Pursue What You Love Before You Pursue Love with Jay Shetty [From the Archives]

Today we're revisiting one of IMO's most memorable episodes. World-renowned life coach, podcaster, and former Hindu monk Jay Shetty joins Michelle and Craig to dive into a listener's question about professional ambition and dating. The trio discuss money in relationships, finding balance between work and romance, and Michelle shares her advice for choosing a life partner. Is the pursuit of perfection — in work or dating — worth it? 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.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  If you can't see something in your mind, you can't create it in your life. And so instead of looking at life through these two extremes, maybe there's a middle path. And the middle path could be that, wait a minute, maybe I don't need to quit my job. Maybe I can stay at my job and then build my passion and build my skills and learn and expand my network. And maybe this thing that feels like a big risk and feels like a big jump and a big leap, maybe I could make it feel like a series of steps that make it feel seamless and smooth. Maybe it doesn't need to be, if I don't go all in, then I'm not gonna make it. And I think sometimes also,

• 0:44Speaker 00

  our mindset today is if I don't go all in, then it doesn't matter.

• 0:59Craig Robinson?

  Well, it is great to see you.

• 1:01Michelle Obama?

  Hi, you.

• 1:02Craig Robinson?

  I missed not recording with you and spending time with you.

• 1:07Michelle Obama?

  Welcome to one of my favorite places to be.

• 1:09Craig Robinson?

  I know it is. We have to figure out how to get here more often.

• 1:13Michelle Obama?

  You know, I keep telling you all that. Like, this is a great place for the boys at this age. I know you all are busy with basketball and all the things. But last time they were here, they had a ball.

• 1:24Craig Robinson?

  Oh, they, they, listen, it's not their fault. It's, it's, it's our fault. Between basketball and music and school, it just, it makes it tough. But, I mean, I really appreciate you having us here. How about this?

• 1:38Michelle Obama?

  Yeah, yeah, we're lucky. I mean, I can actually walk, you know? I can get on a bike and ride for hours. I can walk on my own. You know, you can see the ocean. The towns are just very quaint. So I'm, I'm glad you're here.

• 1:53Craig Robinson?

  I am glad to be here. And our listeners should know that you have, your oldest nephew got married this summer.

• 2:00Michelle Obama?

  I'm just so happy for Avery.

• 2:02Craig Robinson?

  It was really neat.

• 2:03Michelle Obama?

  Avery and Emily.

• 2:04Craig Robinson?

  Another Mrs. Robinson.

• 2:05Michelle Obama?

  Another Mrs. Robinson. Yeah, that's, that's strange.

• 2:08Craig Robinson?

  That is.

• 2:09Michelle Obama?

  How does it feel having your first child married?

• 2:12Craig Robinson?

  I will tell you that Kelly and I were so focused on the wedding because we didn't hear anything about what was going on. So we thought it was gonna be a disaster, of course.

• 2:23Michelle Obama?

  No faith, no faith.

• 2:24Craig Robinson?

  No faith in your own kids who you've raised to be well. And when we showed up and everything was so well done and so tastefully done, and so many of the little things, like the name tags and the menus, were all done by hand by Emily and Avery. It was such a wonderful and beautiful ceremony. I left there feeling proud.

• 2:47Michelle Obama?

  Yeah, yeah. Well, you did a good job, dude.

• 2:50Craig Robinson?

  Thanks. Thank you.

• 2:51Michelle Obama?

  Hey, way to go. Way to go.

• 2:54Craig Robinson?

  Well, and speaking of jobs, we have a great question today.

• 3:01Michelle Obama?

  We do. We do. Good segue. Way to go.

• 3:04Craig Robinson?

  Thanks. I'm, I'm, I'm, I'm, I'm working hard to be like our first guest, Jay Shetty. I'm trying to be Jay.

• 3:11Michelle Obama?

  Okay, okay.

• 3:13Craig Robinson?

  But the question deals with leaving your current situation to try and find a job in something that you're passionate about. And you know, I've, I've dealt with that.

• 3:26Michelle Obama?

  Yeah, passion versus family versus...

• 3:29Craig Robinson?

  Versus financial.

• 3:30Michelle Obama?

  Financial, yeah, yeah. It's something that we've all dealt with, but...

• 3:34Craig Robinson?

  Yeah.

• 3:35Michelle Obama?

  It, it, it's a good question to get us started.

• 3:37Craig Robinson?

  Yeah, yeah. And we've got a great guest for this. And Jay Shetty is a number one New York Times bestselling author, award-winning storyteller. And I happen to be telling my sister all about someone she knows. This is really for me because I'm meeting him for the first time. He's a podcast host, which I've already said I'm trying to be like him.

