IMO with Michelle Obama and Craig Robinson - IMO Live: Swerving Through Life with Michelle and Craig

Episode Date: July 22, 2026

Live from South by Southwest in London, Michelle and Craig flip the script and interview each other! In a vulnerable and revealing conversation, they discuss their journeys through Chicago's South Side, law school, the Oval Office and share what they’ve learned about one another while working together. Plus, a lightning round of questions on beloved British traditions!Have a question you want answered? Write to us at imopod.com.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Bravery makes you brave to try anything at any age. And I think for me, I've just gotten used to, okay, we're going to do this. I mean, I lived in the White House. I was the first lady. That wasn't my plan. I had no training for that. Wasn't my idea. Was not.

But we figured it out. If I can be first lady, I can do a podcast with my brother. This episode of IMO is brought to you by progressive insurance. Hello, South by Southwest London. How are y'all doing? We are thrilled to be here with all of you. A little over a year ago, we launched our podcast IMO with Michelle Obama and Craig Robinson, my big brother, if you hadn't. But we launched it in South by Southwest all.

And that was also the first time we did a live event. And we had so much fun, we thought we'd do it again here in London. Mm-hmm. But just to give you a sense of IMO, what we do, it provides a space for vulnerable and revealing conversations with some pretty amazing guests, some of whom are friends of mine. Mostly her friends. And we talk about everything. Talk about everything. Love, friendship, family, careers, you name it, we've been there. And we hope that by sharing our stories and experiences, we might help someone facing similar

challenges or at the very least to give folks a little boost throughout their day. And there aren't always clear answers. One of the things we say is that there's no one way to live this thing called life, but one thing that we do believe strongly is that connections can help. And that's really why we started higher ground production, me and the guy Barack Obama. You've heard of him, my husband. We wanted to build a platform of programming that brings people together to explore different ideas and perspectives on how to get through life. And we are incredibly excited by several new podcasts that are joining the higher ground family. Talk Easy, which is a cool program. Let me say

this. Two young sisters talking about culture, stories from a stranger, just to name a few, shows that lift up a range of new voices and new ideas and hopefully help people feel just a little at this lonely. So today, Craig and I are going to try something a little different. We usually have a guest, but we cut them out of the action. So we're going to flip the script and we're going to interview each other. You should be frightened. So I'm not frightened, of course.

But what do you guys think of that? Just me and him talk. But first of all, Craig Robinson, how are you doing? I'm doing really, really well. I have not seen you in a couple of weeks. I know. I know. So part of the, so one of the fun things about doing this podcast is that we get to spend a lot of time together and we used to only talk to each other on the phone because we lived far apart. And now we see each other all the time, but don't talk on the phone because we're like, let's save that for the show.

But for anyone who's read any of my books or heard me speak, I talk a lot about the power of swerving through life and careers being able to remain flexible and open to changes. And I learned a lot of swerving from my husband. He has set me off on a path where I've had to adjust. So he was my first swerve teacher, but one of my best role models in swerving is my big brother, Craig, because his career path, as well as mine, is anything but traditional. We've done a lot of swerving throughout our lives.

And so we're going to talk about how we got where we are, because that's one of the questions that we get often from people who are trying to figure out their careers, who are trying to figure out life. And a lot of them are wondering, how did you guys get from the south side of Chicago, from a working class background, to sitting here and doing all the things

that we've done over the course of our lives? So, Craig, I want to start with you. Okay. Just so that people get a little sense of your career trajectory. Can you give folks a brief sense of what you've been doing in life to this point? I will. First of all, thank you all for being here. It's really exciting to be here.

And you should know, I used to live in Manchester. How about that? Yes. I played basketball for what was then called the Manchester Giants. It was the start of my pro career. And the real beginning to the swerve, because when I was in college, I'm old enough where I didn't go to college to be a basketball player. I enjoy playing, but I never thought I could be a professional. And then I got drafted by the Philadelphia 76ers.

And next thing you know, I was trying out for that team. And when I got cut from that team, I came to Manchester and played. And I stayed, I lived in Manchester for two seasons. I came to visit one year. That was my first trip to England. Yeah, that was your first trip to England. And then while I was here, our team did pretty well, and I thought, you know, I could be a basketball coach.

And I went back to visit Mish at Princeton and to see my old basketball coach. And I said to him, coach, I figured out what I want to do. And he said, I want to be a coach. And he was like, you don't want to be a coach. And he was like, you don't want to be a coach. I'll tell you when to be a coach. Go get a job somewhere and coach later.

And that's when I started my trip into finance. And I've worked in finance investment banking for quite some time. And then after 14 years, I switched back into coaching. That's when I started my coaching career. And I did that for another 14 or so years. And then I worked in the NBA in the front office, the National Basketball Association. And I did that for about five years.

And then now I work at the Coaches Association, as well as I'm a podcast host now. So that's a lot of swerving. It's a lot. It's a lot. How did you think about who you wanted to be when you grew up? How did you process it? What kinds of things did you think about? So I processed it by the people and things I was around, right?

So my early role models were my parents, my mom and my dad. My mom was a housewife and my dad worked for the city of Chicago. And then the other people around me were uncles and aunts. And they worked as, you know, policemen, city workers, educators. So I always thought that that would be what I'd end up. doing. Because that's one of the things about figuring out who you want to be. You know, there's no way we're taught that, you know. We just start making up things out of thin air. I know I used to say when I was 10 years old that I wanted to be a pediatrician. Yep. But that's because I like kids.

