The Ambition Monster

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I'm Jane Marie and this is The Dream.

Today you'll be hearing a conversation about work and industriousness and speaking of which, we'd really appreciate it if you went to the show description, today's episode.

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Today, we're talking to a woman who I think spends more time thinking about work, what it means, what it says about us, its value, than I do, especially women's work.

What is it about us here in North America that urges us to equate output with our intrinsic worth as humans?

And no, she's not wielding an axe all day, but I have no doubt she'd be an incredible lumberjill in a pinch.

My name is Jennifer Romolini, and I am a writer and a long time

content maker.

You're a content creator before that was a job.

Yeah, well, that was, that was, that was exactly the swerve that fucked us all.

We don't have to curse on this.

Yes.

That was exactly the swerve that fucked us all.

I remember when it happened, when we started calling any kind of creative art content.

It was exactly like it used to be where I'm making a story.

I'm creating an article.

I'm writing.

I'm painting.

I'm, you know,

doing something digitally that's artistic.

And now

everything is content.

And that was when we got screwed.

Not just artistic, though, but you write like thoughtful articles and you explore parts it's like yes scholarly in a way and journalistic.

And, you know, I,

as far as what I know of your work.

Yes, I've written a lot about work.

That's what I'm here to talk about.

Yes, that's what we're here to talk about.

But you've written about other things.

Can we

go back a ways to how you got started?

Okay.

So

what's going to be germane to this conversation, I think, is that I am a blue-collar kid.

I am sort of the product of the American dream.

My father and my parents had me as teenagers.

We have similar backstories.

My dad didn't have a high school education.

Neither did my mother.

They built a business up, got us out of poverty into a, you know, somewhat upper-middle-class life when that was kind of possible for people to hustle into.

I started late, like you started late in media.

I worked my way up through the ranks of New York publishing.

I worked at Condé Nest.

I worked at lots of women's magazines.

I worked at Talk Magazine.

I worked with Tina Brown, which people who are old enough to know know.

And then eventually I just, I kept rising and rising.

I was in corporate media.

I was in tech companies.

I was contenting and I ran startups.

I just

started running things.

And then I really had like a massive burnout and started writing books.

And now, yeah, that's basically it.

How did that help with the burnout?

Well, I think

no, I mean, you've talked about this a lot.

And I think this is...

so the book is called Ambition Monster, the last book that I wrote.

The first book I wrote was really me grappling with trying to still fit into the system and giving people like a decoder ring.

You know, it was like, it was called Weird in a World That's Not a Career Guide for Misfits, Fuck-Ups, and Failures.

And it was really about, I was still in it pretty deeply.

And I was trying to figure out why everything felt so bad.

And it had to be me, right?

I had to be weird in order for work to feel so bad.

And especially because it was the height of the girl boss movement.

And I felt sad all the time.

I didn't want to like show off my cute office with like the, you know, neon sign that said good vibes only on the wall when it was like, you know, when all it felt was bad vibes.

So I was, I was really trying to write a guide in that first book, which was like,

Here's how to work the system.

Here's how to get through it.

If you feel anxious and sensitive and all of this feels like bullshit.

Here's how to serve your

self in this system.

But then eventually I went back in and I went in for an even bigger job after writing that book.

And I was like, no, no, the whole system's fucked.

Like I,

you know, ignore that whole book.

I want to write about why we're thinking about ambition entirely wrong because there's actually no there, there, here.

There's no satisfaction in the sort of lie we've been told, like, you know, accumulation for accumulation's sake, titles for title's sake, you know, tying up your identity in your work and your value in your work.

Mm-hmm.

Well, so where do you think you got that idea in the first place?

That that was how things were supposed to work.

Like I talk about this a lot about myself where I, you know, grew up in a home where I was told you need to, first of all, you need to bust your ass twice as hard as any man.

That's right.

And it's true.

It is true.

It's if you want to survive, you do.

Yeah.

Especially without a man.

Yes.

Exactly.

So if you're going to do it by yourself, you're going to have to be 10 times better.

But, but where do you think it, like for you, where did it start?

I mean, first off, it's just in, it's just in the ether, right?

Like work is, I mean, we associate work, we associate,

there's a virtuous suffering

with labor.

Okay.

Like, I'm not the first person to say it, but that's a Protestant work ethic.

That is just built into us.

We are

conditioned very early on

to understand that the

easiest way to be liked, accepted, is to achieve.

Right?

Achievement is just built into the whole thing.

And then for me,

I

very actively saw work

as survival,

as redemption,

as the thing that made you worthy

on the planet.

And then there's this other version

as women where it could have been that we saw motherhood and marriage and parenting as that thing.

And that never appealed to me

as far as how I was going to get that satisfied or

any sort of.

I felt like there was probably more of a guarantee that work

would get me that sort of

stability.

Freedom.

Yeah.

Yeah.

The ability to actually live a life, like live a full and rich life,

to see a lot of things,

to have a lot of experiences, to have a bigger life.

Yeah.

My mother's life looked very small to me

and suffocating.

And the bitterness, the wiping down the counters, the cleaning up, just angrily cleaning it.

Like it just seemed so stolid.

Like I couldn't fathom.

I wanted to be my dad

from early on.

He got to leave the house every day.

He had friends.

He went wherever he wanted.

He had the money.

He had the power.

Right.

Right.

And that's what I wanted.

Yeah.

And you were told, well, we're all told that you can have it.

You can't?

Well, yeah, exactly.

Exactly.

But you don't realize nobody tells you.

Well, because, well, because then.

Well, tell me specifically how you're, how, how that worked.

Like, what was your first job?

I started working when I was 13 for my dad.

I sold

at Easter.

we are Italian Catholic, and right down the street from his store in southwest Philadelphia was a church, and I sold Easter flowers.

And

he

would split the profits with me if there were any profits.

The entire reason to put these Easter flowers out, which was like, you know, there are all the kind of masses during the week before Easter.

And so people go to church and they come and they buy, you know, tulips or hyacinths.

And

the entire reason to have this stand was to bring people in to the store, right?

He didn't care if he made a profit off it.

So that's why it was kind of the perfect thing for me.

