Former First Lady (Michelle Obama): This Is A Scam! People Were Running From Us Because We Were Black! I Was Bitter About The Racism I Received!
Guests: Michelle
Full transcript · Read the full conversation in order, with its original context.
§01Transcript — part 1
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People in power who haven't understood their "why" can lead us down some dark tunnels. We are in a really tough time right now.
The one and only Michelle Obama. The former First Lady and her brother Craig Robinson are sharing their rare perspective into a world very few ever get to see.
I grew up in a predominantly Black neighborhood, and we were taught foundational values so that we could function in our society. But growing up, I was just checking boxes. And then I met Barack Obama. He showed up in my life as the opposite of a box checker.
You rejected him at first, right?
Yes! I was even trying to introduce him to some of my friends. He said, "Well, why don't we go out?"
What did you think of him?
Honestly, I was like, he may last two months. I remember Mom saying, "Well, at least he's tall."
But the next thing you know, we were on our way to building our lives together. And my initial reaction was: "Don't do this." There would be death threats. How do you raise kids in the White House? How would we afford it?
Did you ask for any promises if he were to win?
I didn't know what that journey was going to be and what I would need to negotiate for myself. If I had known what I know now, I should have said...
Michelle, I was watching the coverage of your decision to not go to Trump's inauguration. What was the thinking behind that?
The truth was that...
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Michelle, Craig, what do I need to know about your earliest context to understand the adults—and I use that word intentionally because I know that's what your parents were intent on raising—the adults that are in front of me today?
Wow. It starts at 7436 South Euclid. That was the hub of it all, the home that we grew up in on the South Side of Chicago. And it was a teeny, tiny house. We lived above our Aunt Robbie. It was a single-family home, a bungalow on the South Side of Chicago.
Our Aunt Robbie was married to her husband, Terry, and they owned the home. They had a little bit of a—it was almost a one-bedroom or two-bedroom apartment over the home, so it was a two-family home. We were surrounded by extended family. That community of people, probably because people didn't have a lot of resources, lived with each other. You shared spaces; you lived next to one another.
We lived with our great aunt because it helped our parents save some money and get us into a better neighborhood. My father was a city worker; he was a working-class guy and didn't have a college education. Working for the city was a really stable job because it gave you benefits and some stability.
My mom wanted to stay home and raise kids. So, in order to save that kind of money, we banded together and lived with our Aunt Robbie. All of the adventures and the lessons learned—when I think about my foundational values, that house, really, and all the experiences and conversations at the beginning of my kitchen table happened on 74th and Euclid.
I talk about it because you'd think it was a palace, but this was a little home. We shared a bedroom most of our lives because there just wasn't room for us to each have our own room. We shared the space, one bathroom, there was no dining room, just a kitchen.
And the way it was set up, from how it was supposed to be used, it was a one-bedroom apartment. The living room was the room that we shared as a bedroom, and the one bedroom it had was where my mom and dad lived. The whole thing could have been 700 square feet.
You talked about foundational values. What were those foundational values that you learned in that location, and how did your parents teach you those foundational values? I ask that with great curiosity because as I read through both of your books, there are moments in your career as adults in your late 20s where those values show up so clearly over and over and over again.
As I was reading, I was thinking, "Gosh, what did their parents do to orient them in such a clear way?" At key moments in both of your careers, you make decisions not to get a pay rise or to go for the thing that is higher status, and to do something else—either something aligned with your passions and hobbies or something in service of others. So, what were those values and how did your parents instill those in you?
I think our parents modeled it. If I were to think of one word that would describe my father, he was just a decent man. Decent, honest, hardworking, and loyal, trustworthy. I mean, these were the kind of things that we talked about. We didn't have material stuff; he couldn't provide that.
But he provided a set of lessons about what it meant to be a good friend. He was the elder in his family, the oldest of five, and my mom was the middle child. He took care of everyone, even though he had multiple sclerosis and walked with assistance. He had a cane when we were younger; I never knew my father to walk without the assistance of a cane. MS was a progressive disease, so over the course of his life, he just got weaker and weaker. But he was the strongest person in our orbit, with everyone.
Never took a sick day.
Never took a sick day. He was the father that fathered all the other kids in the neighborhood. So when Craig was playing basketball, he was the person that was at most of the practices if he could be, if his shift allowed. He was the dad in the neighborhood where a lot of kids didn't have those kind of role models. Even though we didn't have a lot, there was never a time when my father wasn't going to help somebody.
Those values were: you take care of people. Money doesn't really matter; that's not the thing that makes you great. It's how you show up in the world, it's your word, it's how you treat other people.
To Michelle’s point, he was the guy who was giving kids rides to practice and to games because their parents couldn't go. He would be sharing stories, sharing his values. It was just embedded in his being to pass on knowledge that he had.
With regard to my mom, I think my mom is where I get my philanthropic gene from. Not with money, because we didn't have any, but with our time and with our resources—whatever resources we had. What was behind all of us was unconditional love.
It’s a tool in the toolbox that you sometimes don't even realize is there if you're privileged enough to have it. Because it's that tectonic plate that sits underneath you that you never can really see but gives you a certain sense of risk and go-get-it.
Well, and knowing that it's not just unconditional love, but our parents believed us. They valued our voices. I mean, they really liked to hear us talk. They encouraged us to think out loud and to problem solve, and to come to us with their problems but not be the ones that were going to solve them.
This came in very handy when you're a kid in public school because, you know, in public school on the South Side of Chicago, teaching was kind of uneven. One year you'd get a teacher that cared and invested in the kids; another grade you'd have a teacher that didn't care. I remember distinctly, I started second grade and I went to a classroom that was completely chaotic. The teacher clearly didn't want to be there, and I knew this in second grade.
There was no order; we didn't have homework; we weren't doing regular lessons. I knew that something was wrong. I would come home at lunch and I'd complain about how nothing happened today at school. I don't know what second grade is supposed to be, but I don't feel like I'm getting what I need to get out of second grade.
It took a month of coming home and complaining, and my mom was quietly listening. But she wasn't just listening; she was plotting. A month in, she went up to the school, watched herself, and saw that this teacher not only wasn't teaching but it appeared that she didn't even like kids.
She went to the principal's office and read them the riot act. I don't know what she said or what she did, but three of us were pulled out of the class for testing. I just remember I didn't have to go into that class, and I spent a couple of weeks taking some specialized tests—we were just doing bubble tests, didn't know what it was—got the results, and the results proved that I could skip second grade. And it was a lifesaver for me.
But I'll never forget, my mom finally did—I would hear her complaining to my dad about "these teachers who don't care about these kids." She had gotten us out, but she was worried about the kids who were stuck in that second-grade class who didn't have parents who were their advocates, who were going to spend probably a wasted year in second grade missing whatever they were going to miss.