I mean, you base things off of things like that. And then when I was in Princeton and I had to figure out what to do next. I was like, I don't like math. I read. I like to talk a lot. So I'll apply to law school. I mean, that's how I picked going to law school. Because there's really no way that we teach

young people, you know, as they're growing up. Well, certainly not how to think about it. Not 40 years ago. 40 years ago. We're old, y'all. 40 years ago, it was sort of go to college. And then most of

our parents and friends of parents didn't go to college. So it was like, go to college and get a better job than what we got. And that's sort of what we did. But, Mish, you've had your share of transitions. Can you tell the folks what you learned from your transitions? Well, you know, did some. I tried to do the traditional checking the box thing because I was good at that. I was a good student.

I understood that if you got good grades, you went to college, from college. If you don't know what you're doing, you go to grad school. And I could check the boxes. I was good at that. I could achieve in that way. But that wasn't enough because I didn't have any experiences. I mean, I had summer jobs, babysat, did all that sort of. stuff, but when I got to the law firm, and I worked at a big corporate firm in Chicago,

what you were supposed to do after Harvard Law School, and I got to that firm, great firm, and I realized, oh, my God, I don't like law. I don't like it at all. It wasn't even close. I was, and thank you to all the lawyers. I mean, no shade, but, you know, it just wasn't for me. And I realized I didn't know anything about the law. I didn't have, parents in the law. I'd never clerked. I didn't, you know, only in my summer associate experiences, but that was very different because they were courting you during that time and not giving you real work. So one of the things that I learned through the transition is that gaining experiences are more important than I thought they were. Because back then in college, we just went straight

through. And now I know that I encouraged Malia and Sasha, and I encourage a lot of lot of young people, do not go straight through. Don't be afraid to slow it down and have some experiences. If I were to do it again from college to law school or grad school, I would have done a gap year or two. And you were kind of leading the way. I mean, quite frankly, your time in Manchester playing European pro ball was kind of like a really cool gap year where you got some experiences, just being out in the world and working and learning about what you liked, what you were good at, not just what you were able to do well. Because that's all I did. I just pursued something that I could do well. And I didn't know anything about passion or purpose or, and the

truth is, I didn't know what other careers were out there other than the traditional careers. You know, you grow up, you can be a doctor, you can be a lawyer, you can be an engineer. They're like six things. And here I'm at Princeton and Harvard. And in my mind, I only know six things I can be. And I think a lot of young people are limited because you've got to get out in the world to see what else is out there. So that's one thing I learned. Was your decision to go pro scary for you? I mean, because here you were at Princeton and there's the pressure, especially in your class, your year. We graduated. You were 83, I was 85. Economically, the country was doing great. And if you got out of college, a good school with a degree,

you were going to make money. You could pretty much write your own ticket, which I know is not the same now, at least where we live in our country. Was it scary for you to sort of see your peers going into finance and all those things while you were going to take this interesting leap into professional basketball and how did you think about that decision? So probably not how most of you think I would have thought about it because it was scarier for mom. Our mom was like, why on earth would you go all the way over there to play, just to play basketball. And it wasn't scary for me because as I progressed in the sport and got better,

it was a dream that, oh, okay, maybe I can play professionally, so I wanted to go try it. And it's a tribute to my parents that they never held us back because of their own fear. So as scared as my mom was, they both were like, all right, Go and do it. Now's the time to do it. So it was not a hard decision for me to make at that time. Secondly, because mom and dad encouraged us to go to a place like Princeton as opposed to go on some place else where you could get a good education,

my dad always emphasized that one of the, of the things you get from a good education are options and the ability to try things, which he didn't get a chance to do. You know, when you're a black man from the south side of Chicago growing up in the 50s and the 60s, you got the post office, the army, you know, you have certain things that you're allowed to do. You don't get to travel to be a basketball player or work at Morgan Stanley or. some other bank. So I felt really comfortable, and it helped that I came to England where everybody

spoke English just about. And really, really friendly, really friendly. So I have to mention that. This episode is brought to you by Progressive Insurance, a company committed to helping people move forward and live fully. Mish, I've been thinking about how over-war, big life decisions can feel these days between the endless stream of information, social media, and that constant fomo the kids talk about, do you feel like people are overthinking things more than they used to? Or is it just harder to make a choice when we have so many options? No, I think it's a little bit of both. You know, I think with so much information coming in, we just have so much more to process. And, you know, there's only so much the human

brain can take in. And then, yeah, we feel inundated with choices. We feel like there are too many options. So, yeah, I agree. I think it's a little bit of both. I feel that. I feel that. With your public image, how do you tune all that out and actually make the big calls? Are you relying on a gut feeling or is it more about leaning on the people you trust? Well, there's a lot of gut that goes into it. you just get used to making hard decisions. You, you know, you start to trust your instincts, but most importantly is having a strong team. You know, learning to let go that I can't make every big decision, you know, by myself and I shouldn't. So I surround myself with really smart people that I can count on. I let go of a lot and trust that they're going to, you know,

