Pursue What You Love Before You Pursue Love with Jay Shetty [From the Archives]
45m 49s
Adrienne, a 38-year-old tech professional, faces a dilemma between pursuing a high-risk entrepreneurial dream or securing financial stability for a family. The conversation reframes this binary as a false choice, emphasizing that both ambition and family can coexist. Jay Shetty, a former monk and motivational speaker, shares that his personal journey—mediating his parents’ relationship as a child—taught him the value of empathy, balance, and emotional resilience. He stresses that true fulfillment comes from understanding one’s “why,” not simply checking societal boxes. The hosts argue that success isn’t linear or perfect; it’s messy, evolving, and shaped by relationships. They encourage Adrienne to stay in her current role, build skills and passion incrementally, and open herself to dating and community connections where she can meet like-minded people. The key insight is that a fulfilling life isn’t defined by career titles or financial success, but by authenticity, emotional honesty, and shared vulnerability. The podcast highlights that life is long and fluid—what seems like a choice between career and family may instead be a journey of growth, where both can flourish through mutual support, openness, and real human connection. The message is clear: don’t fear risk or failure; instead, embrace the imperfect, evolving path of becoming the person you truly want to be.
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.
I think sometimes also our mindset today is, if I don't go all in, then it doesn't matter.
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.
Martha's Vineyard.
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.
And 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?
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.
I'm 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.
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.
Wow.
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 a great question today.
We do.
We do.
Good segue.
Way to go.
Yeah, thanks.
I'm working hard to be like our first guest, Jay Shetty.
I'm trying to be Jay.
Okay.
Okay.
But the question deals with leaving your current situation to try and find a job in something
that you're passionate about.
Mm-hmm.
And you know, I've dealt with that.
Yeah.
Passion versus family versus-
Versus financial.
Financial.
Yeah.
Yeah.
It's something that we've all dealt with, but-
Yeah.
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 time.
Mm-hmm.
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?
Mm-hmm.
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.
Thank you so much for having me.
Oh, thanks for being here.
Grateful to be here.
Thank you so much.
It's great to see you.
Thank you.
So good to see you.
Thanks so much.
Craig, it's wonderful to meet you.
It is so nice to meet you, man.
I listened to the show you did with my sister, and I couldn't stop listening.
Oh, that's very kind.
Well, that's because of her.
Everything she said is beautiful.
No, no.
That's because of you.
We already know.
We already know.
Jay, 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, I am.
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?
That's true.
That's 100% right.
I did my research.
What I want to ask you about is, what have you done?
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.
Like I said, I'm trying to be you.
I'm trying to be you.
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.
Mm-hmm.
And the fact that you're a monk.
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.
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 and 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.
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 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.
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. 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 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. 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 Adrienne 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.
That's 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.
It sounds like a familiar dilemma, you know, and the first thing I think about is, you're
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. 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 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, the right salary, the right school, that there were like these answers,
and none of it had to do with happiness.
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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. 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 either or. Like 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 is that I've been in this world for a long time. And I've been in this world
for a long time. And I think 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
maybe this will help me. And I think that's a good place to start.
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'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, 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? 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,
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, 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
have all done it and we're all okay in the end. I have had four or five different careers. 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 want to know, why aren't you dating? I mean, what are you doing?
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 you're going to be able to do that? I don't know.
I think that building a business is. the only thing that's going to be required of finding a good mate.
Let me just help Adrienne 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?
I married one.
Don't you like that alley-oop 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.
I think you-
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-
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.
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 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-
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.
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.
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.
No, that answers it.
And I'm going to ask Jay to referee again.
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.
Why not?
Why not?
It's 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.
It was now my wife.
How old were you?
I was just. I was 25, going on 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, 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. 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,
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?
Like normal, in the wild?
I love it.
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.
We're old.
No wilder place.
There wasn't.
It was all wild back then.
So, you know, I'm interested in. in knowing how Adrienne 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 dogma.
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 dogma.
But the thing, you know, I want Adrienne to think about
the power of building something with someone.
You know, because I also worry that, you know,
Adrienne'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 Adrienne 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.
Yes.
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 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.
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 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. 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 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 Carrillo, 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. And I stop off and I see Coach Carrillo. 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 making 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.