But that was one of those instances where I knew that if a cry for help from me was heard by my mother and acted upon. She could have been one of those mothers who said, "Well, just, you know, life is life, just get it together." But she knew there was something different in what I wanted and what I needed, and she made it happen.
Does that teach you to respond to others who cry for that help?
It probably does. I mean, I still think about the kids who were left behind. There's just something that really touches me about kids who are as bright as we are because we grew up with them. My mother saw them, and the only difference between me and them was that they had a mother that cared. A lot of their lives look totally different from ours because of that.
I find myself being that advocate for those kids, the kids who are underestimated and undersupported. That turns out to be kids—most kids all over the world. So I do find that that moment for me was defining in a pretty fundamental way about how I fight for kids in the way that I saw my mom fight for me.
Race. One of the startling things with these two photos—mainly because I think it's this way round, but this was I believe what, second grade or something?
That was first grade.
First grade. And then this is eighth grade?
Seventh or eighth grade, yeah.
There's a lot less white people in the second photo, which means that—which assumes that—white people started leaving your school.
Oh, absolutely. They were leaving the neighborhood, leaving the whole of South Shore.
My question really is about what role did race play in your childhood? Because I think about my own childhood and it's quite a prominent, persuasive force in who I became and what I thought about the world, and really what I thought about myself. So race as an issue as young people in Chicago—what role did it play?
I think there was a lot of race pride in our family. There was this feeling, this understanding that because of people's prejudice, there would be a lot of white people that would underestimate you, that would mistreat you, that would assume things about you.
Our family, our entire family on both sides—really smart, talented, gifted people. To have a family that big and but all working-class people, right? So we lived among sort of real, regular excellence. People who were teachers and who were engineers. All of our cousins were people who were expected to do well in school.
So we were taught like, "No one's better or smarter than you. You're capable." My father was that voice for a lot of our cousins if they didn't have that kind of energy in their lives. It was always like, "You got this and you know what you're doing." So in our home, there was race pride.
But when we moved into South Shore, into Robbie's house, our Aunt Robbie's house, most of my neighborhood friends were white kids. Rachel Dempsey and Susan Yacker and Sophonat Kansapon, who was a Korean girl because we lived by a hospital and her mother was a nurse. So it was a very mixed—the Stewarts who were a Black family but could pass for white. It was just sort of some of everyone in the neighborhood. Miss Mason, who was the little old white lady across the street, and our neighbors were the Mendozas, the Mexicans. It was sort of everywhere all around us.
And everyone got along. Neighbors knew one another, we played with each other. I went to Rachel's house for lunch. But then one year, it was like the lights went off for the white people and they were gone without a trace.
They call this white flight.
This was white flight in action. Yeah.
For anyone that doesn't have context on white flight, what is that?
It's the sociological occurrence of what happens in communities when Black people sort of start making their way up socioeconomically and can buy homes or rent homes in neighborhoods that are predominantly white. So instead of white people accepting it, they sell their homes en masse. There's a sort of undercurrent of "we better get out because these Black families coming in are going to ruin the neighborhood and bring down property values, so you better sell now and go further south into the southern suburbs."
And so when you're young, you kind of know something is going on. It's not like we were sitting around the kitchen table talking about white flight. But what you do know and you take in as a child is like, "These people are running from us."
It's like my dad, who is this amazingly kind and generous person who would have been good for a lot of these people's kids—these white folks' kids—to get to know and be around us, who turned out to be who we were and we were always going to be that. "You're running from us?" Well, our feeling was like, well, how stupid is racism and how stupid are you for not really looking and getting to know? So race to me and in my household was just a dumb manifestation of ignorant people. But we were taught to keep moving through it.
How do you stop it getting to you? One of the remarkable things I noticed, even when we spent some time together yesterday, was there is no apparent bitterness. And one would say that there's reason to be, because when you're so powerful and so prominent and so well known, you're exposed to everything. And going through that experience in those early years and then going through everything that happened thereafter, there doesn't appear to be any bitterness. There doesn't appear to be any chip on the shoulder, any anger.
Sometimes there is. You just don't show it. But I will say, at least from my standpoint, Mom and Dad, but Mom especially, she taught us empathy almost to a fault. So she always said—remember how she always said—"Put yourself in the other person's shoes." And she would always say, "You never know what's going on in someone else's home." And so I always approached negativity toward me with empathy. That was the first thing.
It's like, "Oh, what happened to you that made you so mean and evil?" The other thing that our parents were really big on was: "Do not care what anybody else who's not sitting at this table thinks." If we ever said somebody said something and it affected the way we behaved, that's when you saw anger from my parents. I mean, you got in trouble with my parents when—it was crackback right away.
What would they say back?
They would be like, "So you're going to tell me that what whoever this is over here said is more important to you than what you hear around this table? Then you can go live with so-and-so."
If our—admonitions in our house were always conversations. It was discussions. And you knew when your parents were disappointed, you knew when you had struck a nerve. And it was never about just making a mistake or, you know, it was about thinking in a way that felt oppressive, internally oppressive. They didn't like that kind of thinking in us.
They wanted us to feel our own power. They never wanted us to surrender the way we thought about ourselves to the rest of the world because they probably understood that they couldn't trust the way the rest of the world would treat us. So you can't—they knew that we couldn't be so locked into what the world would say because the world was grounded in racism. And that a little Black boy even more so, even my brother, they were probably more concerned with him because he was going to encounter it every day as he got taller and bigger and smarter.
Because all of the men in our lives had experienced someone trying to knock them down a peg or two. I think our parents understood that that was waiting for both of us and it was waiting for my brother in particular. So they wanted to arm him with enough self-esteem to fill him up at the table where he was safe, to give him the tools to just embed in him a level of empathy so that he wouldn't become angry, because anger for a young Black boy was dangerous. So there was a real clever way of allowing us to have these conversations but filling us up with empathy so that we could function in a racist society.
Being underestimated. It’s a word that I saw throughout your book and it's a word you mentioned a second ago. You knew you were going into an underestimated world, if I can call it that—a world that was going to underestimate you because of your race and things like that. But it's so clear to me that you had your shoulders back regardless.
I spoke to Valerie. Do you know Valerie? Of course you know Valerie. You've worked with Valerie for many decades. She was a sort of early mentor figure in your life, Michelle. And she actually wrote me a letter about you. She describes that she's never met someone in her life that was so clear on what they wanted to achieve in the world in terms of the social good and the impact they wanted to have, but was so unbelievably confident and high conviction.
When I think about when you went to Harvard and studied law, there was what, 30% of the people attending were women and then a tinier percentage were Black women. And you were aware again of being underestimated, but again shoulders back, it seemed. Where does that come from in you?
