Right. The fashion is overdo everything, right? Make people look very different than they actually look. And yet, even early in your career, when you’re trying to build a career which is almost some of the most vulnerable time for us. You even then were like. But here’s what I do.

Bobbi Brown 00:07:53  Yes, because I tried it on and I just didn’t feel right. Like, I’m someone that deals more with feelings and gut than thinking.

Bobbi Brown 00:08:02  It just didn’t seem right, like I could. I couldn’t do it to make the people look good. I just couldn’t. Either I wasn’t talented enough or I just didn’t like the style of it. So I just started kind of doing it my way and at the same time, like shifting some things. Like so I couldn’t work with some of the same people that I was trying to work with. I had to find my people. I had to find people that understood me, appreciated me, liked the kind of makeup, liked my personality. You know, walking into a studio with a fabulous fashionistas back in the, you know, in the 90s was kind of terrifying, you know, because I would walk in and I really couldn’t be myself, or at least I didn’t know that I could be myself.

Eric Zimmer 00:08:50  You mentioned in the book that you chose normality over fabulosity. Yeah, yeah. Do you think that that choice you were able to make because in the one situation you could just be yourself, and in the other you had to pretend to be somebody else, and that just really rubs you the wrong way.

Eric Zimmer 00:09:08  Right. It feels uncomfortable.

Bobbi Brown 00:09:09  It feels uncomfortable. And I realized in my life, being comfortable is the most important thing in my clothes. By the way, whatever I’m wearing, I can’t be an uncomfortable clothes. Like, it just. I just can’t be. I cannot be an uncomfortable shoes. And I really don’t, you know, enjoy being in situations where I’m really uncomfortable. But I walk into a lot of situations even now where I don’t know what I’m walking into, and I usually find my way. You know, there’s always like a second where you’re like, okay, I don’t know what to expect. Like, I’m going to speak to a, you know, a bunch of women next week. I don’t know if these women are going to be dressed, you know, as corporate women, you know, with fancy clothes, or they’re going to be more relaxed because it’s at the US open. I have no idea if I had a crystal ball, then when I go get dressed, I could kind of decide, you know what, Bobby? I want to be, but I know me.

Bobbi Brown 00:10:07  I’m going to find something that could kind of fit with both.

Eric Zimmer 00:10:10  Yeah. It’s funny, every day before I come into the studio to record an interview, I think about, okay, well, I probably need to shave. I need to look reasonable. Right. And today I thought, well, I’ve just got this t shirt on. Should I put something else on? Because I’m talking to Bobby Brown. And then I went, hang on a second. Bobby would not put on a different shirt for this. So I’m in what I was wearing. So here we are.

Bobbi Brown 00:10:31  I’m wearing a similar, you know, black t shirt and, you know, a black Uniqlo sweater. So I don’t have a fancy outfit, but I did have a little makeup put on because I didn’t have any makeup on this morning. Because now everything you do is like photograph.

Eric Zimmer 00:10:47  So well, I am not is pale as I look in this camera that you have. I look like Casper the Ghost in this particular one.

Eric Zimmer 00:10:54  I don’t know why, but I was thinking.

Bobbi Brown 00:10:56  Bright in your overexposed.

Eric Zimmer 00:10:58  Yeah, I was thinking, I need I need Bobby to come get me. Get me set up right for this. You know, I’ve got I got a book coming out next year. I’m like, I gotta look good on these book interview podcasts. So. Right.

Bobbi Brown 00:11:08  By the way, you know, the thoughts in your head are normal. Yeah. This is what people think about. I don’t care if you’re Cindy Crawford, you know, or Michelle or Barack or, you know, will be will be equal. Trump like. All right. Maybe he doesn’t think about it, but his wife and people you always think about like, what do I have to do to make to be presentable, to be myself. And that’s the difference I don’t want to be. I’m not presentable anymore for other people. It’s for me, you know? And because I have such a busy, crazy life, I not only think about what should I wear to be right for where I’m going.

Bobbi Brown 00:11:44  But then I’m going right to the airport and I’m going to be on an overnight flight. I don’t want to have to change my entire wardrobe. Right. I just, you know, I’ll change my shoes, maybe. And, you know, I’ll take off. I don’t even know what I’m wearing if I’m going to wear a blazer or a sweater, if I have a blazer on, I will take it off because I’m not flying with the blazer.

