Michelle Obama Opens Up: Her Struggle To Feel Like She's “Enough,” Mental Health in the White House & Lessons from Childhood w/ Craig Robinson

Welcome back my friend. We have some big guests today. Former First Lady Michelle Obama and her big brother Craig Robinson are on the School of Greatness to really open up and share in ways they've never shared before. Both of them dive in deep about growing up in a small Chicago apartment together with parents who instilled unwavering confidence in them. And Michelle and Craig offer powerful insights on building self belief, raising grounded children amid privilege, and maintaining your core values through life's most extreme challenges. In this conversation, they discuss navigating the pressures of the White House while remaining authentic to themselves and their perspectives on emotional regulation during high stress situations. Also, Michelle's reflection on finding her deepest confidence at 61 is especially inspiring from my experience in this interview, proving that self discovery is a lifelong journey. And throughout the conversation we have a ton of fun. Some really interesting conversation about Craig sharing how he played basketball with Barack Obama and he had to pass the basketball character test before Michelle would continue dating him. Also story about how he played with Barack and Michael Jordan around the same time, which was kind of interesting. Michelle talking about the importance of emotional regulation and staying in the pocket during extreme highs and extreme lows and how she's been able to maintain this calm, cool emotional state through all the ups and downs over the last 30 years. Why Michelle feels more confident now than ever before and also finally answering the question, am I good enough? She reflects on her time right now in therapy and all the lessons that she's been experiencing and learning about with herself and reflecting on the past 10, 20, 30 years. The whole conversation is inspiring. They both share things I've never heard them share before, and I'm so excited for you to hear this conversation again. Make sure to share this with one or two friends that you know, someone that you want to inspire, someone that you care about. Send them a link to this episode and make sure to follow Michelle Obama and Craig Robinson. We'll have their social media and their podcast linked up on the description of this episode. I'm so excited about this. I hope you enjoy. Let me know your thoughts online when you listen. Please share it with a friend. And without further ado, let's dive into this episode with Craig Robinson and the former First Lady Michelle Obama.

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Welcome everyone to the School of Greatness. We have Michelle Obama and Craig Robinson in the house. Thank you guys for being here. Very excited.

Thanks for having us.

Thank you. This is awesome.

Excited.

Very excited. You're in a brand new studio, the School of Greatness. Beautiful, elegant, beautiful, elevated. We've got an amazing team that helps set this up. And one of the things that right, fake fireplace going over here. I started the school of greatness 12 years ago because I wanted to learn the lessons that I feel like I didn't learn in school.

Okay.

That I wanted to learn how to overcome insecurity, how to deal with failure, how to deal with navigating intimate breakups and getting into relationships consciously. And all these things that school didn't teach me. You guys both went to Ivy League schools and you have done incredible things since college. But what I'm curious about is what is one lesson each one of you has taught each other as adults that you didn't learn in school? Craig, I'll start with you. The biggest lesson that Michelle has taught you as an adult that you didn't learn in school?

I will tell you. I've learned a lot from my sister and you know, people now that she's iconic. People think that my sister is older than me, but she is really 20 months younger than I am. And she is so full of wisdom. I could probably tick off about four or five different things. But recently, not in. In the. Not in the recent past here you said to me to make sure. Because I have four children, two adult kids, but I have a 15 and a 13 year old. And I am, as she will tell you, I'm the charter member of the odc, which is the old dad's club.

Okay.

And being a charter member, you're continuously parenting. And she said to me, make sure that you're taking your wife out on dates. And, you know, my wife is a coach's wife, so she's used to handling 20 kids, 20 student athletes at a time, you know, or 20 people in our house at a time, and not saying a word about what her needs are.

Putting herself last.

Putting herself last. Like a lot of women do. Like most women do. I can even say that. And it was such nice advice to hear from her because it enabled me to do it before my wife had to ask me to do it. And it was. It's really. And we.

If I talk to Kelly now, she'd say, you're doing it.

You can. You can check in.

Yeah, yeah, no, this is really good.

Really check. And we don't do anything but sit and talk about the kids, you know, when we go on these dates. But it's fun. They're old enough, we can leave them at home on their own. And so she gave me that advice probably about nine months ago, maybe. Maybe it was a year and a half ago.

And how has the relationship grown or thrived from that?

It feels like it's the same, but we're having fun when we go out, you know, we're having fun. And. And it also allows us to let the kids sort of have the place to themselves and not tear it up and give them some. Give them some rope. And so it's a growth. It's a growth region for all of us.

That's a beautiful lesson.

Yeah, it's a good lesson I've learned.

So what's, Michelle, what's the biggest lesson your brothers taught you about life or anything that you didn't learn in school?

Craig is. There's such a youthful, joyful innocence in him that you've never lost. And that creates a lightness, you know, that I think other people feel. I mean, I joke that everyone loves Craig, you know, and I'm among them. Right. And if he were a different kind of brother, I'd probably hate him because everybody loved him so much. I Teased that my mother loved him more than she loved me. It's like all I, you know, I'm in the White House. She's living in the White House, you know. When's Craig coming here? He showed up, you know, we're at his house in Milwaukee, in Maquan. Milwaukee. And she's Mequon somewhere in. Near. Off. Outside of.

It's cold there.

It's hard to speak the words, you know.

Exactly.

It's freezing.

Exactly. I know.

You know?

Yeah, yeah.

And she's raving about the wine he has in Wisconsin. I was like, mom, you live in the White House. What more do I have to do? I'm first lady of the United States. Right? But any little sister could be resentful, but retaining that joy, retaining that kindlet kindness. And he's different as a coach on the bench. Sometimes he scares me, and I'm like, who is this dude yelling at these little boys? But I'm trying to hold on and, and, and embrace more of that, because in my line of work, you know, you know, there's a lot of cynicism. There's a. There's, you know, there are a lot of problems. There's a lot of in your face reasons to, to, to be less than optimistic. And when I'm around you, Craig, everything is just, like, wonderful and new. No matter how many times he's seen it, he enters a space with this level of joy and, and awestruckness that, you know, it's. It's important to, to keep.