• 4:00Michelle Obama?

  You can learn a little something here.

• 4:01Craig Robinson?

  And a former monk.

• 4:03Michelle Obama?

  Yeah.

• 4:04Craig Robinson?

  How about that? Dedicated to helping people train their mind for peace and purpose every day. And he hosts the popular podcast On Purpose, which you were on, by the way. I'm very excited to have him with us today. And Jay, why don't you come on out? It's good to see you, man. Thanks for being here.

• 4:27Speaker 00

  Great to be here. Thank you so much.

• 4:28Michelle Obama?

  It's great to see you. Thank you so much.

• 4:31Speaker 00

  Craig, it's wonderful to meet you.

• 4:32Craig Robinson?

  It is so nice to meet you, man. I listened to the show you did with my sister and I was, I couldn't stop listening.

• 4:38Speaker 00

  Oh, that's very kind. Well, that's because of her. Everything she said is beautiful.

• 4:42Craig Robinson?

  We already know. We already know.

• 4:44Michelle Obama?

  Jay, I am, I'm just grateful that you're here. After our conversation, I don't know if you remembered, but I was like, I could talk to you forever.

• 4:53Craig Robinson?

  Well, I, let me tell you this. I've been thinking about what I wanted to talk to you about. And I know we have to get to this question, the, the question that we have from our listener. But I wanted to know, Jay, I'm sure you've been on a number of shows. I can imagine that people wanted to ask you about being a monk the most.

• 5:15Michelle Obama?

  Is that true?

• 5:16Speaker 00

  That's true. That's 100% right.

• 5:18Craig Robinson?

  I did my research. What I want to ask you about is, what have you been asked about in your experience the least? And how has that informed who you are as a person now?

• 5:33Speaker 00

  Wow, that's a great question. That's a great question.

• 5:36Craig Robinson?

  Like I said, I'm trying to be you. I'm trying to be you.

• 5:40Speaker 00

  Well, you're doing better than me right now. You've stopped me already. The thing I'm asked about least probably is my family. And the fact that you're both doing this together just shows how important family is and how, how much it shapes us and how much it molds us. And I would say my family experiences are a huge part of why I do what I do today. And I've never spoken about this before, but I have a really beautiful relationship with both my mother and father. But I, I mediated their relationship ever since I was a young boy. And so I found myself at 10 years old, sitting with them individually, listening to them, trying to understand them,

• 6:24Speaker 00

  giving them a shoulder to rest on, to feel seen, heard, and understood. And I feel that all the work I try and do today to try and help and serve the people online or wherever it be through my books or my podcast, comes from, I feel I've just played that role my whole life. I remember doing it for my parents and recognizing that they were both beautiful, wonderful people, but had their differences. And to be able to recognize that at an early age, I think has allowed me to not have this divided thinking of it's one or the other.

• 6:57Michelle Obama?

  I'm just picturing 10-year-old Jay sitting down between mom and dad. Okay, now, tell me what you're thinking here and what did you mean? But kids do find themselves when, with the level of sort of precocious empathy, you know, oftentimes kids do become the mediators in the family and that you were 10 years old doing that.

• 7:20Craig Robinson?

  And I would, I would venture to say that there are more people who are in your position who turned out a mess because they were refereeing their parents. I mean, I, I think you gotta, you, you gotta feel pretty good about where you are, given the position you were in.

• 7:39Speaker 00

  I would like to think that I took good notes and that helped a lot of what to do, what not to do. And I think I'll be happy and satisfied if I figure out how we can help more people get to that. I think that's the hard part.

• 7:54Michelle Obama?

  And, yeah, that's why I wanted you here. The reason we're doing these conversations is to, to talk, you know, to talk through things with people, to talk through things in person, you know, with us here, hopefully shedding some light, giving people tools and, you know, some kind of direction because everyone is looking just for a little bit of direction. It's like, how did you get here? How did you, how did you not mess that up? And as you know, we don't have the answers. But oftentimes, it's just the conversation that people find helpful.

• 8:29Craig Robinson?

  That actually leads to our question from our, our listener, Adrian.

• 8:34Speaker 03

  Hi, Michelle and Craig. My name is Adrian and I'm a 38-year-old man who works in tech. I've been considering recently whether to take a major career risk, which is starting a new company, or to stay in a high-paying job that will afford me the opportunity to have a family. These dreams seemingly are at odds. Given my experience in an emerging industry, I feel like I have a real chance at starting something big and making a difference. In the long run, I think it will pay off, but it will require years of hard work, long hours, and financial instability. Not the best circumstances for having a family. The alternative is putting my career dreams on the back burner

• 9:17Speaker 03

  and prioritizing financial security so that I can support a family in the future at some unknown time. I'm currently single, but I'm also serious about settling down when I do meet the right person. At my age and knowing I do want a family one day, how should I approach this decision? Should I prioritize my career dreams or financial stability and starting a family earlier in life? Thanks, Adrian.