Eric Zimmer 00:12:03  Yeah. I think that one of the things that you’re kind of making a point of, and I think it’s a valuable one, is we often think that authenticity is like we’re always just one way. And what you’re sort of showing is that there’s a way to be authentic, and there’s also a way to show different sides of yourself depending on the sort of circumstance or situation that you are in.

Bobbi Brown 00:12:28  Well, and your mood and how you feel. I mean, I have a tendency to feel sleepy when I’m not, when I am not trying. You know, I go out of the house, my hair is wet in a ponytail.

Bobbi Brown 00:12:40  I’ve got my, you know, Lululemon tights on and a sweatshirt. And if I had to like flick a switch, which I do a lot and, you know, shoot something, I look really sloppy. So some days I’m okay with that. And other days, you know, I’m like, you know what? I gotta give myself five minutes to put makeup on, all right. Like, today I had my hair done. So, you know, to me, that’s a game changer. Looks great. Thank you. To me, it’s a game changer. I need, you know, and I also had my nails done because we have a manicurist that comes once a week to our office. So. And those are, those are days. And you know what? Everyone’s got to figure out what they could do that makes them feel a little bit better.

Eric Zimmer 00:13:21  Right. You can’t see the lower half of me, but I put on certain pants every day that I go to work. No one, no one sees them.

Eric Zimmer 00:13:29  I mean, my entire career, everything I do is, you know, chest up. But for me, they signal something in my brain. They signal like, okay, this is time to work. It’s a different thing. And anyway, yeah, I think that sort of idea of recognizing that the inside drives the outside, but the outside also influences the inside. They they work together ideally.

Bobbi Brown 00:13:52  Right. And you know it. Look, I’m not going to lie, it takes a lot of work to be comfortable with yourself. And you’re not always, you know, but figuring out what makes you feel better. And you know, I’m in the business of helping people look a little bit better. And also, you know, it has a lot to do with how you feel from your health to you, what you see when you look in the mirror like that, that all matters.

Eric Zimmer 00:14:35  I was thinking about something that you say in the book early on as you’re talking about sort of the style that you became known for, which was I always wanted people to look like themselves, only a little healthier.

Eric Zimmer 00:14:46  And I was thinking about the kind of work that I do with with clients and people coaching and in my programs. And I was like, I think that’s exactly what I’m trying to do. Like, it’s not to make yourself into something you’re not or be someone you’re not. But how do we be a little bit healthier versions of ourselves.

Bobbi Brown 00:15:03  Right. And it’s it’s the little things that make a difference. Like there’s no big giant you know. And I’m sure in your business to change that you’re going to do. But it’s the little things that make a difference.

Eric Zimmer 00:15:13  Yeah. I’m thinking jumping around a little bit here to you after your company, Bobbi Brown, was bought by Estée Lauder. And that went really well for a number of years. And then it didn’t go so well. And you had a period of time sort of in between. And you chose to be a functional health coach trained for it, which I found really interesting. But one of the things that you mentioned in the book is that you understood this idea of biomimicry is that, no, that’s not the right term.

Bobbi Brown 00:15:41  Bio individuality.

Eric Zimmer 00:15:42  Thank you.

Bobbi Brown 00:15:43  I went back to school, got my degree as a health coach, and I am, you know, the kind of person that thinks, well, if I just do this, it’s going to make a difference if I just do this and, you know, and I tried all those different things, you know. Okay, I’m going to just be a vegan now. Okay. Well, that I think that lasted maybe one day. You know, I tried keto maybe that lasted a day. And then after taking the course, you realize none of these things actually work for me because it’s just about figuring out what works for me. It’s not about what’s working for the influencer down the street or my husband or my kids. What is working for me and how can I do it the simplest way and the best possible quality of things. And that’s, you know, bio individuality.

Eric Zimmer 00:16:31  Yeah, it just means that we all respond differently to things. You know, paleo might be a great diet for me, but a terrible one for you, right?

Bobbi Brown 00:16:40  Are you paleo?

Eric Zimmer 00:16:41  I’m not.

Eric Zimmer 00:16:42  No, actually. Actually, what I am mostly right now, and it’s sort of surprising that I’m able to do it is I’m mostly keto, but the reason is that it seems to really do something for my mood and energy. Like, it makes an actual pretty significant difference for me. Right.