do their job and bring me the information that I need to do my job. So I, I've just learned that it's no victory for me to do these things alone, making these big decisions alone. As the kids say, facts. For me, knowing I have a solid circle to talk things through is usually what helps me get clarity. Progressive knows that big decisions at any stage of life can feel daunting. That's why having the right support and resources makes all the difference. Progressive's up payment program falls under their board. broader Open the House initiative, a multi-year effort focused on helping more people achieve

homeownership. Right now, they're expanding the uppayment program offering up to $13,500 each in down payment assistance to at least 200 eligible first-time buyers. They've already committed more than $16 million since 2024 to help make home ownership more accessible. At the end of the day, Progressive wants people to feel seen and as individuals whose needs matter. Because this is your life and it should be taking seriously. Learn more about the uppayment program and Progressive's commitment to first-time homebuyers at progressive.com slash open the house where homebuyers can access more housing resources and support to empower them in their housing journey. I have to, we have to take a moment just give tribute to our parents.

You know, they were uniquely gifted in pushing us to do things that they wouldn't do themselves. And sometimes, you know, we're parents now and, you know, the hardest thing in the world to do is to let your kids try hard things. You know, I think a lot of people wind up picking careers because they feel the pressure of parents wanting them to do something that feels safe and secure. A story that I tell often is during the Becoming Book Tour. I would do a lot of things in colleges, and I was sitting with a set of seniors who were graduating from Spelman College at a historically black school in the south in Atlanta.

And this group of girls, they were about to graduate. They were excited, but incredibly frightened about the next step, because they were sort of like me. They had box-checked their way to a college degree. And now, once they were done, you know, because you don't learn this, is that once you get through with the box-checking, the things you're supposed to do,

you're still faced with figuring your life out. And nobody kind of told them that. They, like many young people, hit senior year and it's like, how do I figure this out? And this one-year girl said, my father wants me to go to law school. And she's like, but I just don't want to go.

And she was in tears because her father, who was probably like our dad, just wanted her to be safe. He didn't know that a law degree cost $70,000 a year. He didn't realize that she was going to come out of that degree with so much debt that she would be limited in making choices about what she wanted to do because she'd have to pay down that debt.

And so I explained to her, your dad wants the best for you because he's scared, but he has no idea what you're facing. Because we don't know what our kids are facing. We, being us, we still can't relate to what our sons and daughters are going to face. It's a different market. It's a different situation. And so I find even with my girls today that I have to step back

and not try to push them to where I want them to go. I have to trust that they know their own market and can make certain decisions. Our parents were way ahead of the curve on that. And I say that because I know that there are kids who are trying to follow the dreams of their parents, sometimes to their own detriment, their parents out there that are really trying to push their kids to do a certain thing because it feels safe. And part of life, part of this thing called life, is creating the optionality, you know, getting the best foundation you can get, which we both did by going to good schools and then, you know,

developing some skills along the way. I mean, I didn't regret going to law school because taught me how to write, how to think, how to communicate. It gave me a level of confidence to just be able to go in any place and figure anything out, right? Those are the skills that were more important to everything that I do in the years ahead than simply just learning the black letter law. So I think that our parents unknowingly, probably more knowingly, they kind of knew that. And so they let us try hard things. And let me tell you, when you've been working at a corporate law firm where I started working

at Siddeley in Austin, I was making more money than both mom and dad combined. So you imagine how they felt when I walked up to them to say, hey, I don't like this career. Doesn't give me passion and purpose. And I'm going to leave and do something else, right? And to have them both say, all right, we trust you. Give it a try.

Well, let me just say a couple of things. One, she didn't learn how to think at law school. She could always think. Oh, thank you, little boy. She has been this personality since she was three or four years old. And she didn't learn how to write there either, because you all should know that my little sister used to write these wonderful short stories that entertained our family.

And you think I'm talking about like Jane ran to the market. No, these were intricate stories that were mysteries and funny and filled with livelihood. So she's being a little bit modest. Well, Harvard did teach me something. It didn't teach you that much. Didn't teach you that much. So how would you say our parents prepared us to be? be brave enough to do the kinds of things that you're talking about. I always, you know, I think about

the fact that they, they taught us how to think for ourselves early and to own our lives early. And by early, I do mean four and five. I mean, I talk about this. Our mother, once we started kindergarten, gave us alarm clacks and said, this is how you work it. You're a lot. You're in school now. It's your education, not mine. This is kindergarten, y'all. And she's like, you know, learn to wake yourself up because no one should have to wrestle you out of bed to build your own life. That was day one. And it wasn't like we were shocked or scared. We were like, yeah, give me an alarm clock. Yeah, look at us. You know, so a lot of what mom and dad did was hand us our lives early in appropriate ways, right?

It wasn't like my mom was asleep in bed while we were going to school, you know. She was up, but she wasn't going to come and be like, you're awake, you're awake. She'd wait for that alarm, and it's like, okay, let's see how you do it. And then she sent me off to kindergarten by myself around the corner. I was like, lady, I'm five. She's like, you can do it. But the beauty of our parents handing us our lives, it was them showing us that they had confidence in our choices.

And sometimes we tend to do the opposite if we helicopter a bit too much, if we're trying too hard to prevent our kids from failing or feeling fear, you know, what tends to happen is that you're kind of signaling to them that you can't do this without me, you know. And our parents were like, no, you can do this. This is just life. And everybody does it. And you're pretty smart kids. So you'll figure it out. And that came to everything from working out situations with teachers that were unfair, you know, clashes with friends, and that's very different from how people parent today.

