Previous: Ask Polly’s Heather Havrilesky On Self-Help, Tim Ferriss, & Getting Healthier With Money
Next: Our 10 Most Asked Money Questions, Answered



View count:25,400
Last sync:2024-05-29 21:00
This week, Chelsea sat down with Heather Havrilesky to talk all things money, work, work-life balance, and the realities of marriage. Heather is the voice behind the popular advice column "Ask Polly" and author of the books "What If This Were Enough" and "How To Be A Person In The World."

To get started using TurboTax and Intuit's suite of products, click here:

Subscribe to The Financial Confessions podcast here:

For our favorite moments from The Financial Confessions podcast, subscribe to our highlights channel here:

Heather Havrilesky on Twitter:
Heather Havrilesky's website:
Ask Polly the column:

The Financial Diet site:

Hello, everyone, and welcome to a new episode of The Financial Confessions, with a guest that I'm very excited to introduce because I have been excited about having her on the show for some time now.

And we've already gotten into a very interesting conversation right before we turned the cameras on. But before I introduce her and say hello to her, I'd love to say hello to our beloved partners with whom we make every episode of The Financial Confessions.

So as you guys know, we make every episode of The Financial Confessions in partnership with Intuit. And if you are not familiar with Intuit, I know that you're familiar with some of their awesome products. They make things like QuickBooks, TurboTax, Mint, Turbo, basically these amazing apps and programs that help you live your financial life better.

All of the things that can feel complicated or overwhelming, like doing your taxes or starting a budget-- they make the tools that help you do that in a way that's intuitive but also just generally not that overwhelming. For example, I used to be incredibly resistant to the idea of making a budget. And seven years ago, before I even started TFD, I downloaded Mint.

And they basically just like-- it made my budget for me, and put it into nice little pie charts, and asked me questions, and basically prompted me through the process in a way that allowed me to do it for the first time ever. And Mint is totally free, so why not give it a try? Anyway, that's just one of their amazing products.

And if you want to try all of the rest of their awesome products, check out the link in our description or the show notes. So as I mentioned, our guest today is someone that I've been excited to meet for some time, got to be honest. I've been reading her column for years and years.

Her name is Heather Havrilesky, a.k.a. Ask Polly. She's an author, a columnist.

Anything else? Human freak. Oh, I thought you were going to be like, wife, mama, tribe leader-- Oh, no.

No. --whatever people put on there. There are so many titles that I don't want to go down the list. I just get lost.

Angelino? I never have called myself an Angelino, actually. Do people even say that?

Not really. Not here. Got it, yeah.

I mean, actually, maybe. Maybe if you're born here, you call yourself that. Yeah, because people are very into calling themselves New Yorkers.

Oh yeah? Yeah. I would like to call myself a New Yorker.

It sounds chic. I know. It just sounds right, somehow.

Yeah, but Angelino. You go to New York sometimes? No, I haven't.

You've never been to New York? No, no. I've been in New York a million times.

OK, good. I would like to move there immediately. You would?

I really would. I've been trying to move there for, I don't know, 20 years. It's terrible.

Oh, my god. Wait. Well, do it.

I'm very stuck here. I'm married. Married, kids, house.

My husband's a professor. Oh, chic. Hey, hey.

What does he teach? He teaches science education at UCLA. Tell us about Ask Polly, for those who may not know.

Oh, OK. So let's see. Polly is an advice column for people who-- I would say it started out as like a-- I pitched it to The Awl very casually when I was in a lull.

I have had a strange, bizarre writing career that's had to shift gears many, many times. So at the beginning of my career, it was during the dot-com boom, and I was a cartoonist. Oh, how cool.

My father's a cartoonist. Who is? My father's an Illustrator.

He's a cartoonist, yeah. Oh, nice. [INAUDIBLE] I worked with an illustrator, but I wrote the-- Oh, you wrote the cartoons. --characters. Yeah, I didn't draw.

Got it. And that was for, which was one of the first online magazines, actually. Very cool.

And then I wrote for Salon for seven years. I was their TV critic. And then I wrote cultural essays and book reviews for a while.

And then, right around the time that I basically didn't have any kind of steady column, I pitched Ask Polly to The Awl, because I was like, what can I do that doesn't include having to read something, having to watch something on TV, where I'm just inventing everything from scratch? And so I was like, oh, people could write to me, and I'll be like tough love, mean, obnoxious. But what the hell qualifies you to give people advice?

Nothing. I have no qualifications whatsoever. Do you ever feel a sense of who the hell-- do you know what I'm saying?

Who am I to say? Yeah, yeah. I went through a phase, yes.

I mean, that's the overriding feeling of writing my column, for sure. I do select letters pretty carefully based on where I am and what I have a lot of good, intuitive movement around. But I would say that I've learned a lot from writing the column.

About yourself. Yeah, I mean, when I started out, I wrote a lot about dumping boyfriends. All I really knew was how to dump a boyfriend.