Bobbi Brown 00:17:00  So it doesn’t do that for me. It just makes me hungry and angry. And I know, I mean, I don’t like I can’t do a lot of carbs, but I need carbs, my brain needs carbs and I don’t. And I’m not talking donuts. I’m talking the, you know, the best quality, but not. But I’ve learned not a lot. Yeah. If I, you know, not a lot.

Eric Zimmer 00:17:22  I’m still trying to figure that out a little bit. I’m trying to figure out like, okay, is it like truly being in ketosis that makes the difference for me or would simply be low carb. Make a similar difference. I don’t quite have the answers to all of that yet, so.

Eric Zimmer 00:17:42  But for right now, it’s been working for me in that it hasn’t been too hard to do. I’ve been able to find ways to do it that I don’t feel like I’m deprived, and it helps. So we’ll see. But but for plenty of other people, it would be a terrible.

Bobbi Brown 00:17:55  Choice, right?

Eric Zimmer 00:17:56  And I think that’s there’s a certain humility in recognizing that we’re all different. I remember my partner Jenny and I at one point were a continuous glucose monitor to see what happens with our blood sugar, and it was fascinating for me to see we would eat the exact same food at the exact same time, and her blood sugar might spike really high in mine would be fine, or vice versa for the same food. And that really, for me, sort of shattered this idea that there’s a right way to do it for everyone, right?

Bobbi Brown 00:18:25  But there’s so many elements right in your day, how you slept the night before. What was your day like? How aggravated were you? And you know what? It doesn’t.

Bobbi Brown 00:18:35  My whole theory is it doesn’t always work all the time, and you just sometimes have to just say, okay, reset. You know, I’ve been in situations where there’s really not not the kind of food that’s going to make me feel good, but. Okay, Bobby, what are the best choices you could do? You know? And if there’s no best choices, let me just have a little bit of something that I know is probably not going to make me feel great. Like I had a piece of pizza, okay? And I can’t just eat one piece of pizza without eating, too. Yeah, but I have two pieces of paper, right? I could not. I mean, honestly, the old Bobby would have eaten three pieces of pizza or even four and said, oh, you know, I blew it.

Eric Zimmer 00:19:15  F it.

Bobbi Brown 00:19:16  Yeah. Two pieces. I’m like, okay, my pants will be tight in the morning, but I won’t feel awful. So, you know, you figure it out.

Eric Zimmer 00:19:25  Yeah. I really love what you said there, which is like that. You know, nothing works all the time, right? Life is just a it’s a dance and it’s we get presented with different circumstances, different situations. We have different capacities at different times, at different moments. And, you know, a lot of this, I think is just like you’re saying, you do the best you can in the situation you are in and move on.

Bobbi Brown 00:19:49  And if you make a choice that maybe isn’t the best, just reset it in the morning, say, okay, it’s a new day. Let me go back to, you know, for me, it’s like two eggs and some oatmeal is gonna make me feel good in the morning. And there’s times where I don’t feel good eating oatmeal. And so I’ll have, you know, a half a piece of sourdough toast or something. But, you know, I can’t just do a smoothie because I’m ravenous afterwards, you know? So. But you just do the best you can.

Eric Zimmer 00:20:16  I’d like to talk about a phrase that I believe you actually got painted on your wall at one point, which is, well, I’ll give the whole sentence where you set it up. You say, I’ve always been open minded. I see possibilities, not obstacles. Rarely do I have a grand plan. I just follow what interests me. At crucial moments in my life, I have always asked two questions what if and why not say more about that?

Bobbi Brown 00:20:39  You know, I’m really naive, and it’s actually a quality that I don’t know how to teach people to be. And I’m proud of that, because being naive, it’s like, I don’t think things aren’t going to work out, but if they don’t work out, I don’t feel bad because I’m like, all right, that just didn’t work. Let me do something different. Let me try it differently. But if you don’t try, you don’t know, right? And it’s like, if you’re always afraid of failing or looking like a, you know, an idiot or dumb or something, you’re never going to do it, and then you’re not going to say, what if you’re just going to say, why? Why didn’t I? So what if and you know, oh, I mean, that’s more why not, I guess, you know, what if is like, hey, I never thought of that, but what if I do this? Like, I once had this crazy idea.