To the grocery store.

To the grocery store, exactly.

Sorry, my dad owned a grocery store.

So he would set me up outside and I would do it willingly because I was like, if I can make $300 at the end of this week, I'm 13.

I can buy all the Garfield shirts I've ever wanted.

You know what I mean?

So I was learning to wheel and deal.

I knew how, I knew the cost of the flowers.

I knew how much we needed to charge to make a profit.

I knew how much I could cut the price to, you know, to make a bargain with somebody, but still make a little bit of a profit.

And I'm in a perishable goods like business.

They're like, they're literally like wilting around me as the week goes on.

By the time Easter Sunday came every Sunday, it was just, it was a massacre, flower massacre.

And I'm just pushing like, you could plant them as bulbs.

They'll come up next year, you know, whatever.

Right.

And then I never stopped working after that.

I loved, I mean,

I do get off on working.

I don't get off on money, which is really the fucked up thing because that's what you need to have to be the person who's like, oh, now I just want to accumulate for accumulation's sake.

And I don't have that.

Or a combination of, I really love working in a place where I make money or in an industry where I make money.

That's where I hit myself in the head all the time where I'm like, Jane,

really?

You picked public radio?

Yes.

You know, like I could have gotten an economics degree

just as much fun.

I could have become a plastic surgeon.

I mean, that's really where the money is.

What were we doing?

I don't know.

Why am I not injecting Botox and making, you know, $10,000 a day?

I don't know.

But I think that what's important to say here is

the world was different when we made these decisions, right?

So

you could make a living.

Like,

I was never hot for wealth.

And I don't think you were either.

Still not.

And

I went into magazines and I just wanted to be somewhere in magazines.

I wanted to be part of people making something.

And at that time, people were making a fine living because, you know, real estate was cheaper in New York.

So you could live in New York on a magazine editor salary.

Salaries were better.

Magazines, you know, were robust and had budgets.

I think we also grew up in a time where magazine, there were magazines like Sassy.

Right.

And we can talk about Kim and

your relationship to these magazine editors who are adjacent to all this stuff.

Yes.

But I remember at, I think I was 13 or 14 when they did the

reader-produced issue.

And a girl from my high school was chosen.

Wow.

And got to go to New York for a week or two.

Yep.

And create this issue of this magazine where it was a bunch of girls, teenagers, saying,

here's what's cool.

And here's what I, what interview I want to do.

And here's, and just all these ideas flowing out and being printed in a glossy magazine that I could buy at the drugstore.

Yes.

And I felt at that time like that was my first glimpse of, oh, ideas

are valuable.

Yes.

And

I think I have some ideas.

Yes.

Yes.

It didn't really make sense, but it gave me a dream of like, oh, if I just come up with some good ideas and I learn how to write.

or tell stories or edit or whatever.

And I can have a lot of people.

And you need to be curious.

Yeah.

These people are curious.

They are out there looking at things and finding the coolest stuff.

And they're sourcing it for me and sharing it.

And sharing it.

And I mean, sassy really was the dream, right?

I mean, that did the number on a whole generation of women, which is why Kim France, who is my podcast wife, who I do a podcast called Everything is Fine With, she was an original sassy editor.

And

her life, she's nine years older than I am.

We missed this by by nine years.

Like

she made more money in every single job she had.

It's not talent.

She is very talented, but I'm as talented.

It was just the business had

changed and everything had changed.

You know, rents have changed.

Like everything was changing by the early 2000s.

Everything was just,

life was not set up in a way that you could survive as that kind of mid-level creative.

And even her following is very different than mine.

Everything's so diffuse now, it's just not the same.

And she didn't have to sell herself.

Right.

She didn't have to create a giant following on Instagram or whatever.

Yeah, she didn't have to become an influencer.

They just got to do their jobs.

And they just got success from doing their jobs well.

Right.

So the eye, so that we had the idea that that's something that would have worked for us.

And that was every industry.

That was every industry.

It's just not the case anymore.

Yeah.

Yeah.

And I mean, I don't know.

I guess if you are really good at being an influencer, you have money, but that feels so unstable to me.

Yeah.

Because it's built on somebody else's platform.

Even though those were built magazines, it was kind of, that was different.

It felt more collaborative.

So, yes, that's where I got the idea that work,

the work would save me.

I also really loved hiding in work.

I found that to be such a powerful drug, such a way to numb out was just, and I still do.

It's still a place I'll turn, like I will just create more.

I have five jobs.

I will just create more and more work for myself if I'm anxious,

if I don't know how to be in the moment, you know, like, oh, well, I'll just go over here and I'll just, you know, type something up real fast.

You know, I'll put out a quick sub stack, you know.

Or an email to friends saying let's start this thing let's start exactly yeah exactly exactly so

okay so you go from selling flowers on easter someday to

then what

well i was a bad student i didn't know i had adhd and i was a bad student like i was a curious kid but i just could not follow the rules of school i couldn't keep up with homework i was constantly getting behind i was disorganized So

I got into one state school.

I failed out.

I stoned out.

Who knows?

I mean, I was doing, I was doing drugs.

I was just, you know, whatever.

I was drinking and smoking a lot of weed.

I wasn't really a big drug person other than that.

And then I got married, which was dumb.

I got,

I just, I married, like, I was working at a hotel restaurant and I married the hotel manager who had a Miata because, you know, you just had a Miata?

Yeah, you had a fucking Miata.

That's hot.

He had a Miata.

Like I, at those days, I was like, I don't even, he was just like a Ben Stiller, like reality bites type to like, you know, every Ethan Hawk I had dated, you know?

And so I married him and I was so bored immediately.

But then I felt like I couldn't leave him.

But I was so bored.

He like played golf and like listened to Rush and like watched golf on TV.

Absolutely not.

Like that was not the life I wanted.

And he was like, let's start having kids.

And I was like, no.

How old were you?

I was 21.

I was 26 my first, my first try at marriage.

So stupid.

And the judge was like, these are good ages.

She even told him, her name was Nancy Drew.

No.

Yes.

Amazing.

I know.

That gave me confidence somehow.

I do think

that's so funny.

Why?

I know she was like, she was solving the mystery of of whether or not you should get married.

