When Success Becomes Empty: Rediscovering Purpose Beyond Ambition | Jenn Romolini
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I am ambitious to feel content. I don't expect happiness every day, but I am ambitious to feel a sense of equanimity in my life. You can't find when your life is out of balance. And I am ambitious to invest in friendship, which is something I've really lacked for the majority of my life and is so important, especially as you get older, right?

And just being a good person, how do I show up every day? Those are things you need space and time to think about. We don't just come out being good people who know how to manage ourselves in the world. And many of our childhoods don't help with that, right? So it takes work and it takes effort. And that's something to be ambitious for. Being a person who means something in other people's lives.

All of those things. That's how I calculate if I'm a success now. So ambition is this loaded word. It's often associated with this relentless drive to succeed, trampling over others as you scrap your way to the top, ignoring your well-being, your relationships, any sense of groundedness or meaning or peace or joy along the way. It's what helps you achieve, quote, success, we're told. But

What if that was not only wrong, but it also kept you from the work, the relationships, the health, the life, a different kind of success that you didn't just want, but that was actually worth wanting, that would make you feel the way you want to feel? Well, today's guest, Jan Romolini, shares her deeply personal journey, rising to the very top of the New York media world, up in the C-suite, then untangling from that toxic drive of

and letting go of an ambition that didn't align with who she was, her core values, her aspirations, to reclaim something deeper and better.

Jen is the author of the raw and emotional memoir, Ambition Monster, a memoir about her reckoning with workaholism and obsession with work that really just stemmed from her childhood experiences. And first as a rising star in the near publishing world, she really appeared to have it all, the coveted career, the money, the status. But beneath that picture-perfect exterior, the relentless ambition was disconnecting her from her truest self and what really mattered most. And

And it took a health crisis to forcibly hit pause and have Jen reassess everything. In this intimate conversation, she shares how losing her voice, I mean literally losing her voice, became a wake-up call that allowed her to find it again, but in a different way. From realizing her workaholism was a trauma response, to grappling with external measures of success, and finally breaking free and realigning with her core creative calling as a writer. It

Jen's path shows that there is another way. One where blind ambition doesn't crowd out relationships or well-being and what you value most. So if you've ever felt confined by others' versions of what ambition and success should look like, Jen's story offers some real hope for rediscovering and living congruently with your own authentic aspirations. Her perspective will really inspire you to get radically honest

about what truly constitutes a good life for you. So excited to share this conversation with you. I'm Jonathan Fields, and this is Good Life Project. Ryan Reynolds here from Intmobile. With the price of just about everything going up during inflation, we thought we'd bring our prices down.

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I feel like the word ambition, the experience ambition, conversations around ambition, success, what they mean, what they don't mean, and how we're wired for them has entered the zeitgeist a lot more since we found ourselves coming out of the pandemic. And maybe that's just me, but I feel like that was this moment where so many people really reexamined what is a thing called work that I'm doing? How will I bring myself to it? What's it giving me back to me?

And this ambition I've been striving for, like the work, work, work, I'm going for the brass ring. Is that really what I want? I'm curious whether you feel like there's been sort of like a reemergence or reexamination the last couple of years too. Oh, I think for sure. I mean, I think we see it with all of the burnout books that came out a few years ago. I think we see it as a correction to the sort of girl boss of the 2010s. I think we see it as...

the midlife crisis of Gen X, who were really the recipients of the women's rights movement, and really the first generation that fully was working, you know, just all out ambition. And I think that there was a sort of collective during the pandemic feeling about

work as a highest measure of a life success, this feeling of, is that all there is? Wait, is that it? I'm not sure that's really it. I do think to some degree, I mean, and certainly there's the trend of quiet quitting and there's, you know, the lazy girl job, all of those things. I don't know if we've gotten it quite right yet because now I think the pendulum is swinging a little too far to the other side and

Because what we're not talking about is the gratification that can come from ambition and achieving goals. If those goals are personal and if those goals are not about some external idea of what you're supposed to be. No, I think that is such an important part of the conversation and I agree completely.

I feel like it isn't getting centered nearly as much. I think we tend to look at ambition or success and say, it's either good or bad. It's a binary thing. It's like, eh, not so much. You know, it's like, what's driving that? What's underneath that? If you're devoting yourself to something really deep and profound and meaningful and joyful, it can be incredibly powerful. But it also doesn't protect you from things like burnout and overwork and workaholism. Like you can experience all those, even doing something that

on the most fundamental level is you would think would be pretty nourishing. Yes and no, I would say.

Because I think that there is a situation that happens when you are doing work for yourself and you know, this is the path I want to be on. This isn't about external validation. This is, I've really examined myself in my life and I've thought, what do I really want to do before I die? Right. And you sort of backed yourself from there. I have found, because I am certainly a workaholic and I absolutely love work.

And I have found that when the goal is personal and I am just hustling for it, I feel rejuvenated by the energy that I'm putting into work, even if it's excessive.