Bobbi Brown 00:21:26  It made no sense to anyone except me. And I had a friend that knew Howard Schultz from Starbucks, and I was still at Bobbi Brown Cosmetics, and I said, people go into Starbucks in the morning and they’re like, so tired. These poor girls, they get their coffee and they go to work. And I’m like, what if we sold an eyeshadow palette and called it Wake Up Your Eyes and you know, all the eyeshadows had names of coffee like Cafe Espresso. I thought it was such a cute idea. I got someone in my office to draw it all up. I found Howard Schultz through a friend of mine I pitched him. He couldn’t have been nicer, but he said, I just don’t see it. And he said, let me bring it into the marketing team. And he brought it into the marketing team. And this was years ago now, I think they would have jumped all over it. And they they just said, no, not the right thing for us right now.

Bobbi Brown 00:22:17  I’m like, okay, no big deal. But I tried it. If I didn’t try it then and, you know, it’s okay that it didn’t work.

Eric Zimmer 00:22:24  Yeah, that’s a great story. You mentioned you’re you’re naive, which I think what you mean by that is you don’t think everything through like an experienced lens, right? Are there downsides to that for you, or have you found that to be a personality trait that’s really just served you very well?

Bobbi Brown 00:22:40  I think it served me well. I mean, you know, because it gives me a little like, I’m not afraid. I’m not afraid to reach out. I’m not afraid to connect. I’m not afraid. And, you know, there’s times I don’t, you know, I’m ghosted. I don’t get an answer back. And sometimes, you know, I find a different way to reach the person. And they never got my email, you know, or other times, you know, I move on because, you know, I also get bored really easily.

Bobbi Brown 00:23:06  You know, some things I have a very long time commitment and and focus and other things I’m over. So and it kind of depends. And I’m not afraid to do like too many things at once. You know, my friends don’t understand how I’m able to do what I do, but I just my mind’s on a lot of different things. And I think why? That I’m able to do these things. I’m pretty good with having a team around me that I kind of say, Will you do this? You know, let’s do this. And then I go to someone else and say, okay, let’s work on this. And I keep checking in to see what’s going on. You know, I think that’s the entrepreneur in me.

Eric Zimmer 00:23:43  Check in for a moment. Is your jaw tight, breath shallow? Are your shoulders creeping up? Those little signals are invitations to slow down and listen. Every Wednesday I send weekly bytes of wisdom, a short email that turns the big ideas we explore here in each show things like mental health, anxiety, relationships, purpose into bite size practices you can use the same day it’s free.

Eric Zimmer 00:24:11  It takes about a minute to read, and thousands already swear by it. If you’d like extra fuel for the weekend, you also get a weekend podcast playlist. Join us at One Coffee. Net newsletter. That’s One-Year. Net and start receiving your next bite of wisdom. All right, back to the show. You early in your career. did maybe this is a phrase from the makeup world. I don’t know, but go sees a lot. not not ghost. Sounds like ghost. Go see. What are ghosts?

Bobbi Brown 00:24:48  It’s something that I. I learned when I came to New York. And I tried to figure out how am I going to get hired. Who’s going to hire me to be a makeup artist? Like there was no jobs. You don’t go and apply. Oh. Guess what? I got a job as a makeup artist. You know, unless you are someone that works, you know, at NBC or ABC, then you get a job. But most in the fashion industry are just, you know, one off jobs.

Bobbi Brown 00:25:13  And when I moved to New York, I opened up the yellow Pages, looked up modeling agencies, models, all sorts of things. And I went to a modeling agency and I said, okay, how do I break into the fashion industry? She says, well, you need go seas. I’m like, what’s a go see? That’s when you go see someone and you show them your portfolio. And, you know, I just made sure that my calendar was filled with go seas and most of them did not, you know, turn out to be jobs to hire me because I was such a young makeup artist that I didn’t have anything in my portfolio to show my work. But then I started doing go sees with models and photographers, and we would do a photoshoot together and I’d build a book and eventually someone would hire me for a magazine. So I started to be able to put more things in my book, and that’s how I started getting hired as a freelance makeup artist.

Eric Zimmer 00:26:11  Yeah, I love that you just keep asking.

Eric Zimmer 00:26:16  You had a phrase somewhere in the book where you were like, I’m relentless, but nice. Yeah. Which sounds like a great. You know, like a really good strategy.

Bobbi Brown 00:26:24  It is. Being nice has definitely served me well. And. Look, I’m. I think I’m emotionally intelligent enough to know when I am when it’s. I’m not liked. You know, the person I’m pitching is not exactly, you know, into me. And then you got to find someone else, you know. So again, you find your people and you find your posse, and that makes a big difference. And you know, many it’s funny, many, many of the people that I think turned me down in the beginning that had, you know, no time for me or just, you know, dismissed me when I went to see them, when I started to make a name for myself, all of a sudden they’re like, oh my God, I’ve always wanted to work with you. And, you know, I’m like, do you don’t remember me? Do you? You know, I remember this one photographer.