Did you ever lose that when you were in the White House? Like, being in awe of how far you had come and how far you and Barack had, you know, created your lives together, or did it. Did you ever just be like, oh, this is the norm now.

And I think we practice just staying level, not getting too high, not getting too low. I mean, and I think that became a habit. My husband's nature is that he is very cool, calm, collected. He's an athlete. But he's the slowest walk in person I've ever.

I'm no urgency.

Do you walk that?

Island time.

He's an island. Island time goes.

And he's like, why are you walking so fast? It's like, if I walked any slower, I'd be walking backwards. I don't even know how you do it. So he has a natural calm. My temperament, I'm a little more fiery. And if I were to let my emotions guide me, if I got too pumped about the good times and too down about the bad times, I'D be a mess. So I think there has been a little of. Yeah, that's fine. Yeah, we just did that. Okay. Great Wall of China. All right, what's next? Meeting with the Pope. So good to see you. Let's move on.

Really?

A private meeting with Nelson Mandela. That was really cool. But okay, now we have to do. You know, it's just because the lows were like, we're mourning kids that were shot. You know, we're at a site where people have lost their homes in a horrible tornado. We are grieving with military families. I'm visiting Walter Reed, and, you know, in the midst of the war and seeing rooms and rooms full of young men with their legs cut off and young wives with babies wondering, you know, how are they going to live going forward? I mean, you talk about the peaks in the valleys, and I think getting through that, you just. I've just learned to remain a little unplussed either way, just to get through it. And then in comes miss here. Whoa. Wow. Look at this. And it's like, that's so sweet. You know, I mean, there's. Sometimes you need to just be like, this is the coolest thing ever. So, yeah, I do think that I practiced a little more.

That's so interesting.

Staying in the pocket because you had to really.

It sounds like you had to keep your nervous system steady at all times. Otherwise, the highs and the lows could have made you exhausted emotionally, it sounds like. And as a basketball coach, you have to motivate and keep people steady as well when there's momentum and it's going. And when you're down by 20. So did you now. But as siblings, this is actually the first brother sister combo that I've had on the show in 12 years. I've had siblings, but not brother sisters. So this is interesting. Were you able to just be her big brother in the height of all this while she was in the White House, or were you trying to coach her like you would your athletes?

Oh, the former. Because I could not coach her like she's an athlete. Because I'm not saying you're not coachable, but.

But it's not in tennis right now, you know?

No, I was more there for support.

Okay.

Right. I was there. I was. I was coaching her up on the side to get her. Her spirit up rather than technical things. Here's what you should do. I'd like to think that when we came to town, my family, my wife Kelly and the kids was like, all right, it's time for us to have Some fun like the old days.

Bring the lightness, the familiarity.

Yes, yes. Bring the.

The normal.

The normal. The normalcy that we used to have when we were in Chicago when our mom picked up all four of our kids and took them to one of our houses and we had a barbecue on, you know, Friday night. So that was. I felt that was my role when they were in the White House. And then, you know, I would say being able to sit with Barack and watch a basketball game, although he. He's such a good multitasker, he'd have so much stuff going on and then have the game on, and he would know exactly what's going on in the game while he's doing all this other stuff. Interesting. But it just was nice to sort of have normal family time, albeit in the White House.

Yeah, yeah. Try to make it familiar.

In a nutshell, ignore all of this.

Yeah, exactly.

Bump proof.

Class.

I also heard that you asked your brother to play basketball at Barack. Is that right? To, like, feel out if he's a good guy or if he's.

Yeah. Well, Louis, you can appreciate this because being an athlete, and I know you're.

A football player, But I played D3 basketball, but not D1.

I was just going to say, most football players fashion themselves as basketball.

Of course, I was a basketball player.

First, and then that's what they all.

And then I stopped throwing, and I was like, I'm not going to make it in the NBA, so let me go try football. I did.

So my dad used to. My dad and I talked basketball. Now, my dad wasn't a basketball player, but we talked about sort of basketball and how the game brings out your real character.

It does.

Especially pickup basketball because you have to call your own calls.

Oh, I know that.

And so my sister heard us popping off about that, and she said when they first met, hey, will you take Barack out? Because I really like this guy. I want to see if he's really real, if you like him based on what you and dad said on the court.

And how long have you known him before?

It was the first year.

Oh, God.

It was the first year that we were dating because it was like, I like him. He's. He's cute, he's funny, he's smart. We're starting to get close. But who is he?

What's his character?

What's his character?

What's inside of him?

And, you know, and when you're with the family, you know, everybody is going to perform, you know, at Thanksgiving dinner or if they were just to go out for drinks. I mean, Barack was smart enough to. To know how to. He presents well. Right. But. And it wasn't just overhearing them talk about it. I mean, being the sister in a basketball culture. Right. I was dragged along to all the sports. I spent my life in gyms.

I was absolutely salty about it, but.

You know, but it was just the norm. We weren't going to cheer him on in a sport because at the time, title nine hadn't kicked in. And even though I was kind of a tomboy, very athletic, there wasn't a place for me to put that energy. Nor was it cool for girls to be athletes, especially if you were tall, because everybody assumed that. So I was the sister on the sidelines, got to meet all the cute basketball guys. So I wasn't complaining. But I know sports and I understood the game. And I dated people that were on, that were on Craig's team. And I'd hear about them, like, how were they in practice? How were. Were they coachable? Were they. So I believe that myself, that, you know, you learn a lot about a man in particular and how he engages in the game. Right.

100%.

So I was like, take him out. Really? So in the first year, Barack said he was a basketball player.

Like, oh, let's see if he's a real player.

Yeah.

And if you say you're a player and he didn't talk himself up, but he is a basketball fanatic. And I kind of wanted to know, was he an athlete? You know?

Yeah.

Is he really an athlete?

Is he not?

I don't know if I'm gonna.

I wouldn't mind. I wouldn't have minded if he wasn't, but I would have been suspicious if he had said he was. And then he couldn't even dribble the ball.