Oof. Living through the incorrectness of that underestimation. First of all, I grew up fortunately in a predominantly Black neighborhood after white flight happened where everyone assumed I was smart. I grew up as the salutatorian in my grammar school, I went to a top high school. I had the fortune of growing up in a validating Black environment, which is—we talk about that a lot with Black students whether they should be going to HBCUs and what happens when you get pulled out into a mixed environment where you are so underestimated so early.
You start—we talked about the messages that you start telling yourself. I didn't have that because when we were young, my mentors, my teachers, the coaches, my dance teachers, they were all people who if I made a mistake or if they doubted me, it was because—not because of my race, it was because I disappointed somebody in some other way.
By the time I hit Princeton, thankfully I had enough internal data that I could do a lot of things. That I was better, smarter, sharper than they would give me credit for. And then it was confirmed when I walked onto Princeton's campus as an undergrad, feeling a little intimidated because it was an Ivy League school and I wasn't a great test taker although I was an outstanding student. I wasn't a good standardized test taker. All those numbers said that I shouldn't do well at Princeton.
And so I came in as an affirmative action kid, sort of feeling like maybe I don't belong in these ivory towers and maybe these kids coming from these other schools are really so much smarter and better than I am. And then I sat on that campus and I looked around and I was like, "Oh my God, well, there's all kinds of affirmative action that they never talk about." There's wealth and legacy, there's athletic affirmative action. There were a lot of kids that were on that campus and as I learned, continued to gain access to these seats of power that had nothing to do with their raw academic ability.
There are a lot of bright kids who go to these schools, but there are a lot of bright kids whose parents get them into these schools. And when I got on campus and I came out of my first semester with straight A's, I was like, "Well, what's the—what are you talking about? What—who are you? Why are you trying to mess with my head in this way when you guys are—you're not even working as hard as me."
But that was—it was infuriating, but it was freeing. Because I was like, "I get it now. This—you're just trying to get in my head. You're scared of me. You don't want me competing with you." And I think it was at that period, going to one of the top schools, that I was like, "I'm done. I am done worrying about whether I belong here. This is a scam."
So that, I think that really—I came out of Princeton just feeling like, "Graaar! Let me at 'em!" Forget all this stuff, and now I'm trying to tell other kids that. It's like I'm coming down from the mountaintop with the tablet of truth and going, "Do not let these people scam you. This is all a racket."
What's the scam?
That you don't belong. That they're smarter. That they work harder. That they know more. That they deserve this more than you do. That's not—it's just not true. And so from then on, I was like, "You prove that I don't belong here. I'm going to sit at these tables and I am going to run it from now on. Why am I listening to you? Why don't you listen to me?" I think that experience for me was freeing in an odd kind of way. And a lot of kids don't get access. They're just blocked out and it's sort of like they're told, "Don't look behind the curtain because you don't belong," and they want us to think that way. I stopped thinking in that way a long time ago.
The journey you've both been on is really remarkable for so many reasons, but it's also remarkable for the pivots along the way. I was reading about a bit of an identity crisis that you had when you were 27, 28 years old, Michelle. You were a lawyer at Sidley & Austin.
Yes. Beautiful, high-paid corporate attorney that allowed me to buy a nice Saab. A Saab-driving attorney. First real job I'd had right out of Harvard. Because that's what you did, right? After you go to law school, top school, you're recruited by the top firms in the country and they offer you exorbitant salaries. So at that age, as I started as a first-year associate, I was making more than my parents made combined.
Which seemed like something you didn't turn down, you know? If you have the opportunity to do that, it's like, "Well, yeah, sure, I'm going to work for a firm." But that's what I was really doing all my life; I was box checking. I was just, because I was a good student and I could do certain things, that's what I did. I sort of understood that there was a formula: be a good student, show up, do the work, check. Got that, get good grades, go to a competitive high school, went to a magnet high school, was class treasurer, top of the class, check. Got it, because I can do this.
Just marching through life, check, check, check. Apply to a top college, got into Princeton, right? I'm in, graduated at the top of the class, go to law school. Why? I don't know. There wasn't really a thought to why I went to law school; it was just I don't know what I'm going to do after graduate school. Not going to be a doctor because I don't like science or math. I like to talk, I like to argue, and so why not go to law school? So I applied to Harvard, get in. Well, you go to Harvard!
That was—that was my thought process. There wasn't purpose, there wasn't "what do I care about?" I didn't know what being a corporate lawyer meant; I was just checking boxes until I became a lawyer. And a lot of stuff happened in that year besides me just joining Sidley & Austin. In that period of time, we lost our father. He died very suddenly.
One of my best friends from college, Suzanne, died of lymphoma. And it was sudden; she was diagnosed in December and she died in May. Really the first time in my life where people that weren't expected to die died. We had lost grandparents and great-grandparents. And I was really having kind of an existential crisis sitting on the 47th floor of my beautiful office with a secretary and a Saab in the garage, thinking, "Why me? Why am I here rather than Suzanne?" Because she was also the dreamer, the person who wasn't box checking. She went to Princeton, but she traveled the world, she didn't go to business school right away. And I always thought, "You got to get your life together, you got to be on a path."
And I thought, "Thank God she didn't do that." Because she didn't know she was going to die. But instead of sitting in some office building, she was living life and trying on new things. And I realized I hadn't done that for myself. All I was doing was following a game plan. I wasn't trying to figure out my purpose.
And at the same time, I met Barack Obama. He showed up in my life as the opposite of a box checker, but somebody I describe in my book as an ultimate swerver. He did nothing by the book. But he was brilliant and interesting. He didn't go to law school right away; he worked as a community organizer, he lived in different parts of the world. He was really trying to unpack life in a way that people in my generation weren't trying to do. You were just—I was with the Black bourgeoisie, right? And people were buying their homes and getting their cars together and trying to make partner at a firm. There was a very finite path.
And I hadn't explored anything else but that. And I thought, "I have to do something more before I settle on this." And I think Barack helped give me the courage. He was the person in my ear that said, "Why would you want to just stop here and settle on this career when there's so much out there that you haven't tried? You can do this." And I was like, "But I'm loaded down with debt!"
And right around that time, we knew we were going to be together, we knew we were going to be engaged. And he was like, "We'll figure that out." He was like, "Don't settle on becoming a partner at a law firm because of money. You need to see the world in a different way, and we'll figure this out together." And so I started swerving. I started trying other things in life and never looked back.
Craig, when was the first time you heard that your little sister had met a guy called Mr. Obama?
Well, she called me up and said, "Hey, I met a guy. I want to bring him by." My mom, my dad, and I were sitting on our front porch, and she pulls up in her nice Saab 900 that you've heard a lot about. And he gets out of the car, and that was the first time we met him.