You know, everybody's trying to curate their kids' experiences, and ours was just not. I mean, our parents did not feel like our lives were theirs to manage or to make better or worse. I mean, look, we had food on the table and lots of love and lots of attention, but like some parents I know, they weren't riding on our highs and lows. You know, our A's, our grades were our grades, you know. Our failures were our failures. They were there to help pick us up and add a boy and push you right back out there.

We could talk about anything, but we were required to figure things out and go to them for counsel, but not for... intervention. And so, you know, you leave home having practiced those skills, and you start thinking at a very young age, there isn't anything I can't figure out. I got this. And I think that, what about you? No, I, everything you said, the one thing I'll, I'll say to you folks is, our parents always had room for our voices at an early age, at the kitchen table, when we had meals. We were expected or we were allowed to voice our opinions, and that was really important at an early age. And to Misha's point about advocating for learning how to advocate for yourself, my dad, who was disabled,

I'm sure everybody those of you have read my sister's book know all the stories but he walked with a limp that got progressively worse as we got over and we found out he had MS but

he wasn't an unhappy disabled person and he always talked to me about finding something you'd love doing and it won't be work And he did that at an early age. So I was getting it hammered into me. Let me figure out what it is that I love doing. And again, I said this earlier.

Our parents never let their fears get in the wave. I remember going to my first basketball tournament when I was 12 years old to Poplar Bluff, Kentucky in a van with a coach. who was 19 years old. And my mom was like, yeah, go ahead. And then I found out that she was so nervous that my dad had to comfort her

and remind her that I'll be back in a few days. But it's not the sort of helicoptering that you see today. When you decided to get off the basketball track. and go into finance and then leave. Talk about how scary that was and how risky that was and why it was so for you. Yeah, so that was the scary point

because I took a job in finance when I came back from playing basketball solely because it was the place you could make the most money. Growing up poor like we did, I was like, all right, I'm going to use this Princeton degree and I'm going to get the job that I can get. and get paid, right? And I was doing that, and I was off on my way, as you remember, on the partnership track,

and it was time for me to move to New York or maybe even London. This was back when Morgan Stanley first moved to Canary Wharf over there. Now, I haven't been back in 40 years, but I know a lot about it. And he was living, you were living large. Yeah, it was ridiculous. had the red Porsche that I was in when his former wife crashed it.

It wasn't, you know, it was a fender bender, but she was picking me up from the airport and somebody ran into her and she ran into somebody and all we were doing was sitting in that Porsche going, oh, man. So he was, he was

Mr. Corporate. He was a finance bro. But what I realized in that is that because you know when you grow up poor you think money fixes everything right and I learned

now that my ex-wife it wasn't the means to happiness and so I'm making this money and doing well and my life doesn't feel like it's where it's supposed to be and it's because I'm not doing something

I love and so I get this opportunity from my old basketball assistant coach gets the job at Northwestern University, which is in Chicago. And he offers me a job as an assistant coach. Now, you can imagine being an assistant coach as opposed to being a bond trader on Wall Street. It was about a tenth of the salary. And I was really, really nervous about making the change. So I talked to Mish about it.

What was I doing at the time? I in life. You had already gotten out of the law. You had already decided to take a and a pay cut. So here's the two of us going to our parents. We're going to

make less money. Each of us. Every step we take is less money. Our parents are just like okay. So one story for you. I can't pull the trigger.

on this job because I've got an eight-year-old and a four-year-old and I'm thinking to myself as I told you, their lifestyle is going to change. And so I talked to them both and I said, I brought them together and I said, you know, Daddy's

getting a new job, he's going to be a basketball coach and they both looked at me like this. And my eight-year-old said, does this mean that your office is a gym? And I said, yes, it does. Not quite. It's next to a gym. And my four-year-old daughter said, they have a pool there? And it was at that point that I realized I was worried about the wrong things. I was worried about

their lives changing and they could care less. They just wanted to spend time with me. So that allowed me to make that swerve, which was nerve-wracking. But again, my mom said, listen, I get it. You got custody of the kids. You have to have a place to say, come move back home. You can pay rent when you can, and I just start it over again. And the lesson I learned from that is there's a couple. One is money ain't the best thing all the time.

And two is if you're not afraid to start over, you can do anything. And I just started over it. And it couldn't have, I couldn't have made a better choice. I just got back from London. We taped an IMO live show. I had a little bit of downtime, so I explored. I did this Airbnb experience while I was there, a walking tour around the city,

and it was one of those things where you learned something every five minutes. We hit Trafalgar Square and got the full story on Vice Admiral Horatio Nelson. We caught the changing of the guards. We walked through Ben Franklin's actual house, made it out to Greenwich, the literal center of time, and the city was already buzzing getting ready for the King's ceremonial birthday celebration outside Buckingham Palace. Oh, and random fact I couldn't stop thinking about those stripes on American Navy uniforms?

Direct nod to the British Royal Navy. Yep. Now here's the thing that got me. London was packed for this conference. And I'm thinking, if you live in a city that draws big events like this, you could be making real money those weekends. That's the whole thing about Airbnb. When people list their homes, it lets travelers like me actually live like a local. So if you've got travel coming up, think about listing your space. Your home might be worth more than you think. Find out how much at Airbnb.com slash host.