• 9:45Michelle Obama?

  Sounds like a familiar dilemma, you know? And, and the first thing I think about is how I wasn't a risk taker. I think because of the stability that we had in our family, I thought that that was the way you led a life, that there, that things were linear, you know? If you did the right things, if you checked certain boxes, that you were winning in life. And as a result, I think my view of what life could be was way too narrow. But I was on, I was off on that path, not really thinking about anything but checking the boxes. So I did what, what I was supposed to do. I went to grammar school, got great grades,

• 10:29Michelle Obama?

  went to the best high school I could go to, got great grades, applied to an Ivy League school, got in, did well. Never asking myself, why? What do I care about? After graduating from Princeton, went to Harvard. Why? Because I got in. And I thought, well, maybe I want to be a lawyer. But it seems like it's a very linear thing. And it wasn't until I was practicing law that life hit me in a certain way and I started to think about my why. And that sort of made me stop and think, wow, I've been kind of stuck on this path that isn't even mine, thinking that what was important was a good job,

• 11:13Michelle Obama?

  the right salary, the right school, that there were like these answers. And none of it had to do with happiness.

• 11:27Craig Robinson?

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• 12:12Craig Robinson?

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• 12:34Speaker 04

  Wayfair, every style, every home.

• 12:37Craig Robinson?

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• 13:22Craig Robinson?

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• 14:05Michelle Obama?

  So when I think of Adrian's question, I think he's got a narrow way of thinking about what a happy life can and should look like. And so my first thing for Adrian is to think about, why does he think that? Why does he think his choices are either or? That I can either have a family, or I can have a career? Or if I'm gonna have a family, then I have to have a certain set of things? I think a lot of young people, a lot of people in general, because of their narrow view of what's possible, they find themselves limiting what life could look like. And I always challenge young people now to first think about your why.

• 14:50Michelle Obama?

  You know, don't think about the what. Don't worry about numbers and titles, because you can have all that. And I've seen people have it all, and they're still not happy.

• 15:00Craig Robinson?

  Right.

• 15:01Michelle Obama?

  He could have a big, high-paying job, a great career. Maybe he decides to get married, have kids, but then he'll have no time for them. And then he'll be disgruntled about that.

• 15:14Craig Robinson?

  Sounds familiar.

• 15:15Michelle Obama?

  Sounds familiar. Stop checking boxes, first of all.

• 15:20Michelle Obama?

  You know, and start thinking a little bit bigger about what a happy life can look like.

• 15:25Craig Robinson?

  That's a good place to start. Jay, what are your thoughts?

• 15:28Speaker 00

  Yeah, I'd have to agree. I think everything that Michelle just said, I think really summarizes the challenge. And he used a line that said, seemingly at odds. And I think that's exactly what it is. It's like, we live in this world now where it's either either or. Like, I can either have success and ambition, or I can have love and relationships.

• 15:51Craig Robinson?

  Right.

• 15:51Speaker 00

  I can have an amazing family and home, or I can have an amazing career. And what's fascinating about it is that it's actually a block in the mind. And I feel like if you can't see something in your mind, you can't create it in your life. And so, instead of looking at life through these two extremes, maybe there's a middle path. And the middle path could be that, wait a minute, maybe I don't need to quit my job. Maybe I can stay at my job and then build my passion and build my skills and learn and expand my network. And maybe this thing that feels like a big risk and feels like a big jump and a big leap, maybe I can make it feel like a series of steps

• 16:35Speaker 00

  that make it feel seamless and smooth. Maybe it doesn't need to be, if I don't go all in, then I'm not gonna make it. And I think sometimes, also, our mindset today is, if I don't go all in, then it doesn't matter. But then if you don't go all in, you're just all out. You never try. You never gave it a go. And I think also, the perception of thinking that, if I have a family, it means I can't take risk. Going back to your point of the why, Michelle, I feel like a lot of us don't realize that maybe the partner you're going to be with is gonna be attracted to your ambition. Maybe they'll be attracted to the fact you wanna take a risk. Maybe when you're honest with them about who you are, they'll say, you gotta go for your dreams.

• 17:19Speaker 00

  I don't wanna be with someone who's settled. And so, I think you can't preempt that. It all depends who you attract and who you choose.

• 17:26Craig Robinson?