But when it's for something else, for a way that I think I'm supposed to be in the world, whether it's for checking boxes, you know, oh, I should go for this promotion. I should take this dream job. I would be crazy not to. Those kinds of things, those kinds of motivations, those are the things that deplete us. Yeah, it's almost like, are you crazy?

Building something that is an emanation of you, or are you trying to fill a hole that was probably dug, at least in part, by any number of other people? Yes, yes. Are you living a life of purpose that aligns with your values? Are you able to grow in whatever you're doing?

You know, I think that especially for women, I would say, work is so intertwined with this idea of being good, with goodness. And I'm going to go above and beyond, not because I have to, and not because I have to.

And not even necessarily that I'm going to get a reward that's going to sustain me or my family, but because I want to be considered good. I want that validation. And again, that's external. And that's when we get into trouble with ambition, I think.

Let's deconstruct those stories that we, I think that where the seed gets planted when we're pretty young about work and ambition and success. And you write so powerfully about this in your book. You had very specific experiences and stories coming from your family culture, like certain ones coming from your mom and a sense of competitiveness with playfulness that could also sometimes go off the rails. And then on your dad's side too, with sort of like a really, an interesting framing around strength and vulnerability and winning and,

Take me into this a bit, because it's really fascinating the way that those sort of like showed up in your life and then almost like laid down patterns that stayed with you. I am most certainly a product of the American dream. My parents were teenagers when they had me. They didn't, neither of them had high school educations, but they lived and they built from that.

a business or my father did got us out of, you know, what was lower class, lower class life, not necessarily poverty, but certainly lower class poverty.

into an upper middle class life, which took a lot of hustle and took everything that we are told about the American dream. It was nonstop work. It was persistence. It was, you know, all of it. I don't know if that was work that was satisfying to him, but that wasn't really part of the equation, right? It was about survival and salvation. And

my parents had very traditional gender roles. My mother ran a household. She wound up having two other children after me and my father worked. And my mother had me when she was just turned 17. She was always telling me, never be relying on a man, always make your own money. They had a

but he had all the power and he had the power because he made the money. And I watched that for sure. And then the other side of this, I had this really hardworking. And let me say, my parents are people of immense integrity. I love them very much. But of course, you know, you get to a certain age and you start to examine, you know, how did I get here? Right. And you start to, you start to pick things apart a bit. My father just had more power in the house and,

And he just had more freedom because of how much he worked. But also, our extended family and our immediate family, we all sort of exalted him because he provided for us. He provided our lives. But he worked constantly. I had very little relationship with him growing up.

I craved a relationship with him. And so when I was 13, I said to him, you know, can I start working for you? I just, I wanted to be close to him. I wanted to be in his world. And I did not want my mother's life, which was about cleaning up after everyone. And it seemed so thankless what she had to do and running a home. And that messaging really brought me into...

the working world. But then, of course, a blue collar life and a working class life and what ambition looks like in those environments is very different than what it looks like in a white collar world, which is where I eventually landed. I mean, you go from there, seeing like a very strong work ethic and a devotion to family and like providing and do what you need to do,

And then you land eventually over a period of years, it's really the New York City magazine, media and tech world, the blend of all those in different, which is a radically different work culture and radically different work environment. On the one hand, it gives you all the opportunity in the world to effectively work until you die. Absolutely. Yes. You know, which if you're wired in a particular way, which you were coming into this, you're like, okay, here we go. Well,

Well, I had a lot to prove too, right? Because I didn't have a pedigree. I was really a fish out of water in those, in, you know, sort of upper class environments, you know, especially in magazines, especially in lifestyle magazines where, you know, you're selling sort of prestige to other people. You're an arbiter of taste, you know, it was a...

But the thing that surprised me the most in white-collar environments was I really had expected work to be a meritocracy because in a lot of blue-collar jobs, that's kind of how it is. Like, you work hard, you are rewarded. I was a waitress for a decade. The more work I put in, the more money I made. It was a very simple equation, and that is not the case in corporate America. In fact...

you might actually be worse off the harder you work, you know, because you become like a sucker. You're a receptacle for everybody else's slacking off or, you know, you just, if you don't know how to play the game and you're just like hustling, hustling, hustling, it really doesn't reward you that much unless it's incredibly strategic.

Yeah. I mean, that makes a lot of sense. And I think so many people have probably found themselves in that spot also where they're like, they show up, they work incredibly hard. Other people see them working incredibly hard. They're like, oh, here's somebody who's going to get everything. Well, it's that classic phrase, right? And like, if you want to get something done, give it to a busy person, which is

Hey, great for you as the giver. But like that busy person becomes known as the person that get stuff done person. And all of a sudden they're just getting crushed because everybody's starting to say, oh, I'll give it to the busy person. I know they'll do whatever they need to do to get it done. I feel like oftentimes it's sort of like corporate culture that people,

That person gets pigeonholed as being that person. And nobody wants them to leave that sort of pigeonholing because it means that the work comes back to them. Well, corporate systems, from my experience, they don't really reward competence as much as they reward survival.