It was just the three of us in a room.

And so I was like, I didn't have anyone else to look to for like,

really?

Is this okay?

Oh, I had the whole thing.

I had the big Catholic wedding.

I wore gloves.

I had like the meringue.

I knelt in front of the statue of Mary.

Like I did the whole.

He was like an altar man.

He had been an altar.

He was an altar boy so long that he was an altar man.

Like it was a very Catholic experience.

But let me ask you this.

Okay.

I have come to believe that marriage is just stupid.

That's our next episode.

Okay.

It isn't unrelated to what we're talking about with work.

No, it's not.

Right.

Like I said, like there's, I know that at least for my mom, marriage was the job and was supposed to afford you.

a comfortable life.

Yes.

If you're a good housewife, right?

And a good mom.

Yes.

And you're supposed to be taken care of.

Yes.

Even though you're doing more work than they are.

Oh,

so much more work.

Yeah.

Like the unpaid domestic labor.

The physical domestic labor, the emotional labor, the accounting,

just

so much of it.

But what's so funny is

even when you're working, even when you're the breadwinner,

you're still doing

80, 90% of it.

Yeah.

And that's not you making that up.

That's real statistics.

Like, I mean, I know.

That have been studied.

And it doesn't matter who the man is.

Like, I have so rarely seen it in any other way.

I say that often to people and they're like, well, I know a couple.

No, it's like a, this fucking drives me crazy.

It is when it is like a.

When we see men doing domestic labor, emotional labor, it is always a dog playing a saxophone.

It is always like, oh, but he changes diapers.

And it's like, oh, fucking great.

It's like Ben Affleck is a director.

It's the same fucking thing.

It's just like, oh, and also he could do this.

I didn't know his species could.

But

I...

I am also very sick of hating on men.

Like, it's obviously the system.

Like, I'm not interested in being a bitter middle-aged lady.

Like it's it's in some ways not their fault.

Like it is their fault but not, but this is societal conditioning.

You know like they don't survive in the same way that we're taught to survive.

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You check your feed and your account.

You check the score and the restaurant reviews.

You check your hair and reflective surfaces and the world around you for recession indicators.

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What I find

difficult is that the world is built on the idea that they're the most capable and that they're the drivers of the economy and all of this stuff.

And all of us women who really

run things,

quote unquote, behind the scenes or whatever, are seen as accessories to that as opposed to

like people aren't seeing reality.

You know what I mean?

Like the story that's been sold.

So, oh, wait, so let's get back to the conversation so that we don't completely confuse everyone.

Yes, yes, yes.

Um,

and we will come back and talk about the scam of marriage.

Yes, please.

But I want to have regular guests.

I will talk about it for four years straight.

And motherhood.

Oh, my God.

The scam of motherhood.

The scam of motherhood.

Oh, my God.

Yeah, I screwed that one up big time.

I mean, I have a great kid.

So do you, but whoa.

Yeah.

It's a lot.

So, okay, so you are working in

magazines.

How did you get from dropping out of school and being a stoner?

I got myself back into college.

And honestly, because there were some

pretty good

incentives for a student in my position, for a non-tread student, like I walked into the financial aid office at Emerson College in Boston, which is where I was living.

And I was like, my husband and I just split.

He's not going to give me any money.

This is what our taxes look like.

He's literally let, you know, he's let me leave with a fork and a futon, which is the truth.

He was like, you can't have anything.

And

I'm a waitress.

And they were what, 23 years old?

I was 24.

And I walked into this office of all women in this financial aid office.

And they were like, okay, honey.

Like, they really took care of me.

And they were like, there's a Pell Grant.

There's this.

There's that, you know?

And I still had to work, I still had to take out student loans, and I still worked full-time as a waitress.

My same experience, yeah, full-time as a waitress, like worked every night as a waitress, had two internships, and was also going to school full-time.

And I was just on, like, it was, I was just out of my mind.

But I did it, and then I got to New York.

That was a whole nother story.

And I had to get interviewed by every

snotty female

elite

generational wealth

white editor

who literally one of them said to me, We expected to get all people like you coming in for this job, but instead we're seeing all these Harvard grads.

And I was like, That is fucked up.

So there was definitely a massive culture shock for me coming from being blue collar Italian in a very aggressive city of Philadelphia to moving to New York into these super white worlds of New York media.

It was,

I was really out of my depth.

I didn't understand that the world was not a meritocracy until I got into this situation.

I was like, oh, wait, this person does no work, but her dad is important.

You know, it was a lot of that.

But I wanted it.

I wanted it.

There was, there was like a, I had a fire in me.

It was, I had such an I'll show you.

Yeah, you had an axe to grind.

I did.

And do you remember exactly where that came from?

Or approximately?

I think failing young, I think getting in that marriage.

I think even I was married for three years from 21 to 24.

And

he didn't really want me to go back to school.

He really wanted me to have baby.

Like just that that like short jail time of that, you know, that sort of heteronormative like confinement of that

made me like, I have to live.

Like I have to get out there.

I need to make something of my life.

Also,

having no skills, no marketable skills, no money, and feeling like I couldn't leave because I had nothing,

I knew I would never put myself in that position again.

Now, going back to what we were just talking about, I chose poorly if I was looking for financial stability.

Well, I was going going to say, I mean, yeah, becoming a writer or an editor seems like a wild choice to make when you could have

become a phlebotomist.

I know, but it was what I wanted to do.

And I knew I was good at it.

And that's always fucked up.

Like it's fucked up to say that when you're young, especially as a, as a woman, it's like, I knew I was a good writer.

Like I knew it really early on.

And it felt really high flutant to me.

It felt really

like I had no understanding of what a path to that would look like.

And coming from what I came from, there were no models of that kind of a life.

But I was like, yes, this is, I'm just going to do it because also I had nothing to lose.

I had like $200 in the bank.

Like and I was 24 years old.

Like what was I, what was it, what was going to happen to me?

So I got to New York in my late 20s.

Magazines were starting to go, but I didn't know that yet.

So I got laid off.

It took me so long to get a first job.

And then I got laid off from the first three jobs I had in quick succession.