And then I got into how to feel your feelings more. And then it became how to stop beating yourself up over everything. It was almost like I had to monitor my own progress constantly in order to have content and to have advice to give.

And there's something about giving people advice that makes you very aware of what you have going on. You have to show up and be this strange, perverse non-expert and lay yourself bare. And I mean, there's a little bit of me in every column.

So yeah, I've evolved through writing the column. I like it when people are blind to themselves in ways that I can bust in and-- And be like, hey-- --be a little bit of a dick about it. --get it together. I mean, it's hard not to love that.

Satisfying. Yeah, but it's also-- I think that probably the best combination is when you can start out a little rough and then kind of-- making it sound a little sexual. Yeah, well, hey.

Oops. But it's like you-- I mean, I like to start with a blast of, hey, hey, wait. And then it's like you move into a place of, but I understand.

I mean, I never really pick a letter that I don't relate to at some level. Oh, yeah. That's interesting.

There's some level of desperation or need or longing. Recently, there was one about this woman who moved off grid with an emotionally unavailable man. Have you read that one?

No, but yikes. Oh, that's right. I want to talk about emotionally unavailable men.

Because you know what's funny? I was talking about my husband, and I was like, what I love about him most is that he feels intrinsically unknowable to me. He's a very self-contained, mysterious-- he's very cerebral, very withdrawn, but unconditionally available to me in the sense of I never for a second doubt that he's very present and loves me but is also a little obscure as a human being.

I never really feel like I understand what he's thinking. And I feel like that's the ideal combo to me. Yeah, well, I think that's a very straight-woman thing to want, right?

Well, I am a straight woman. I mean, I'm a straight woman too. And I think that understanding that difference, like, oh, I like that I don't know everything, I like-- Right, but to the emotionally unavailable point, that to me-- no patience.

A guy who I'm like, does he love me? Does he want me? Is he interested in other-- no, none of that, because I just feel like life's too short.

Oh, yeah, no. I mean, it's very difficult to exist in some kind of state of-- I think you just have to be-- I don't know. Should I say unhealthy?

How so? To be wavering in some kind of state of, how could I get more love? I'm not getting enough love.

I mean, I have lived there with different-- And you like that? --boyfriends. No, it's a bad-- No, it's a bad. It's just like something's wrong if you're living there, right?

It's not comfortable. But if you have experienced that-- It's sickness. --I feel like a lot of people don't know-- they don't trust the feeling of someone who is-- Loves them. --in love with them, yeah. Well, I think that the distinction you make is really important between having someone who can give you emotionally what you need but still has their own separate self.

I mean, I think it takes a strong person, actually, to accept someone who has boundaries, right? Right. I mean, to respect boundaries and to be interested in boundaries and to notice that you like boundaries is a very boundary person or at least just an independent person's way of-- Of approaching a relationship.

Yeah, and I don't think that I was there even when I got married. Interesting. And I'm a little bit more there now.

I'm more impressed with boundaries than I used to be. I'm writing a book about my marriage right now-- Nice. --which I might just throw it in the fire and give the money back. Don't do that.

I'm always a little tempted to do that, because I'm like, do I want the world to know everything? As a writer, having to write about falling in love with someone and how much they matter to you-- you get bored with-- it becomes a boring subject, where you're constantly trying to not-- I mean, this book is going to be really strange. I don't want it to be a sentimental book about what a great marriage I have.

I have a marriage. Who wants to read that? Yes, and also, having a marriage means being in some kind of tedious hell at some level, no matter what kind of marriage you have.

Just being around another human being all the time and raising kids with that person and being with them for 15 years is its own kind of hellish-- I'm more into capturing the hell than I am into capturing the-- I'm into capturing the acceptance and the boundaries and the digging through the shit to get to the good stuff. But I'm not as into capturing-- I mean, I've struggled to capture the falling in love. And I don't love writing about sex.

It's like it doesn't belong somehow to just go into-- ironically, right, because it's like, here's my marriage, but talking about your sex life in that seems insane. I just don't want to hear about anyone's sex life. I don't want to know about other people's, especially within-- Yeah, no thanks.

Yeah, no. One of my biggest things before I married my husband was I was like, it is very important to me that you have intimate, platonic male relationships. He says I love you to his closest friend.

They have little phone dates. I was like, you must have strong friendships, because I do not want to wake up one day and be your only emotional resource, which I feel is very common. But the other thing is I was like, you should have a best friend.

You should have a closest platonic relationship which is love and which is powerful to you and which is a different resource than your spouse. Because ultimately, at the end of the day, I feel like your relationship with your spouse is totally unique and shouldn't also be your best platonic relationship. I don't know.

I'm not an advice columnist. Well, I feel like my-- I hate to go into the generational thing. But I do think that my generation, Generation X, is a little less skilled at that.

Interesting. At maintaining really strong platonic relationships? Yeah, I mean, I think that we don't have a good culture around friendship, I don't think.

Interesting. I mean, just based on casual observation, I think that-- it would never have occurred to me to say something like that to my husband, but I should have said it a long time ago. Really?