And what did you think of him? Honestly.
Honestly, I was like, "You know, he may last two months."
Because of who?
Because of her! She'd be like—he'd do something and she'd be like, "Oh, that's a deal breaker," and he'd be on his way. And my mom, I remember my mom saying, "Well, at least he's tall." We were just meeting him like we would meet anybody she'd bring by.
But I never brought—I didn't bring a lot of boyfriends by, so that's why they thought it wouldn't last that long, because she didn't bring too many guys by.
Yeah, but why would you think it wouldn't last? The people that didn't last you didn't meet.
But we heard about them.
Yeah, but you never met them. Yeah, well... I have known my sister a long time. Michelle's so hard on men!
I didn't say she was hard. I brought them home, and I think there was one other boyfriend that you met, even though I had plenty of boyfriends. I just didn't bring them home.
That's because we went to school together. Right. Those guys didn't—but they didn't come home. Well, okay, well, I met them. Yeah, but they didn't meet Mom and Dad. No, they didn't meet Mom and Dad, but that's because we weren't in Chicago. Anyway...
It all that matters is really how it turned out, right? This is the sibling—it's like, ugh, you know. You rejected him at first, right?
Yeah, yeah. Because Barack was—I was assigned to be his advisor. And that didn't mean I was his boss, but every—I was a first-year associate, so they tried to pair first-years with new summer associates just to help them get acclimated and to kind of give them advice, to sort of mentor them for the summer. So I was his mentor, right?
So he comes in, he's late. So I'm thinking, "Okay, this guy's trifling," because we didn't in the Robinson family, we didn't do late. But it was raining, and he didn't have an umbrella, and so he was a little wet. So I was a little annoyed. But he stood up and he was tall, and he was more handsome than his picture. So I sort of thought, "Oh, okay, not what I expected."
So I took him around the office, got him settled into his office, took him out to lunch for that first day, and we talked for like hours. And I knew that we were going to be friends. He was smart, he was funny, had a good sense of humor, didn't take himself too seriously. So we clicked right off the bat.
And over the course of the summer, we actually became really good friends. I was even trying to introduce him to some of my friends, my girlfriends, saying, "There's this really cute guy who's my advisor," because in my mind, there wasn't any way that the few Black associates there, who both went to Harvard, were going to date. In my mind, I was like, "That's going to be tacky. That's expected," right? And I was just sort of into doing what wasn't—not doing the expected, right?
So my mind went somewhere else. I was like, "Ah, meet all these wonderful, beautiful women that I know," you know? And after a couple of outings, he said, "Well, why don't we go out?" And I was like, "No way are we going to go out. That's just not going to happen. We're friends." And he was sort of like, "Huh, well why?" And he made the case. I said, "Well, you know, I don't think it looks right." And he said, "Who cares about how it looks?"
And so he made his Barack Obama case over a couple of weeks, and finally I was like, "Okay, we'll go out on one date." And so he planned the—after that, it was over. It was a full day date where he pulled out all the stops. I'm sure I picked him up because I had the nice car.
And we went to the Art Institute where he showed me his suave view of art. And we had lunch at the museum, and then we walked from the Art Institute down Michigan Avenue north. So we walked hand in hand, talked slowly, and then we went and had dinner on top of Lake Point Tower, which was a beautiful view of the city. And then we, I think, ended the evening watching—going to Spike Lee's "Do the Right Thing."
So I mean, he had planned culture, art, a lovely stroll, and slowly I was like, "Okay, maybe I—you know, I spoke too soon. Maybe there is something more here." But yes, that's a long way of saying I did say no for a good month or two. But by the end of the summer, we were, I think it was that summer, by the end of the summer I was introducing him to my family.
You both have that through line through your story of ticking the boxes. And then eventually—it's kind of what we were talking about yesterday on your show where you have sometimes—your preconception has to fail you. And you have to feel it for you to understand that maybe a pivot is needed in your life. And that was the same when I was talking about my early journey.
Valerie. This very interesting character in your life. This is the letter I found it that Valerie wrote into me. And she's talking about the pivot you made from being a lawyer to leaving that law firm and going in pursuit of something else. What was the something else you were pursuing before I read what Valerie said to me?
I had no idea, because I didn't know anything. But I started with what I—I had spent some time thinking, journaling about what did I care about.
What was the journal question?
What brought me joy? You know, of all the things that I was doing in my life, what was the thing when I had it on my calendar that I would jump out of bed for, that would change my—the way I felt about the day? And it always had—it went back to mentoring. Because while I was doing all this stuff in law, in my education, I was always finding ways to help younger kids understand how to get here.
So it was the mentoring piece that Craig mentioned—we never talked about that when we think about our parents. That brought me absolute joy, you know? So I started really trying to listen to that self-interested part of me. It's like, "What made me happy?" I never asked myself that. I always did what I thought I was supposed to do.
And making money was one of the things that you were supposed to do if you were anyone who had an opportunity to get an Ivy League education. That was really all they talked about, that's all they showed you. There wasn't a course or major in helping people. There wasn't a course on working with young kids. There's no major for that, especially in the Ivy Leagues. So I knew—I knew nothing about the nonprofit world, I knew nothing about NGOs.
Well, Valerie said—she said the opposite. I'm joking, I'm joking! "The day I met Michelle Obama changed my life forever. I'll never forget the moment she strolled into my office for an interview dressed in all black, hair elegantly pulled back. I was struck by the confidence that she carried herself with. She looked me right in the eye when she shook my hand. She was so poised and self-assured that it was hard to believe that she was only 27 years old.
Michelle told me about her life, how she grew up on the South Side, how much love and support her parents poured into her and her brother, Craig. I asked her why she was considering public service rather than a much more lucrative path as a partner in a law firm, and she said that she had recently lost her dad and her best friend within a year, and their deaths were a painful reminder of the finiteness of life and the importance of making it purposeful.
And how she knew that her abilities could lead her to make a difference in the lives of others, to serve and to give back to the city that she had grown up in. I was so in awe of her clarity of purpose, determination, and vulnerability that I offered her a job on the spot."
That was close, right? It was the same! He's like, "Ooh, what did Valerie say?"
And at that time in your life, you know, those early 30s, what's—what's going on with Mr. Obama?
Oh, by then he was—he had written his book because he was the president of the Harvard Law Review. The president of the Harvard Law Review is the top student at the top law school in the world. And he was the first Black student to be elected president of the Harvard Law Review. And that garnered a lot of attention for him. We were dating at the time. And so he got a book contract to write a story, "Dreams from My Father."