  So your refereeing relationship ability is coming to light here, because he's not even in a relationship yet. And he's determined, he's determining that his partner wants one thing or the other. Why do we think the norm is either make a whole lot of money or be happy? Why can't you do both?

• 17:50Speaker 00

  I think there's a feeling we have that if I do one thing, then I'll do it perfectly. And so that perfectionist mindset, we feel, well, if I just focused at home, I'd build a perfect home. Or if I focused on my career, then I'd build a perfect career. And the truth is, we're gonna do both imperfectly, whether you gave them 100% attention or 50/50.

• 18:11Craig Robinson?

  Yeah, that's a great point.

• 18:12Speaker 00

  And I think what I hear in Adrian, and I empathize with it, I genuinely do, is we're all struggling to give ourselves permission to make mistakes on both.

• 18:21Michelle Obama?

  Yeah.

• 18:22Speaker 00

  And there's this feeling today that I have to get it 100% right. And the truth is, we're gonna fumble, and we're gonna fall. And maybe one day, I'm not gonna be the best at work. And maybe I am gonna say something to my wife that I regret and I wanna take back. And maybe, I'm not gonna be present at every recital. And maybe, and that's the reality. And I think we've stopped looking at life as this real, honest, transparent, flawed-filled dance. And we almost want it to be like, well, if I devote my life to this, then I will be able to eliminate all forms of trauma, pain, and stress. And I just don't think it's real. So I think we're seeking that permission.

• 19:04Speaker 00

  I think that we're looking for someone to say, it's okay.

• 19:08Michelle Obama?

  I think it's incumbent upon us as adults and people with platforms to talk a lot about the fail. You know, just to own up to the fact that, as you said, Jay, life is full of getting a whole lot of stuff wrong. We will get more things wrong than we will get right. And we've all done it, and we're all okay in the end. I have had four or five different careers. You know, I would want Adrian to understand. It's like, few people pick a career at the age of 10, or 12, or 15, or 21, and stick with it forever. I wanna know, why aren't you dating? I mean, what are you doing? You know, you're almost 40 years old. Is that all you're doing is working?

• 19:53Michelle Obama?

  And how are you gonna ready yourself for a partner? Do you think that you're, you know, building a business is the only thing that's gonna be required of finding a good mate?

• 20:03Craig Robinson?

  Let me just help Adrian out here. And feel free to jump in here, Jay, because Adrian's probably thinking, I am 38 years old and I don't have somebody. Is it because I don't have enough money? Or is it because I don't have this thriving career? And it begs the question that I have for a lot of these women out here. If you had, and I'll say it to you too, would you be attracted to a guy who's not financially sound when you meet him?

• 20:43Michelle Obama?

  I married one.

• 20:45Craig Robinson?

  Don't you like that alley-oop I just threw you?

• 20:50Michelle Obama?

  No, that was a good.

• 20:51Craig Robinson?

  In basketball, you just point. You don't even have to say, you just point and run down the court. And let me say, one more thing before you give your answer. Most, you have to admit, most of your sister-in, not just.

• 21:04Michelle Obama?

  Women, other women?

• 21:05Craig Robinson?

  I'm talking about women in general. Typically are not like you at that age. They're looking to, they're looking to catch, they're looking for a good catch.

• 21:17Michelle Obama?

  Mm hmm. And there's a, a clear definition of what a good catch is.

• 21:23Craig Robinson?

  And to Jay's point about, maybe you can find somebody who's attracted to the hunt with you, which I think is hard to find these days. If you, if you disagree, feel free.

• 21:35Michelle Obama?

  I, I mean, I think you make a good point, and I think we can't generalize across the board for women. And I, I think women are also confused about what they want and what they should be looking for in a mate. I have a lot of friends who will ding a guy because, you know, he doesn't have a college degree. So there are a lot of people who aren't looking deep enough. They aren't thinking broadly enough about what makes for a good partner. And instead, we all just look at the superficial things. The first question we ask if we're on a blind date, so tell me, what do you do? You know, just starting with that question, you know, arguably could put somebody on the defensive, because what are you looking for?

• 22:20Michelle Obama?

  Why is it the first place that we start? Are we trying to get some idea of how much money they make? And that definitely happens. And I think on the flip side, with men, sometimes I think they're maybe a little bit too visual. I think there are a lot of women who are open to a lot of different kind of men and a lot of different kind of lifestyles. Women want a partner. They want to feel loved. They want to feel desired. They want to feel chosen. And I think a lot of women, I would tell Adrian, if you, if you're just straightforward with who you are, you know, you're going to find a mate. You're going to find somebody that wants to go on that journey with you and will be excited about it.

• 23:01Michelle Obama?