Does he have very good friends? He has good friends, but they're just-- I mean, it's just like straight guy friends. No.

They need to cry sometimes. Oh, my god. I mean, he goes to our hairdresser and has the time of his life.

Because he gets to talk. Yes. I think that he needs-- this is great.

Sorry, Bill. I think he needs gay male friends. I think he needs female friends.

I mean, I'd like for him to have a kaleidoscope of friends the way I do. Because I have a ton of friends, and I'm constantly like, you're a friend, too. I'm at a stage where I'm a friend hoarder.

Yes, well, I feel like there's so many interesting studies that show how beneficial it is to women as they age that they have a lot of friends and that they have a lot of people with whom they feel truly connected. That's the last time I want you to say "as they age" to me. No, I'm literally, when I'm thinking of this-- As you get very old, Heather-- No, I mean, senior women have a lot of friends-- Yes, absolutely. --which becomes incredibly important as their husbands die younger.

I mean, it's a whole thing. But I do feel that feeling of-- especially when I read columns like yours, because it's probably-- I mean, I don't know the statistics, but it seems like mostly women who write in and mostly women who read. Mostly, yeah.

I don't know about read. I think they did some little sneaky thing where they figured out that it was a lot of men, more than they thought. The men don't blab about it that much.

Right, but they should. They should be writing in. They should be asking these questions.

My number one political platform-- all boomer men should be in therapy, every last one of them. Oh, god. How much better would the country be if every boomer man was in therapy?

Oh, my god. That's hard to even picture. What would they do in therapy?

Cry, express vulnerabilities. Weep? Crawl into a fetal position and just weep and suck on their thumbs?

I don't know. I mean, obviously so much of what you do is about examining the machinations behind behavior that can often otherwise feel on autopilot. And I feel like that just doesn't get done enough.

No, and also the intersection of the way that our culture teaches us to be, the way we metabolize our culture and believe that it's a part of our bodies and a part of ourselves, and we don't question it. Understanding even what culture is is sometimes hard for people, just how much of what they do is conscripted by and limited by culture. But then the intersection of those things-- right now, I'm in this phase of, how do you accommodate your truest desires in the context of a culture that is not really into desire?

We're in a moment, especially I think right now, that is very into self-denial and a moralistic space. So yeah, I mean, I think that there are all these ways that people just don't even feel comfortable exerting their will in the world. Especially women, I think, struggle with that, just taking up space and owning who they are and doing what they want to do, and also even just locating what you want.

And just to segue way to money as an issue, I think that, in some ways, money clouds all of these things and makes it-- it can be extremely difficult not to-- I mean, when I had less money, I really struggled with the idea of doing anything that involved money. And I drew a little, narrow-- it almost became an excuse to be a hermit, that everything that I could do when I left the house would cost money, so I shouldn't leave the house, essentially. I mean, there are just all these layers of guilt around serving yourself in our culture, I think, ironically, because the culture is all about, you need more of everything to be happy.

Well, you have an essay in your book that I wanted to talk about, because I feel like it so taps into what we talk about at TFD. It's an essay that looks at Mad Men and Fifty Shades of Gray as these dual explorations of people who are constantly yearning after more, usually in a consumer/class sense, and they represent opposite approaches that-- you make the point, which I think is a great point. Another writer I really like talked about that as well, Ashley Ford who was recently on the show, that the ultimate sexy thing in Fifty Shades of Gray is just that he's extremely fucking rich.

And that's the real point of lust. But you also explore how, in Mad Men, which is my all-time favorite show-- I've seen every episode, like, 15 times. The point is that all of Don's yearning for more and getting more leaves him feeling emptier and worse.

And yet, in Fifty Shades of Gray, the takeaway is that getting more is awesome and makes you feel great and makes your relationship better, even, to a large extent. Oh, walking into a really nice bathroom in a restaurant with good lighting practically gives you an orgasm in Fifty Shades of Gray. That's the takeaway.

Because she documents every little moment of luxurious service. "He stepped up and quietly poured the champagne and stepped back. 'Thank you, Mrs. Gray,'" or whatever the hell. Yeah, and I found that so interesting, because one of the things that we talk about a lot on TFD is the concept of lifestyle inflation and the concept of-- because you don't have to be a billionaire in order for you to get slightly better tastes of everything.

And then now the thing that you did yesterday that used to be fantastic-- you're like, ugh, could you even believe I ever did that? Do you find in your own life-- and you mentioned that you went from having less money to having substantially more of it-- that you have been able to combat lifestyle inflation? Yeah, but the way that I do it is through neglect.

How so? Just for example, I bought my house in-- well, my first house I bought in 2003. I had a little bit of inherited money from my dad who died young, when I was 25.

Sorry to hear that. Yeah, so I first bought Apple stock in '97. Whoa.

Just a little pat on the head. And then I sold it in 2003-- Oh, no. Boo-- and bought a crappy house instead.

Isn't the worst time to have sold it? Wasn't that during the jobs exodus? It wasn't down.