Break that down more for me. So say a job has a set of goals and expectations, right? You can sort out how to do those and just those never going above and beyond, but also work strategically to curry favor with a boss,

to understand the corporate political system. And that employee who puts in minimal work, but understands the politics of the system and is strategic is going to succeed far more than the employee who is constantly working, nose to the grindstone,

And doing more and more in that role. Because like you said, we want to keep that person in that role. We don't want to move them up. Why would we? I moved up quite a bit. I was kind of both. I was both strategic and I worked maniacally.

So I rose through the ranks because I also kept thinking, well, with the next promotion and the next raise, I'm going to feel satisfied. If I could just get there, then I wouldn't have all this other stuff they don't like doing. Maybe I'll like that stuff more, but also power. I thought, you know, I just need to get a little more power and then I'm going to feel less disempowered. But none of that turned out to be the case. So as you find yourself in that world, in that life, what's,

like crazy, rising up, like being in some levels rewarded for at least externally. What's happening on the inside for you? There's, I think it's the Buddhist phrase, external riches, internal rot, you know,

I was so on the train, in the wheel, on the ride, however you want to say it. I couldn't think about anything else. It became all consuming for me. And it was to the deficit of, and to the detriment of, and to the neglect of almost everything else in my life. I think the only thing that I managed to eke out as successful as work is I managed to be a present parent as much as I could be.

That's really all I had though. And I didn't really have any fortifying friendships outside of work, which, you know, I had friendships with my employees, but then you're just in it and in it and in it because you're just talking about work all the time. I wasn't really tending to my marriage, but more than anything, I just wasn't an interesting person anymore. I only cared about work and work is so boring, really? Like,

The ins and outs of work are really kind of boring. And it was all I would really talk about to anybody. And I would see, I could tell that like it wasn't landing, you know? Who wants to know about your internal, like your CEO and how you think they're messing things up? Like nobody wants to talk about that. But when you are fixated, I was hyper fixated and I had no escape. I had nothing outside of, I really lost everything.

so much of the breadth of my life. And we'll be right back after a word from our sponsors.

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Have you heard or become familiar with the research around harmonious versus obsessive passion? No, no, but I'm interested. This was shared with me by a friend of mine who also, he's a positive psychology guy and teaches at NYU also. And apparently there's this fascinating research around passion and divides it into these two different types of passion. One is harmonious. One is labeled obsessive. The obsessive kind of sounds like what it is, like obsessive.

You take an interest, you develop it into something which is all consuming. You go all in, like basically everything in your life, but the pursuit of that passion vanishes away. This is the only thing that exists for you in life. And you just, you immerse yourself in it. You get completely and utterly lost in it.

The other version is harmonious passion, which I'll kind of bastardize the way I'm describing it, but it's basically, it's something that is a deep interest for you. It's a passion. You love doing it. You devote yourself to it. And at the same time, you make room in your life for all the other things, for the relationships, for the other interests and passions and hobbies, for taking care of your physical and mental health.

So it exists in harmony with these other things that if you look at your values, you say you hold dear. Yeah.

He said, the research actually says no. The harmonious passion is the one who's more likely to. And the reason looks like it's because you're going to have a ton of adversity when you're going that hard and trying to be the best in this one thing and achieve the top. You're going to get knocked back a whole bunch, which means you need resilience. And to really have a wellspring to build on, to have that resilience to navigate those moments, you need something outside of the work.

to actually turn to, to be able to breathe again. I'm curious what your take is on sort of like that. Even now as you're saying that I'm a little torn because in my line of work, it's so much about detail and it's, it is obsessive to a degree that period should not go there. That image does not sell that story as well as it could. All of those small details that add up to a really quality product.

And if you don't have the fire for that, then you're kind of churning out mediocre work, in my opinion. However, I see the point when you're not in balance and you're dysregulated, and particularly if you keep going obsessively, you will burn out. And once you reach a place of burnout, then your effort toward the work

It's not what anyone would want. So I feel like it is all about balance. And of course, that balance is harmony.

When you think about the way that you were driving towards the work that you were doing, it sounds like it was pretty much on the obsessive side of things. With that one exception of trying to be a present parent as much as you could. This all comes to a head at some point. Yeah. You write about actually in your books are like a moment where you're delivering a speech and it doesn't actually go the way you planned. Well, no.

I'd been neglecting my health and I had had a number of things and I just was blowing through the signals. You know, your body, the body keeps the score, whole thing. I was blowing through a number of signals. You know, I'd had a lot of, I'd had a classic like 80 stockbroker dad, like ulcer. You know, I had had, I had really terrible headaches. I, you know, I was grinding my teeth. I like, I chewed through like a couple of mouth guards, et cetera.

But I kept going because those actually, I could keep going. Didn't matter. And then what happened was I had...