He talked a big game and he couldn't back it up.

Exactly.

You know, so wait, so he would dribble the ball? So can you walk through the scenario of how this. Did you call him and say, hey, let's go hoop it up. Let's play a pickup game? Is it one on one? What's the scenario?

Let me start with how she asked me. She said, hey, I want you to take him out and I want to know what he's really like. And the first thing I said, I'm not doing your dirty work.

No.

Because I was worried that if he turned out to not be a good basketball player, I'm the one who has to say, oh, no, this guy's a complete jerk.

But you're Also, you were an Ivy League, like mvp. You were a professional. You got drafted.

Let me get to that.

You were a pro.

So listen, that. So, so it would be the guys I worked out with. He, it wouldn't be fair for him. So I said that to her, she was like, oh, come on, please, you gotta do it. So I called up some guys that I knew who were like me but were, weren't gonna be trying to kill them, right? So, you know, if, if you were in Chicago at the time, I would have called you up. I called Arnie Duncan up. I called my friend John Rogers.

Athletes, but not like NBA guys, but.

Not the, the summer league guys that I'm working out with. And so, so I, I, and I called him up and said, hey, we're playing up at, you know, I forgot where we were. University of Chicago.

Yeah, yeah, yeah, yeah, yeah.

University of Chicago. Okay, let's, let's go play. He came and it was, we, we started playing and I'm just, you know, we're playing a nice friendly game and it's fine.

Is this five on five? It's two on two.

No, it's three on three and four on four.

Half court, okay.

No, you can hide in a full court game. You're not good.

You can cherry pick.

You can. Yeah.

Half court game, half court game, you have to be engaged or you'll get called out. But he was terrific, right? He was a decent player. And I always say he's a real lefty. So he dribbles to his left and shoots with his left hand. You know how some lefties are really right handed, they shoot with their left hand.

Yeah, yeah. And like for your audience, my best.

Friend Matt is that way.

I do.

The athletes know, the athletes know.

But here's what I liked. You know how when you follow a guy, you know, you follow a guy and in a gentleman's game, you just say, hey, you're ball. I follow you, you're not.

You call it.

Yeah, you call it as the defender.

Yes.

And he did that. And I was like, that's a really good sign. Early on. And then the other thing is he didn't shoot too much, but he didn't pass too much. Like, he took the open shots and he passed when he wasn't open. But the thing that really put him over the top was he didn't just pass me the ball knowing I was her brother.

Yeah, let's make you look good.

Listen, you know how that is, dude. To be like, hey, hey, gracious you, you take the shot. And I'm like, oh, come on, man. So I was able to go back and report the Robinson basketball got married.

So it worked out.

Yeah.

Now here's the thing.

I'm just saying, if it hadn't worked out, I might not have kept dating.

Really.

I, I, you know, I don't know.

Your brother would have said something about, you know, his character was really nasty. Like, he was really mean.

They wouldn't have gotten married.

Really.

I would have addressed it. I would have, I would have had the conversation. It's like, so I hear you were kind of a jerk on the court. What's that about? Right. Why would you do that? Or, you know, I mean, I would have had a discussion and then I probably would have been looking for other signs. He didn't show. He, yeah, you know, he is. The outcome of that pickup game was consistent with what I was. That's good, right?

His behavior matches exactly.

Exactly. So it's, and it's continued to be.

That's beautiful.

Is who he appears to be, you know, and he shows up. Well, he's somebody you want on your team.

That's beautiful.

And that was, that was important to know as a woman who grew up in sports culture. Right. That's important. You know, that's a value that I hold dear. That's something, that's something I respect, not just in my male friendships, but in all my friendships. Are you who you say you are? Do you show up? Well, do you? Are you a team player? So, yeah.

That's beautiful. That's beautiful. Great story. I love that.

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But growing up, you know, you guys, I, I think I heard you say in your podcast, which is an amazing show, I want people to go download it and watch it. But you're talking about. You grew up in a one bedroom apartment together, essentially with like a living room as your guys's bedroom up until you went to high school.

Yeah.

Oh, yeah.

So you shared a room for like 10, 12 years together?

Oh, yeah. We shared a room our whole time growing up.

Wow.

Until I went to high school. And then we turned the back porch into a bedroom.

Yeah.

You know, finished it off and enclose it and insulated it. And that became my kitchen, my bed, my bedroom. But the I would say our entire apartment apartment was as big as this, this come on area right here. And that was the kitchen. And in the kitchen had a table. So it wasn't a dining room.

Yeah.

You come through the hallway, that bathroom would have been right there. And the stairs down would have been across this, which was considered the living room was really the dining room. But we used it as a living room. One bedroom in there, and then the living room was there that we use for our bedroom.

Incredible.

We started out with our beds head to head like this when we were really little. And then when we got older, my grandfather, my paternal grandfather, Southside, who we called him that because we had a. He used to live on the west side. We had two grandfathers. And we would say, who's. Which house are we going to, west side grandpa or Southside grandpa? We say west side. And then he moved to the south side. So we named him south side. He built a paneling, a paneled T down the middle of that room. So that turned into one bedroom for me, one bedroom for me, and then a common room. So, yeah, we shared.

My father was a. He was a city worker. He's a blue collar city worker, worked for the water filtration plant. And we lived off of his salary until I went to high school because my parents thought it was important for my mom to stay home. So in order to make that work. And my father was very financially responsible, even though he didn't earn a lot of money. And they made sacrifices. So their view was, it doesn't matter the size of the house. It's more important for you to have your mother there who is, you know, so we could come home for lunch. And she was a room parent and she knew our friends and. But we didn't have a lot of money. We didn't grow up with stuff. And so, you know, when I talk about this with parents, when, you know, you hear young people waiting, it's like, well, I want to make sure I have a 6,000 square foot house and that we have Savings for college already lined up before I can even think about getting married. You know, my. That. That wasn't what made us who we were, you know, and. And living in that little bitty space with four people in one bathroom, that built character for us, and it created a level of closeness and intimacy, and it. It's a reminder to us today that no matter how successful that we get home is about who's there, not where we are. Which was something I had overcome with the idea of moving into the White House, which was amongst my biggest fears. When Barack said he was gonna run, I was like, if you win, how can we raise a family in that environment? You know, that's not normal to us. That weightiness was not, to me, something that could sustain a healthy family. And I'm worried about it. The weight of.