It was up. But it kept going up from there-- Oh, man. --a lot, a lot, a lot. And I remember talking to this-- I talked to some kind of investment person, friend, and I was like, I really just want to hold onto the Apple stock.

I was just planning on holding it for 10 years. I just feel like I believe in Apple. I just want to hold onto that.

Shouldn't I just hold into that? And he was like, whatever. You can just buy it back.

And I was like, you don't quite understand. Once it's gone, I'm not going to be able to buy it back. Who was this person who told you that?

A rich person. You can't get advice from-- Rich people. --people who have enough money that they're just like, yeah, I just buy the stock again, no problem. Oh, my god.

It's just a bet. Who cares? Sue that man for malpractice.

I didn't have an extra two dimes to rub together for the next decade. There was no buying back. Plus, it shot up immediately, of course.

But by the same token, you weigh that against the lifestyle of, like, I had my first house. I fixed it up. It was my full-time project.

I loved it. I was able to dump the boyfriend who lived in the house and kick him out. And I still owned the house.

Wow. It's emotional freedom to own your own property. Totally.

Totally. I had a dog, and that became my partner, sort of. Emotionally, not in all ways.

No, no, no. I know it sounded not quite right. No, just-- well, slept in my giant bed with me, like all dogs do-- They do do that. --if you're not married.

Unfortunately, then you get married, and your dogs get kicked onto the floor-- Not mine. --and your life is worse. Oh, really? My dog has a place of prominence.

And it's funny, because my husband's-- we've got to have a bell for any time I say this. My husband is 6'4". It is relevant to this anecdote.

You like to bring that in at all times? Listen. I would, too.

It's not even that I seek it out. But in this case it's relevant, because we share a queen bed, which is not that large for two people, especially if one is a gentle giant. And we have a small dog in the bed, but she's eight pounds.

So how do you-- let's get back to the neglect as a means of avoiding lifestyle inflation. So you just basically keep-- Oh. Oh, right. --a low level of life quality?

Well, OK, so I had this house that I fixed up by myself. I mean, I got it to where it was nice, and I was able to sell it. The market was down.

It was 2010. Timing has really not been your thing in this story arc. Well, I was buying another house, so it's fine.

Oh, OK, yeah, so that one was also depressed in value. Yeah, so the other house is worth twice as much now. And it was just barely affordable then.

And it was bigger. At the time, my stepson lived with us, and we had two little kids, and we had two giant dogs. And I had a 1,300 square foot, little, scrappy house.

So we moved to-- That's enormous. I live in New York. That's a mansion.

Well, yeah. OK, so yes. I mean, we had a big yard, actually.

It was nice. Whatever. It was great.

But we moved to a public school district that was good for the kids. And I don't know. It just sound so Karen-y, doesn't it?

What does Karen-y mean? Karen. Who's Karen?

Like, I'm a Karen. OK, Karen. Shut up, Karen.

But that's good. That sounds very-- Good? Karen's not good.

No, but you seem like a very-- your decisions seem sound. Oh, I have made solid, very practical decisions for most of my life. I would say from age 32 till maybe last year I was making incredibly just solid decisions.

And before that, chaos. Before that, drunken chaos. Nice.

And now I long for drunken chaos again. I'm moving back towards chaos a little bit. How old are the kids?

My youngest daughter's 10, my older daughter's 13, and my stepson is 23. All right, well, they're moving into independence, and you can reintroduce a little chaos into your life. Yes, exactly.

Do spontaneous, crazy things. Part of this is just making enough money that you actually feel like you can just do what you want to do a little bit, within limits. Speaking of you having a 13-year-old, drop the skincare routine.

Oh, well, can I just say the dumb thing about my stupid house, about saying dumber-- Oh, yes, yes, yes. I always forget to finish the point. I find myself down various tributaries.

I have a bathroom that is exactly the same as when I moved into my house. It is bright red. There's a volcano-y cut mirror that's got rough edges.

There's a black toilet in this bathroom. This is the main bathroom in my house, OK? And so when I walk into this terrible bathroom, I'm like, I know I'm not going-- I know I'm not wasting a lot of my money because I still haven't done anything to the shitty bathroom.

That's good. There are aspects of my environment that remind me that I'm not that Bourgeois, right/ And I feel like that's a grounding thing. That's good.

Some of my house is kind of nice, and then other things-- I don't really believe in having a hotel-like house, like, every inch of it is perfect. Yeah, I don't like that. Because that's lifestyle inflation, too.

Everyone feels like they have to have-- once they have some money, they have to make sure everything is perfectly designed. Recognizing that you care about how things look is important if you care. And I do care.

But also, balancing that out with-- things don't have to be perfect. I mean, my book is a little bit about that. Yeah, no, it is.

If you really rebel against, oh god, this space is so-- the lighting is bad in here, something's going wrong in your emotional state if you can't just exist in an imperfect place or look at a dirty window. Oh, have that, though. My home is my life.

I love my home. I'm very into home. And I hate my bedroom right now.