Bobbi Brown 00:27:11  He’s, you know, I he was so dismissive of me and not very nice and said, I don’t think you’re right for this. And then years later, you hired me. And he said, I’ve been trying to hire you, you know, for for a long time. And I said, you don’t remember me, do you? Let me tell you what you said to me the first time I met you. And he was like, oh my God. But, you know, it happens.

Eric Zimmer 00:27:32  Yeah, but you let that go and give people another chance.

Bobbi Brown 00:27:35  Well, of course I did. You know I did. I let it go. You know, look, I was different. He was different. And, you know, look, I probably wasn’t ready to work with him back then, so it’s a good thing. I probably would have failed. And, you know, and whatever, he could have been a little nicer in the beginning, you know, but, yeah, you know, there’s there’s tons of rejections, you know, on a daily basis when you were a young makeup artist trying to get your, your career going.

Eric Zimmer 00:28:01  Yeah. Yeah. And I think it’s just that it’s so important that we learn how to, depending on the field you’re in. But lots of fields. I think we just have to learn to know that rejection is part of it. I mean, I’m in the place right now where I mentioned I’ve got a book coming out next spring. So I’m in that place where I’m starting to ask people, Will you blurb my book? Would you be willing to do this? Would you be willing to do that? Right. And and I’m just I’m it’s funny because I feel a little bit like I’m back in high school in a way. Like, can I be in the cool kids club? But I’m just having to be like, you know what? You’re just going to ask a lot and you’re going to get a whole lot of no’s, right? And that’s fine. You know, it’s like when I started the podcast, I asked so many guests. Nobody knew what a podcast was at all even then, let alone who we were.

Eric Zimmer 00:28:50  And I just kept saying, well, I just keep asking and keep asking and and not let not let the rejection wear you down. And sooner or later people start saying, yes, yes.

Bobbi Brown 00:28:59  And as you get better, hopefully your audience gets better. And then people are like, okay.

Eric Zimmer 00:29:06  Then someday you’ve got Bobby Brown’s people reaching out to you and you’re like, wow, look, now here we are. I want to spin around to the difficulty that happened when, as I briefly alluded to what you could tell the story. You were Bobby Brown, you got bought. You tell the story. I don’t need to say it out, but I kind of want to get to the difficult part.

Bobbi Brown 00:29:37  Yeah, well, you know, it’s kind of the center of the book is is much about this. But my husband and I started Bobbi Brown Cosmetics together, basically from our kitchen table, and we ended up selling it to Estee Lauder after four and a half years. I stayed as an employee 22 years.

Bobbi Brown 00:29:56  And, you know, the day I left was a pretty tough, you know, emotional time for me, filled with sadness, anger, excitement, you know, all of those emotions one by one, you know, kept coming in and, you know, I somehow got through it, but it wasn’t easy. And, you know, I didn’t have a psychologist, a therapist. I didn’t, but I ended up, you know, working with, believe it or not, a chiropractor that did energy release. And so he just kept helping me get the negative energy out of my body. And it was so incredible. And then I started working with a life coach, which I didn’t know what the hell a life coach was, who kind of just helped me practically figure out how to start doing things and figuring things out. And so the, you know, very unusual path. But those two things really helped me. And plus, I just kept doing a ton of projects. You know, I just kept jump.

Bobbi Brown 00:31:00  Something would come up and I would jump into it. So, you know, it was like starting over again, right?

Eric Zimmer 00:31:06  Because you basically left. It didn’t end well at Estée Lauder. It sounds like there had been problems for a little while before. Just different a vision. Things have a way of doing things and eventually they basically more or less, you know, gave you a role that didn’t matter, that you didn’t want.

Bobbi Brown 00:31:25  Well, there was really no role. They, you know, they canceled my work contract and offered me to be the face of the brand. Yeah. Which was not what I was, wanted to do or be.

Eric Zimmer 00:31:38  So as a guy who doesn’t know much about the makeup world, did your brand, Bobbi Brown, continue with Estée after you left?

Bobbi Brown 00:31:46  It’s okay. It’s still.

Eric Zimmer 00:31:47  Still.

Speaker 4 00:31:47  They’re still there?