My voice basically failed. I wound up having several polyps on my vocal cords. And a doctor had told me, you know, you need to slow down. You need to not be talking so much. In the meantime, I was giving a couple of speeches a month, plus running several meetings a day on the phone all day, you know, talking in loud coffee shops with the writers I was trying to recruit, just talking, talking, talking, talking. And I was standing on this stage giving this keynote speech and

And I went to say a word and I couldn't. And it was just like, like a strange haunting, like gasp, like came through instead of a word. And it was terrifying. And,

And then I wound up after that, long story short, I didn't really follow the doctor's instructions. It got worse. My vocal cords started bleeding. It was, you know, it was in danger territory and I had to get surgery. And after the surgery, I,

I couldn't speak for two weeks. You have to absolutely be silent because when you speak, your vocal cords touch. And if they've been in surgery, you could now damage them permanently. So I took this very seriously, but it didn't stop working. And

And once I couldn't be a participant in the game, I got to watch it as an audience member and I didn't like what I saw. It was the best thing that ever happened to me because I really don't know that I would have taken a step back and really examined my life in that way if I hadn't been forced to. It changed my whole life. What was it that you did see? What were you seeing? I just...

I just saw the jockeying and the callousness of, you know, the people I worked with, my bosses. It's like a game that I wasn't interested in playing. You know, a lot of what I really regret about my years as a, you know, as a high level manager, I was in the C-suite at this point, was that I made decisions that

that were maybe good for business, or I was kind of forced to make decisions that were maybe good for business, but didn't align with how I felt and who I was. There are people who are really good managers, leaders, who have no problem making those kinds of hard decisions. But I did have a problem. I didn't like when I was asked to fire somebody who was on maternity leave, for example.

I didn't like a lot of the things that I did. I didn't like, you know, laughing along with like some flaccid jokes from a boss just because that's what we have to do here. I didn't really love playing the corporate game ever, but because I wasn't being mindful as I was climbing the ladder, by the time I got there, I just felt kind of wedged in and stuck. You know, I hadn't really thought like every step of the way I wasn't thinking, is this what I want?

Is this right for me? I was just doing it because I thought I should. And so when I was able to take that step back, I was kind of shocked. I was like, wait, I don't belong here. This isn't right for me. And even then I didn't leave because I was too afraid. Afraid of what? Of the world.

I was afraid the way it would look on my resume, which seems ridiculous now because I've endured so much tumult in my resume. It doesn't matter. Like none of that matters. You think it matters so much, like intention matters so much more, you know, it's, it's

I was afraid of losing my health insurance, which was a big deal. I didn't realize at the time like, oh, well, if you just earn an extra amount of money, you just, I can pay for health insurance out of my own pocket. I just need to like rearrange some things and like, you know, cut some things and maybe stop outsourcing so many things in my life. Like I could earn a lot less. And I think you don't realize that either when you're earning more. Hmm.

And I had scarcity issues. I had big scarcity issues from growing up. My sister and brother grew up upper middle class, but I grew up lower class. And I had real scarcity issues around money. And so once I started making some, I was very scared that I wouldn't be able to survive without making that much. Which is completely understandable. These are the patterns that get laid down. The tracks that we have when we're kids...

And unless and until something happens to really rewire those, it's like they stay with us until we actually do something to sort of like question them and say like, huh, is this true? Like, do I actually, is this the only way to be? Yeah. And I had sort of lost that. And it was really interesting because it was the provider thing. You know, once I had a child, I was the breadwinner of our family and I was just

I felt like it was what I was supposed to do. And I abandoned myself completely in the process. You know, I was a creative person. I was a writer. I always wanted to write books. And at some point, I just got so far off path and I missed myself, honestly.

Did you have a sense? I think having this conversation now, I think you probably have a really strong sense for who you are and who you've always been. If you can take yourself back there to this moment where you're starting to really wake up to something's not right here. Did you have a sense for really who you were back then? Or were you so far from it that you couldn't actually really connect to it in that moment? And I think this happens to a lot of kids who...

It's, you know, it's called, there's a connection between workaholism and something called parentification, right? Where you have, you come from a tumultuous home, chaotic home, you have expectations put on you from a young age. I was a very sensitive, creative, weird kid in a tough working class family.

And I think that I never really embraced who I really was because I didn't think it was the right way to be in the world. And also, I thought that the way I really was, the soft, tender way I really was, the creative, gentle person I was, was not going to survive. I mean, I was told that overtly. But also, it was just something I gleaned from my surroundings.

When I was in corporate environments, when I was in rooms full of all men, and I could hold my own, and I could out-tough them, and I could be as ruthless as they were, I thought, well, this feels bad, but look at me doing this. This is amazing that I can do this. And

And then part of it was gender too. I felt a responsibility. I was one of the few female corporate leaders in my department. You know, I felt a sense of responsibility and accomplishment that even if it wasn't satisfying, I felt like, well, if I can do this and I'm really good at it, clearly, maybe I should do it. And I think that's something that's really difficult is when you are really good at something you don't like.