  And it might make taking the risks a little easier because you're not doing them alone. You know, I left my corporate firm when I met Barack. And I had somebody who was like, I got your back. The risk you think you're taking, they're not that crazy. And I'm here to help you. That's when I said, I would rather have that in a partner than a higher income. I'd rather have somebody who was ready to do some hard things with me. But that meant I also had to be ready to do some hard things with him. I just think we shouldn't assume.

• 23:42Michelle Obama?

  You know, you just got to kind of get out there and meet people and come to people with your truth. And then let them decide. But I feel like Adrian may be just too afraid. He's making some assumptions without even testing the waters, that there is a, there is a partner out there for him that will embrace everything that he wants to be. And it could make the ride a lot more fun and easy than it would be doing it alone. So I don't know if that answers your question.

• 24:13Craig Robinson?

  No, that, that, that answers it. But, and I'm going to ask Jay to referee again.

• 24:32Speaker 00

  No, I was, I was listening to Michelle and just relating in, in our own unique and different way to so much of what you said. When I met my wife, I'd just left the monastery and I was in debt. I didn't have a job. And even though I was a first class honors degree graduate, I couldn't get a job because surprise, surprise, no one wanted to hire a former monk.

• 24:54Craig Robinson?

  Why not?

• 24:55Speaker 00

  So it was like, what are your transferable skills? Like sitting still and being silent? Like, we don't need that. But, but it wasn't valued. Like, I remember going, I wouldn't even get a job interview, actually. I was applying online and I wouldn't even get invited to the next stage. It was quite hard on my own self-worth. And I was starting to date this girl at the time who's now my wife.

• 25:15Michelle Obama?

  How old were you? I was just.

• 25:16Speaker 00

  I was 25, going on 26. And so I was, I was younger than Adrian, so I understand that there's, there's a difference there. But there was a part of me that just thinking, will I ever get a job? Like, who's ever going to give me a shot? And I'm so grateful to my wife for, you know, sticking through all of that with me and navigating it with me and never, ever making me feel pressure. I think that's what I'd give her credit for, is I've never felt pressure from her for a certain type of lifestyle, a certain set of things, even today. And I think that's what allowed me to take more risks. It's what allowed me to dream bigger. It's what allowed me to try new things and fail and go backwards and forwards.

• 25:57Speaker 00

  And for Adrian, I would encourage him, like I think we all are, of be honest about who you are, be transparent about what you want. And if you're not out there meeting people and having these conversations, you're going to assume that everyone wants you to be set up, steady and stable, rather than ambitious, dreaming and navigating what that looks like. And so one of the things I think would be helpful for him is to start meeting people, is to start dating. And also talk to friends who are in those environments. Talk to his friends who are entrepreneurs, who have left the world of work. Talk to them about who's friends with their circles, who's connected, because you're also going to find them in similar spaces.

• 26:40Speaker 00

  It's going to be more likely that one of your friends says, oh yeah, I just met this person. They're also trying to be an entrepreneur. They also want to be with someone who's figuring it out. And I think that culture today is growing compared to when you met or when we met. I feel like the culture today of people building interesting lives together is spreading further.

• 27:00Craig Robinson?

  Did you meet your wife in the wild or did you meet her online?

• 27:05Michelle Obama?

  Is that what it's called? Like normal, in the wild?

• 27:07Craig Robinson?

  I love it. I love it. I'm taking that. I'm using that forever.

• 27:11Speaker 00

  Based on that, it would be in the wild.

• 27:12Craig Robinson?

  You met her in the wild.

• 27:13Speaker 00

  Yes.

• 27:13Craig Robinson?

  And you met Barack in the wild.

• 27:15Michelle Obama?

  Yeah, because there wasn't.

• 27:16Craig Robinson?

  There wasn't any. We're old.

• 27:18Speaker 00

  No water place there.

• 27:19Michelle Obama?

  There was, it was only the wild.

• 27:21Craig Robinson?

  It was all wild back then. But, so, you know, I, I'm interested in, in knowing how Adrian is meeting people. Because I agree with you. You, you got to get out there and, and open yourself up to failure on a relationship side to find that right person. And I think it feels like in this day and age, to your point, people are living more alone and being comfortable with being alone and doing things a certain way and don't venture out into the wild. And you, you might step in some dog mess every now and then, and you clean your shoe off. You can't be like, you can't be like me and throw your shoe away when you step in some dog.

• 28:05Michelle Obama?