Which I thought was, "Who writes a book at your age?" But he was like, "Yeah, I might as well tell them a story" and, you know, and it was money, right? He got an advance and we were engaged, so he was working on that project. But he was still trying to figure out what he was going to do. And when you're the president of the Harvard Law Review, basically the world of law is open to you. The normal path is that you clerk for an appellate judge for a year or two and then you go on to clerk for the Supreme Court. Then you go on to do appellate work, you have offers from every law firm, you are in demand. Or you can do policy or whatever. That was the normal path.
I was like, "So are you going to clerk?" He was like, "Why would I clerk?" So he didn't work at any of the big firms. He went to a very small firm that was doing public interest work. So he wasn't making a lot of money. He was doing what I was doing; he was going the opposite direction of all the things that were supposed to make us money. But he was like, "Money isn't why I'm doing this. I'm trying to figure out how I can best use my skills to impact the most people."
So he was doing 50 million jobs, and we were cobbling together our payments for our student loans at the time, which were more than our mortgage. We had bought a condominium, we were on our way to building our lives together, but we were in deep debt. So while we were both pursuing our deep love of being in the community, our incomes were going in the opposite direction of where they were supposed to go.
But we were in this together. Politics hadn't really come into the fold yet; it wasn't a part of the conversation. But we were both kind of on these parallel paths, kind of figuring out how do we take all these skills and all this energy and help people. I was working in the city, he was working everywhere else and writing a book. And we were just kind of, we were sort of plotting ahead.
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I guess I'm seeking advice from both of you on love and romance and relationships, because in your—I'm in my early 30s now. And when I looked at both of your stories of love in your 30s, it's not a straight line.
Oh no. It’s not a straight line to say the least.
Michelle, you talk about going to marriage counseling with Barack. What does someone like me at 32 years old, who is in a relationship, who is aggressively pursuing a career because I feel like I've got to build and build and build and set my family up for the future—what advice would you both give me about navigating love through that part of your career where it's go, go, go, go, go?
For somebody with your personality in particular, my advice would be that I could see you thinking, "If we're—if I've got my stuff together and I've got my path going over here and you've got your path going on over there, as long as we're both trudging along and pushing, we're going to be good."
And generally that can work because you can be two independent beings out there with—basically slaying your own dragons, making the choices about which dragons you slay and how much armor you want to use. You're independent people, and that feels good right now until your first and most important joint project happens, which you told me you want: you have kids.
That's oftentimes when the rub happens. Because when you—when you bring life into the world, that's the project where you can't do that independently. You can't—you can't be on one path and your partner on another. Because raising those kids and making them as whole as you'd want them to be has so little to do with the dragon you're slaying now than it does with how you partner and engage and make choices together on these little creatures that you're going to love more than anything in the world.
And you're not going to want to get that project wrong. But you've got to work with your partner, you got to communicate, and that's when it gets really hard.
Is that when it got hard for you and Barack?
Yeah, yeah. Because, you know, when you're independent operators in the world, he's off, he's traveling, I'm traveling. Maybe I don't see him during the week and then on Saturday, whoa, it's great, I love you, I missed you, this was so cool, tell me about your life and ooh, this is sexy and it's all of this, right?
And it feels—and you're moving and you also are okay having a break. It's like, let me miss you for a little bit, so I don't care that you're traveling or that you're everywhere. But the minute there's a little baby that is waking someone up, and if there's one person that's carrying the burden of that—if one person's dream stops because they are taking on the lion's share of things, and you're still going to the gym and you're still slaying your dragons at the same rate, and you haven't looked over at your partner who maybe is now stuck at home because she's breastfeeding or she made a set of choices to make this little creature work—and you guys haven't had a conversation about that and what that balance looks like because you're just slaying your dragon at the same rate... Oh, there's going to be problems.
There's going to be resentment, there's going to be fatigue, there's going to be measuring and counting and all the things. So I think it's just important to communicate now, to start doing the work of making sure that you guys are defining your one life together. That you're deciding together now what dragons are going to be slain and who gets to do what when. And what does that feel like? Are you going to be working all the time? Are you going to be traveling all the time on the road? Is she coming with you? How does she feel about that?
Did you have that conversation?
No, no we did not. No, because I didn't know that that was the thing that you had to worry about. Because when you're in the midst of it, it—when you're in the midst of pursuing your own independent journeys, it's beautiful, right? It is. It's like I'm independent, he's independent, we get along, and then all of a sudden someone's legs are cut off from under them. Someone is making a different set of sacrifices that weren't negotiated.
Because of children?
Because of children and because of life.
You had some pregnancy struggles. And I've spoken to many women on this show who have been through similar pregnancy struggles, and it's something that I've—it's actually a big conversation in my life at the moment but also just some of my friends in my life around trying to get pregnant and the IVF journey which you went on. What do women who are struggling need to understand, and how did you feel when you were contemplating the IVF journey and when you started to have struggles conceiving without IVF?
It's the thing—because we don't talk about our bodies and women's health and there's just not a lot of conversation about marriage or pregnancy or any of this. Our parents don't talk about it, their parents before them don't talk about it. So you imagine your life as you're checking boxes: I'm waiting, I've delayed having kids until I found the love of my life and now I'm going to get pregnant. And no one tells you that there is really a biological clock; that's not false.
We have partner in podcast Dr. Sharon Malone who wrote a book "Grown Woman Talk" where she's talking—she's sort of ripping the curtain off of women's health questions. And in a conversation with her, she reminded us that women, we are born with a finite set of eggs and we don't get any more. And every month we're losing them. And so there is a period of time, usually, and it's different for everyone, usually in your 30s where you go from fertile to not. And it's like falling off of a cliff.
And I'm like, "Why didn't anybody tell me this?" Why wasn't—why weren't people talking about this? So by the time I—we started really trying, which worked perfectly for our careers and maturing and having everything set, right? Because that's what we're—we're trying to get everything set. Unlike our parents who had us, we lived in a little bitty apartment, one income. Our generation, we're worrying about "I want everything set." I guarantee you, you have things way more set than any of our parents had before they started having kids.
But we're waiting for everything to be perfect, no friction. We don't want any friction, right? And while we're waiting for our lives to be perfect, that biological clock is ticking. So you start trying and it's not working. That's when you go to the doctor and they tell you, "Oh, you're—you're running out of eggs. This is normal. I mean, you're going to have trouble getting pregnant." And so try a little bit, and then now it's time for IVF—if you can afford it, which it wasn't covered by insurance at the time.
So it's just a shock to the system. And as people who like learning and like knowledge, you really sort of feel gipped that why is this such a secret? Which is why I talk about it openly and I talk about miscarriages. Because the other thing I learned is like most pregnancies—a good percentage of them end in miscarriage. That people have been having miscarriages for years but not talking about it. So when it happens to you, a box checker, somebody that thought life was going to be so and you did all the right things, to have things not work out and to know that it was going to be that way and nobody told you so that you could be prepared for it, it just—it was a blow.