The weight of it all.

The weight of it. But what I came to learn, even in that environment, that it wasn't the house as big as it is. It was us in that house.

So interesting.

So we had to find a way. And, you know, creating family is doing it in a small way. You know, if you think about it, it's like it's creating closeness. That's why everybody in families, they gather in the kitchen, right? I mean, in real close households, no matter how big the house is, everybody's in the kitchen. Because if they're really talking and wanting to connect, they want to be with each other, right? And it was that way in the White House. We would all wind up gathering this one center space. No matter what was going on, especially if Craig was over, you know, we wanted to be together. So you. You know, it doesn't matter if you have 6,000 square feet or 600 square feet.

Wow.

You know, the kitchen. We gather the kitchen because we're always hungry, Chris. Right. You know, I'm just like, we're always going there. Then everyone else follows us and like, hey, you want to hang out with us? We're in the kitchen. Here's what I'm curious about, Michelle. And both of you, both, you've had successful careers and made big impacts in the world in your own way. How did you build belief in yourself that you were worthy of the success at such a high level, you as a coach and in the business world, in the NBA and. And even going from a small little apartment with both of you to being in the most iconic house in the world? Like, how do you believe you're deserving and worthy of that life when you come from such smaller, humbler beginnings?

Well, it's a step by step process. And if you got good, smart parents like we did, you know, who don't even know what's coming, but they understand. They understood for us that they wanted to make us feel that way at our little kitchen table. So you begin feeling that because you feel it. You see your excellence in the eyes of your parents. Like, we have parents that really thought we were smart and funny and interesting, and they reflected that back to us. They wanted to hear what we thought. So we grew up thinking, we're so funny. I'm so smart, you know, we're so interesting. You know, I know you want to hear what I have to say. I know I'm five. But let me tell you my opinion about these things, right? So it starts there, and especially when your poor black kids from, you know, on the south side of Chicago, I think our parents knew that what was coming for us was the absolute different message, that at every turn, what was awaiting us, regardless of who we were, there were going to be teachers and people who would be constantly lowering our bars for us anyway. So I think they fueled us with a level of can do it, must do itness.

Interesting.

That would arm. That would give us a kind of armor as we went out and sort of started getting dinged in the world. In the world.

Yeah.

Yeah.

So what did they instill in you to keep your self confidence high when the world was trying to take you down?

So I'll give it to you in coaching terms. Before people were coaching confidence, they were coaching confidence.

Interesting.

What would that look like? What would they say or do or react?

This is what it would look like. Mom, how do you learn how to read? And I'm four years old, Instead of saying, you put letters together, she said, here, go get a book. I'll show you how to read. She taught me how to read when I was 4 years old because I asked her, how do you read? And every time I asked her, how do you do something? She stopped what she was doing and she showed me. So then I felt. And then she would talk about how wonderful it was that I could read or that I could tell time or that we could go around the block on our bikes by ourselves. And that it's really interesting because today people talk about coaching confidence and leading with confidence. When we grew up, leaders didn't do that. They broke you down to build you back up.

They yelled at you.

They yelled at you. And it was just a different mentality back then. Even in corporate America, back then, people put you through the gauntlet and didn't coach confidence. They told you how poorly you were doing, and then they hoped that the cream would rise to the top. Our parents did the exact opposite.

How did they learn how to do that?

Like, they were ahead of the game.

And as mom said, she tried to do the opposite. What was done for her, because she came out of a generation of a generation of, you know, they didn't know what they were doing. With parenting, there was no philosophy. Kids were seen but not heard.

There was no conscious parenting.

There was no conscious parenting. And our parents were smart people. They weren't college educated, but they could have been. You know, my mother could have been a teacher. She could have been a professor. You know, she just didn't, you know, there was no pathway that she saw for herself. So just like all of us, I mean, while there's some insecurity there, there's also in each of us, this level of. I know more than they're giving me credit for. Right. I think it's. It's already there. And then it gets beaten out of you. It gets abused out of you. It gets. There are other things that get in the way. I think my mother always felt like every kid has the power and the ability to learn if you get out of their way and if you fuel it and you don't suffocate it. And my parents were sane people and just. We were blessed in that. And so that established a foundation for us to then go out in the world with this belief of. I. I'm. I'm pretty sure I'm pretty confident and competent because that's what our parents get. And they forced us to be that way. And every time you succeed, you know, and sometimes we. We rob kids of that. Parents today, because we're trying to make sure kids don't fail. We're trying to avoid our hurt and our embarrassment with them failing. So we never let them. We never really hand them their lives. And so they don't get those experiences. And so they miss out on those early, you know, sort of building blocks of confidence that you need. Our parents handed that to us.

That's beautiful.

So then there were the experiences that went along with it. We were. We came into the world as good people, polite kids. We knew how to engage with teachers that multiplies that confidence and competence, because teaching your kid how to be socialized helps them, because better socialized kids, they get better feedback from the world. And we were always the kids that the teachers liked and loved. And so now you get a little bit of that. And then now you learn how to do that. And then so you just keep succeeding. And for me, one of the aha moments was actually going to Princeton because I wasn't confident then because I wasn't a great test taker. I was a great grade getter, but I wasn't good on sat, so I had good grades, not great scores. So all the scores said, you don't belong at Princeton. And there were people who saw me, saw the color of my skin and said, you're aiming too high. Right. So luckily he went, yeah, you were.

Already there for two years, right? Or a year or two.

Yeah, I was there for two years. And. And she. What? She's being nice, but what she really said was, if this dude can get.

In, yeah, I'm smarter than him.

She is a better student than I was. I was a guy who could do well on tests I never studied.

