IMO with Michelle Obama and Craig Robinson - Pursue What You Love Before You Pursue Love with Jay Shetty

Episode Date: April 2, 2025

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.You can watch Jay in person as he takes his podcast On Purpose on the road. Tour tickets available HERE.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 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.

This episode is brought to you by Indeed and Pinesol. Well, it is great to see you. Hi, you. I miss not recording with you and spending time with you. Welcome to one of my favorite places to be. I know it is. We have to figure out how to get here more often. You know, I keep telling you all that.

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. Listen, it's not their fault. It's our fault between me. basketball and music and school, it just makes it tough. But I mean, I really appreciate you having us here. How about this? 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. I am glad to be here. And our listeners should know that you have your oldest nephew got married this summer. I'm just so happy for Avery. It was really neat. Avery and Emily. Another Mrs. Robinson. Another Mrs. Robinson. Yeah, that's strange.

That is. How does it feel having your first child married? 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 going to be a disaster, of course. No faith. 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. Yeah, yeah. Well, you did a good job, dude. Thanks. Yeah. Thank you. Way to go. Way to go.

Well, speaking of jobs, we have. we have a great question today. We do. We do. Good segue. Way to go. Thanks. I'm working hard to be like our first guest, Jay Shetty.

I'm trying to be J. Okay. 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. Yeah, passion versus family versus financial. Financial, yeah, yeah. It's something that we've all dealt with. But it's a good question to get us started.

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. first time. He's a podcast host, which I've already said, I'm trying to be like him. You can learn a little something here. And a former monk. Yeah. 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. Oh, thanks for being here. Grateful to be here. Thank you so much. It's great to see you. Thank you. Thanks so much. Craig, it's wonderful to me. 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. Oh, that's very kind. Well, that's because of her.

Everything she said is beautiful. We already know. We already know. 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. 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. But what I... That's true. That's true. That's 100% right. 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? Wow, that's a great question.

That's a great question. Like I said, I'm trying to be you. I'm trying to be you. You're doing better to me right now. You stump 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 would 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 an early age, I think, has allowed me to not have this divided thinking of it's one or the other. 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 with the level of, 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. And 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 think you got to feel pretty good about where you are, given the position you were in. 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 lot.

And yeah, that's why I want to hear 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 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 our question from our listener, 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. Sounds like a familiar dilemma. 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 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 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 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, while 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. This segment is brought to you by Indeed.

Hey, Mish, you remember your first job? Oh, yeah, yeah, I do. It was working on the line at a book bindery. Yes. I got that job. I was my high school boyfriend at the time. His mom worked at the binder and got us summer jobs. And it was the kind of job where whatever you did, that one thing, you did it 10,000 times.

You know, I remember it was like because they made binders for school and things like that, like the paper binders. And you'd have the three-hole punch and you'd have to punch the metal thing that would split the papers open. I would be responsible for putting the metal thing in the hole. And then I would hand it to my boyfriend who would put it in the machine and it would stamp it. Do you remember my first job? Working at Soldiers Field where the Bears played. Yes. That was a great first job for me.

Consolidated concessions. And what we did were, you know, the. The vendors where the guys were, hey, peanuts, hey popcorn. Well, we supplied those guys with their basket of stuff, whether it was hot dogs. I remember the smell of boiled hot dogs. We would take the hot dogs right out of the hot strainer, slather it in mustard, throw it on the bun, wrap it up, put it in the canister. So you were actually handling food. Handling food with no gloves.

This was back in the 70s. I remember is that you were excited because you got to drive. Yes. Before you had a license. I was 14 years old and they had these trucks and Cushman. They were called Cushman's. They were small carts that you drove around to restock all of the concession stands. It's just a great experience.

But the world's changed so much, but the hiring process is still stuck in the past. That's why we've partnered with Indeed to discuss how better work helps create better lives. Indeed is helping job seekers elevate their skills so that they can match with employers better and faster. In turn, employers get qualified candidates. Job seekers are working harder than ever, but struggling to find the right opportunities. At the same time, employers are screening out qualified candidates without realizing it and struggling to fill their open roles. That's why Indeed is focused on skills first. hiring, helping people get jobs based on what they can do, not just where they went to school or who they know. Mish, for example, there was no school that taught me how to be a basketball coach.

It was a lot of skills that I had picked up while I was working in corporate America. You know, you think about project management, communication, understanding how to manage people. those were things that I had to learn before I started coaching. But it's not just about getting hired. It's about finding a workplace that actually supports you because a great workplace impacts overall happiness. Another way indeed is championing better work is by conducting the largest study on work well-being

and actually creating the work well-being score, which is a score based on the current employee's real, experiences at a company measuring happiness, purpose, stress, and satisfaction. Finding the right opportunity can change your life and indeed is helping match those looking for better work to those offering it. From encouraging equitable hiring practices to empowering employees, together we can create a world that really can work better. We're so thrilled that Pine Saul is a partner of IMO. Pine Saul has been connected to our family forever.

To this day, whenever my sister and I catch the scent of Pine Saul, we automatically feel better about life. The smell of Pine Saul has always taken us back to our childhood home. It is amazing how smells can transport you to a place or a moment in time. Another smell that takes me back is cherry blossoms, which always remind me of visiting Michelle in D.C. That's why I'm excited for Pine Soles' newest scent, Cherry Blossom. The cleaning power you know and love from Pine Soll is available in a new scent this spring.