  But the thing, you know, I, I want Adrian to think about the power of building something with someone, you know? Because I also worry that, you know, Adrian's on this path. He's going to have the perfect, everything will have bought the house. And he might get suspicious of bringing someone into that who hasn't been part of the climb. You know? I, I think, I, I think in my marriage, we're stronger because we, we've been through a hard climb together. I mean, we've seen it all. I loved my husband way before there was any idea he might be president of the United States. In fact, if I thought that, I probably wouldn't have married him.

• 28:49Michelle Obama?

  But the beauty of, of just trudging through some hard stuff together, you know, it can, it can bind you in a unique way. I, I don't want Adrian to rob himself of, of having a good partner along that journey because he could achieve all that, meet some, some woman, and then he'll wonder, well, do you love me just because I've got the house and the nice job? I mean, so back to the point of, there isn't really one right answer. I mean, he could do all of that and then grow suspicious of somebody who's just glomming on, you know, rather than knowing that somebody is marrying him for him.

• 29:30Speaker 00

  Yes.

• 29:30Michelle Obama?

  You know? And then he might find himself trapped in sustaining something that he might not even enjoy. But he's married a person who married him because he does have a big bank account and a, you know, a big house and has created this financial stability. He could decide in 10 years of being an entrepreneur or trying something big that he doesn't even want to do that. You know? I mean, there, life is long. And that's the other thing I'll, I'll say to Adrian. Life is long, you know? He might be interested in this big job now or being an entrepreneur, but in 10 or 20 years, he may want to do something else, you know? He may have kids and decide like you did.

• 30:14Michelle Obama?

  I mean, and Craig, you should tell your story.

• 30:16Craig Robinson?

  Yeah.

• 30:16Michelle Obama?

  About your transition. Because I, I will joke that we stopped checking boxes sort of at the same time in our lives. We started at these high-salaried careers and ran away from it. Because I know I was running towards fulfillment, not the salary. And Craig, you did the same thing.

• 30:39Craig Robinson?

  Well, my situation, Jay, was a little bit different, but similar philosophically. I was fortunate enough to get drafted, but I didn't make the NBA. So I didn't make a whole lot of my, I went overseas to play for a couple of years. And I was fortunate enough to play for a coach over there who said to me, you know, you went to Princeton, you played for Pete Carill, can you show my guys how to play a little bit of that offense? And I did. And we went from being the 12th place team out of 12 to being in third place.

• 31:13Michelle Obama?

  Wow.

• 31:14Craig Robinson?

  And I thought, you know what I'm going to do? I'm going to be a coach. And I went back to Princeton to go visit her because she was still there. And I stop off and I see Coach Carill. And I said, Coach, I know what I want to be. I want to be a coach. And he said, you don't want to be a fucking coach. Why would you want to be a coach? Here you are, a black guy from the South Side of Chicago with a Princeton degree, and you can't give up this basketball. Now, he wasn't doing that maliciously. He was being a mentor and saying, there's more for you out there than being a coach. And of course, I was like the dutiful player.

• 31:56Michelle Obama?

  Like, okay, coach.

• 31:57Craig Robinson?

  Straight out of his office and to Wall Street. And I began to work my way up. The whole time, I'm thinking, I should be a coach. I should be teaching kids. I should be teaching them the lessons that I learned from my first coach, who was my father. And my, one of the former assistants from Princeton offered me a job, being an assistant coach at Northwestern University. This is where I come to my sister and I'm like, I just got offered an assistant coaching job. But I go from making what a trader makes to making about $45,000 a year. And I'm going through a divorce. I've got two kids, four and eight.

• 32:40Craig Robinson?

  And I'm trying to figure out, should I make this move? And that was when you said, what did the kids say? And I was like, I haven't told them yet. And she's like, you should talk to them. At least you'll know where they stand. And so I put this decision basically in the hands of an eight-year-old and a four-year-old. And I said, Daddy's getting a new job. And my eight-year-old said, are you moving away? And I was like, no, we'll still be here, but I'm gonna be a coach. And he looked for a minute and he said, does that mean that your office will be a gym? I totally didn't expect that from him.

• 33:23Craig Robinson?

  And I said, well, it won't be the gym, but it'll be right next to the gym. And my four-year-old daughter said, do they have a pool there? And all of the agita that was inside me just went away. And that's when I made the decision to go into coaching. So for Adrian, I'm like, do what you love doing if you can. Now, he doesn't have a family now. So to me, he's in the perfect position to try some stuff.

• 33:50Speaker 00

  I think sometimes when Adrian's sitting there going, do I have to quit my job and start this out? There's things at his great company that can fuel that passion. There's something there for you to learn. And actually, when you try and make that leap or that jump without this healthy transition, you rob yourself of all the time that you get to learn, make mistakes. When I was at Accenture, I got to see how corporate companies build programs for mental health. We had 500,000 employees at the time. I got to think about what that looked like. How do you scale mindfulness across a company? I got to ask questions without the risk, without the fallout. And so I think Adrian's in a great position. And I think he could be throwing it away.