Interesting.

So my first years at Princeton, I got killed because you have to be able to study there.

Wow.

But my sister is studious and smart, and just the bad she get. She got frazzled on the test.

Yeah.

Yeah.

And me, I was like, you know, process of elimination.

You imagine going to these schools, being told that you're not ready. And that was my first insecurity of thinking, well, maybe I don't belong here. And that's the world telling you that you don't belong. Even though it's like, well, all my experiences up until this point say that why wouldn't I belong. Belong here?

So how did you overcome that belief that you don't belong or that other people are telling you you don't belong?

You. I got there and I looked around and went, oh, my God.

Sat in a few classes.

Sat in a few classes and sort of realized that affirmative action isn't just the color of your skin. But there were a lot of kids that were legacy kids. They were athletes. They were. It was like. And then you sit in class with people, a lot of bright people, but there were a lot of people that were just so. You wonder, well, how'd you get here? You know, who told you you were ready? Right. And then doing well in that environment for me, it sort of. It sort of took the curtain off of this elitism.

It lifted the veil.

It lifted the veil is. That's. That's the phrase I was trying to come up with. It lifted the veil for me in a pretty. So if I'm here at the top schools in the world and I am succeeding, then all this other stuff is a lie.

Interesting.

You telling me that I can't. This is the scam. Like you want me to think I don't belong here when I actually do. And so that was the first step of. Let me just. Let me trust my gut again. Let me go back to the foundation. The things that my parents were telling me that I thought maybe they just loved me and start believing what's actually happening in the war. Let me trust my experiences. Interesting. And so I experienced my way into confidence. And the White House is just another Princeton. Right?

Really.

And the experience was just the same. You have a lot of people saying that there's no way that this black couple is capable of representing our country. You know, they are not patriotic. Look at their fist bump. You know, did. Did she really get into Princeton? Is he really from this country? You know, did he really go to Harvard? Is his. You know, it's the. It's the same kind of let. Because we can't see past our own prejudice. Let's question. Because we were told that there is an order and that you don't belong at the top. You know? And what I soon realized is that's not about me. That's about them. Which goes back to what we learned at our kitchen table. It's like you cannot base who you are and how you think of yourself on what anybody else other than who's at this table and knows you thinks. Because everybody's bringing their own stuff to their opinion of who you are. So you have to do the work and let your work speak for itself.

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That's fascinating, because if you're at, you know, the position you were in for eight years during that time, how are you able to keep the core nucleus of your closest friends and family to just only focus on what they think of you rather than what the world thinks of you? Both at the extreme high high and others extreme critical. Like, how did you not own your own hype of half the world or whatever, or most of the world? And then the extreme criticism, like, you.

Can'T listen to either. Interesting. And so that's not to say that I didn't look at any press. Especially when you're campaigning, you can't help but know what things are. But what I learned was that I have to filter it. So the beauty of being in the White House is you have a comms team, a communications team, and I just get to the point where tell me the things that are objectively are things that I need to hear. And I just had to practice. And I wasn't always good at it because I'd look through the clips, I'd look at stories. Every now and then I dig a little too deep, you know, good and bad.

Yeah, feed the ego and then also the criticism. Ah, that doesn't feel good.

Exactly. And it's like, well, I. I can't believe one and not the other. So let me just do the work. So I tried to develop a habit of getting my information not firsthand, but thirdhand. So my comms director tell me in this meeting what I need to know, what I need to be paying attention to. If there's an article or something about the girls or something that I need to know in preparation for speech, give me that information. So I do what I tell young people do. Do not read the comments section. You know, just don't go there. If you. If you're in social media and you're doing this work, do not let that stuff feed you. You have to be disciplined enough to just put your head down and do the work and let the work speak for You. So I would read things about the work. You know, did the speech work? Is the program working? Is it having impact? But all the other stuff, the op EDS and the commentary, it's like good and bad. I can't take it in because it would cloud the work.

That's interesting. And so it's really about, you know, was I effective? You know, that's right. And as a coach, you're seeing, were we effective? Maybe it wasn't pretty, maybe it wasn't perfect, but did we accomplish our goal? Did we win the game? Did we move the initiative forward? And really not looking at the praise or the feedback too strongly as well, on either spectrum, which I'm hearing you say is you had to regulate your emotions. And it's something you probably have to do as a coach. As a coach is like get student athletes or athletes to not react when someone gut punches them under the, you know, and doesn't get called the foul. And also not own their own hype too much.

Exactly. Especially in the age of social media. All these guys want to read about. About themselves.

Oh, yeah.

And it was, it was a real challenge to try and get them to stay off the. Their phones and reading because most of the feedback is going to be negative. That's just the nature.

Somebody's going to take time to write.

It's going to be bad.

The criticism.

Yes, yes.

Yeah.

The critiques. And I also. I got to ask you off camera, did I hear you also played with Jordan when he came back?

Yeah, I'm happy to tell.

I mean, you can share real quick what was. So. You're. So Jordan retires play baseball.

Jordan retired to play baseball. And when he came back, people were hearing he was working out and he wanted some guys to work out with who could play enough but weren't like gorillas while he was getting in shape. Tim Grover, who was his workout guy.

Tim's a buddy of mine, so Tim.

Knows the story because Tim is the one who called.

Come on.

Arne Duncan, myself, John Rogers and a couple other guys. And we start play two on two or three on three. And then when he got in shape, we play five on five. And then when he was ready, when he got past us, he went to the real dudes to work out with.

Summer league. Yeah.

Cause, you know, I think I was in my late 30s probably then, so we could give him a safe game. We knew the game. We knew how to guard him without tools. Jumping into his landing spot so he'd get a twisted ankle. And it was, it was just And. And he was so gracious.

That's cool.

But he was. He was as tough as he was on. On the last dance. He.

He didn't want to lose anything, probably.

He was trying to beat us every single time. And he was the opposite of Barack.

Yeah, he was. He was like. Yeah, he was. He wasn't passing the ball. He was.

He.