And we've only lived there for two and a half months. So it's like, who am I that it's already-- the rest of it's exactly what I want. But by my bedroom, every time I walk in there, drains my will to live.

My bedroom's shitty too. Yeah, but I just feel like, in that case, just pick a long weekend-- Pick a thing, yeah. --and just do it. But it has to be a concerted, dedicated time that you totally redo the room.

You can't half do it. You've got to get in there. Because living in any kind of transition is worse than living in a room that's bad, I feel.

Oh, a transitional, half bad, yeah. Yeah, that's like one wall's painted. Stuff isn't on the wall yet.

It's leaned up. But you know what's interesting about-- if you're going to save up for your house, I mean, I hate to say it, but you're also going to have to pay those taxes. It's tax time, baby.

It's that time. And nothing feels worse than entering into tax time feeling totally unprepared and overwhelmed. So I cannot recommend enough that you guys check out TurboTax so you can go into that tax time with a peace of mind.

TurboTax is basically software that walks you through the process of preparing your taxes in a really effortless and intuitive way. It prompts you on all the questions. It helps you make sure you're doing it correctly.

And it helps ensure at the end that you're getting the maximum possible refund that you're entitled to. Nothing can feel more scary at tax time than potentially not getting all the money you're entitled because you didn't know how to file your taxes properly. So don't leave it to chance.

Use a program that will help you walk through the process and feel confident that you've done your taxes right. I've used TurboTax many times in my life and can highly recommend it personally. Check TurboTax out at the link in our description or our show notes.

So I'm not letting you off the hook. Drop the skincare routine. Skincare routine?

You have good skin. Skin? Good skin?

Those of you listening on podcast, turn on YouTube so you can see the skin. OK, so first I'm going to go straight for like the mega-expensive old lady thing. Is that OK?

Please. Drive right into this insane thing. I'm looking for excuses to talk about this all the time.

And I'm sure someone will say, no, that's shitty for you, it'll kill you, or something. And I'll be like, oh, no. What's going on?

OK, so I have acne rosacea, and I have blepharitis. I have rosacea. You have rosacea too?

High five. OK, you might want to hear this part, then. I'm listening.

I had a cyst, a "chiz-ayl-eun--" a chalazion-- a "chiz-ayl-eun--" a chalazion on my eye, like a witch thing. A stye? I would get these little styes, and I ignored them.

And I wasn't washing my makeup off enough, which is not good. Not good. And so this one stye turned into this marble in my eyelid.

And they had to do this Clockwork Orange style thing where they opened my eyelid and clamped it open while I was totally awake. I mean, I assume numbed to some extent. I think I took some kind of-- I did take something to relax me, because that was horrendous, horrendous.

And they had to cut this thing out. Anyway, so in order to avoid that, the eye surgeon said, you need to get IPL. It's a laser thing where they laser your face, and it burns off-- it sounds terrible-- any red and any brown, OK?

And I actually just had it done a few days ago, so I have these big black patches right here-- Oh, well, I couldn't tell. --that are covered in makeup. I did this last year. I mean, it sounds like such a middle-aged lady thing.

But it actually got rid of my acne completely. What is it called? IPL.

IPL. How much does it cost? It's like $350 in LA. $350?

Yeah. OK. So you go in, and it feels like a rubber band snapping.

And all of the brown and the red stuff comes off. And you just think, who gives a shit about red and brown, right? But it totally evens out your complexion.

It kept me from getting any more of this red-eyelid horseshit, which was a nightmare. It got rid of my rosacea, pretty much. I mean, I do use a medicine for it.

It makes your skin porcelain-y, which I've never had. I mean, I break out. I don't really break out anymore.

It's insane. Shoutout to friend of TFD-- she'll be at our-- well, it will already have happened by this time. But Amanda Mull at the Atlantic wrote a fantastic article about the best skincare just being money.

It's messed up. It's so unfair. The thing is, you go to a dermatologist, and you say-- especially at a certain age, you're like, I don't know, my skin-- they're like, what are you dissatisfied with?

And you're like, I don't know. I don't trust you. I don't want you coming up on my face and injecting shit.

People do crazy, crazy things at my age. But this is like-- it makes your skin look younger. It somehow minimizes wrinkles.

I'm actually writing this down. Repeat the name for me one more time. It is all of the things in one.

I'm a little bit religious about it. It's called-- IPL. IPL.

Something something Laser. And I guess there are three different kinds. Nice.

Anyway, so I have to say that, because I don't want to just say, oh, I buy this one cream. Well, no, it feels a little bit deceptive. Any products you love, though?

Yes, I love Fresh Black Tea Corset Cream. Yeah, I have some in my bag. It's Fresh.

I don't know. What's Fresh? You can buy it at Sephora.

It seems pedestrian. Drag them. Well, it's just like, who cares?

I never really believed in creams. Yeah, I'm all about the creams. But when you break out, you think that creams are going to mess you up.

No, cream's good. See, I've had bad skin my whole life. It's been my thing my whole life.