And then as a woman, you're walking around owning the blow as if it's your fault. And so you're carrying around that burden, and that can become the first pressure point in a marriage. Because emotionally, you've got a woman that is carrying all of this, feeling like a failure, feeling not having anyone to talk about, having her hormones go up and down literally, right? Probably dealing with depression and maybe some postpartum—still working, still slaying dragons, still on the path, but she's carrying it all on her own.
And then if you do IVF, the bulk of the work, the shots, the—we are the petri dish in the IVF process. You show up, you come in a cup, and "Oh, yay, good for you," right? And you're a little mad about that too because women have to get shots every week and you have to go back and forth in between having your job, your high-powered job and keeping it all together. You're at the doctor's office every month trying to count your eggs and hoping that you're producing eggs, and then you have to go through the procedure.
And then you have to be pregnant for nine months as your partner is going to the gym and keeping his figure and all of that. So it's a long way of saying there are just many natural reasons why marriage, infertility, trying to have kids makes things difficult. It's like I try to tell couples: of course it's hard! Just listen to what I said, right? Like, if you're having some issues in your marriage, it's not you; it's the process of marriage. It's just all hard.
Because guess what happens when it all works out right? You know what you end up with? Babies! Little people with their own sense of everything. They mess you up. You love them dearly, but they're a hassle. And they're demanding and they have their own whims, and now they're in your world, in your partnership. They are factored into everything. So even when everything works out and you have the 3.2 kids and you got everything right, it's still going to be hard because now you're developing a life.
So I talk about these things because I think that people give up too quickly on marriage because there is so much friction built into the equation. And if you're not getting help, talking about it, going to therapy, just understanding how things are changing and how do you continuously renegotiate your relationship with your partner, I just see people quitting because they look at me and Barack and go, "#couplegoals," you know? And I'm like, it's hard. It's hard for us too.
But I wouldn't trade it. He is, as the young people say, he is my person.
Was there ever a moment where you thought...
You know, there are the moments where I'm like, "Eergh!" Right? But was it real? No, no, no. There was never really a full moment. There are moments when I was resentful, there are moments when I was mad, there are moments when I didn't feel like I got enough attention. But it's like, don't you feel that in your relationship right now? So it's just me understanding, "Yeah, I was mad, but I forgot even why I was mad," right? That's—it's like, "Was I really that mad? Oh, did I say that? I'm sorry, I didn't really mean that."
So no, in the end, no, we're—and the beauty of my husband and our partnership is that neither one of us was ever really, ever going to quit at it, because that's not who we are. And I know that about him; he knows that about me. So no.
Both of your lives change because of a decision that former President Barack Obama decides to make, which is to run for public office. And that has a profound impact on both of your lives because it's the most powerful job in the world, you become the most famous family in the world. When he said that he was going to do that, did you believe that he was capable of it?
Yeah, that was the problem. I knew that—in my heart I knew that he would make a phenomenal president. And as I've written in "The Light," the truth was that my initial reaction was like, "Oh no, oh my God, don't do this." It had everything to do with having the foresight of knowing what this would do to our lives. I mean, I was projecting that if you win, which I thought he could and should—he would be somebody that I would want as my president—it was all about: our kids are little, we're going to have to move, how do you raise kids in the White House? It's dangerous, as the first Black potential president we knew there'd be death threats, there was just all—how would we afford it?
Because it's expensive to live in the White House. As many people don't know, I mean, much is not covered. You're paying for every food—every bit of food that you eat. You're not paying for housing and the staff in it, but everything, even travel. If you're not traveling with the president, if your kids are coming on Bright Star, which is the First Lady's plane, we had to pay for their travel to be on the plane. It is an expensive proposition, and you're running for two years and not earning an income.
So all of that was in my mind: how would we manage this? So my fears were—what came from the fact that I thought he could win. Because if I—maybe way in the back of my mind, I was hoping that maybe he wouldn't, you know, that this would be the last thing he would do. But I knew he had it in him to make this happen.
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This has never been done before: a newsletter that is run by 100 of the world's top CEOs. All the time, people say to me, they say, "Can you mentor me? Can you get this person to mentor me? How do I find a mentor?" So here is what we're going to do. You're going to send me a question, and the most popular question you send me, I'm going to text it to 100 CEOs, some of which are the top CEOs in the world running $100 billion companies.
Then I'm going to reply to you via email with how they answered that question. You might say, "How do you hold on to a relationship when you're building a startup?" or "What is the most important thing if I've got an idea and don't know where to start?" We email it to the CEOs, they email back, we take the five-six top best answers, we email it to you. I was nervous because I thought the marketing might not match the reality, but then I saw what the founders were replying with and their willingness to reply and I thought, "Actually, this is really good." And all you've got to do is sign up—completely free.
Did you ask for any commitments or promises if he were to win?
I—it wasn't very thoughtful. I told him that he definitely had to quit smoking because he was still toying with smoking—he was in it and not in it. And we had to have enough of a nest egg so that we wouldn't be just financially broke at the end of it. And you know, I thought that was going to cut it, right? Because we weren't in really—we were just starting to make decision moves where we were recovering the income that we lost making our purposeful moves. So I kind of thought that was going to be the deal breaker.
But then he was chosen to give the speech at the Democratic National Convention and he just blew up. And as a result of that—and maybe I'm getting it out of order—"Dreams from My Father" went back on the bestseller list, he wrote "Audacity of Hope," so there was all this income that was being generated from his book sales. He kind of looked at me like, "I think we're okay." And I'm like, "Darn, drats."
So I didn't know enough to know what to ask for. We were flying blind. I didn't know what that journey was going to be and what I would need to negotiate for myself. And that was a bit problematic—problematic not to know what I needed.
What should you have said?
Oh... I should have said that I needed his team to really, truly value that he had a family. That I shouldn't have just said, "Well, this is what it takes to get this done." I mean, it was almost like the consultants that sit around; it was almost like "this is the way it has to be."
Remember, the legacy of presidential office doesn't recognize families. It is not designed. You get in there and it all revolves around the commander-in-chief, who has always been a man. And the whole system of it doesn't really take into account that there's a wife and kids and their needs and the demands on them.
So I wound up having to fight for a lot of stuff on my own. If I had known what I know now, I would have asked for different things. But ultimately, I had to push to get the things that we needed to be able to operate as a family. Even when it came down to how the Secret Service protected little kids.
The girls had to have a detail, right? So they started school in second grade and fifth grade in armed cars with primarily men with guns, going into a new school—strangers that they did not know. And the detail—these weren't—they weren't practiced on going to Sidwell's second-grade schoolyard. So we had to basically work on: how do you do this for little kids?