Like

one magazine went under.

The next magazine I got to went under.

The next magazine I went to went under.

Then I went to Time Out New York.

It was like the best job I ever had, but they paid $35,000 a year.

And it was an amazing job.

But like in order to have that job, which was a full-time job and pay my rent, which was only $900 a month, but that was two weeks' pay.

You needed a husband.

I needed a husband, or I had to write quizzes for kitchen and bath magazines on the side.

So I was always working.

I was never not working.

I was like, I was reporting stories.

Target had a magazine for a minute, an in-house magazine.

So I was like reporting stories for Target.

Like

I was just never not working.

And years later,

I would be on panels with, you know, girl bosses after I became like a lady who people wanted to hear things from.

And the girl boss ladies were almost uniformly people who came from wealth or had wealthy husbands.

And we would be sitting on the stage in front of all these young women.

And these young women would be like, how do you make this work?

Who maybe didn't come from generational wealth or had wealthy husbands.

And the rich women on the stage would say, well, just get a side hustle.

Just, Just, well, you know, I mean, and they would all talk about their first apartment in New York as if it was the worst suffering because their first apartment was a studio with like a bathtub in the kitchen.

Ha, ha, ha, chopping.

By themselves.

By themselves.

Exactly.

I lived with four roommates.

One was a clown, you know?

A literal clown.

A literal clown.

Oh, that's funny.

He used to hide things in my bed because he thought it was funny.

It is kind of.

Not really.

But I would watch them and I would be like, you're just, you're just telling people to burn out.

But also as if they don't already have three side hustles.

They're trying to become like a journalist.

They're trying to become you.

Yeah.

You rich lady who had the book that you're promoting ghostwritten by somebody else for $70,000 and you have four nannies and everything else.

They're trying to become you and you're not telling them the truth about what it is to become you.

Right.

You're saying stop buying your Starbucks in the morning.

You're saying yes.

Or, you know, just, you know, do something something on the side.

Like, that'll be fine.

Then you can, you cobble it together.

That's not what you do, bitch.

Your husband's in finance.

You don't pay your credit card.

Exactly.

You're telling these women how to have a balanced life.

How to have a balanced life is have money.

But these parents pay, you know, and they pay for the apartment and they pay, you know, it's a very different.

Well, no, and then you start to realize, I mean, New York Magazine just did that story about how many people.

So

like, I forget the percentage, but how many people who own apartments in New York, their parents gave them a down payment.

It's a very high percentage.

It was like, it was like over 60, 70%.

LA too.

Yeah.

I mean, because how else?

I don't know.

You don't save that kind of money by cutting back avocados.

Like, that's not.

Right.

Right.

Like, I don't know math that well, but I know it well enough to know that.

Anyway, for the first couple of years when I was in New York, I made less at my job than I had made as a a waitress.

And I made about $60,000 a year in fine dining waitressing because that was really a meritocracy.

That was really, this is how much you put in.

This is, you can upsell.

You treat the customer well.

You're going to like, you understand what to do.

Plus, it was a cash business.

So, you know,

I've never really gotten over.

starting out my career as a waitress for the first 10 years.

I've never really gotten over the economics of that.

Like, oh, I'm short on rent.

I'll pick up three more shifts.

Or I'll just be more charming and faster.

And faster and make sure the order's right.

And I'll never bring a plate to a table that isn't exactly right.

And as soon as I hear it's wrong, I'll fix it.

You know, like those sorts of things.

Exactly.

And I'll be checking in and I'll have all my timing correct.

And I'll tip the bus boy really well so that he really serves my section better than other sections.

And I'm always nice to the chef because I don't ever want him to fuck me over.

And if something goes wrong, I am going to need him.

That is an ecosystem that makes so much sense to me.

And everything since then has made no sense to me.

Publishing?

What?

What is it?

What are they doing?

So, what was the impetus for your first book?

My first book,

I was working at

Hello Giggles, I'll just say it.

I was working at Hello Giggles, which was a Zoe Deschanel startup.

It was a happy place on the internet.

It was geared toward, at that point, they were young millennial women in their 20s.

And I had a lot of young female employees.

Nobody was older than 25.

And they didn't know how to do anything.

They didn't know how to write an email.

The thing is, it wasn't their fault that they didn't know how to do anything.

What I realized when I was working with them is that mentorship steps had been cut out.

Like it used to be you were an assistant for a really long time or an intern for a really long time and you kind of learned the basics.

You know, part of your boss's job was teaching you those.

Exactly.

And it was like swim lessons almost, you know, you didn't get thrown in the deep end the first day.

And so what I was realizing is that these these young people were only as good as they were out of the gate because they were not being taught skills slowly.

And those jobs suck, those grunt work jobs where you're also getting coffee, but you're also learning.

Even if you're answering phones or, you know, taking messages or whatever you're doing, you're learning.

You're seeing business etiquette.

You're getting the basics.

You're watching how somebody who's been doing it for 20 years is doing it, right?

They didn't have any of that.

My classic example of this was how just

out of their depth, one of my employees who I liked a lot and I knew she liked me a lot, she had got, she was getting poached from another company on LinkedIn.

She brought her laptop into my office, showed me the message and said, what should I do about this?

And I was like, okay,

this person is trying to hire you to go work another job.

You now have a decision to make.

And you're showing your boss.

So I really took it very seriously.

You call your mom.

You could say you call your mom.

You call a friend.

Something.

Because also they all called their moms too much.

Something.

You have a professional network.

You discuss this.

Or you use this as leverage with me and say, hey, I'm getting poached.

I want to make more money.

So those kinds of maneuvers,

I wanted to teach people how to do that.

Especially people who felt like this feels weird to be in an office like the weird like office birthday where we're all eating cupcakes together and like you know

standing around like I never knew how to do that I didn't know what to do with my hands you know what I mean like I had to be told to stop tying my sweatshirt around my waist during like greeting guests at this American life in the lobby like you know stop looking like a child skateboarder that doesn't actually have a job.

Yes.

Yes.

Brush your hair.

Yes.

Those sorts of things, you know?

And I feel a little bit bad about those things.

And I also think that book is incredibly dated now because I think the pandemic changed work completely.

