Jay Shetty on Pursuing What You Love, from IMO

Summary

Podcast Summary: Happier with Gretchen Rubin – Episode Featuring Jay Shetty on Pursuing What You Love

Release Date: April 3, 2025

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1. Introduction and Guest Overview

In this episode of "Happier with Gretchen Rubin," host Gretchen Rubin introduces a special guest, Jay Shetty, a renowned New York Times bestselling author, award-winning storyteller, former monk, and podcast host dedicated to helping people cultivate peace and purpose in their lives. Gretchen sets the stage by highlighting the episode's focus on balancing career ambitions with personal fulfillment and family aspirations.

2. Listener's Dilemma: Career vs. Family

The core of the episode revolves around a listener named Adrienne's dilemma:

Adrienne's Question (10:43–10:54):

"I'm a 38-year-old man in tech considering whether to start a new company or stay in a high-paying job to afford a family. My career dreams and the desire for financial stability and family seem at odds. How should I approach this decision?"

Adrienne is torn between pursuing a potentially impactful entrepreneurial venture that demands significant time and financial sacrifice and maintaining his current stable job to build a foundation for future family life.

3. Perspectives on Balancing Ambition and Stability

Craig Robinson's Insight (10:54–13:38): Craig shares his personal journey of realizing the pitfalls of following a linear, checkbox-driven career path devoid of personal fulfillment. He emphasizes the importance of understanding one's "why" rather than solely focusing on external markers of success like job titles and salaries. Craig encourages Adrienne to broaden his perspective on what constitutes a happy and fulfilling life beyond societal expectations.

Michelle Obama's Contribution (13:38–19:08): Michelle recounts her own experiences with career transitions and the importance of following one's passion despite external pressures. She illustrates the value of family support and authentic connections in navigating significant life changes. Michelle underscores that true happiness often stems from aligning one's career with personal values and relationships.

4. Jay Shetty's Insights on Creating a Balanced Life

Jay Shetty on Middle Path (01:08–02:07): Jay introduces the concept of finding a "middle path" between extreme choices. He suggests that instead of making an all-or-nothing decision, Adrienne could consider staying in his current job while gradually building his passion project. This approach allows for skill development and network expansion without sacrificing financial stability or personal well-being.

Key Quote (01:08):

“If you can't see something in your mind, you can't create it in your life... maybe I don't need to quit my job. Maybe I can stay at my job and then build my passion...” [01:08]

Personal Reflections (06:41–27:41): Jay delves into his personal story of transitioning from a monk to an entrepreneur, highlighting the challenges of societal expectations and the importance of supportive relationships. He emphasizes authenticity, vulnerability, and the courage to pursue one's true calling despite external judgments.

Practical Strategies (32:01–39:47): Jay advises Adrienne to approach his dilemma with flexibility, encouraging him to explore his passions alongside his current career. He advocates for making incremental changes, fostering meaningful work environments, and leveraging existing roles to cultivate personal growth without immediate drastic shifts.

Key Quote (13:38):

“If I don't go all in, I'm not going to make it... you're just all out. You never try. You never gave it a go.” [14:37]

5. Advice from Michelle Obama and Craig Robinson

Michelle Obama's Guidance (28:51–32:01): Michelle shares her experience of making a significant career switch to coaching, emphasizing the role of family feedback in her decision-making process. She illustrates the importance of aligning career choices with personal happiness and family support.

Craig Robinson's Counsel (18:28–35:41): Craig encourages Adrienne to engage in deep self-reflection to understand his true desires beyond societal pressures. He highlights the significance of emotional well-being, relationship-building, and the flexibility to pivot career paths as life evolves.

Key Quote (22:37):

“A happy life looks very different than what we think it looks like... every way of being is good.” [22:37]

6. Practical Takeaways for Adrienne

Jay Shetty's Takeaways (38:25–39:47):

1. Adopt a New Perspective: Move away from binary thinking and explore integrated solutions that allow for both career and personal fulfillment.
2. Embrace Flexibility: Be open to pivoting and making incremental changes rather than seeking perfect, all-encompassing solutions.
3. Engage in Self-Reflection: Continuously assess personal values and desires to ensure alignment between career choices and life goals.