You know, like when we excel for whatever our makeup is.

And I would say, not to throw the T word around, but I think that the majority of my success was because of trauma response. I'm incredibly hypervigilant. All of these things, right? So I was basically dysregulated all the time. I was hypervigilant. I was always looking for danger everywhere. So it made me an incredible employee. I've often used the phrase, just because you could doesn't mean you should. It

It's such an interesting conundrum. If you are really good at something, whether through hard work and skill development, or maybe just naturally like this is your gift, there is this sense of obligation that we tend to have to be like, oh, this is, I have to do this thing. And especially if you see that that thing is well rewarded, it gives you status, it

It genuinely helps the organization or community or someone that you want to be in service of. You're like, this is the thing I'm here to do because I wouldn't be so good at it if it wasn't that way. And I feel like we give so much energy and oftentimes so many years or decades of our lives and our careers to doing that out of a sense of obligation, not genuine interest or passion or meaning or purpose.

For sure. I mean, the whole system is set up to reward exactly that behavior. By the end, I was really rewarded for this. You know, I remember like Cosmo called me up and they said, you know, we want to feature you in this regular column we do called Get Her Life. And I was like, are you kidding? Yeah.

You're like, if only you knew. You know, it was like I had a dream job. I had this coveted life. I almost felt ungrateful that I was so unhappy. And it's hard to break yourself out of that. It takes a lot of courage to bust out of that kind of societal norm, I think. Exactly.

And convention. I feel like for a lot of people that you can sort of layer on shame. Like I shouldn't feel this way. So many other people would quote, like want to be in this position, you know, like, and for me, I'm just sitting here feeling miserable about it or complaining about it, even if not externally, internally, like to myself. And who am I to be complaining about this? You know, that's shameful behavior. And it just, and then it creates an even worse spin cycle. Yeah.

Exactly. Or, of course, I have agency. I can change this. I can take these skills and I could go to another place and maybe that will be better. And maybe, you know, there has to be a way to fix this, right? It can't be. It can't be that I just shouldn't be doing this. That's silly. Of course, I'm an executive. Look at me. And then, of course, you get some clout and you get a reputation and all of those things. And all of these things, all of these like majorities,

micro addictions sort of add up. You know, work is a behavior addiction. It's a process addiction. So eventually you do feel a sort of sense of helplessness and you feel like it's carrying you away in a way. When you end up having surgery on your vocal cords and you have this two week window where you go back to work, you're there, but you're forced to observe and not sort of like fill the space with your voice.

it sounds like this is almost like a forced time of reflection and observation. And I wonder if the fact that actually you were physically unable to contribute vocally to

Yeah.

the mood, like the affect, the energy of people. I wonder if that all started flooding in once you were forced to create that space. Absolutely. That's absolutely correct. I think that I quieted my mind. I literally quieted my mind because I wasn't talking, right?

And I could feel things more profoundly. And I had a visceral disgust from what I was hearing because I wasn't trying to win the game. I was just looking at the game. I just remember sitting in these meetings and watching like...

Ill thought out strategies. That's a big thing that happens in jobs, right? Like somebody is just presenting one ill thought out. It's like they're just trying to get on the board, right? Nobody's thinking, is this going to work? Is it not? Or this one person's making a big case and it's so much noise, right?

So much of these dynamics in these meetings are just noise. And when I wasn't concerned, or I couldn't be concerned about, you know, when it came to my turn, what noise am I going to put out, you know?

I really just was like, this is stupid. This is all stupid and silly. And I am getting very stressed out by something that is stupid and silly. And I am spending the majority of my life, of my waking hours, thinking about something and contributing to an organization for work I don't really respect, I don't believe in, for people who don't really respect me. And

And don't align with how I think the world should be. And in that moment, I was not courageous. I didn't like have some big, you know, network speech and storm out. I just stopped working quite as hard. And then within six months, I was fired. Like,

I had reputationally been brought on because everybody knew that I would do anything. I would plow through a wall to get it done. And I stopped being that person, which meant I was no longer right for the role. And I was fired. And we'll be right back after a word from our sponsors.

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We all have dreams. Dream home renovations, dream vacations, or sending our kids to their dream colleges.

But finding straightforward ways to turn those dreams into realistic goals, that's where things get tricky. Merrill understands that. That's why with a dedicated Merrill advisor, you get a personalized plan and a clear path forward. And having the bull at your back helps your whole financial life move with you.