He was working on his game seriously, and working on his. His sort of emotional and mental attitude, too. And he has been absolutely gracious. Every time I run into him, you know, when I was working for the Bucks, I run into him, work for the Knicks, I run into him and be at All Star, and, hey, Craig E. And he's just. He is just the same person that he is. He has always been the same person.

That's cool.

Yeah.

What a cool experience.

But, you know, I had played against him in the summer league in Chicago when I was. When he first came. So Chicago had one of the best summer league basketball leagues because Chicago was one of the few places where you had pros, college players, and high school players. So when Jordan got drafted by Chicago, we played up at Chicago State University.

And you guys probably heard about him kind of like, growing up and all this stuff you were in that.

We were in the world. And then he shows up after he gets drafted and he's playing in the summer league, that.

Playing it.

Wow.

Yeah.

That's crazy.

It was. It was. It was. It was fantastic. It was just. The place was packed.

Great time to be in shock.

Amazing. You guys were living the dream.

Yeah.

Now, I'm curious about this, Michelle. I'm curious. Did you ever struggle with your mental health while you were in the White House? Did you ever feel like the pressure is too big, the anxiety is too much, or I'm having it, the weight of it all was too much? Or do you feel like you were pretty steady throughout the whole time?

Yeah, I mean, I. I think we were surprisingly equipped for it, you know, and that's not to say that I didn't have my bad moments. We didn't have our bad days. We did, you know, but I didn't feel like, we can't do this. We'll never make it through this. That's not, first of all, how we were raised. Right? I mean, you're in it. We're gonna make this. It's gonna work. We're gonna. We're. We're gonna show up every day. Every day we're gonna show up. And you also. I found that it's important for me and Barack to Keep our sanity, our even keeness because we were raising little kids.

Gosh, that's gotta be so challenging. Like being a parent without the world looking at you constantly and having to make big decisions every day. It's got to be one of the most challenging things ever.

Right?

But then doing it and how can you be a great mom, a great wife, a great, you know, leader in the world as well and take care of your health and your mindset? Like, how do you do all that at once while raising kids?

But it also helps to have them because guess what kids are. They're a big distraction and they're very self centered and they're very much about, you know, okay, dad, that's nice about the Middle east, but let me tell you about little Susie from what we did. I mean, they keep you grounded and.

Because you gotta be in the present.

You gotta be in the present. That's where they are. It's like, I don't really know who Putin is, but let me tell you about Ms. Cherney. Okay? I mean, their worlds are real. And it was Barack, you know, he reveled in that normalcy. Right. Really just coming home from a day at the office, you know, and being able to sit down with two chatty little girls and hear about their lives and remind him what's important. Right. That helped. So it was a stress, but it was also a very grounding thing.

And it probably brought a lot of joy to your life too. It's like when you're dealing with heavy, stressful things all day long, to have children bring love and joy and play and just wonder.

Yeah.

You know, more of like what Craig brings to the world.

Right.

Just that joy, like curiosity and awe in the moment.

One of the best stories about my husband is that he, he became a co coach during his White House years. He coached Sasha's fourth grade basketball league.

Really?

The Vipers.

And how'd he do? How was his.

He did let her finish.

Okay.

Yeah.

Yeah.

So he didn't start out as the coach, but she. We signed her up for rec basketball and it's at some local YMCA in Chevy Chase. And of course we're going to the games because it's basketball.

Of course you have to yell and it's my baby.

He's got one that maybe will do it. Right. So we're all going to the games. And also on the team was Maisie Biden, Joe Biden, the then vice president's granddaughter, who the Biden girls and our girls grew up together. Friends. So imagine that rec league on any given Sunday, because we all went, right? The president, the vice president, secretary, Secret Service.

Two details.

No, like gate details. Because all the had details.

So they have their own bodyguards also.

Ambulance helicopters, SWAT people all over the gym. Right.

It's like a little middle school gym. Like. Yeah, two rafters. Like nothing.

Yeah, right. And of course, they're all still young. Basketball. Amazing. And I'm just like, Joe, you gotta lighten up, yo. You know, Barack, sit down, sit down. But it was a parent coach league and the two parents of the Vipers weren't professional coaches and they really didn't know basketball. And it was very evident by game number two as Barack would just start sliding down to the coach's bench and just say, you know, have her block that one and get them to tie their shoes. So he was sort of side coaching. And at the time, his eight was Reggie Love. Reggie Love was a Division 1 guy. That was his body guy. So it's he and Reggie. And they come out of the games really critiquing what wasn't going right. They weren't running plays. There were no know practices. So they started making these side. Giving side advice to these two parent coaches.

Oh, my gosh.

So how do you, you know, well, what do you do with that?

With the president dude giving you some coaching advice? Eventually your little whistle as a coach.

No, he starts offering to run practice for the Vipers. So they come to like one of the depart one of the downtown gyms in the Department of Agriculture or the interior or whatever. So Takeover gym. Every week they're coaching the Vipers. They teach them two plays. One was box and one was something else.

Not the triangle offense.

Not the triangle offense. Because these little girls weren't even tying their shoes.

Just tuck your shirt in, you know.

So eventually Barack's on the bench with Reggie with the parents, and they're running plays.

That's incredible.

Long and short of it is the Vipers won the championship.

That's cool.

Vipers won the championship.

Well, we have. Me and your daughter have something in common. We both played on a team called the Vipers. My arena football team was called the Vipers. So we have something in common there. That's amazing.

So you imagine what, how, you know, what that does to, you know, just to alleviate stress, that once a week you're just a parent and eventually, no matter who they were playing, he was just the Vipers coach. It was good for him. It was good for his relationship with our daughters. It made us focus on something other than the world crises that he was facing. So the girls brought us down. And he went to every parent teacher conference, really every single one motorcade and all, which embarrassed the hell out of the girls. It's like, dad, the SWAT guys are on the roof. They've got the machine guns out. And we were just like, like, just ignore it. This isn't about you just trying to make them focus on their lives. It's like this president stuff. This is one thing. Your life is your life and we are entering into it just like every parent. We're going to go, I'm going to the potluck. I'm going to stand on the soccer field. I'm going to, you know, watch your tennis game. Tennis was a hard sport to watch. So I would stay in the car in the motorcade and kind of look, because it's hard to watch high school tennis, which Malia played without showing up with all the.