Craig Robinson's Takeaways (39:51–37:40):

1. Define Personal Happiness: Understand that happiness varies and isn't confined to societal norms.
2. Build a Supportive Network: Cultivate relationships that support personal and professional growth.
3. Prioritize Emotional Well-Being: Focus on self-awareness and nurturing authentic connections to foster a fulfilling life.

7. Conclusion and Final Thoughts

The episode concludes with heartfelt exchanges between the hosts and Jay Shetty, emphasizing the importance of authenticity, vulnerability, and supportive relationships in navigating life's complex decisions. The collective wisdom shared offers Adrienne—and listeners at large—a nuanced framework to approach the balance between career ambitions and personal fulfillment.

Final Quote (40:53):

“Don’t be afraid to be an old dad... those kids will keep you young.” [40:53]

This episode serves as a comprehensive guide for anyone grappling with similar life choices, providing actionable insights and empathetic support to pursue what truly brings happiness and fulfillment.

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For more episodes of "Happier with Gretchen Rubin," subscribe wherever you get your podcasts.

Transcript

[Gretchen Rubin]

Hey, happier listeners, I am dropping into your feeds with something a little different and really special. It's a new show from my friends at Higher Ground, hosted by Michelle Obama, called imo. You know, on Happier with Gretchen Rubin, I give practical advice meant to lift you up and help you reach goals and fulfillment. Similarly, on imo, Michelle and her big brother, Craig Robinson tackle real questions from real folks just like you, offering practical advice, personal storytelling, and plenty of laughter. Each week, they're joined by a guest bringing candid perspectives to the everyday. Questions shaping our lives, relationships, and the world around us. Topics range from dating and relationships to family and faith. Michelle and Craig share stories about being there for each other throughout their lives. From first crushes and fraught college years to landing at the White House to losing their mom. For six decades, they've been each other's most trusted counsel. And now they want to be that counsel for you. Okay, here comes the preview. You can find more episodes of IMO wherever you get podcasts.

[Jay Shetty]

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 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 going to make it. And I think sometimes also our mindset today is if I don't go all in, then it doesn't matter.

[Michelle Obama]

Well, it is great to see you.

[Craig Robinson]

Hi, you.

[Michelle Obama]

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

[Craig Robinson]

Welcome to one of my favorite places to be.

[Michelle Obama]

I know Martha's Vineyard. We have to figure out how to get here more often.

[Craig Robinson]

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.

[Michelle Obama]

No, listen, it's not their fault. 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, huh?

[Craig Robinson]

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 glad you're here.

[Michelle Obama]

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

[Craig Robinson]

I'm just so happy for Avery.

[Michelle Obama]

It was really neat. Emily, another Mrs. Robinson.

[Craig Robinson]

Another Mrs. Robinson.

[Michelle Obama]

Yeah.

[Craig Robinson]

That's strange.

[Michelle Obama]

It is.

[Craig Robinson]

How does it feel having your first child married?

[Michelle Obama]

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.

[Craig Robinson]

No faith. No faith.

[Michelle Obama]

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 and the menus were all done by hand by Emily and Avery. Wow. It was such a wonderful and beautiful ceremony. I left there feeling proud.

[Craig Robinson]

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

[Michelle Obama]

Thanks. Yeah, thank you.

[Craig Robinson]

Way to go. Way to go.

[Michelle Obama]

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

[Craig Robinson]

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

[Michelle Obama]

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

[Craig Robinson]

Okay, okay.

[Michelle Obama]

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

[Craig Robinson]

Passion versus family versus. Versus.

[Michelle Obama]

Financial.

[Craig Robinson]

Financial. Yeah. Yeah. Something that we've all deal. But it's a good question to get us started.

[Michelle Obama]

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.

[Craig Robinson]

You can learn a little something here.

[Michelle Obama]

And a former monk.

[Craig Robinson]

Yeah.

[Michelle Obama]

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, which 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.

[Jay Shetty]

Grateful to be here. Thank you so much.

[Craig Robinson]

It's great to see you. Thank you.

[Jay Shetty]

Thank you so much, Craig. It's wonderful to meet you.

[Michelle Obama]

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.

[Jay Shetty]

Oh, that's very kind. Well, that's because of her. Everything she said, we already know.

[Michelle Obama]

We already know.

[Craig Robinson]

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

[Michelle Obama]

Well, 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 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. Is that true?