But I have incredibly dry skin, like painfully dry skin. So creams have been my entire life's quest. Yeah, but you should honestly-- I love it.

If you had to live in my face with the tightness and the dryness and the flakiness-- I think I had that too, and I didn't realize it-- It's painful. --because I have oily skin, but I also have red, combination and red and-- Not a good combo. And also, in LA, you need a lot of cream. But let me just also say the mask, the overnight mask-- same thing-- My mom uses the Fresh overnight masks. --Black Tea Corset Cream overnight mask.

I like that one. It's kind of stretchy. It's like jelly.

It's like putting jam on your face. It is delightful, and I strongly recommend it. Interesting.

Yeah, I do it every day. I'm weirdly self-conscious about-- when I'm sleeping, I want to look decent. What?

Why? I have an irrational fear that I'm going to die in my sleep, and they're going to come get me, and I'm going to look-- You're going to look bad? --bad. I just recently stopped sleeping in giant, Archie Bunker-y-- you don't even know who Archie Bunker is.

Goddammit. Of course I know who Archie Bunker is. OK, good.

Like rags. Rags. And now I sleep in a lingerie type thing.

It's soft. Yeah, I like a good pajama, yeah. I'm so proud of myself.

Like a sexy-- it's soft but sexy. I mean, Ryan just saw me walking around in my-- I wear a Berenstain Bear-- I have a little striped pajama dress. That can be sexy.

Yeah, no. But I also have sexy stuff. No, I usually am wearing stuff that like-- I should be wearing one of those little caps and carrying a candle on a tray.

Anyway, god knows I shouldn't be found in that if I die. OK, so you have another essay in your book that I think our audience would love to talk about, because we are-- we're not in the exact same space as this gentleman, but he really overlaps with a lot of the personal finance, self-improvement universe. And that's Tim Ferriss.

And you wrote a chapter that's mostly focused on him and his books but is more broadly about the concept of gurus and life-hacking, and mastering your own life and body and self, and a lot of the-- maybe not necessarily the shortcomings of that approach, but the hollowness, in a lot of ways, of that approach. And first and foremost, tell us, especially for those who haven't read the book, what your take on what a guru is and how Tim Ferriss plays into that. Well, I mean, OK, so gurus-- I was struggling with the concept of gurus, because my last book before this was really about-- it was Ask Polly columns, right?

So it was really a book of advice. And so I was toying a lot with what my role in the world should be and how I could navigate as a person who represents-- I give advice, I'm a person who knows a few things, without either being totally disappointing physically and emotionally and everything when you show up at a reading, and there she is, and Jesus, why would I ever take advice from that type of person? Stop.

So that was part of it. But then when you get into that space of, well, what should I be? How should I seem if I'm going to bestow wisdom on people live?

Shouldn't I be prettier and more fashionable? And then when you get into those layers of, how do I game my body to be better, and also just when you're obsessed with self-improvement, which you tend to be when you're giving people advice all the time and you're trying to solve the problem of how to fix their lives, you start to understand the folds of where you could easily become just a mutant who is so fixated on optimizing every dimension of their reality that you almost become like a cyborg who can't just exist in a moment and be imperfect and accept the imperfection of other people also. I think that there's a space in our culture where people just feel like, Jesus, I'm really doing this.

I'm firing on all pistons. Oh, look, the secret doors are opening up. I'm meeting interesting, amazing people who have money and are fabulous, and they want to know me because they read my shit.

And it's easy to get into this glam-- I mean, it's not that glamorous, but into this space of, in order to be with these people, I'm going to need to be living my best life and being my-- and if you're a neurotic person, which I am, your brand turns against you because it's like, hold on. You give people advice? What the hell are you doing?

Why are you wearing that underwear? Yeah, everything is called into question. Everything's called into question, including, like, there's a dust bunny in the corner.

Why are there smudges on your windows? What's going on with you? Why are your roots gray right now?

What does that represent? I think that we're in a time in history where-- I mean, here I am, on camera, right? You hear my voice.

What if I had a weird voice? You can see me now. It's intense to be a writer who's also supposed to be a brand that represents-- I mean, everyone is in this-- I mean, you don't have to be a writer.

Our world is making brands out of all people. And in order to survive, especially as a writer, you need several income streams. You have to be managing your business and owning your brand and promoting and all these layers of things.

So in the process of looking through that, the main thing I think that I dedicated myself to was not selling other people on a way of life that-- I mean, avoiding selling people something that was basically just enabled by money or enabled by whiteness or enabled by-- Maleness. --yeah, I'm married to a professor, and I'm fine, and I live in the suburbs. Trying to understand-- not a, hey, it's so easy. You just work this amount, and then you go surf in Costa Rica.

It's fucking fun and great, man. Go with your friends, Steve Jobs and Mark Cuban. Cubes.

We've hacked life, man. We've figured it out. And then to also call your privilege-- hey, I'm the best life-hacker there is.

And also, there's the feminine version of that. I mean, not to dogpile Gwyneth, but Goop is-- Fucking dogpile her. You point out something.