Oh, yeah.

With all the agents and stuff so that I wouldn't do. But soccer you could do.

Yeah.

You know, back far enough.

Yeah, stand back far enough and interact with the parents in a normal way so that people would understand. I'm a mom, you know, and these are my daughters.

You want the best for them?

Yeah, I want the best for them. And we'll have sleepovers at the White House and the girls will come over. So that helped. You know, that's a long way of saying that having young kids helped us stay normalized and it helped us with our mental health as a family.

That's interesting.

Yeah.

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Now, how did you. I mean, you guys grew up with parents that weren't famous, that didn't have a lot of money, that weren't in the public eye, that weren't in, you know, universities or politics and the world was paying attention to. But that wasn't the case for both of you. You're both public people in your own way and had a lot of fans and critics, and you had more money than your parents, more success, more opportunities, all these different things. How do you raise both of you? How do you raise healthy, conscious kids to be good, loving, generous when they are given more financially success opportunities, networking when they're given more opportunities than what you were given?

Yeah, that's a, That's a terrific question. And the way we approach it is you all haven't done anything yet, so you can't.

This isn't about you.

It's not about you yet. You got to earn your keep and you do your chores and, and you get good grades and you behave, then you start to get rewarded.

But because you don't want to rob the confidence of them making mistakes, building their own thing. Right. So how do you do that?

Well, we're trying to do it like our parents did it. Give them, coach them for confidence and hard work. The results will come. And I always thought that my parents did me such a justice. When I got older, I realized there were a lot of kids who I went to school with, both in high school and in college, whose parents were cracking the whip for them to get good grades, and it prevented them from getting good grades. And my parents always said, look, if you do your best, I trust that you'll get good grades, so don't worry about it. Just do your best. And, and whenever I didn't do my best and they asked me, I had to say I didn't do my best because it might come back in evidence at the end. But it was rare because they trained us to just do your best. That's all we want. We don't forget about the grades. Do your best. And it was the same in sports. Just do your best. And I'm trying to do that with our kids, even though we have more than what we did growing up, up does mean our kids have to have, you know, four times as much as that they would have had. Right? And it's not like, you know, we. We would get pizza growing up when we got report cards. That was the, that was our reward for good report cards. Italian fiesta pizza.

Let's go.

We do the same with these Kids. But we have pizza more often than when we did. Okay, that's, you know, we have.

We do.

We go out to dinner.

Yeah, yeah, of course.

You go on better vacations.

Sure.

But when it comes down to just working, just. Just work hard. Work hard and you'll be rewarded. And yes, that, That's. That's, you know, and. And it's. It's lovely to see between my two older kids and her two older kid or two kids, they're all adults out on their own in their, you know, in their early 20s and early 30s, not in our basements.

Right.

So it's. And. And they figured out budgets. They figured out their relationship with money. And that's the one thing that my dad spent a good amount of time with us, showing us the value of money. And I think that's important too, in this day and age, because we do have more money than I did growing up and. And helping our kids understand. Like, my wife, Kelly, is a. She only buys stuff on sale. So our kids look for things when they want something. They know it's gotta be on sale or they gotta spend their own money.

Interesting. Yeah, that's cool.

I think you've gotta know who your kids are. Right. And that starts really early. I think all of the. That work starts way earlier than a lot of parents. Parents think because it's about boundaries. It's about respect. It's about teaching your kids how to hear. No.

Not giving them everything.

Not giving them everything and being okay with their disappointment. And that starts at 3 and 5. It started way before we entered the White House, even though they were really young. It starts with discipline and not being afraid to discipline your kids. Doing it with love, but still doing it and being consistent. So our kids even coming to the White House were already at 7 and 10, those kids. Right. So then the worry became like, I don't want. And for all of our kids, I don't want you to think that you have to be this Right. Because the pressure can go the other way. And our kids are Obamas. Right. They entered the room with a name and a face that, you know, makes them have to prove something. So I'm for my kids because of who they are. They're already hard workers. They're already good people. They, you know, I hear this everywhere they go. They know how to enter a room and treat people kindly. They're gracious. They've learned how to be diplomats in this process because this whole experience that I was worried about also taught them how to maneuver in the world so now I worry about them feeling like success has to look like what we.

Did, getting the White House, or.

I mean, come on. Like, this is unusual. Right. This is not the norm.

And did you. Did your parenting style shift or evolve pre White House during the White House and post White House, it evolved not.

Because of where we were, but because of their ages. Right. You know, our. My kids lived in the White House longer than they lived in any house, so they came in at 7 and 10, and they came out the year that Malia graduated. She graduated from high school and took a gap year in our last year because she didn't want to go to college. As the president's daughter, she didn't want to have a detail.

Interesting.

Right. So she took a gap year for that reason. Sasha graduated from high school when we were, you know, posted White House. So they were different people. So now you move from creating boundaries to being an advisor. Right. And slowly letting. Giving. For me, I felt like my job is to, every year give you more rope, every year give you more control over your life, every year step back even more to get out of the way. And I wanted to do that before they left my house because I wanted to see, what do you do when you have all the roof? And some. And mistakes were made. Let me tell you. And mistakes were made.

Yeah.

But it was better for me to see those mistakes so we could come home and talk about it. We could, you know, we could institute punishments. We could, you know, I. I didn't want to know that when they were out of the house. And so I gave my kids a lot of their ropes, each. With each phase. But that had more to do with who they were and how I wanted them to develop, because we also. They weren't going to have Secret Service their whole lives. So it's like, you got to learn how to drive. Yeah. And you got to learn how to drive with your agents. So we had to switch that around. It's like you're driving in the car by yourself, and your agents are following.

Wow.