Bobbi Brown 00:31:49  Yep. Still there. Yeah.

Eric Zimmer 00:31:50  That’s got to be really difficult in a way, to have this thing that has your name on it going in directions that you don’t have any say in.

Bobbi Brown 00:31:59  I’m not going to lie, in the beginning it was really difficult. It was such a tough, emotional thing for me that even as a makeup artist, I wouldn’t use any of the makeup. Like so from the day I left the brand, I don’t even think I donated it. I threw it all out and I didn’t, and I just needed to start over. Differently. And you know, I’m also not going to lie. The success of my new company, Jones Road, has made those feelings okay.

Eric Zimmer 00:32:25  It’s I often joke that, like, there’s a lot of work you can do in getting over a breakup that you could do on your own. There’s lots of really valuable work. And then when you find your way into the next good relationship is like the actual real, like, okay, now I’m really over it kind of thing.

Speaker 4 00:32:42  Exactly.

Eric Zimmer 00:32:42  So, it sounds like a similar feeling.

Bobbi Brown 00:32:44  And there’s always things that come up, you know, but it’s amazing as we get older and we get a little bit more self-aware, you know, you’re able to look at things differently.

Eric Zimmer 00:32:56  Let’s talk a little bit about that period of time. After the time with Estée Lauder ended, you got a the life coach, you worked with a chiropractor. You talk a lot about sharing with your friends. Well, I think we often have this view that moving forward productively through that sort of thing, which I think you did sounds like in many, many ways. I think we often have a really tidy view of that. We think like, oh, well, you should, you know, we just moved on. She just moved on. But I’m wondering if you can share about the lingering aspects of that in the ways in which, if it did, it kind of kept coming back to you and take us into the real difficulty of that period a little bit.

Bobbi Brown 00:33:38  I mean, really the hardest part were the people because, you know, they were most of the people were my people that I hired my posse. And, you know, we were not supposed to be talking to each other.

Bobbi Brown 00:33:52  So that was that was tough. And I felt, you know, some people reached out to me anyways. Some people called me from their kids phone and some people didn’t call at all. That was the hardest part. People that I really thought were my people, you know, I understand now. They needed their jobs, right? And they couldn’t. You know, and they would have been in trouble if they didn’t listen. But I moved on. And, you know, I feel really good now because a lot of those people who aren’t there anymore have, you know, we’ve rekindled and they’ve apologized and, you know, we’ve we’ve moved on. So and and by the way, you know, the more room you have in your life, you could bring new people in. So I’ve, you know, rebuilt my posse. And I love, love the people I work with, like every single person on my team. You know, they’re kind of family. And it’s and it’s really nice. And also they’re really young. And I really like being around young people.  I do.

Eric Zimmer 00:34:53  Feel for those people that were in that situation. Right. That’s a really difficult position to be in. Like I feel torn between my probably mentor in many cases, you know, this this mentor of mine, this person who means a lot and keeping a job and that’s, you know, that’s just a lousy position to be in. You mentioned that as you were getting ready to start these other projects, you hired a woman right out of an Apple Store because she was very persistent in in helping you. When you’re hiring someone, what is it that you are keying in on? Do you even know or is it just so intuitive to you?

Bobbi Brown 00:35:31  Well, look, I’m not always right. You know, I make mistakes like anyone else. It’s usually someone that I could talk to, someone that I’m comfortable talking to, someone that is curious. Someone that you know has a pulse and a personality. Because sometimes you interview people and they are either nervous or they’re duds or something. Like, I like to see a spark. I could sense if they’re genuinely into what I’m doing, or if they’re just kind of full of it, pretending that they are. You know, I interviewed one person for a, you know, a pretty big job. And she had never used the products. If you had an interview with me at Jones Road, would you not go into one of the stores or order online and at least try to understand what this company’s about? So, you know, that was a deal breaker.

Eric Zimmer 00:36:25  I certainly would.

Bobbi Brown 00:36:27  I mean, you would think.

Eric Zimmer 00:36:28  Seems like. Yeah, it seems like basic.

Bobbi Brown 00:36:30  Basic.

Eric Zimmer 00:36:30  Sort of common sense.

Bobbi Brown 00:36:32 And there’s a store Like five minutes from my office. You could have gone in there and had your makeup done, right. Like. And, you know, you come in looking great and. Wow, you look. You look the part.