This episode is brought to you by Progressive Insurance, a company committed to helping people move forward and live fully. Mish, what is one of the biggest swings or leaps of faith you've taken professionally or otherwise? I've had a lot of big swings. I mean, you know, me leaving my job at the law firm where I was making a ton of money in corporate law and deciding to go and work in government and public service where it cut my salary in half. And I remember how guilty I felt for going to mom and dad and even expressing an interest to do something that I cared about rather than something that would make the absolute most money. I mean, at the time I was making my salary was more than both mom and dad's salary combined. Right. I remember the first time I ever bought a house. One of the biggest leaps you ever take, I was really intimidated by the whole process. Progressive understands the hurdles first time homebuyers are facing, including housing

affordability challenges and a lack of straightforward education that could make the home buying process feel less intimidating. Progressive's Open the House Initiative is committed to breaking down these barriers, and making first times a little easier. Since 2024, Progressive has committed more than $16 million towards making the dream of home ownership more achievable. This includes a $3.5 million investment this year towards the Up Payment, Progressive's down payment assistant program aimed at first-time homebuyers.

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Cost of medication not included. Final pricing depends upon program selection. to empower them in their housing journey. Yeah, the one thing about swerving is that it gets easier over time. You know, that first leap is the hardest. Mine was when I left law and decided that I, you know, and I had to figure out then, if not a lawyer, who do I want to be? And I had to start over and figuring that out.

I had to start that process. And what it was going on in my life at the time was that dad, had just died. And one of my best friends from college died suddenly of lymphoma. And I mean by suddenly she was diagnosed in December and died in May. And this was a young, healthy, beautiful girl. And it made me stop and think, oh my God, life is short. And it is unpredictable.

And nothing is really guaranteed. And if I were to die tomorrow, is this where I've been. want to be on the 47th floor of a corporate firm working for corporate clients looking at my I could see the neighborhood where I came from from my fancy office but I wasn't connected to it I was like is this who I want to be have I even thought about it or was I just checking boxes and I thought and I also met Barack Obama at the time who was the master swerver because he did the opposite of everything you were supposed to do. He had been a community organizer. He had, you know, he went back to law, not because he wanted to do the corporate firm thing, but because he thought it would give him tools to help the

community. He had no interest in Supreme Court clerkships, even though he was the president of the Harvard Law Review, and that was the path. So I was meeting other people who were showing me different ways of making decisions in life. And we started dating, and he was like, if you don't want to do the law, leap now. I got you. We're going to be okay. And so I left to work in the city, to work

in city government. I was an assistant to the mayor, then was in economic development. And with every move, I just realized that I was walking more into my reality, into my truth.

Not being in sort of a sterile environment, but being in the grit and the scrum of city work and helping people and that that is what got me up every day feeling really excited and nobody taught me that or teaches young people that in college you know nobody teaches you even the process of figuring that out for yourself um and that was an eye-opener. But once I did that first leap, the others were easier, you know, because number one, I had freed myself from the financial belief in the same way that Craig did. It took us longer to pay down our loans, but we were able to pay them down. And I hope this isn't so

disheartening to people that were saying money doesn't matter, that people are leaving. No. they're like wait a minute money doesn't matter we're in the wrong seminar I don't agree but it doesn't but it doesn't look

you know the thing is is that it comes along the way right we're both doing well you know but I try to talk to young people about one thing we learned with IMO, one of our guests, favorite guests, was Dave Chappelle. And he said something about, because he lives in a little town, Yellow Springs, Ohio,

in the middle of nowhere. It's his little dot of blue and a lot of red. And that's where he grew up. His parents were professors at Antioch College, which is a small college in that town. I mean, it's a farm town. And we were like, we went and visited it because we did the interview out there. We did another live out there, and we had an amazing time. Dave Chappelle is one of the smartest people on the planet. Funny is all get out. Yeah, you can clap for that one. For that one. It was good. But when I asked why, because once he became himself, he moved back, bought a farm, has raised his family on this farm, and one of the questions was, why here? And he said, I wanted to have the financial freedom to be courageous.

And I was like, ooh, ooh, bars, bars, you know. And that's a truth I think Craig is talking about, which what I would say to young people, and I say to my girls, live smaller than you need to, you know. I know, look, I saw your face, girl. What should do? You got loans. It's not too late. It's not too late.

Because I wasn't living small either. He had a Porsche. I had a sob. That was the first thing we got with nice cars when we got these big fancy firms. Big houses, all of that. It was just, and it wasn't happiness. But living small financially allows you to stay free of the golden handcuffs. Because that was the thing I saw in my firm.

I was figuring this out. I would talk to junior associates, senior associates, and people were there, and not across the board, but folks felt were there because they got used to the money. And everybody had a mortgage or this or that. And that led them to just stay, just let me just make partner and let me just do this because now I'm living up to the salary that I'm making, right? I didn't want to be stuck because making choices in life because of the money. So I tell my daughters, get used to living smaller than you need to so that you can do the things you want to do when they present themselves. And then you can build from anywhere.