So now you have to learn how to manage and communicate with a group of grown men on how you're moving in the world. Because you have to do this.

Yes.

You know, you have to learn how to get gas. You have to learn how to get on a bus. You have to learn how to. How to get on a plane by yourself. And I can't be there to do that with you because I still have all that. Right? Yes.

Right.

So it's. So the. The. The. The changes were really Based on the kid, what they needed and the age. And my motto was your life is soon going to be yours. So let's start now.

That's beautiful. That's beautiful. I've got about five minutes with you guys left. They're telling me so I've got a couple. I know we'll have to do another one in the future. So many more basketball chat I want to have and everything else, you know. But I've got a couple final questions so hopefully they'll let me finish these few ones up. But before we ask them, I won't be able to download you guys new podcast imo. I listened to the first episode where there was gist of you two. I thought it was fascinating hearing these stories you guys share about early childhood, growing up, the lessons you learned, how you were able to instill confidence in each other, support one another and overcome challenges in the world. World. I just think it was really cool. And all the other conversations you're having with people I think is really needed right now. So IMO with Michelle Obama and Craig Robinson, I want people to go down that download that they can go to imopod.com imo podcasts everywhere on social media and all the good stuff. We'll have it linked up as well. But really inspiring and I'm glad you guys are doing this. So congrats on the show. It's really cool. This is one more question I have for you. Then I have a couple for both of you to wrap it up. I'm curious about your confidence pre White House, during White House and then in the last decade since you've been in the White House. And I love your reflection on this as a brother and what you've witnessed. Do you feel like you're more confident now in the last 10 years, the eight years in office or the kind of four to eight years before leading into the office?

Easy answer now really. I think I'm my most confident now, I think. And by confidence I mean I feel, I feel, I feel like I can claim my wisdom. And I've said this before, I think maybe it's a little bit different for women. Maybe I can only speak as a woman because I'm a woman. But, but I feel like throughout my life, you know, like a lot of women, I was reticent to claim what I knew and I was always sort of, well, maybe I don't know what I'm talking about. Maybe I won't speak up or yeah, maybe, maybe this idea, it seems that way. Maybe you know what I'M saying to these guys in the west wing doesn't make any sense. I was, you know, while I was doing my thing and having my own proofs, it still took until now for me to kind of go look over all this life and say, I kind of got. I kind of know a few things. I think. I think I can now sit in my wisdom at 61. And I think a lot of that has to do is with the fact that I am. I'm, of course, still a wife, but I'm not the. I'm not the first lady of the nation. I'm not the primary parent of Malia and Sasha. They are adults out there on their own. This is the first time in my life when every decision, good or bad, is mine to own.

Interesting.

And I feel good about owning it. I'm still working on it, though, because there's still guilt, there's still a sense of obligation. There's still a sense. There is still always the sense of, am I good enough? Really? Because while I'm confident, I think it's. I think it's there in so many of us. Like, that's what I've come to.

But you think, am I good enough? You've created and accomplished so much, not only professionally, but personally. So at 61, you're still feeling that.

But is it enough? And that's the work that I'm doing. Like, if it's not enough now, I'm telling myself and my therapist, then it won't be enough. So now I have to determine for myself, because this is all an internal conversation that I'm good. Right? I'm just now really. I just really now have the time to do that work.

Interesting, right?

Because when you're climbing, slaying the dragons, you're just feeling the feelings. You don't have time to assess it. Right. Raising kids, getting through hard times, writing books, doing book tours, you know, working on the library with my husband, blah, blah, blah. But the decade that I was talking about, that just went by just like a flash. When was there time to reflect and.

Work on that stuff, do the healing.

Work, to do the healing work, because after all that work, there still is healing from it. That was, you know, that was a mighty experience that we had. Right?

Yeah. It's a lot to unpack.

And so in these last years, I've been unpacking it, and I'm becoming better with my choices, feeling the most confident in myself and the. The most settled in that question of am I good enough? And I'm finally starting to answer it. Yeah, I think I'm. I think I'm there. I think I'm there.

That's beautiful. I feel like this is. We're just getting started, but unfortunately, I'm gonna have to wrap this up. So I want to ask you guys both a final question, and that is, what is your definition of greatness? And I'll start with you, Craig. Your definition of greatness.

I think greatness is the ability to both have an impact on your own life and on other people's lives. I think if you can find a way to develop yourself and coach yourself up, you can inspire and develop and coach up others. And that's kind of what sort of my life's work has been. Even before I was coaching, when as a. As a player, as an executive, as a corporate worker, I always felt like we didn't inspire each other enough. Everybody was sort of an independent contractor, and if we could all be team players, we'd be in a better position.

Oh, that's cool. That's cool. I love that.

I think mine is similar because we were raised in similar. Greatness is giving more than you get, you know, because what. What's it all for? You know, greatness, I think greatness, greater good, good. You know, we should be all. We all should be working for our greatness to affect the greater good. And then we all experience that greatness. Because greatness as an individual feat, I mean. Yeah, I guess, right? I mean, you can sit in your own greatness and have all the stuff and be really alone, but the bigger greatness is putting that energy out. Amen.

Thank you both for being here.

Thanks for having us, man.

Appreciate it. Michelle, thank you so much.

12 years. We can see the experience.

Let's go.

You know, let's go.

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Moving forward.

We have some big guests and content coming up. Make sure you're following and stay tuned.

To the next episode on the School of greatness.

I hope you enjoyed today's episode and it inspired you on your journey towards great greatness. Make sure to check out the show notes in the description for a full rundown of today's episode with all the important links and if you want weekly exclusive bonus episodes with me personally as well as ad free listening, then make sure to subscribe to our greatness+channel exclusively on Apple Podcasts. Share this with a friend on social media and leave us a review on Apple Podcasts as well. Let me know what you enjoyed about this episode Episode in that review. I really love hearing feedback from you and it helps us figure out how we can support and serve you moving forward. And I want to remind you if no one has told you lately that you are loved, you are worthy, and you matter.

And now it's time to go out.

There and do something great.

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