A lot of times details just float through, they continuously move through. It was important for me that we find two detail leaders that stayed with the girls for most of their time until they became teenagers, because it was sort of like you know these people, right? At least they get to know—they couldn't just have strange men coming throughout. And we had to kind of fight for that.
So those—that's just one example of the—what living under those things and trying to raise small children—the kind of things that the guys in the West Wing weren't thinking about as they were fixing the financial crisis and dealing with Syria and on and on and on. I was trying to make sure that our kids came out of that process not crazy and whole.
Being the first Black First Lady in the White House, the public scrutiny that that comes with is a unique type of scrutiny. Being the First Lady anyway comes with tremendous scrutiny.
Absolutely.
Since stepping reluctantly into public life, I've been held up as the most powerful woman in the world and taken down as an "angry Black woman." I've wanted to ask my detractors: which part of that phrase matters to them the most? Is it "angry," or "Black," or "woman"?
I've smiled for photos with people who call my husband horrible names on national television but still want a framed keepsake for their mantel. I've heard about the swampy parts of the internet that question everything about me, right down to whether I'm a woman or man. A sitting U.S. congressman has made fun of my butt. I've been hurt, I've been furious, but mostly I've tried to laugh the stuff off.
Craig, if that was my little sister, public scrutiny elevated to the highest office in the land—I'll ask you the question: how did you feel?
Let me back up because I had been a basketball coach at a big conference. I always had to tell them, "Don't worry about what people say in the newspaper. I am doing exactly what I love to do, and that doesn't bother me at all."
But then once they got in the White House, I had to tell myself that. Because I knew that they were doing the best that they could do for the most people, no matter what anybody said. But because it's my little sister and brother-in-law, and my mom was in the White House and my nieces, I would find myself becoming enraged and I'd have to coach myself to: I know they're doing the best they can do for the most people, and I would not want anybody else sitting in that seat but my sister and brother-in-law.
And that's how I got through eight years of that. Because it's relentless. It is relentless, it is global, it is unfair, and it's mean. It's just mean. And you know, I lean back on the lessons I learned from my parents a long time ago. I wasn't worried about what anybody said who wasn't at this table.
And I coached—I counseled my family, my immediate family, the same thing because our kids—our older kids were old enough to read the papers and read the news and things online. Michelle always talks about this: in order to get through that, she always says she needed the village of her friends and family. And I just wanted to be a supportive piece of that, and we tried to get out there as much as we could and make it as normal as you can—you know, having Thanksgiving in the White House. That's an oxymoron, almost: having a normal Thanksgiving in the White House. But we tried to make it as normal as we could.
And yourself, how does one deal with such scrutiny? The scrutiny occurs for eight years as the public are at war with different opinions and ideas, and often the president is seen as the villain or the hero in that context, and the family is obviously impacted by that. But then even beyond the White House, it's relentless. Is there a framework? Is there an underlying belief? Is there a set of values?
You know, it goes back to what we learned earlier. I think I approach everything with empathy. And Barack does too, and he helps keep me in check because he is so smart and he believes in ideas and he understands context and history.
We are always putting these times, these moments, into a greater context. We're trying to understand where people's rage, ignorance, hatred, whatever it is, where it comes from. And it usually doesn't have anything to do with us. It has to do with the state of the world.
And the world and this country is unfair for way more people than it is fair to, and it impacts people of all races. And folks are angry and they're scared, and they don't have enough opportunity. And when people are put in that position, they lash out, they're mean, and we otherize people because it gives us a sense of stability. We pick on someone, someone has to be a little more oppressed than us.
But that doesn't make what they say or feel true. Just because you say it or think it about me, in the way that I had to overcome the racist low expectations of us in our childhood, it's the same thing. It's like: you're not mad at me. You don't understand a lot about the world, and you've been told a lot of things about who people of my skin color are. You've been taught to fear me because of the history of our country, because of what you're going through.
And when you put yourself in other people's shoes, I do get why people are afraid, I do understand it. And also Barack helps me remember, which I experienced myself: he says this is still the country that elected Barack Obama twice. And people in this country are proud of that. There's a very small percentage of people who would never, ever in their lifetime want a Black man to tell them how to get down the street to the grocery store; they can't hear it.
But this country is bigger than that. And we saw it, we experienced it. As much hatred or conflict or ridicule as we had, we also had so much love, so much goodwill. So many people who tell us even today, "We miss you guys." And it doesn't look like any—you'd be surprised at what corners of the world. And our daughters felt it and feel it. That is true too.
We are in a really tough time right now, and we are being led sadly by people who are not being, in my opinion, their best selves for whatever reasons they have—whatever is moving them to push this country in this direction, whatever hurt they have. Billionaires have their hurts too, you know? Business leaders, people in power who want power and haven't understood their "why" can lead us down some dark tunnels, right?
But it's that empathy for me, that ability to kind of give it some perspective, that allows me not to take all that hate in and to really see the light in people. It's just the better way to live. It keeps us from being embittered and it keeps us hopeful and it keeps us working for people. So it's kind of a necessity to get through it.
Marion, your wonderful mother. She was a prominent figure throughout that time in the White House. What did she give you that helped you through that journey of being thrust into the very, very highest mountain in public service? What role did she play, what force was she at that time for you both?
For me, she continued to be that soft place to land. The place where she always saw me—always, always saw who I was. And she was that soft place for our girls. She was common sense right in the middle of the White House.
In that big house, people, just with her sheer presence and her wisdom, that old-fashioned wisdom, she was the center of that house. Everyone came to her door and sat in her room and sucked up her wisdom. The butlers, the florists, the housekeepers, the chefs—they were all mothered in some way by her. And so she was that for me, for sure.
§02Transcript — part 2
I can still see her in your face as you reflect.
She's there. She is there. I see it in his face more—you know how you don't see yourself in your—like I don't think I look like him at all, right? But he looks just like my mother!
How did that loss impact the family? It’s 2024, so it's fairly recent.
Yeah, yeah, it's still painful. But again, I'll go back to what I said at the very beginning when you talked about the values we had: the underlying value was unconditional love. And Michelle and I knew that our mom loved us. And even more importantly, she knew we loved her, she knew her grandkids loved her.
So while her dying was traumatic and disappointing and sad, I always feel like she knew where we stood. And it was right before she passed away—we knew she was going to be leaving us—and I said, "You know, Michelle and Barack are on their way." And she was like, "Oh, that's nice." And she just said that.
There was nothing left unsaid. Yeah. And there was just a peace. I just miss her. But I feel like she knows how we feel about her, and that's always comforting. And speaking of comfort, that's how I felt when she was in the White House for them. Because I didn't have to worry about them when she was there.