And Craig, you know, one thing a lot of people didn't realize that you knew was that there's a hierarchy even financially, even in coaching. that you start out as an assistant coach or working with kids, but if you make your way to Division I coaching, they make ridiculous money. It's way too much money that you were making as a coach. On another note. The first leap is the hardest,

and keep yourself financially as free as you can. So how much of our journey do you think prepared us to be podcast hosts together? None of it, no. You know, I think it's that courageous thing, right? The feeling that, okay, I guess we can do this because we did all these other things. The bravery makes you brave to try anything at any age.

And I think for me, I've just gotten used to, okay, we're going to do this. I mean, I lived in the White House. I was the first lady. That wasn't my plan. I had no training for that. Wasn't my idea. It was not. But we figured it out.

If I can be first lady, I can do a podcast with my brother. But I think the staying courageous and curious and open, and vulnerable, and willing to share. I think the one thing that I learned through my journey was like a lot of people just don't tell young folks stuff. I mean, it's like, why is so much of life a secret?

You know, why are we pretending like, I got it, I get it, you know, and nobody's got it. Nobody knows what they're doing. And so I've kind of offered a lot of my experiences up really is kind of like, I feel like I have a responsibility, having had opportunities and exposure, and to have sat at every powerful table there is. I have seen it all. Every table, I've been at it. And I feel like it's my job to come down from the mountain and be like, y'all, this is a mool. It's not all that, because there's so many people like me, like you,

women, minorities, folks who aren't supposed to be at these tables, because they are sitting around thinking that they're impostors. I've never heard a white man talk about imposter syndrome. I haven't met. I haven't met one who has felt it. I'm just

wondering if you guys know what we're talking about when we talk about imposter syndrome, this feeling that you don't belong at the powerful table you're sitting in. Y'all are like, nope, never felt it. Never felt it. But it's, you know, I think my honesty and vulnerability,

the kind of conversations we have in podcasting, that's a good, I think it's a good space to share some of these experiences so that we demystify all of life, all of it. You know, marriage, raising kids, what was hard, IVF, let's talk about it. Let's talk about it so that people aren't growing up unaware of like some obvious things and mistakes. And so I think you have to be willing to be vulnerable to be in the space of podcasting.

And I think my life has prepared me for that. What about you? I'm only in this because our team asked me to do it, to give her to do it. It is true. It is true. I wasn't, you know, I was like, I don't need to do it. I'm half joking.

No. No, it is true. They're like, your brother will do it with you. I was like, oh, really? Craig? I love my brother. I do. Oh, and that's sweet. He's my big brother.

But pivoting to this was easy for me. But, you know, one of the pivots I took in between working in college basketball and working in the NBA. I worked at ESPN, which is a sports channel in the United States. I forgot all about that. See, he swarves so much. I totally forgot about your broadcasting experience. She was busy in the White House. Yeah, that's right.

That's what we were doing. So it wasn't something that I had planned to do, but it was one of those things where my agent was like, don't go back into coaching right away. Why don't you go work on TV and just think about it? And I did that. And my wife says that we're doing this podcast. second wife, by the way. But yeah, my second wife. Well, we want to clarify that.

We're honest. Remember he got divorced before the Porsche? My sister and my second wife get along really well. I got along with your first wife too. We crashed a Porsche together. Yeah, I'm still mad about that. But she says it's because I just like talking to people, which is true. you know what's really been interesting about this pivot is that I've been able to sort of

culminate all the experiences I've had throughout my life and then use them philanthropically because as Mish said early in the in her introduction you know we get questions from our listeners and then can impart some opinions um to try and help them. And being philanthropic with our experiences is such a wonderful feeling. And people have been so gracious. You go through the airport. I'm still coaching my kids in basketball tournaments.

People come up to me all the time and say how much they love the show. So that's been really good. The second thing is, and I don't think we talk about this enough, because I'm used to being on teams, you know, having been a player and then gone and worked at, you know, when you think about bond trading, it's very individualistic. So for a big part of my life, I was sort of a sole survivor out there. And then I got back into sports and it's back with a team. You know, working on this podcast is like having a whole new team.

in a completely different genre than I've been comfortable in. So I'm like the rookie on the team again. I mean, we've got, you know, our staff is peppered through here and in the back. They really are the ones who make this show for us. They get our guests. They, you know, help produce us. And it just is a really neat feeling. And every time we get together, it's like a reunion.

And so this is really been a pivot that's been a whole lot of fun. And it's really nice to hang out with my little sister again. And the most remarkable thing is because I know how you guys look up to her. That's how our guests are. Well, some of you do. Right? Wait. And it is mind-boggling to me.

Mind-boggling. I mean, you know, sometimes people get so emotional, and I'm just, like, shaking my head like... Her? No, but it's been really fun. This message is a paid partnership with Apple Card. You know, I like keeping things simple, and that's exactly what Apple Card does.

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You know, I just think the pace, we stack up a lot of interviews at once because he works and there are other commitments. So it's just doing. You know, so she said he works and then other commitments. Well, he's got a real J-O-B in a traditional sense. And I'm just rambling around the. country doing stuff. But I have more control over my schedule than he does. So we, you know, it's doing the work to be prepared for your guest, whoever it is. I mean, the one thing I've learned in college, one of the skills that I've brought along the way that has helped me as

first lady is, is just preparing, you know, just being ready for whatever job you're doing. and I tend to over-prepared. So I think it's really trying to make sure I know enough about every guest, about every aspect of them, so that I can forget about any notes and then be engaged in the conversation when it happens. So it's like talking to a friend that I've known all the time, and I can remember, ooh, you said this one thing.