[Jay Shetty]

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

[Michelle Obama]

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?

[Jay Shetty]

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

[Michelle Obama]

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

[Jay Shetty]

Well, you're doing better than me right now. You've stumped 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 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 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, giving them a shoulder to rest on, to feel seen, heard and understood. Wow. 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.

[Craig Robinson]

I'm just picturing 10 year old J 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 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.

[Michelle Obama]

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

[Jay Shetty]

I would like to think that I took good notes and that helped a lot of what to do, what not.

[Craig Robinson]

To do, what not to do.

[Jay Shetty]

Yeah, 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 heart.

[Craig Robinson]

I feel you and yeah, that's why I wanted your heat here. The reason we're doing these conversations is to talk, you know, to talk through things with people, to talk through things in person, you know, with us here. Hopefully shared, 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 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 that actually leads to.

[Michelle Obama]

Our question from our listener, Adrienne.

[Adrienne]

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 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, Adrienne.

[Craig Robinson]

Sounds like a familiar dilemma, you know, 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 things were linear, you know, if you did the right things, if you check 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 off on that path, not really thinking about anything but checking the boxes. So I did what I was supposed to do. I went to grammar school, got great grades, went to the best high school I could go, 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, the right salary, the right school, that there were, like, these answers, and none of it had to do with happiness. 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. 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. You know, 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.

[Michelle Obama]

Sounds familiar.

[Craig Robinson]

Sounds familiar. Stop checking boxes, first of all, you know, and start thinking a little bit bigger about what a happy life can look like.

[Michelle Obama]

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

[Jay Shetty]

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, right? 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 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 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 going to be attracted to your ambition. Maybe they'll be attracted to the fact you want to take a risk. Maybe when you're honest with them about who you are, they'll say, you got to go for your dreams. I don't want to be with someone who settled. And so I think you can't preempt that. It all depends who you attract and who you choose.

[Michelle Obama]

So your refereeing relationship ability is coming to light here because he's not even in a relationship yet.

[Jay Shetty]

Exactly.

[Michelle Obama]

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?

[Jay Shetty]

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.

[Michelle Obama]

That's a great point.

[Jay Shetty]

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. And there's this feeling today that I have to get it 100% right. And the truth is, we're going to fumble and we're going to fall, and maybe one day I'm not going to be the best at work, and maybe I am going to say something to my wife that I regret and I want to take back, and maybe I'm not going to be present at every recital. And maybe. And that's the reality. And I think we've stop 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. I think that we're looking for someone to say it's okay.

[Craig Robinson]

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

[Michelle Obama]

Let me just help Adrian out here and feel free to jump in here, Jay, because Adrienne'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?

[Craig Robinson]

I married one.

[Michelle Obama]

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

[Craig Robinson]

No, that in basketball, you just point.

[Michelle Obama]

You don't even have to say, you just point. That's a good alley that run down the court. And let me say one more thing before you give your answer. Most, you have to admit most of your sisterin not just women, other women 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.

[Craig Robinson]

And there's a, a clear definition of.

[Michelle Obama]

What a good catch, what that, what a good catch is. And to, 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 disagree, feel free.

[Craig Robinson]

No, no, I mean, I think you make a good point. And I think we can't generalize across the board for women. And 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? 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 Adrienne, 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, 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, you know, you just gotta 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 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.

[Michelle Obama]

No, that answers it. And I'm gonna ask Jada referee again.

[Jay Shetty]

No, I was listening to you, Michelle, and just relating in our own unique and different way to so much of what you said. When I met my wife, I 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.

[Michelle Obama]

And so why not?

[Jay Shetty]

So it was like, what are your transferable skills? Like sitting still and being silent, like, we don't need that. 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.

[Craig Robinson]

How old were you? I was just.

[Jay Shetty]

I was 25 then. I'm 26. And so I was younger than Adrian. So I understand that 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 gonna 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. 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 gonna find them in similar spaces. It's gonna 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 wanna 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.

[Michelle Obama]

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

[Craig Robinson]

Is that what it's called?

[Michelle Obama]

Like, normal in the wild? I love it.

[Jay Shetty]

I love it.

[Michelle Obama]

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

[Jay Shetty]

Based on that, it would be in the wild.

[Michelle Obama]

You met her in the wild.