So I put this decision basically in the hands of an eight-year-old and a four-year-old. And I said
to them, 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 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.
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
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.
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 Misha, 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 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.
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 now. He's trying to figure it 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. 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, 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. People who can look
you in the eye and say, like I did with my brother. You really are not that dude.
You really love coaching. 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,
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. 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 J's 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, 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.
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 is 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.
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, 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.
He may fall in love with a partner who doesn't believe in marriage.
I mean, life be lifin'.
That's the other saying I like that my kids say.
Life just be lifin'.
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.
And I can't add.
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 you had your second set of kids.
How old were you?
Just to.
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 it up?
That's inspiring for me, too.
48.
I'm not a dad yet.
And I think about that often.
Yeah.
So I'm going to be hopefully joining the ODC.
Yeah, listen, Ben.
And you see, you got your hair now.
Just wait.
That stuff is gone once you have kids.
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.
Isn't he amazing?
He's just amazing.
I just.
You see, and she was going on.
And 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.
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.
And that's our next.
We're going to call Amy.
It's very grateful.
We're calling her.
Thank you so much.
Yeah, thank you.
Thank you, man.
This has been terrific.
I'm Emma Greed, host of Aspire with Emma Greed, 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 Greed, available wherever you get your podcasts.
Podcast Summary
Key Points:
Life doesn’t have to be an either-or choice between career ambition and family; a middle path allows growth in both areas.
Starting a passion project doesn’t require quitting a stable job—small, incremental steps can build skills, confidence, and networks over time.
Authentic self-awareness—especially understanding one’s values and “why” behind goals—is more important than pursuing external success metrics.
Relationships and partnerships can be drawn to someone’s ambition and authenticity, not just financial stability or comfort.
Vulnerability, honesty, and sharing personal struggles with trusted friends or partners build stronger, more resilient connections.
Life is inherently flawed and full of failures; embracing imperfection allows for deeper emotional honesty and growth.
Building a life with purpose means prioritizing emotional fulfillment over perfection in career or family outcomes.
Meeting people and stepping into “the wild” increases the chance of finding a partner who shares your values and journey.
Summary:
Adrienne, a 38-year-old tech professional, faces a dilemma between pursuing a high-risk entrepreneurial dream or securing financial stability for a family. The conversation reframes this binary as a false choice, emphasizing that both ambition and family can coexist. Jay Shetty, a former monk and motivational speaker, shares that his personal journey—mediating his parents’ relationship as a child—taught him the value of empathy, balance, and emotional resilience.
He stresses that true fulfillment comes from understanding one’s “why,” not simply checking societal boxes. The hosts argue that success isn’t linear or perfect; it’s messy, evolving, and shaped by relationships. They encourage Adrienne to stay in her current role, build skills and passion incrementally, and open herself to dating and community connections where she can meet like-minded people.
The key insight is that a fulfilling life isn’t defined by career titles or financial success, but by authenticity, emotional honesty, and shared vulnerability. The podcast highlights that life is long and fluid—what seems like a choice between career and family may instead be a journey of growth, where both can flourish through mutual support, openness, and real human connection. The message is clear: don’t fear risk or failure; instead, embrace the imperfect, evolving path of becoming the person you truly want to be.
FAQs
Yes, you can build your passion gradually. Staying in your current job allows you to gain skills, learn, and expand your network without financial risk, making the transition smoother and more manageable.
Absolutely. Life doesn’t have to be either/or. By embracing imperfection and being open to change, you can build a life that includes both ambition and family, growing together through challenges and shared experiences.
Start by exploring your current work to find meaningful aspects of it. You can build skills and confidence within your current role, and gradually integrate your passion without making a sudden leap.
Be honest and transparent about your goals. Many people are attracted to ambition and growth. A partner who’s ready to share the journey with you—through both success and failure—can strengthen your life together.
Yes, taking risks is essential. Life rarely goes as planned, and being open to pivoting helps you grow. Start small, like launching a side project or meeting new people, to build confidence and real-world experience.
Self-reflection helps you identify your true values and desires. Instead of focusing on external goals like salary or status, ask how you want to feel each day and what kind of life aligns with your core values.
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