Have you processed the grief? Have you been able to?
I'm sure I have more than he does because he doesn't process stuff; he just keeps working through it. But yeah, I think I probably—for me, making choices for me, I feel like now I have permission to do what I want to do. I think part of our podcast is part of that legacy because, at least for me as a woman, I think at 61 I'm finally owning my wisdom in a way that I don't—I think it takes women until we're about 60 to be like, "I think I know a thing or two."
But that wisdom comes from her, and she's our last line of elder wisdom. And so now we're up. We're next up, believe it or not. Me and Craig and our family, we're the ones. So I.M.O. [In My Opinion], our podcast is sort of that offering back. It's like, all right, let's—let's keep up the mentoring that we were taught. Let's create our table and be a place where people can come for the little bit of advice and conversation in the same way that you're doing, Steven.
It's like when you—when you learn something, the way you hone in on it is that you keep teaching it to other people. You said that, right? And so this is sort of helping us continue to, by helping others—which is a thing we both get great joy from, that mentoring, just being able to have this conversation here and maybe somebody's going to get something from it that I missed when I was their age.
That brings us joy. It's like we're here for a reason other than making a bunch of money and living a nice life or being famous. It's like, maybe we can help somebody.
Permission. Yeah. I was watching the coverage of your decision—your decision to sort of take back some of your control and not go to Trump's inauguration. Is that one of those key moments in your life where you did take back control?
Absolutely. Absolutely. What do I want to do in this moment? As a box-checking person who has been box-checking her whole life, doing the right thing, trying to always be an example, always going high—I think I now earned a little bit of "well, how do I feel?" Do I want to upend my life and take this trip and leave my peace and my children for this?
I don't—I didn't have to. That was my choice. And I was not—I would have never made that choice. I would have always done what I thought was the right thing to do for other people to set an example. And I think I just told myself, "I think I've done enough of that." And if I haven't, then I never will; it'll never be enough. So let me start now. This is the perfect time to start. So yeah.
Obviously, off the back of that, people start to swell rumors that there's an issue with you and Barack and there's a divorce coming. I can, I mean, you can say it yourself, but I don't think that needs to be addressed.
What I will say—you know me now well enough, Steven—is if I were having problems with my husband, everybody would know about it! I’d be like, "And let me tell you!" And then he would know it and everybody would know it. I'm not a martyr. I'm not, you know. And I would be problem-solving in public and be like, "Well, let me tell you what he did!"
They've got a podcast now as well, so we would know! Wait, but if they were having a problem, I'd be doing a podcast with him!
Your podcast is incredible and I highly recommend everybody goes and checks it out. I'm going to link it below on the screen. I was fortunate enough to be invited on it yesterday, and we had a wonderful conversation in there.
We surely did.
I.M.O. [In My Opinion], it's a reflection of this kind of conversation. It's human, it's a discovery of life. You're bringing people on there that have wisdom to share, but you're passing through that to understand the world that we're all living in and the struggles that we're all contending with. So it's a wonderful, wonderful space on the internet. I highly recommend my viewers go and check it out on Spotify, on YouTube, wherever you get your podcasts.
It's a must-listen in my opinion because it's so rare that we get an insight and a window into the family but also just the human story of everything that you've both been through in your lives as a really successful coach, as a stockbroker, as the First Lady, as a mother. And then everything you're going to do thereafter. You're helping me navigate the world and you help other people navigate the world because not everybody has that foundation. Not everybody has the parents at home, not everybody has—especially in Black communities—not everybody has the mentors. And you're vicariously mentoring the world through that show. So please do continue. It's a wonderful thing to get to podcast and I was so happy to hear when you joined the industry.
We have a closing tradition. And the closing tradition on this podcast is that the last guest leaves a question for the next guest, not knowing who they're leaving it for. So the question that's been left for you both is: **If there is one person in your life that you have been afraid of putting up a boundary with, but know you need to, who would it be?** Now, you don't have to name them, but I guess this question is just about boundaries.
The inauguration might have been the one! Yeah, I think I've kind of done that. Yeah. At this age, we got our boundaries well set. I think that's—that's—it's the act of practicing setting boundaries, period. And I'm having that conversation with my daughters now.
I mean, it takes a lot of work to learn how to say no and how not to be people pleasers, which I think there are more of us out there than we like to admit. It takes practice and it takes decades of practice. And I am constantly giving my girls tips on how to do it. How to politely do it, how to not jam yourself up, how to not say yes right away, how to take a moment and say, "Let me think about that."
Some of a boundary is just saying, "Wait, I don't have to give you an answer right now. Let me go back and sit in the request and figure out whether it works for me." And so many of us as pleasers, we're trying to give people an answer right away and it's hard to look someone in the face and say no. So I think it takes practice, even practice in the wording of it.
And then the older you get, the easier it gets because guess what you realize? Your "no" doesn't usually change anyone else's life. They might be disappointed, but guess what? It all—they will find the next person that they'll ask. The world continues; none of us are that important. And people can deal with a little disappointment every now and then.
And with that, I thank you both. It’s such an honor to get to meet you and to learn so much from you. And yeah, the rise of your family, the grace, the humility, and the way that you've conducted yourself has been a huge source of inspiration for me as a young Black man that's navigating the world and that's looking up to role models that aren't often as in close proximity in our lives. So thank you so much. I can't tell you how much you had a profound impact on me, thousands of miles away in a small little village in the Southwest of England. It had a profound impact on me in shaping the man that I became in my life, and that's a credit to your family. It’s just the greatest honor that I got to speak to you both today. So thank you.
It's been a pleasure.
Absolute treat to be spending time with you. Thanks for having us on.
And hopefully it won't be the last.
I hope not. Yeah.
I find it incredibly fascinating that when we look at the backend of Spotify and Apple and our audio channels, the majority of people that watch this podcast haven't yet hit the follow button or the subscribe button wherever you're listening to this.
I would like to make a deal with you. If you could do me a huge favor and hit that subscribe button, I will work tirelessly from now until forever to make this show better and better and better. I can't tell you how much it helps when you hit that subscribe button. The show gets bigger, which means we can expand the production, bring in all the guests you want to see, and continue doing this thing we love. If you could do me that small favor and hit the follow button wherever you're listening to this, that would mean the world to me. That is the only favor I will ever ask you. Thank you so much for your time.
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The Diary of a CEO is brought to you by Progressive Insurance. Do you ever think about switching insurance companies to see if you could save some cash? Progressive makes it easy. Just drop in some details about yourself and see if you're eligible to save money when you bundle your home and auto policies. The process only takes minutes, and it could mean hundreds more in your pocket. Visit progressive.com after this episode to see if you could save. Progressive Casualty Insurance Company and affiliates. Potential savings will vary, not available in all states.