[Jay Shetty]

Yes.

[Michelle Obama]

And you met Barack in the wild.

[Craig Robinson]

Because there wasn't.

[Michelle Obama]

There wasn't any. We're old.

[Jay Shetty]

No wilder place.

[Craig Robinson]

There was.

[Michelle Obama]

It was all wild back then. But so, you know, I'm interested in knowing how Adrian is meeting people, because I agree with you. You gotta get out there 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 might step in some dog mess every now and then, and you clean your shoe off. You can't be like me and throw your shoe away when you step in some dog.

[Craig Robinson]

But the thing, you know, I want Adrian to think about the power of building something with someone, you know? Cause I also worry that, you know, Adrian's on this path. He's gonna 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 think in my marriage we're stronger because 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. But the beauty of just trudging through some hard stuff together, you know, it can bind you in a unique way. I don't want Adrian to rob himself of having a good partner along that journey, because he could achieve all that. Meet 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.

[Jay Shetty]

Yes.

[Craig Robinson]

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, their 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 wanna do something else. You know, he may have kids and decide like you did. I mean. And Craig, you should tell your story about your transition, because I will joke that we stopped checking boxes sort of at the same time in our lives. We started at these high salary careers and ran away from it because I know I was running towards fulfillment, not the salary. And Craig, you did the same thing.

[Michelle Obama]

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 money. 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 Carrill. 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.

[Jay Shetty]

Wow.

[Michelle Obama]

And I Thought, you know what I'm gonna do? I'm gonna be a coach. And I went back to Princeton to go visit her. Cause she was still there. I stop off and I see Coach Carrill and I said, coach, I know what I wanna be. I wanna be a coach. And he said, you don't wanna be a fucking coach. Why would you wanna 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. I went, okay, coach, 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 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. To making about $45,000 a year. And I'm going through a divorce. I've got two kids, 4 and 8. 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 said, 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 to her, I said, daddy's getting a new job. And my 8 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. 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 Ajita 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.

[Jay Shetty]

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 the 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. 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.

[Craig Robinson]

Yeah, yeah.

[Michelle Obama]

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 miche your point, we want to just be able to help folks like Adrian understand that you're going to get a lot of messages from a lot of different places. Here's what we think is the healthiest way to go about it.

[Jay Shetty]

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 going to appear weak, Weak, lose my leadership. I'm going to 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 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, 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 are your only stability and foundation. Which is where Adrian's kind of at right now.

[Craig Robinson]

That's right. That's fair.

[Jay Shetty]

He's trying to figure it all out on his own.

[Craig Robinson]

All out on his own. 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 going to 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? I would want Adrian, and I think I would want all men to do a little more of that soft soul searching, 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. 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, Adrienne, 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, 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, Ajita, you know, he'll be struggling alone for a long time.

[Michelle Obama]

But we need to train ourselves. Speaking as men, we're not as good at being empathetic. 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 Js of the world, like me, like all of us 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.

[Jay Shetty]

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.

[Craig Robinson]

Yeah.

[Jay Shetty]

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

[Michelle Obama]

Terrific. Anything else to add to your.

[Craig Robinson]

Just to emphasize that a happy life looks very different than what we think 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'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.

[Michelle Obama]

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, okay? And be in our odc, which is the old dads club, because those kids will keep you young.

[Craig Robinson]

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

[Michelle Obama]

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. Does that add it up?

[Jay Shetty]

That's inspiring for me, too.

[Michelle Obama]

48.

[Jay Shetty]

I'm not a dad yet, and I think about that often. So I'm gonna be hopefully joining the odc.

[Michelle Obama]

Yeah. Listen, and you see, you got your hair. Now just wait. That stuff is gone once you have kids. No, but listen, this was Adrienne. 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.

[Craig Robinson]

Isn't he amazing?

[Michelle Obama]

He's just amazing. And 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 absolutely want to have you back at some point.

[Jay Shetty]

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. And that's our next.

[Craig Robinson]

We're gonna call Amy. It's very grateful they're calling her.

[Jay Shetty]

Thank you so much.

[Craig Robinson]

Yeah. Thank you.

[Michelle Obama]

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

[Gretchen Rubin]

That was a preview of I Am with Michelle Obama and Craig Robinson. You can find more episodes wherever you get podcasts.