• 34:34Speaker 00

  And I would encourage him to first fall in love with where you are. Make work meaningful. I think it's okay to want to change where you work. But first, make your work meaningful, wherever you are.

• 34:45Craig Robinson?

  Yeah.

• 34:59Craig Robinson?

  How do we change that? I mean, I know you're doing what you can. You're talking about it. You're having some quality people on your show. And to me, to your point, we want to just be able to help folks like Adrian understand that you're gonna get a lot of messages from a lot of different places. Here's what we think is the healthiest way to go about it.

• 35:22Speaker 00

  I think it has to be top-down and bottom-up. And so I was speaking to a client of mine a few years ago, who's a CEO at a large company. And we'd worked on some really tough stuff with him. And then I'd said to him that the next stage of his growth was for him to share what he'd been through with his team. And he said to me, he said, Jay, I can't share it. And I said, what do you mean? And he said, well, if I share it, I'm gonna appear weak.

• 35:50Craig Robinson?

  Lose my leadership.

• 35:51Speaker 00

  I'm gonna lose my, I'm gonna lose the clout and the authority I have. And I said to him, I said, you sharing your weakness makes you strong. Like, you being able to tell them, I went through this. I found help. And I've come out the other side, is the narrative we need to hear. So I think one of the biggest challenges for men today specifically is leadership position men either not making the space, not having the time. Maybe they were never given the opportunity. And I think that's what I see the most compassionately and empathetically is, most people who don't give people the opportunity are people who weren't given the opportunity themselves. And so I think the best thing we can all do is turn to both men and women in our lives

• 36:33Speaker 00

  and all genders in our lives and just look at someone and say, what are you going through? Where's that space for leaders to openly share? And I'm thankful that people have come on the podcast and shared those stories. I remember, Michelle, you were talking about your kitchen table being the place of stories. It's like, this has to happen in informal settings, not just on TV. I think it's important, but it needs to happen everywhere. And then bottom up too, I think that a lot of us today are really scared of asking for help when we're going through a tough time. We're scared of even asking our parents. We're scared of asking our friends. We're scared of asking our brothers and sisters because we're scared that our problems aren't big enough.

• 37:16Speaker 00

  They're not real enough, that they're not valid enough. And we keep questioning whether anything we have to say is enough, only to realize that if we don't ask for help, that's the biggest weakness. And our greatest strength is our network, is our community. And so don't put yourself in a position where you're your only stability and foundation, which is where Adrian's kind of at right now. He's trying to figure it all out on his own.

• 37:44Michelle Obama?

  And I would want Adrian to spend some time, not just thinking about the achievements, but to think about the kind of life he wants. And not in terms of just job title, but how do you want to feel about your day? You know, is it gonna be enough for you to, you know, have a big bank account and work all hours and never see or have time for the people that you love? If you have kids, do you want to spend a lot of time with them? Would that bring you joy? You know, do you want to go to their games? Is that something that you care about? He, I would want Adrian, and I think I would want all men, to do a little more of that soft soul-searching,

• 38:28Michelle Obama?

  that it's okay to identify and nurture those real, true feelings. It's like, who are you? And it's okay if you're not a hard-driving, competitive mogul, you know? That's okay. We don't need all of that in the world. In fact, I think we have too many men striving for one kind of leadership. We need a broader cross-section of men in the world. So who are you, Adrian? You know, deep down? And then work to build the life based on that truth. And that may require a little counseling. It's definitely gonna require him to talk to more people, to find some community, his kitchen table,

• 39:11Michelle Obama?

  and to actually have conversations, people who know him and can say, Adrian, man, you're really not that dude, you know? People who can look you in the eye and say, like I did with my brother, you really love coaching, you know? And you'd be a great coach. So go coach. We got your back. But if he never taps into that and doesn't learn how to share some of this agita, you know, he'll be struggling alone for a long time.

• 39:40Craig Robinson?

  But we need to train ourselves. Speaking as men, we're not as good at being empathetic. We, we're locker room guys, right? And as soon as you're vulnerable in the locker room, you get attacked. And sometimes it's in a humorous way, but it's an attack. We need more people, like the Jays of the world, like me, like all of us who are, who understand this issue, to be out in the world doing it at the kitchen table level, to your point. So with that, So we've talked about a lot of things. I would love to hear what you would think, a couple of or a few takeaways for Adrian, based on our discussion.