Talk more about that or get into that. You know, sometimes it's work to make things look effortless. And so just making that time is one thing that takes up a little more time than I thought. Yeah. But it's good. For me, the most challenging thing is keeping up with my sister's wardrobe. That's hard. You're doing okay.

Look at his socks, though. He doesn't know that he should steam his jackets before he comes out, but we're working on it. We're working on it. Nobody can see the back. Yeah. Spoken like a boy, a non-fashioned boy. No, for me, it is keeping up with pop culture is hard, you know, because... Which is just regular conversation, right?

You know, I mean, pop culture, if it's not basketball, you know, it just can't be all sports. You know, you got to know what the real housewives are up to. You've got to know. And I don't know what the... real housewives are up to. I don't. So he's left out of a lot of conversations on the podcast, y'all. But we've talked about, you know, this third act. And you guys are young out there. There are a lot of young faces, but I think there'll be some people here who understand, you know, that next, that what for me, and I do say this, is probably my last child.

I mean, from a career standpoint, don't look like that. I am 62 years old, and you're older. I'm 64, yeah. 64, 62. Our grandparents, we could be grandparents, but we are not. If we had sat down for a few minutes, we could be grandparents. It's true, yeah, yeah, if we had slowed down a minute. But I do think, I have been trying to,

to be very mindful in this next chapter. And I get my staff all upset when I say this, and we just lost our mom. And one of the things that mom said, and our mom was very practical about life and all things, and she's like, I don't want to live to forever. Old people need to die and get, I mean, these are her words. It's like, we don't know what we're talking about.

We need to keep moving on, and I'm just going to be fine. when I get older and, you know, she's been dropping dead for 20 years. She's like, oh, I'm going to be dead, and you need to be able to get yourself together with me not here. I mean, she's telling us this and we're 10 years old. And I'm like, Mom, this is scary.

But when she was sick and getting worse, she was with me for about a winner, and it was clear that she wasn't, that this was, she might not recover from this. And so we, you know, fortunately had some time to kind of all come to grips with the fact that mom wasn't going to be here forever. And even with her jaded and, you know, stoic approach to things, I was sitting with her on the couch and we were watching TV. And we'd just come back from a doctor's appointment, didn't get great news. And we were watching Judge Judy, as we often do, as she did.

And she just looked over at me and said, while that was quick. And I was like, what are you talking about, mom? And she said, life. And I was like, and she said nothing else. You know, like even this cynical sort of stoic woman felt like, you know, when you're living a good life, it's fast. And I felt like that in our lives when you're busy and moving. I mean, this last, we've been out of the White House for 10 years. And I swear it went like that.

And most people are, my daughters will be 28 and 25 this year. I mean, so my thing is like this next chapter, I want to be mindful about it so that it doesn't just slip away. I want to be clear about how I'm spending my time, how much of it I'm giving away to others, what I'm choosing to do, you know, how it makes me feel. you know, how the choices that I make are now going to be for me, not for my husband, not for my kids, not for the country, not for the world, because this is it. And at some point, it's important for us, our generation, to step out of the way and be prepared to step out of the way so that the next generation really can sit in these seats.

So that means that this is our, you know, this is our third act. I don't know how do you think about your third act, Craig? Well, I wasn't thinking of it as a third act until everybody started talking about a third act. No, it's all the more important to reiterate what I was saying about finding something you love to do because it's not easy to do. it's not easy to find, I should say. And we have been really fortunate and being able to do a lot of things. But my sister always reminds me.

She said on one of our episodes, she said, you know, we only have about 19 summers left. Which is a lot of summers. But it is 19. We're 62. When you think about it, that's not many. That's not many, but it's, you know, so I want to start counting, so I don't lose track. Yeah, yeah.

I don't want to waste a summer doing something silly. It's like, dag, one of my summers just went to doing something silly. So this part of our lives is just, we just taking more control over it and being able to spend it together and our families are getting, together way more often now. It's just, you know, if I could impart any opinions or advice to you is don't sleep on this third act. Because they're, you know, at this age, we are not the same as our parents were. We are vibrant and lively and can still run around a little bit.

We're cool. She's cooler than I am. but we're cool so it is just embrace the third act is what I'm saying because the fun doesn't

have to stop and the learning doesn't have to stop and you know people talk about they throw around this lifelong learner term

it's true one of the best parts about doing this is that my brain has been re-energized I'm learning something every single time we sit together with one of our guests. And to the young people out there, too, because all of this is earned and has to be earned.

And so, you know, it's important to know that there was a process for us to get here. And, you know, and that process takes time. and it takes some level of investment. Because even though we swerved, one of the things I know you and I did was that wherever we were at the time, we put 120% in what we were doing, and none of it was a waste.

And that's what I want young people to understand that every experience, everyone, the bad boss, the boring assistant job, the job that you thought you weren't appreciated. The one that didn't give you the assignment you wanted when you wanted it. All of that is learning. You know, it's learning to be resilient, you know. It's like one thing that's important to learn is how to do something you don't like to do and be good at it. You know, I think a lot of young people, they want to just, now they want to do what I want to do and what I'm good at.