First and foremost, Tim Ferriss's brand and his approach to life is just fundamentally not for me. I'm similar to you in that I like a life that feels imperfect and open to the messiness of reality. I like all that stuff.

And I don't like looking at myself through a prism of optimization, because I think that easily, for a lot of people, can spiral into a mania where it's never optimized enough. --and also dissatisfaction. And dissatisfaction with any natural imperfections. But I think what was most compelling to me about it was the point that, for so many of these gurus, Tim Ferriss only being one of them, there's such a lack of any kind of analysis that extends beyond the self, almost by necessity.

Because you can't really bring into question, what are your structural advantages and disadvantages, or what should you do if you have crippling medical debt or can't afford to feed your-- or any of these things, or having a harder time getting hired for the same job because of the body that you might be in, all of these things. There's nothing around it. It's all in a vacuum.

But then, a step further, it's not really going toward anything. There's no intrinsic motivation of, I want to-- because it would be understandable to say, I want to have 60 hours free a week because I want to work on this very specific problem that needs solving, and I need to dedicate all of my resources. And there are people who are that way, to give as much as they can of themselves to a specific thing.

But a perfect example for me-- so I've done intermittent fasting for almost four years now. And I initially lost 25, 30 pounds doing it, and then I've just maintained for the rest of it. But it's funny because I initially did it for a very specific reason, which continues to be the specific reason, which is that I need a certain amount of calories per day that's kind of low, and I really want to be able to eat a big dinner and have dessert and not really worry about it.

And that's basically the only way to do it, because otherwise I have to cut up my meals into three really shitty, low-calorie meals every day. So what do you do? You just don't eat for 12 hours a day or something?

So generally speaking, I won't eat until around 1:00 PM. I have a very small lunch, high protein but relatively low calorie. And then I just literally eat whatever I want for dinner and don't think about it.

But for me, that intermittent fasting is and always has been a very specific means to a very specific goal that is centered in my own enjoyment of life. And when I read about intermittent fasting-- god forbid I go on those fucking forums, because it is just nothing but people who are interested in doing it for some sort of bio-hacking self-optimization. But I'm like, are you even enjoying this?

Are you even getting anything out of it? And of course the reputation, because of these gurus, of intermittent fasting is a terrible one. But ultimately, I think it can get that way because you're not really doing it for anything.

There's no goal. I think the broader thing, though, is that ultimately-- and this is something that we talk about in the prism of money, is there are a lot of people who become obsessed with money as almost sort of a game or as an abstract concept. And it becomes about the number, and it becomes about what you're able to do with that number and the manipulations and the machinations.

But ultimately, at its core, money should either be a very direct means to living a life that you enjoy and that is healthy and good for you, and really, much beyond that-- I mean, listen, I believe it should be redistributed. But more, even if you're not going to say that, at the very least you should not be giving up more of your time and more of yourself to just accumulate more of it. Money should be about life, but so should any, quote unquote, "optimization of the self." Well, OK, I do understand the obsession with numbers.

I'm a numbers person, and I love numbers. So watching numbers grow is just, whee, especially if you're into investing. I mean, I'm not now, but I have in the past, at times, been just into watching the numbers and making charts and saying, if I save this much, how much will it grow by the time-- And that can be enjoyable.

And everything stays exactly the same. But I just want to say that's its own strange sport. But where it becomes corrupted to me is when you don't understand why-- you have so much excess, and you don't even know what the-- like you're saying, you don't even know what the goal is.

And it's corrupting in a sense of, I wouldn't want a single drop of this to be-- if I can choose between paying more taxes and paying less taxes, of course-- not having the principles in place where you're like, please, someone make me pay more taxes. I'm probably not paying enough. Or just not paying attention, like, look around you.

No one can afford to pay their gas bill, and look at how you're living. Why do you need this pile? And actually, we're in a space now where I think people are using, ironically somewhat, climate change and the apocalypse as an excuse to stockpile more money to ensure that their children are safe from the tides or whatever the fuck.

I just think that people are in this anxious state around-- it's like the college admissions scandal is one reflection of that culturally. And the corruption in that-- I mean, the reason that people are drooling to see these people go to jail-- Lori Loughlin, I think, is going to go at some point. And it's just such a delicious story.

Because, I mean, she's a human being. We all make mistakes. But it's just the embodiment of, my kid deserves this golden path-- And all that I have is not enough --even though I'm just some jackhole that wandered up to a giant pile of money.

I mean, whatever. I don't know her story. But I think that taps into something that really dovetails-- whether it's with money and the accumulation of it or with the perfection and optimization of your life, ultimately what it boils down to is an obsessive focus on the self.

And I personally believe that life is automatically better in almost every way-- and I think a lot of studies bear this out-- when your focus is on communities and your focus is on the group. And that can be many different groups. That can be the wellness of your family, of your friend group, of your colleagues, of your neighborhood, just a focus on, let's lift all boats.