• 40:25Speaker 00

  Yeah, I think what Adrian needs is practical advice is how can you look at this differently? How is there not only two choices? We've all said this today. What's that third choice? What's the middle path? What's that version that puts them together as opposed to separates them apart? And so I think that's the most practical advice for Adrian is let's approach this through a new lens where we're now not looking at it in a divided way and wanting a harmonious life. That's not going to happen.

• 40:53Michelle Obama?

  Yeah.

• 40:54Speaker 00

  The second practical advice I'd say to him is stop trying to predict, project, and assume everything. There's this feeling, and we all do this. We plan, project, and predict the partner we're going to meet, how our profession's going to go, how things are going to be. And I think, or both of you would say, having lived life more than I have, it rarely goes to plan. Like, it pivots so often. And so be open to the pivot. I think we place so much emphasis on making the perfect decision that we sometimes don't even ever make one. And so I think be active. Start that company on the side. Get out there and date. Stay at the company and keep doing well.

• 41:39Speaker 00

  Start putting things into practice and then pivot rather than trying to theorize perfectly in your mind how everything's going to play out.

• 41:48Craig Robinson?

  Terrific. Anything else to add to your?

• 41:51Michelle Obama?

  Just to emphasize that a happy life looks very different than what we think it looks like. Once I stopped checking boxes and started thinking about who I wanted to be in the world, not what I wanted to be, not only that, you know, I realized that there's so many ways to be happy, you know? I mean, maybe Adrian will decide that he doesn't want to get married at all. You know, he may decide to have a partner and not have kids. He may fall in love with a partner who doesn't believe in marriage. I mean, life be lifein'. That's the other saying I like that my kids say, life just be lifein'.

• 42:35Michelle Obama?

  And be open to it. There is no perfect way to be, you know? Every way of being is good, you know? And if you're showing up in the world as a good human, kind, trying to do the right thing, that's what a good life is, as far as I'm concerned.

• 42:53Craig Robinson?

  And I can't add to either one of those. The only thing I will say to Adrian is don't be afraid to be an old dad. And be in our ODC, which is the old dads' club, because those kids will keep you young. And.

• 43:09Michelle Obama?

  You had your second set of kids. How old were you? Just to.

• 43:12Craig Robinson?

  So I was, see, I don't know how to think that way. I just know that Austin is 14 and I'm 62, so I was 48. Right? Is that, does that add up?

• 43:26Speaker 00

  That's inspiring for me, too.

• 43:27Craig Robinson?

  Forty-eight.

• 43:28Speaker 00

  I'm not a dad yet, and I think about that often. So I'm going to be hopefully joining the ODC.

• 43:32Craig Robinson?

  Yeah, listen, and you see, you got your hair now. Just wait, that stuff is gone.

• 43:39Craig Robinson?

  No, but I, listen, this was, Adrian, I hope this was helpful for you. But Jay, I want to thank you for being on. Man, it just is an absolute treat for us.

• 43:50Michelle Obama?

  Isn't he amazing?

• 43:51Craig Robinson?

  He's just amazing. You see, and she, she was going on and on. I'm like, he can't be this good. And then I heard you and I was like, oh my God. Now I'm with you in person and I'm just so thrilled that you're a part of the family. And we will, we absolutely want to have you back at some point.

• 44:09Speaker 00

  Oh, I'm so touched by that. But honestly, I think it's, the pleasure's all mine to sit with you both, to learn from you both, to hear about your stories. And I'm so grateful you're doing this format because I think there's something special about siblings sitting together and sharing their journey and the amount you know about each other. I think it's beautiful. And I think this will inspire a lot of siblings, a lot of family connections to improve. Thank you for being such a wonderful example. Thank you for inspiring me to want to do more with my sister now.

• 44:37Michelle Obama?

  That's our next, we're going to call Amy.

• 44:40Speaker 00

  It's very grateful.

• 44:41Michelle Obama?

  We're calling her.

• 44:41Speaker 00

  Thank you so much.

• 44:42Michelle Obama?

  Yeah, thank you.

• 44:43Craig Robinson?

  Well, thank you, man. This has been terrific.

• 45:08Speaker 05

  I'm Emma Grede, host of Aspire with Emma Grede, the podcast where I sit down with people who don't just dream big, they build big. If you love Michelle and Craig on IMO, just wait until you hear their episode on my show. Michelle told me about the moment at 26 when she lost her father and her best friend in the same year. It made her walk away from her corporate law career to figure out her why. That's the kind of conversation you get on Aspire. We talk about mindset, ambition, and doing the work that actually moves the needle. So if you're ready to raise your standards and take charge of the life you're building, Aspire is where you start. Follow and listen to Aspire with me, Emma Grede, available wherever you get your podcasts.