You got to earn that, you know. You got to earn, you know, carrying some bags. And, and, you know, and having some tough times and having people treat you unfairly, right, and not giving you the raise when you think you deserve it, you know. There's character building that comes that gets you ready down the line for, you know, being your own manager, being your own leader, you know. So one of the things that a lot of our guests say that are good at what they do is that they are more enamored with the process than the outcome. And so I would say to young people, learn to enjoy the process,

whatever your process is, because that's where you develop the skills that then lead you to the things that you want to do. The process of developing programs in the White House, it takes time. It took a level of persistence. There was a whole lot of backlash. Was I prepared for it? Was Barack prepared for it? Heck yeah.

We were. From all the other things that we had done, it all leads up to being ready for the thing you don't even know that you're going to do. So I want young people to be a little more patient in the process. You don't have to start counting your summers yet. You know, you got a lot of them. And that's the other thing.

Life is long. I mean, we have had between us. We've had dozens and dozens of careers. You know, it's like the ability to remake yourself is there. If you're good at what you do, and that's another reason to work hard, is because you leave your job well, you can go to the next one. Everything we've done, I hope people say they were good at what they did, you know, so that we got the support and the encouragement

to go to the next place, even if you didn't like the job. I worked hard at Sidley and Austin. I had great relationships with those partners. They're still in my life. Some of those people back when I was 26 years old are still people who respect me now. And that's the kind of investment that I think everybody here,

young people early in their careers, wants to be thinking about making. What are these people, whether I like them are not going to say about me, in 10, 20 years. What are they going to remember about what I left behind? But it's the process.

I don't have too much more to add. All right, well then, it is time for... Yes. We've covered a lot of ground. This is something our team loves for us to do, which I'm like, okay, I don't know whether this is going to be fun for you.

Yeah. Yeah. Yeah, see, my sister's a curmudgeon. I can be. This is, we want to end on a bit of a lighter note, and our team has written up some fast money lightning round questions. Oh, do I, I think I lost mine. That's okay.

I'm prepared. I didn't do that on purpose, Crystal. Yes, you did. I swear, I swear. So we're going to do some fast rounds to each other, or maybe I'll do them for both of us. I'm like, where's my card? Lost their cards.

But we're going to name, some British favorites and see which ones are our favorite. You ready? Okay. Yeah. All right. So I'll go first. Okay. Sausage roll or fish and chips? Fish and chips. I had a plate. Got in late 1030.

Fish and chips waiting. Vinegar. Tartar sauce. Best thing. Best thing. I mean, it's always smacks. Fish and chips. All right. I'm fishing chips. American biscuits or British biscuits. Okay. It depends on what I'm doing, but British biscuits are cookies and American biscuits are bread. So I'm going British biscuits. Really? Okay.

All right. I know what I'm talking about. They still sell Jaffa cookies around here. Jaffa? Yeah. Okay, little Mr. Manchester. You're next. You ask me.

Tea or coffee? Tea. Although I had a cappuccino because I just come back from Australia. So I'm like, I'm holding up. I needed coffee today. Marmite, beloved delicacy or edible prank? Edible prank. What is it?

It's like vegemite. What is that? It's like a spread, right? What is it? What is in it? It's like yeast spread. It's a yeast bread. Why are you all eating yeast? What is going on here? And who was the first yeast eater?

Who tried that? It's actually good for your gut. What do you know? All right, here. Pub at 2 p.m. on a Tuesday? Concerning or community building? Um, I'm a problem with 2 p.m. Pub. Nothing wrong with a pint.

Assuming, you got your work done. And it's not happening every day. Oh, it's just Tuesday. Yeah, yeah. That's fine. That's fine. Um, what's a spotted dick? I really, what is it? What is that? I don't know what that is. Did you? What is it?

A pudding. Like a cake. Okay. Is it good? Is it delicious? Is it like my wife? Okay. Is it yeast again?

That's why I don't know about it. It's not delicious. I thought you knew. Okay. Big Ben or the London Eye? Uh-oh. Is there a right answer to this? No.

There is. Okay, let me guess what it should be. Big Ben's been around longer. It's a historical feature. whereas the London Eye is a ride. Is that pretty much... So you should care about the history and not the ride.

Although the ride sounds fun. It's a Ferris wheel, right? Yes, it is. The London Eye is a Ferris wheel. It's a ride. Yeah, yeah. All right. Okay, you can only listen to one for the rest of your life,

Elton John or Paul McCartney. Oh, so, yeah, that's a hard one, right? But let me tell you, Hell John was my mom's favorite artist. Yes. And for her funeral, he re-recorded, was it a candle in the wind? One of her favorite songs for her. Oh, and love Paul.

Hey, Paul, we're coming for you. Okay, we're running out of time, so we'll do one more. Okay, you do it. Favorite British word? Bloody brilliant. I love it. Like, brilliant. I keep intending to use brilliant.

Like, but I forget because I'm American and we don't have beautiful language. And bloody is worse than the F word. Is it really? No. No, it used to be when I lived here. It was worse. No. I think the fact that anything can be brilliant, it's so, it's like, it's just brilliant.

Like this time with you all, brilliant. Brilliant. Thanks, love it. It has been a treat. It's good to be back. We love you all. Thank you. And to my big brother, Craig Robinson.

Thank you all.