Like if I had to go back and rework that, it would be totally different because it also.

So that book was advice.

It was advice.

It was advice.

It was, it was what to do if you want to leave your job, how to look for another job, what your resume should look like, what your cover, like a cut, like all just the foundational things, but not in a lean in way.

Because I recognized even back then that what she was selling and what, you know, girl boss was selling was trash.

I knew it.

And I wanted to teach girls like us, who maybe didn't come from a lot, who weren't polished, who didn't have a pedigree, how to move through the world of work.

And, you know, I think that, you know, I think I said in there, and I probably wouldn't say this again, but I said, wear a bra.

And I might not say it again, but I did say wear a bra because people were not wearing bras.

So actually, I think it was like problematic.

But to me, I was like, I want you to set yourself up the best in this system, right?

But you have to wear, I do want to pause on this for a second.

I mean, I really did have those conversations, but I did have a colleague who's very wealthy and didn't wear a bra.

And,

you know, when you don't wear a bra and your buttons go like like this, so you can see the button down.

Yes, Jane's doing like you know, the

spread on the button down, right?

If you're bra, if you don't have a bra on, it just kind of like there's gaps, and then

especially if you have side boobs like I do, yes, yes, there's gaps, and then everyone can see that you don't have a bra on because they can see your skin.

Yes, yes.

Um,

but those folks didn't have to wear a bra

because

daddy had their rent or whatever, you know, like,

it really wasn't an issue.

It wasn't survival.

No.

And so those survival tips, I think in your first book, I found them to be very,

very

useful for folks that didn't,

that didn't grow up with a huge safety net and couldn't take the risks of getting fired because they don't wear a bra.

Right.

Right.

And just wouldn't have thought about it because they didn't, they didn't have a father or a mother, a parent who got dressed every day and went to work in an office and could advise them.

I also wanted to teach people how to negotiate.

Every single time, up until about,

I'm 52, up until about 10 years ago, every single time I got an offer.

like a salary offer.

You say, yes.

I said, yes.

Oh my God, thank you so much.

I can't believe you're hiring me.

Wow, that's more money than I ever imagined.

I've since learned that they expect you to negotiate.

They go low.

They go low.

That is just something, that is just a class difference when you are working class versus when you are a white collar.

You have just no idea.

My first real raise,

I had a cost of living raise when I moved from Chicago to New York, but then I got a raise after that

that I could not believe

was possible.

Yes, yes, yes.

I felt like the luckiest girl.

I felt like, wow, I must be amazing.

I made, I made one, the first time I ever made real money.

And the thing, what really was fucked up is because I made all of those mistakes.

And again, this is wealth building, right?

If I was making more money all those years that I didn't know this, I would have more money.

Like it's crazy.

You know, I would have a lot more money.

I was making.

I think $70,000 as a Condé Nast editor.

Yeah.

This is what I made when I moved to New York.

That was more money than I could ever conceive of.

People in my same position were making $120,000.

Yep.

I saw it on the printer one day.

I saw it on the printer one day.

Someone a few years older than me, a little less experienced, et cetera.

I saw a paper come out on the printer and I went, hang on, what?

Like $130,000, and I was making $70,000.

And it was a real

kind of moment.

Yes.

But I also found out I was the only person on staff who was doing the 100%

maximum pension matching.

Wow.

No one out.

We had like a, if you went up to 10% of your income, they would match five.

So it was like a that was smart.

Well, that's the only way I could get a raise, I thought.

Right.

It looked like a raise to me.

Like it looks like that's how I'm going to make the extra money.

Not going to ask for it, but I'm going to do the matching, the employee matching thing.

And so I maxed that all the way out

rather than, or I probably would have done it no matter what.

Yeah, yeah, yeah.

But rather than say, hey, how does 80 sound?

Because

I live alone in New York.

And, you know, we work in Manhattan and blah, blah, blah, blah, blah.

And I work way too many hours and I'm here all night and I have to order three meals at work.

And

all the stuff, all the reasons.

I didn't dare.

I was also so scared

that I was replaceable.

Exactly.

Oh my God, I'm too expensive.

Yeah.

No, but that's the thing.

That is where the ignorance just damns you, right?

Yeah.

And I had family who were like, we had a safe.

We had a cash business.

That's where my parents put their money in a safe.

Like my parents were afraid of the market.

They like discouraged me from a 401k, you know, like you lose money that way.

Yeah.

So I had no concept.

So then when I got to Yahoo, they offered me $100,000.

Right.

And I was like, six figures?

Which these days, I know we're laughing.

It still makes me nervous that we're laughing about it.

It makes me feel like

a snob.

I know horrible.

Like $100,000, but we lived in cities.

We lived in massive cities.

And still, like, but the reason why that's so $100,000 is a lot of money.

But the thing was, is that two years later, I was in that job.

I had been promoted with no raise and I was working harder than anyone.

My section was doing better than like many of my male counterparts.

And then I found out they were making $250,000.

And like, I tried to at that point get an adjustment, but they're never going to bring you up that high.

So think about that.

That was, I was in that job for six years.

I lost.

$600,000 because I was an idiot.

And like, or I was ignorant.

Let's not say I was an idiot and I was a woman and maybe they wouldn't have given it to me, but the men were making over two for the same job, but doing worse.

And doing worse.

I found out also after, like, when I worked at Gawker, when I was at Jezebel, I was not in the New York office.

I was remote.

And I found out after

the whole thing fell apart for reasons that were out of my control.

Yes.

That I was on the leaderboard every single day, all day long in the office, and my articles were charting higher than most every day.

And I got paid.

I don't even want to say, tell me, tell me.

56.

Stop it.

Stop it.

I'm not joking.

As if it was a part-time job.

But I didn't, I wasn't able to see the evidence that I was doing a good job.

I had no idea what to compare it to.

That this was a new subsection of the website that had never been tried before.

But no one was alerting me to the fact that I was doing a good job.

Right.

And I was just, I was recently divorced.

I needed the money so badly.

That's right.

That's right.

And I feel like women are also often in that position where it's like,

we just, I need, I'll just take it.

We play small.

Yeah.

We play small.