Eric Zimmer 00:36:41  As you were working through this transition period, you kind of got your health together and all of that. And then you say at one point in the book, like you realize something was missing fun. And I’m curious, did the realization that you were missing fun come from the fact that you now have a time to think about it? Did it come from that you were having fun at your previous role and hadn’t quite figured that out yet. I’m just curious how that evolved. I mean, certainly one for me that I have to consciously prioritize. Like, I can get so focused. And I actually do think so many of the things I do are fun, but they’re not fun with like, a capital F in the same way. Right. So it sounds like that was a later in career kind of thing for you to realize, like, hang on a second, there’s something I’m missing here.

Bobbi Brown 00:37:30  Well, it’s so interesting because yes, I had more time on my hands because I was so overscheduled, you know, for years and years and years.

Bobbi Brown 00:37:37  And when I wasn’t working, I had things to do with the kids. I had doctor’s appointments or, you know, tutors or I just was really busy. And, you know, I also realized I don’t like golf. I don’t like tennis.

Bobbi Brown 00:37:53  I don’t really like those things that everyone else is doing and seems like so much fun. It’s not fun for me. So then I had to think, what is? What do I love? What is fun? For me, that’s not work because my work is fun. And, you know, it was it was hip hop dancing. So I started taking, you know, these exercise classes. And then I did a bunch of privates. And, you know, I kind of evolved from there. But to me, I love exercising, you know, that’s it’s it’s fun, but it’s a job. You got to get this done. But dancing, you know, I danced by myself in my bedroom or in my gym sometimes.

Eric Zimmer 00:38:31  You still hip hop dancing then?

Bobbi Brown 00:38:33  I’ve been listening to or watching a video out of the UK where he’s phenomenal and he’s got all these, like, very regular people behind him dancing. And I, you know, it’s it’s as short as 15 minutes and I and I do it, I really enjoy it.

Eric Zimmer 00:38:47  I’d like to circle way, way back actually to the early parts of your story. You talk a lot about your family early in the book, and there are really good and inspiring stories in there. There are stories of your your papa Sam and your Nana Minnie, your Aunt Alice. But there’s also your mother, who had bipolar disorder and struggled a lot. How do you think about taking the good out of that, and also then dealing with the bad parts of that, like how do you think about sort of making all that work for you?

Bobbi Brown 00:39:23  Well, first of all, she’s not with us anymore. Like if she was still here, you know, I probably would have written differently in the book. But, you know, I’m really lucky because my mother had her first, as we call it, nervous breakdown, where we realized something was wrong when I was in seventh grade.

Bobbi Brown 00:39:41  So up until then, I had the most loving, wonderful, you know, mother that gave me so much of herself. And that’s how I choose to remember her. And, you know, then for years, she was kind of up and down on and off while she was figuring out what was going on. And, you know, then she struggled a bunch and that was really tough. You know, so I could think of her both ways. I mean, I spent more time trying to mother her or to help her or to deal with her than I did as a young girl. That got so much from my mom. You know, so, you know, not the easiest, but I am someone that tends to see a glass half full, and I know so many of the qualities that I’m proud of is because of my mom, and she’s the one that, you know, really encouraged me to be a makeup artist. And I know she was really proud of me. And I also know that all the issues that she had.

Bobbi Brown 00:40:47  I mean, it’s a disease. She didn’t she couldn’t help. And, you know, as you get older and you’ve been on medication your whole life, then you deal with other things, you know, So it’s it, you know, definitely a journey. And I think what’s so important about having the story in the book is that people, we all go through things with our families, and it’s what you do with the experience and how you move on or move through it that’s going to make a difference.

Eric Zimmer 00:41:16  Yeah. You say so many people focus on what they didn’t get from their upbringing. I believe understanding and appreciating what you did get is the first step in knowing and accepting yourself. And you go in and say it’s not to minimize trauma or other things, but I really liked that focusing on understanding and appreciating what you did get. And I think this is a dance, right? For some people. It’s like you first have to accept and appreciate the ways in which you didn’t get certain things as a child.

Eric Zimmer 00:41:41  If you’re in a denial sort of story, right? So you almost then have to go and say, well, actually it was kind of messed up for a while, but for me, it has helped me a lot to find my way back around to what I did get from each parent, right? And that has helped me situate things a little bit differently. My father has passed now, so I can talk a little bit more freely about him. But what I realized from him is that that’s where my entire work ethic came from. I mean, I got that, I believe, from him, and it has served me extraordinarily well my whole life. It’s one of my good qualities, like any good quality can be taken too far, but but overall it’s good. And so when I was able to sort of find that and then similar things with my mother, like I love to read and so much of my job, I do what I do because I get to read and I got that from my mother.