So when your plans change, Merrill is with you every step of the way. Go to ml.com slash bullish to learn more. Merrill, a Bank of America company. What would you like the power to do? Investing involves risk. Merrill Lynch, Pierce, Fenner & Smith Incorporated, registered broker dealer, registered investment advisor, member SIPC. You know, on the one hand, you're like, okay, what a fantastic experience or what a great window for you to now step back and say, okay,

Let me reflect on all this. Let me see what I really want. How do I step back into this world of work in a way that feels more holistic and supportive? But on the other hand, as you described, like you're the primary breadwinner. At least there are practical concerns here because I think folks may hear stories like this and like, well, that's great. But I'm like, I've got to pay the rent. I got to pay the mortgage. I'm the person who like actually takes care of the family and all this. You were that person also.

this was on you. So how do you start to navigate, do this dance where it's like, okay, I need to figure out a different way. Where I came from, I can't go back there. Something has changed in me. There has to be a different way forward. But at the same time, you're living the trappings of a life that has built around the rewards generated by working that way and being that person for years. That's not necessarily an easy thing to unwind. Yeah.

No, it was not an easy. And let me say, I think that because I grew up without a lot of money, I'm sometimes confused when I'm talking about things like class. I think that I still think of myself as a working class person, even though I'm not. I'm a white collar person. I made some money.

We had had, my husband and I had saved up enough money to buy a house. And when I got fired, I said, I can't get another job for a while. It was like everything had come up for me. And I felt very like I couldn't get myself back online. I just felt very disoriented. And I knew that I just couldn't proceed as normal.

And so we didn't wind up buying that house. And I took a little bit of a break. I was working a lot freelance, but I never went back to a big job. And I changed the trajectory of our life. I changed us from upper middle class people to middle class people. And we had to make that decision. And I realized being able to make that decision is an incredibly privileged thing to be able to make. And I'm so aware of that.

But it was a decision for the health of our family. I feel like for the health of my marriage, for my relationship with my child, all of those things, it was the right decision for us to make. And we just financially, at least, began living a much smaller life.

And one thing that I did almost immediately coming out of that was I had never really understood money. I didn't grow up having it, so I never really understood it. I was a very self-flagellating person, and I feel like I didn't care about myself enough to respect my money and to consider money.

financial education, a kind of self-care, right? And protection. So I really, for the first time in my life, in my mid forties, educated myself about money. And that was really, really helpful because then I could understand, well, all right, yeah, we can live on less. And all right, well, what are our dreams really? And how do we keep ourselves safe for retirement as we make this transition? Safe-ish, you know?

I had never invested in myself in that way. And that, I think, is one of the most important things that came out of this. Because you can keep making money and just throwing it in a bag somewhere. Like, I didn't, I just didn't understand it. I was like, throwing it in a bag and then throw it in the backyard and burn it. Like, I really, I just didn't, I didn't get what you were supposed to do.

And now I do. And I feel like I really grew up too, because like any addiction, if you are working all the time, your development is arresting a little bit because you're not thinking. You're not listening.

You're not growing. It sounds like also money was one of those patterns that got laid down when you were a kid. And decades later, this was the first time where you go back and revisit that and say, huh, this was a level of understanding that has been guiding me up until this point in life. And maybe it's time to question if that's serving me and the choices that I want to make moving forward and to really understand.

do the research, do the education to be able to say, I need to write my own rules around money so that that can power the decisions that I make moving forward in a way that honors me more, not necessarily the rules that were passed on to me when I was a kid and the mindset probably around it as well so that I can build on that to make decisions about how I now want to step back into the world of work and life in a way that feels right.

more nourishing. It's interesting. You said we were living a financially smaller life, but I wonder if at the same time, you still felt a bigger sense of freedom. Oh, for sure. For sure. I can't tell you the kind of satisfaction that my work has brought me in the past five years. I

and the joy of it, then the freedom for sure. I think that all of the money definitely, but also just my decisions that I now make about my career, it's all about intentionality. It's all thoughtful. It's very personal. My definition of success is very personal. I don't make decisions anymore with my LinkedIn profile top of mind.

I don't care what things look like to the outside world. That's the biggest shift for me. What that's resulted in is a well of deep satisfaction and also a real sense of accomplishment because I've done a couple of things in the last few years that I never thought I could do, but I always wanted to do. That's real success. So tell me about some of those things.

Well, I wrote this book and it's the best work I've ever done. I always wanted to be a quote real writer, you know, and it's a real book and I'm a real writer. I love that you've been writing for like literally your entire double life and you still didn't think of yourself as a quote real writer until you sort of like had this book out.

Well, I think even that, even creative work, even creative projects can be done for you or for someone else. And this book was really for me. And when I finished it, I really had that like, oh, I did it. I knew I had done it. I had satisfied what I set out to do. And so the external reaction didn't really matter to me as much because the success was already there before anyone ever read it. And then, you know, I chased down a project that I had been thinking about for 20 years. I

basically would have been a hobby. I'd been collecting these old magazines for years, and I turned it into a narrative podcast. And so I got to write a documentary podcast. And it was so challenging to write in this new form. And my brain was working in this whole new way. And I was really learning. I was so active and so engaged. And it was really hard work. And some weeks I worked on it every single day of the week.