Yeah.

I still do it.

I know.

I still play small.

I just, I, it's, it's part of who I am.

I can't really fathom it.

And also, you have a poor kid brain.

I do have a poor kid brain.

But also, I've been adjacent to real power and real wealth.

And

I butted up against real power and real wealth and been in rooms and been, you know, not quite a peer, but, you know, there.

Like I have a seat at the table.

And I don't like it.

You're not like them.

I'm not like them.

Well, let's get there in just a second.

Yeah.

Okay.

So your first book was basically a how-to guide for people who don't come from from the world of business or folks who think they don't belong.

Yeah, people who floundered around, who felt anxious, who just felt like they didn't belong, who like, you know, never don't have like a stain on their pants, you know, and are watching all these like perfectly polished people come in who just seem to know what to do.

So that's what that was.

And I loved writing that book.

And Hello Giggles had been sold.

So I had actually made, for the first time in my life, I had made some money.

During the sale?

During the the sale, because I had some equity, because I was smart enough to negotiate some equity in that, even though I really didn't understand what it meant.

You're like, I've just heard that this thing can happen.

It's a startup.

Exactly.

So it actually worked out.

I had some money.

And I got a pretty good book advance.

And I took the year off to write a book.

And I loved it.

And just as I wrapped up that book, I was going through edits.

I got offered a big job.

And I got offered a job that everybody can Google if they want to look at it, but it was a big job.

I was a chief content officer, and they came to me.

And it was one of those things where, and this is one of the most important lessons I've learned in the past six years.

It was one of those jobs that looked good to the outside world.

Everybody told me I'd be crazy not to take, and just seemed like it was just, I should do it.

I should do it.

I had a pit in my stomach from word go, like from the interview, the first drive into the office, I cried the whole way.

I just had the worst feeling about it.

And let's just say it was not a good experience for me.

But part of why it wasn't a good experience was because I didn't want to do it.

I was done.

I didn't want to be facilitating somebody else's dream anymore.

I didn't want to

have somebody profiting off my creative labor.

But more than that, I was only interested in making things that were really good, like really good.

Like I wanted, I wanted every piece that we put up on that website to be

able to be held up anywhere.

I had been in the, you know, clickbait game for so long.

Let's pump out 50 stories a day.

Let's pay these writers $40 for a piece.

I was so over that.

And I also had felt complicit in that, which felt like such an abuse of labor.

I was like, we're going to pay people really well.

We're going to do slow content.

Slow content doesn't make money.

The thing you work on

for three months that is a beautiful story,

it's very rare.

that that does better than, you know,

10 couples you forgot were together.

Right.

Or ways to be grateful today.

You know, I remember iVillage when I was at Yahoo Shine, iVillage.

Remember iVillage?

Yes.

Okay.

So iVillage and Yahoo Shine were in constant competition in CommScore.

Yahoo Shine, which I ran at Yahoo, was the number one women's site in the world, or it was iVillage every other month.

And we just needed that spot because

we needed it as a calling card for advertisers, whatever.

So finally, I went out with the guy from the managing editor at iVillage.

It was in New York.

So I'm sitting there and I'm like, what are you doing different?

How are you making all of this traffic?

I don't understand.

We're doing the same things.

And he said, oh, it's the mullet approach.

Everything in the front.

is all happy homemaker tips and like ways to dress for your body and like how to negotiate a raise.

And the back is all filthy sex.

Okay.

Right?

Like

the kinkiest,

lovely, who cares?

But just the search words that, like, only we are doing.

So he was gaming the system in the back, but had this front-facing thing and had figured out a way to like hide it, but only in the traffic.

The front page.

The front page of the web, the website looked like one thing, but where they were getting all the traffic was from

really specific

gag on a dick.

Exactly, exactly, exactly.

And I'm only saying that because I read an article in Glamour magazine when I was 10 years old that taught me how, oh, yeah, they always taught us how not to gag on a dick.

That was like, you know, you're like 15, something you have to know right now.

Don't gag on a dick.

Or they were also doing like the trashiest like celebrities with cellulite, like the worst shit, the like the darkest, the darkest, you know, like, this person's wife gained weight, like horrors.

Okay.

But in the front, it looked,

it looked like a mommy blog.

Like it was just like a clean, like, you know, whatever.

So the bottom line is, is that since all content is now for profit, you don't get to make good things.

And I was getting pressed to

do a thing that I could not do, which was,

you know, an O magazine.

And I just was, I was done with that.

That was just not where I was at anymore.

And I.

I used to be able to force myself to do things I didn't want to do.

And as I got older, and maybe it was Perry Menopause's brain, I don't know, I couldn't force myself anymore.

And I wound up getting fired from that job.

And after that, I was just in free fall because my identity was so caught up in my career.

And you didn't have an outlet.

Yeah.

So then your next book comes out of that.

My next book came out of that.

My next book came out of, okay,

I don't feel the thing that I've loved to do my entire life, my entire adult and tween life since tweenhood,

I don't want to do anymore.

I have bottomed out of, it was like a serotonin, like just bottoming.

I had no ambition at all.

I didn't want to do anything.

I was very Lloyd Dobbler.

I didn't want to make anything.

I didn't want to sell anything.

I didn't want to do anything.

And I started

sorting out what my relationship with work was.

And I realized that my relationship with work was very caught up in, and I hate to say this, but childhood trauma.

And I started to track the relationship between

growing up kind of rough and tumble,

never feeling like I was good enough, always feeling afraid of myself in some ways, like I was like a monster, and

work

and achievement and success filling all of those holes.

Just like how much I was validation seeking through work.

I wasn't seeking money.

I was seeking somebody to say, yeah, you did a great job.

So I went above and beyond all the time, all the time.

I just needed it so much.

It was, it was, it was akin to an addiction.

And addictions are cumulative, right?

It's an amazing thing to have, like, to just start to understand yourself, right?

And then you're left with, well, what happens now?

And the book was really hard to write in a lot of ways.

Um, because it was really emotional and, like, how much do you write about your family, your family, the you know, people who are still alive?

How can you be fair?

How do you not make yourself such a villain that like people don't

the people are not interested in reading it because it's like annoying to read, but also take accountability?