Cherry Blossom, which is light and fresh and leaves a lasting floral scent while eliminating tough dirt, grease, and grime. You can use Pine Sal Cherry Blossom, multi-surface cleaner, to help deodorize and clean hard, non-porous surfaces, including floors, sinks, counters, stoves, bathtubs, shower stalls, tile, and more. Visit pinesaw.com to find where to shop pine saw, multi-surface cleaner in the new fresh cherry blossom scent. 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,

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 going to 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. Right. 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.

Sounds familiar. 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. That's a good place to start. Jay, what are your thoughts? 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 or I can either have success and ambition

or I can have love and relationships 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 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. 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 it's 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've got to go for your dreams. I don't want to 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.

So your refereeing relationship ability is coming to light here because he's not even in a relationship yet. And he's determined that his partner, once 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? 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 going to do both imperfectly, whether you gave them 100% attention or 50-50.

Yeah, that's a great point. 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 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. I think that we're looking for someone to say, it's okay. 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 up.

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. 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? I married one. Don't you like that alley-up I just threw you? No, that was a good. 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... Women, other women. Is that what you're talking about? Typically are not like you at that age. They're looking to catch, they're looking for a good catch. And there's a clear definition of what a good catch is. 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 disagree, feel free. 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 Adrian, 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 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. No, that answers it. And I'm going to ask Jay to referee again. You know, now that I've been traveling for this podcast and staying in Airbnb's more, it makes me think back to when I was coaching and how much I could have used Airbnb back then.

I would have loved to have put my team up in a house instead of a hotel. It makes for better camaraderie. It makes for better communication between the players. If I could get a place big enough for my whole team, we would have saved on actual hotel rooms, but we would have saved on conference rooms. We would have saved on video and video. And more importantly, we would have saved on food and beverage, which is the most expensive thing when you're traveling. In addition, I would have used this when I was recruiting because you end up in a lot of small towns that don't necessarily have good hotel.

and I would have easily signed up for getting an Airbnb in some of these small college towns. This episode of IMO is brought to you by Theraflu. As a product that was created to provide effective and comforting relief when you're fighting the flu or a cold, TheraFlu firmly believes that the ability to rest and recover when sick should be a right, not a privilege. I think back to the time when my dad was working for the city of Chicago as a stationary fireman, and it seemed to us that he never missed work and he never got sick. But what we realized is that my dad didn't want to take his paid sick time because he wasn't sure if he would keep his job by doing that. And my sister and I realized that my dad was, would.

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to recover. No, I was listening to 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. And so why not? So it's like, you know, what are your transferable skills? Like sitting still and being silent? Like we don't that. But it wasn't valued. Like, I remember going, I wouldn't even get a job interview, actually. I was applying online. Wow. 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.

It was now my wife. How old were you? I was just, I was 25, going to 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 going to give me a shot? And I'm so grateful to my wife for 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 going to find them in similar spaces. 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. Did you meet your wife in the wild or did you meet her online?

Is that what it's called? It's in the wild. I love it. I'm taking that. I'm using that forever. Based on that, it would be in the wild. You met her in the wild. Yes.

And you met Barack in the wild. Yeah, because there wasn't. There wasn't any. There wasn't. There wasn't. No longer place. Yeah. Yeah.

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 got to 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. You clean your shoe off. You can't be like me and throw your shoe away when you step in some dog.

But the thing, you know, 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 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, 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, 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, life is long. And that's the other thing 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. 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-saried careers and ran away from it because I know I was running towards

fulfillment, not the salary. And Craig, you did the same thing. 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 mine. 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. Wow. 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.

I stop off and I see Coach Carrille. 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. I went 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 make in about $45,000 a year. And I'm going through a divorce. I've got two kids, four and eight, 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 going to 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 adjita 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. 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. 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. Yeah. This episode of IMO is also brought to you by Acorns. Acorns is a financial wellness app that makes it easy to start saving and investing for your future. You don't need to be an expert. Acorns will recommend a diversified portfolio that matches you and your money goals. You don't need to be rich. Acorns lets you get started with the spare money you've got right now,

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which is huge when your day is as packed as mine. Instacart brings convenience, quality, and ease right to your door so you can focus on what matters most. download the Instacart app now and get groceries just how you like. 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 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. 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 my, I'm going to lose the clout and the authority 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.

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're your only stability and foundation, which is where Adrian's kind of at right. He's trying to figure it all out on his own. 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? Is it going to be enough for you to 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? 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, 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 going to 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, this adjeda, you know, he'll be struggling alone for a long time. 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 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. 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. Yeah. 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 are the 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. 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 going to play out. Terrific. Anything else to add to your... 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, I realize 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 life in.

That's the other saying I like that my kids say, like, just be lifeing. 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, you know, and if you're showing up in the world is a good human kind, trying to do the right thing. That's what a good life is, as far as I'm concerned. 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 dad's club, because those kids will keep you young. You had your second set of kids. How old were you? So I was, see, I don't know how to think.

think that way. I just know that Austin is 14 and I'm 62, so I was 48. Right? Is that, does that add it up? That's inspiring for me too. 48. I'm not a dad yet, and I think about that often. Yeah, I'm going to be hopefully joining the ODC. Listen, Ben, you see, you got your hair now? Just wait, that stuff is gone once you have kids. No, but I, 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. Isn't he amazing? 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. Oh, I'm so touched by that. But honestly, I think it's the pleasure is 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.

That's our next day. We're going to call Amy. It's very grateful. We're calling her. Thank you so much. Yeah, thank you. Well, thank you, man. This has been terrific.