Eric Zimmer 00:42:33  So while acknowledging the things that were difficult and maybe I didn’t get it has been really important for me to circle back around, like you say and find out, like, oh yeah, I did get some really good things. And I realized recently I was like, you know, I can’t blame them for the negative things and then take credit for the good things myself. Yeah, right. You can’t tweeze things apart that cleanly. It doesn’t work quite like that, because even some of the qualities that I use to turn the difficult things into good parts of me came from them. Right. It’s just you can’t separate the two.

Bobbi Brown 00:43:04  Yeah. And also, there’s things that maybe you not you didn’t get from them that you wish you had. Guess what. You can give them to yourself. Yeah. And you know, you could also have these experiences with your your new family, your kids. You know, and trust me, you know, I’m sure my kids one day are going to be saying all the things that they didn’t get from me.

Eric Zimmer 00:43:24  Of course.

Bobbi Brown 00:43:25  You know, I’m sorry. I’ve worked my whole life. I’ve been home as much as I possibly can. And I’m sure you know they’re proud of me. But I’m sure there’s resentment, you know, that I wasn’t. I mean, I was around more than any working mom I know, but I’m sure there were times where, you know, their stay at home mom friends were always there, and I wasn’t always there. But I made sure we had, you know, the best people supporting our family and, you know, picking them up and playing with them, whatever they were going through. I made sure, you know, we had a Manny for my kids because, you know, three boys and they did all these sports. So it was it made total sense.

Eric Zimmer 00:44:02  I’ve never heard that phrase before. This moment a Manny, it’s genius.

Bobbi Brown 00:44:06  He was in school to be a teacher, and he just, you know, he was the coach of their baseball games. Now his daughter is just babysat my granddaughter.

Bobbi Brown 00:44:15  So it’s just funny, full thing.

Eric Zimmer 00:44:17  How lovely is that? How lovely is that? 

Before you check out, pick one insight from today and ask, how will I practice this before bedtime? Need help turning ideas into action? My free weekly Bites of Wisdom email lands every Wednesday with simple practices, reflection and links to former guests who can guide you even on the tough stuff like anxiety, purpose and habit change. Feed your good wolf at one you feed. Net newsletter again one you feed your net. I guess. Let’s close by me just reading. It may be the last line in the book, or it’s very close to the last line and just let you say a little bit about it as a is a way for us to wrap up, which is a life, after all, is what you make it.

Bobbi Brown 00:45:06  Wow. That’s my last line in the book, I think.

Eric Zimmer 00:45:08  So, I.

Bobbi Brown 00:45:09  Know, I believe you, I haven’t, but trust me, I worked on that book so long I.

Eric Zimmer 00:45:12  Have. Oh, I know, I know the whole, you know. But ridiculous.

Bobbi Brown 00:45:16  Gives me one more time.

Eric Zimmer 00:45:18  A life, after all, is what you make it.

Bobbi Brown 00:45:20  You know, I don’t feel powerless. I don’t feel a victim. Yes, I know I have a lot of luck and a lot of amazing things. Everyone has different things in their life, and it is what you make it. It’s how. It’s how you look at things, right? It’s how you look at things. And I do think the good news about getting older is you realize how all the hard work and all the angst that you put into everything is, you know, you reap the benefits If you do it for a reason, you know, not easy being a mother of three boys. Not easy, but sure. Joyful.

Eric Zimmer 00:45:58  Yeah, well, Bobby, thank you so much for taking the time to join us on the show. We’ll have links in the show, notes to the book and where people can find out all about you.

Eric Zimmer 00:46:09  So thank you so much.

Bobbi Brown 00:46:10  Thank you so much. I can’t wait to read your book too.

Eric Zimmer 00:46:13  Wonderful. Thank you. Thank you so much for listening to the show. If you found this conversation helpful, inspiring, or thought provoking, I’d love for you to share it with a friend. Share it from one person to another is the lifeblood of what we do. We don’t have a big budget, and I’m certainly not a celebrity, but we have something even better. And that’s you just hit the share button on your podcast app, or send a quick text with the episode link to someone who might enjoy it. Your support means the world, and together we can spread wisdom one episode at a time. Thank you for being part of the One You Feed community.