Because I really felt complicit in the systems that I upheld throughout my career.

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One thing I thought reading it, it

reminded me, and I've talked to Dan about this a number of times, that

I have always felt most loved and rewarded by my performance.

Yes.

Not unconditionally loved.

Certainly not for my sweetness or being

a good friend or a, you know,

it was my, and my parents, forgive me for saying this, but I really did get the biggest hugs and the most verbal praise or for performing.

Yes.

Performing with grades, performing on stage, performing, performing for, you know,

and at work, you know,

being the person that gets the biggest tips that night, like, yes, just spinning plates, spinning plates, being indispensable, being indispensable and performing, and

not being rewarded.

You know,

I would see colleagues of mine who are much more successful and wealthier being rewarded for being

quirky or

a certain background or what, you know,

and I never felt like I could keep up.

I still don't.

I feel like, especially in podcasting, like I watch people be rewarded who

are frankly criminals, like literally.

Scammers, people who float by.

People who fail up constantly.

Fail up.

Failing up looks amazing, doesn't it?

I can't imagine it.

Like I couldn't.

I couldn't stomach it.

I couldn't stomach it.

But it happens for some folks.

And I don't know if it's the system doing it or if it's them doing it i don't really know but that's just not the way my brain was formed like my my personality was formed my personality was formed with jane sing that song why don't you recite all of robert lewis stevenson's poems for this party we're having right now but only do it in the corner so that the right people come over and listen you know also when you have parents who are that young you're an accessory

like i remember like my mom and her girlfriends being high because they're in their early 20s and like asking me to like do it, put on a show for them and like put on, like, and there's pictures of me.

And when I look at them, I feel so sad and so tender for that person who was like, needs were just not being thought of.

I just wanted to sit on your lap.

Yeah, I just wanted you to stroke my hair.

Exactly.

And just say, oh my God, I'm going to start crying.

I know.

I just wanted you to look at me and see me.

And I didn't have to learn the dinner you were making.

I just, I'll sit there.

And you said,

I always had to be useful.

And I felt so

desperately unseen.

And how do you work that out?

Right.

So you work that out with drugs and men.

Yeah, that's it.

Oh, the fucking, yes.

And you're bigger, you know, you're bigger than everyone else.

And you're, you know, jazz hands all over the world.

I was fucking jazz handing my whole life.

And now,

like,

you know,

it's like the thing of the invisibility of middle age.

I'm like, hooray,

because I'm tired.

I don't want to be looked at.

And I don't want to be on this.

I don't want to be looking for your approval all the time and you being anyone.

I'm tired of it.

It was, it was, it was exhausting.

I still love work,

but I'm less willing to do anything for it.

And I feel like that's waking up.

I also feel like

I just should have gotten into sex work or something.

No, I mean, if I was going to put that much effort in,

you're right.

I could have charged so much more.

You know,

if I was performing, I could have performed for one person who wouldn't tell anyone.

Yeah.

I don't know.

Yeah, no, no, I hear that.

I hear that.

And that's, no, I think that's interesting.

I think that's interesting where you're going with that.

Now, I don't know what that would have brought for you.

My relationship with sex is so fraught and caught up in the Catholicism and shame.

And I don't know if I could have survived sex work.

I certainly thought about it in my brokest hours.

I thought about, you know, certainly phone sex.

I can't believe I never did that, but I thought about it.

I thought about selling eggs.

I mean, you really start to get this poor brain, right?

And you're trying to survive in white-collar worlds where they have, they have nothing like this right and you're just like i have literally 11 for the week after i pay these bills like what am i supposed to do right

i saw women who had confidence that i didn't have who could move through rooms so they made different decisions like

They also maybe had financial backing, but they went to like Time magazine when I went to Glamour.

And Time paid nothing, but Glamour paid a lot.

But I didn't want to write about stupid, you know, couple time.

Like, I didn't want to write about, I didn't really want to write about serious positions for

bend over and do the dishes.

I didn't want to be fact-checking stories on quefing.

Like, I really didn't.

It's a story I bring up all the time.

I think I've brought it up to you before, but I still think about it.

But I didn't know how to be a serious lady.

Like, I always think about this.

Rebecca Traister and I started about the same time.

And Rebecca Traister had just confidence and she just knew what to do.

Tell us who that is, just for the audience.

Oh, Rebecca Traister is a major feminist writer and she's really smart and she's actually a really lovely person to know and she's super down to earth and she also came from Philly but she came from teachers in Philly and I came from blue cut.

Like I think that's also different.

You know, I had just, I

didn't have a foundational education really because school was not important.

Like my parents were like, drop out in ninth grade, become a hairdresser.

You know what I mean?

It just wasn't.

I was this close.

So was I.

If I had any sort sort of fine motor skills, I might have done it.

Yeah.

I mean, it was

very much like do something with utility and get your bills paid.

But I have friends who, you know, came right out of high school with some, this confidence that like they were going to get a job.

No, I was kind of broken.

I was kind of, I was a broken doll.

I was a broken doll and I tried to fuck the pain away.

I tried to work the pain away.

I tried to drink the pain away.

I did all of the things.

But so I watched Rebecca.

She made so many smart career decisions early and she made decisions,

you know, to advance her creativity and advance her thinking as a writer.

It was a very smart, she was a smart girl.

I mean, look, I spent 10 years at this American Life and up until the very last day, my boss would call me intern from the other room, you know?

It was cute

but nobody else was being called that and i made the least amount of money no and like and i'd been there longer than most people

at this point

i know you're never going to lose your ambition and desire to work yeah is it

Do you have a different goal in mind now?

I've separated art from money.

Okay.

That was step one in some ways.

So my real ambition is for

balance

and contentment.

So I have a day job that I am massively overqualified for, and it's exactly how I want it.

I make enough money that I don't need to worry about money.

I don't make a ton of money.

I make much less than I made at the height of my career, but I make enough

with health insurance and a 401k match.

Okay.

So benefits.

Like I'm a jobs person again.

I understand.

If I, if you can get a job, I'm like, get a job.

Like it's hard out here.

I was just hustling as a freelancer for six years and I

had two successful projects.