But I never got burnt out from it because the brain loves competence. The brain loves acquiring skills, right? We love it so much. And I knew I was no longer stuck. I was like, oh, I'm in a whole new journey here with this.

And every day felt like a delight. It was that beginner's mind, like, oh, how do I puzzle over this? And I was really able to let my ego, put my ego aside, even as like an older, you know, middle-aged person and have like younger people teach me things too, which is not easy to do. I think that's part of why we get stuck as we get older. You know, it's like, I don't know. This is really humbling that I don't know this.

Yeah, it's funny. I had a friend who I hadn't been in touch with for quite a while, actually, but she was in the magazine world in New York for, I want to say, 30 years. You know, like the highest levels also. And...

She turned 52. She decided that she wanted to be a physician. She had to go back to undergrad, take her prerequisites like bio and like basic health science prerequisites for two years to then apply to med school. And I remember her talking to her and she's in class with like 19 year old kids and she's in her mid 50s.

And I was like, how is that for you? And she's like, terrifying and amazing. Yes. Because I know these kids actually don't know why they're here. I know why I'm here. And that's amazing. Yes. And as we get older, it's like so much better to be scared than bored. You know, it's just, it just really is. And just that sense of possibility and that sense of wonder you get from really

Really being interested in something and knowing that you don't know anything about it, you know, just having that desire again, like you did when you were young. I wouldn't trade that for anything. So great. Over these last few years, as you're reimagining so much, what becomes important to you? In your mind, what are the criteria that make you say yes and no?

The number one thing for me is community at this point. Friendships, community, family. That's the number one thing. Protecting that as much as I can. When I got fired, my child was eight.

And I was acutely aware of how fast that first eight years had gone. And I knew how fast the next eight were going to go. So I don't work after three anymore. I work early. I started six, but I never took jobs in the times I was freelance. I never took jobs that would require me to send emails after three that would, I don't want to be in two places at once anymore.

That was the biggest thing. Boundaries around work was really my biggest issue and I really needed to set that. And then, you know, I really think about commitment. Do I want to commit to this? Not just for money, but understanding that my time on the planet is finite and

And do I want to, unless I absolutely have to, engage with something for hours that I don't enjoy, that I might be good at, but I absolutely hate? Now, sometimes you just do work because it is survival and you need to grab that bag. Like freelancers, it's a hustle. Gobbling together a salary is no joke.

But like, I am very clear with myself that there has to be a purpose. And maybe that purpose is, well, this will pay rent for the next six months. But if not, I'm not taking it on. The difference is, is I'd rather not.

be not working than working on something I don't like. And that was not the way it was before. I think I was afraid of myself before and I didn't like time that was not working because I didn't want to be exploring my brain or, you know, chilling out with my husband or whatever it was because I didn't know how to really to be a person.

Yeah, I mean, I wonder if also sometimes when your work absolutely consumes all your waking hours, and you do have this other person in your life, but you're really not interacting with them in a whole lot in a deep and meaningful way, that when you get dropped back into it, if you almost have to relearn,

how to be with each other now that you're actually sort of like, it's a very different context and dynamic. For sure. And the power dynamic for us certainly changed because like I said, in the very beginning of this, the person who makes all the money is in a different power position than the person who doesn't. And our playing field was certainly leveled when I stopped making all the money, which was among the better things that's ever happened to our 20 year marriage. And,

one question I do ask myself all the time is, am I behaving like a person who wants to be married? Is the way I've approached this situation, is the space I'm giving this person, are these the actions of a person who wants to stay married? How is this going to come across to this person? And if you are all consumed with something else and not present,

you don't have time to think those things out. And so you really lose consideration. You wind up like just barking things at a spouse and just being like, well, we just have to get through this. You know, this is just the time. I think having the time to,

The privilege of the time to slow things down in my life has been a big priority for me. I wonder also, and you write about this, you spent some time working with an Irish cannabis media project. I did. But also you being able to just see a different culture, a different way that people explore work and life. Did that meaningfully inform the way that you're looking at the relationship now as well? Yeah.

For sure. Yeah. The company I worked for was based in Ireland.

And it was so funny because I'd get on, you know, and because of the time difference, I'm in Los Angeles. I was dealing with people all the way, you know, in Ireland. And I would get on at 5 a.m. and I would open up the Zoom. I always had a meeting every morning at 5 a.m. And I would open up the Zoom. And, you know, here I am. I'm chipper and ready to go. And like half the people would be missing. And I would say, hey, Johnny, where is everyone? And he would say, oh, well, they have the day off.

And it's because they have dozens of state sanctioned days off a month that they, I mean, a year that they have to take, right? So every month you have several employees out and it's just the way it works. It's just somebody's always out and it's fine, actually. The people I worked with, I don't know if this is how everyone works in say the UK, but the people I worked with, they logged in at a certain time and they locked out at another time. And that was it. If I sent them an email after hours, they were responding to me the next day.