I had a successful podcast, you know, that was written up in the New Yorker, you know, was named one of the best podcasts of the year.

And I had a successful book.

And I was going further and further and further into debt

because the money is just, it's so hard to grab the stupid money.

It's like everything's getting replaced by AI.

Like all the stupid copywriting we used to be able to grab, it's like, it's gone.

So it's just really hard to survive.

So anyway, I have a day job that I do not go above and beyond in.

I do that job well, but that job, I don't have it on my phone.

I don't have Slack on my phone.

That is a boundaried job.

And then I think about,

and this is just like work goals, like I have relationship goals and travel goals and, you know, motherhood goals and all of those things.

But I go back creatively from my death to now and what do I still want to do before I die?

And most recently, I figured out I want to write a novel.

So I write, I wake up 5 a.m.

every morning and I'm working on a novel.

I don't know how people write fiction, but I'm excited to read whatever you do.

I don't either, but it's a puzzle.

And those are the things I've figured out that light up my brain are creative puzzles.

How can I take the bucket of skills I have

and use it in a new way?

Like that's exciting to me.

And especially I feel so scared.

And I love to be a little bit scared, you know, like, oh, God, wow, I'm really failing at this.

I don't know how to do this.

The mastery is also a thing that is very satisfying to me.

Like I'm horny for mastery, really.

And I think that as we get older, it's just so good to give yourself those challenges if you can, right?

Um,

what's the, what's the, uh, my friend Kristen Lasanti, who you know,

and I don't know if this is hers, but she told me about this, which is the, the key to um career satisfaction.

It's just gap, the gap rule, which is growth, autonomy, and purpose.

If you have those three things, you're going to be satisfied in your career.

I don't know if that works, but right now that's what I'm doing.

And

I can feel that the day job would promote me.

And I'm like, no, no, no, no, no.

Just let me stay in my lane.

Let me do a good job.

And let me have enough of my brain left that I can exist in my life.

I can have a social life.

I can show up for people and I can show up for my own creative projects.

Yeah.

That's that to me.

That's that's the win.

Yeah.

I want to say, I think for

as we're sitting here talking about this, I'm getting, I feel this bit of anxiety about how elitist this conversation sounds.

Yes.

And I just want to acknowledge that.

Yes.

That like even being able to say we have creative jobs feels

like I feel self-conscious.

No, of course.

This is an incredible privilege.

This is, this is such a privilege.

Even though we've never made money.

Even though I've never made the kind of money that like, you know, that we thought we were were going to make.

I've never, I've never owned a home.

I've never made, I've never made that kind of money.

I've never succeeded in the way that, but yes, it is privilege.

My car is 14 years old and I don't have one of my side remembers.

And I don't know if I'm going to ever get it.

Oh, I'm driving, I'm driving a beater Prius and I will forever, you know.

But like, what do you value, right?

Yeah.

Well, my other last question is: so we have children.

Yes.

Tell me, Jen, what's the right way to raise them around this stuff?

I,

like, do we, do you feel the pull to raise them to be part of the

ruling class or to be more like us

or something in between?

The problem with what you and I keep saying is, well, why didn't we do this?

Why didn't we do that?

I think that you're not going to live a happy life

if what you do is not aligned with who you are.

I just don't know.

I don't know.

I couldn't even figure out who that would be for me.

It's like, you know, it's not that I wouldn't have married a banker.

Like, they just never liked me.

Like, it was like, I never liked them and they never liked me.

I can't tell the difference between any of them.

I can't.

No, they all look the same.

And the vests, I can't.

I can't.

It's just, no, it's not right.

How do you raise a kid?

I mean,

I'm raising a kid very pragmatically with a lot of financial literacy.

I talk a lot about credit card debt and how you never want to get in it.

I just talk a lot about debt.

I talk about rules about money that I never understood, which is this is what you do with a paycheck.

After your basic expenses are paid, whatever you have left, this percentage goes into savings.

You know?

I drill those things down, maybe a little too much.

And maybe too much, because my kid who's 14 is already starting to talk about.

So, I just want to go to a normal college where I'm not going to take on too much debt.

And I want to live in, like, you know, an affordable city where I can have a two-bedroom apartment, you know, maybe it'll five rooms together.

And I'll have a roommate.

And, you know, for the first couple of years, like, if I do want to be in animation or if I do, you know, whatever they wind up, because I think they are creative.

I mean, their father is a writer.

I think that they're a creative person.

I don't know yet, but so I can work at a bookstore and like afford to live if I'm I'm working in a bookstore while I'm figuring things out.

These are the kinds of things this child says to me.

Like, how much is a sofa?

You know, like

I wasn't asking those questions and I wish I had been early on.

Like, what are taxes like?

Like, we talk about these conversations.

I go in the exact opposite direction with mine where I'm just like, fuck it.

It doesn't matter.

Do whatever you want.

Like, you're going to be screwed either way, kind of.

You are, but God, I wish.

You're not inheriting anything.

No.

That's for sure.

No.

And if you just want to hit the road, enjoi, you know, you're going to have to be a good babysitter or something.

I don't know.

Dog walking.

Which is maybe stupid.

I mean, no, it's not stupid.

I mean, I'm not trying to out there crushing any dreams.

But, you know, I didn't invest in a 401k in jobs that I had that I should have.

I now understand that if I had put $6,000, if I ever had $6,000, if I ever put $6,000 in a bank account when I was 20, 25,

I would have like a couple hundred thousand dollars now.

Oopsie days.

Yeah.

Yeah.

Yeah.

That I did try to do.

I think you were smarter with savings than I was.

I think I was pretty much a moron.

I had like, because my parents were just like,

anytime we had money, they were like, let's get a new TV.

You know, it was just, let's get a Cadillac.

Oh, don't even get me started.

Right.

My dad's like, let's get a blueberry farm and an airplane.

Thank you.

You're welcome.

For coming.

We can talk about marriage and kids next time.

Yes, yes, yes.

Yes, yes, definitely.

Because that's the real problem.

Let's be honest.

That is the real problem.

Okay.

Love you.

Love you so much.

Thanks for having me on.

You're welcome.

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