And part of my job, which was very enticing to me, especially where I was in my life and my brain space, was I had to spend a week in Ireland every two months. So I spent a lot of time in the office and out of the office with these colleagues, and

And I really got a sense of what they prioritized and what they didn't. And salaries there were not very high. Nobody had a lot of money, but there was a lot of support for them. There was a real safety net for them by their government. So that's one thing. But just a de-emphasis of work. It was not...

how they measured a successful life. And I remember sitting with them and really just enjoying my time there, number one, but really enjoying being able to slow down and knowing that even if I had a list of 10 problems that we needed to fix right this minute, nobody was going to fix them. So I just had to ride it out. That was a real learning experience.

Yeah. I mean, it's just, it's a cultural shift that makes you really think about things differently and like circling all the way back to the beginning of our conversation where we're

I feel like ambition isn't necessarily gone. And some people still have the same old ambition for the same definition of success and they're hard charging and they're like doing that exact same thing. But I feel like increasingly we're just ambitious for different things. Yes. We're ambitious for love, for peace, for peace of mind, to be able to exhale, to be able to spend time with people we can't get enough of.

And we're elevating that to the level of this actually matters as much, if not more. You were asking the question, what's in service of what? Yes, yes. I am ambitious to feel content. I don't expect happiness every day, but I am ambitious to feel a sense of equanimity in my life.

You can't find when your life is out of balance. And I am ambitious to invest in friendship, which is something I've really lacked for the majority of my life and is so important, especially as you get older, right?

And just being a good person. How do I show up every day? Those are things you need space and time to think about. We don't just come out being good people who know how to like manage ourselves in the world.

And many of our childhoods don't help with that, right? So it takes work and it takes effort. And that's something to be ambitious for. Being a person who means something in other people's lives, all of those things, that's how I calculate if I'm a success now. It's a good place for us to come full circle as well, so...

I'll ask you the question I always ask at the end of these conversations, which is in this container of the Good Life Project. If I offer up the phrase to live a good life, what comes up? I want when I die for people to say she was a really good person. That's a good life. Thank you. Hey, before you leave, if you love this episode, say that you'll also love the conversation we had with Jen Sincero about transforming your life. You'll find a link to that episode in the show notes.

This episode of Good Life Project was produced by executive producers, Lindsay Fox and me, Jonathan Fields. Editing help by Alejandro Ramirez, Christopher Carter, Crafted Hour Theme Music, and special thanks to Shelley Adele for her research on this episode. And of course, if you haven't already done so, please go ahead and follow Good Life Project in your favorite listening app.

And if you found this conversation interesting or inspiring or valuable, and chances are you did since you're still listening here, would you do me a personal favor, a seven second favor and share it? Maybe on social or by text or by email, even just with one person. Just copy the link from the app you're using.

and tell those you know, those you love, those you want to help navigate this thing called life a little better so we can all do it better together with more ease and more joy. Tell them to listen. Then even invite them to talk about what you've both discovered because when podcasts become conversations and conversations become action, that's how we all come alive together. Until next time, I'm Jonathan Fields signing off for Good Life Project.

Holiday shopping is here and Amazon Live has got you covered. Shop for the perfect gift from the comfort of your home with Amazon Live's shoppable video experience. Discover the hottest products from influencers and shop while you watch. This season, join Kandi Burris from Real Housewives in her holiday Amazon Live series, Generation Face Off.

where Kandi, her mom, Mama Joyce, and daughter Riley share their favorite stocking stuffers and go-to gifts across fashion, beauty, and more. Watch and shop new episodes of Kandi's series, Generation Face Off, now by going to Amazon.com slash KandiLive. That's Amazon.com slash KandiLive. For a limited time, use promo code KandiLive for $5 off an eligible product featured on the first episode of the series. That's K-A-N-D-I-L-I-V-E.

We all have dreams. Dream home renovations, dream vacations, or sending our kids to their dream colleges.

But finding straightforward ways to turn those dreams into realistic goals, that's where things get tricky. Merrill understands that. That's why with a dedicated Merrill advisor, you get a personalized plan and a clear path forward. And having the bull at your back helps your whole financial life move with you.

So when your plans change, Merrill is with you every step of the way. Go to ml.com slash bullish to learn more. Merrill, a Bank of America company. What would you like the power to do? Investing involves risk. Merrill Lynch, Pierce, Fenner & Smith Incorporated, registered broker dealer, registered investment advisor, member SIPC. Hey, it's Mark Maron from WTF here to let you know that this podcast is brought to you by Progressive Insurance. And I'm sure the reason you're listening to this podcast right now is because you chose it.

Well, choose Progressive's Name Your Price tool, and you could find insurance options that fit your budget so you can pick the best one for your situation. Who doesn't like choice? Try it at Progressive.com. And now, some legal info. Progressive Casualty Insurance Company and Affiliates. Price and coverage match limited by state law. Not available in all states.

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