Well, I just want to say-- I mean, I'm doing a devil's advocate thing-- I know. You're really going against the grain of your own book here. Yeah, I mean, I really am in a different space than I was when I wrote the book.

And I do think that we all have eras in our life that are different, right? And accepting the flow of that and making room for different kinds of perspectives within the context of your own life, I think, is really important. That book, when I was writing it-- I really needed to understand what enough was and where the limits of-- because I had been in this striving state, and I really needed to put a cap on it and look around and say, I have everything I've ever wanted.

But now, having gotten my kids to the point where they're pretty mature and having-- I'm looking back and seeing how I have always had this compulsion to stay small and stay hidden, actually. My core personality is a show-offy personality, but I have put a cap on that over and over again in my life. And so I think that after years of the sacrifice of raising kids, which, whatever.

It's a self-indulgent thing too. But just living inside the space of, it's all about community, it's all about what my kids need, it's all about what my husband needs, it's all about friends and how can I serve my friends-- I'm in this era now that's like, what do I want? What do I specifically, me alone, want?

And how do I keep these things together while I also honor whatever the fuck I feel like doing? It's hard to be endlessly generous if you can't honor your own weird ideas about what you need. And I do think that once you-- the more that I've done this, the more generous I feel towards other people and the more at peace I am with the world, in some ways, even as it falls apart before our eyes.

I feel like I have given more to charities since I've become more selfish personally, or not selfish but just since I've started to honor my conflicted desires that are not always just perfect and good and about community. You know what I mean? Yeah, I mean, so what's interesting-- so obviously you're a mother, which is societal role which is very much shunted into being entirely about your children and about sacrificing the self.

I totally get that. I have the opposite perspective in the sense that I'm not a mother, but I am a business owner with a decent amount of employees. And the societal view on that is the opposite.

It's all about valorizing the founder, the CEO, and making them the star of the show and making them the focus and the one who gets the credit and all that stuff. And so I think that it's natural to push against what you're pushed towards. And I also am just disgusted with founder and CEO culture.

I hate it. I think it's gross. So I think that it depends on the-- The mythology of that.

You don't the-- No, it's gross. I talk to founders and CEOs all the time. And some of them, I think, have a similar approach to myself.

We don't run as a co-op, but pretty damn close. And all the staff knows what I earn. They know how much money-- everything is very transparent.

And part of that is because we're about financial transparency, so it would be wrong for us to not exhibit that in our work culture. But it's also because it is so easy, without a strong level of accountability to your team, to just snowball into this mythos and to endlessly justify more for yourself. You don't get to a place where CEOs earn 200 times what their staff earns unless that is cultivated and reinforced.

So I do think that it's natural that, because you've been pushed toward a place where you're so expected to be so selfless and so giving, and you're not getting the credit that you probably deserve, that you would push against that. But I do ultimately feel that outside of, maybe, giving yourself too much to your children, which I think can often be a problem for mothers, in other situations I think the benefits of being as external as possible-- another, I think, good example would be your neighborhood. I don't know how it is in LA.

But in New York, no one gives a shit about their neighbors. You have two kinds of people, right? You have YIMBYs and NIMBYs, either people who want the high rise in their street and to have the whole thing completely gutted by luxury developers or people who want absolutely nothing to change and very-- if you've ever been to a community board meeting, it's hostile territory.

It's like the Kimmy Schmidt, the-- Never seen it. Oh. Well, but either way, it's just a bunch of people-- usually, not all the time-- but a lot of people who are just incredibly self interested and who are attempting to form some kind of cogent group.

And I feel like those types of things-- life, for example, in a physical-geographical community is usually at its best when you can really actively take the self out of it for a little bit. And I feel like we live in a society-- we live in a society-- that really doesn't encourage that, I feel like, of Americans. To take the self out of things-- I mean, my angle on that is, when you are really at peace with your conflicted heart, you can take yourself out of things.

I spent most of my life giving too much but being a total show-off socially and always grabbing more attention for myself. And now that I give myself the kinds of attention that I feel that I need and grab it, in some ways, in social media and some ways on Instagram-- I have ways of grabbing it in my writing. I indulge myself a lot artistically, let's call it, to be charitable.

But I would say that since I started doing that, I listen to people in a totally much more focused way. I mean, I've always been a good listener. But I am so much more interested in people and more accepting of people and full of empathy for people, and I connect with people everywhere I go.

I trust people quickly. Because you have this felt connection to people when you have a really felt connection to yourself. And it sounds like you didn't really struggle with those kinds of connections before.

It was natural for you to serve your team. You know what I mean? You might just be a more connected person naturally-- That's possible. --so it's natural for you to serve.

And you have a lot of values, obviously, and principles. You're principle fixated. I'm very into principles.

I'm very into principles. And I don't mean financially. No, no, I'm very into principles.

And I do think it's funny, because that chapter of your book about the guru and about the self-improvement industrial complex so resonated with me because-- and I think the world that you inhabit professionally is not this world at all. But in the personal finance space, 99% of the thought leaders and people out there-- they're men. That's their shit.

They love the self-optimization thing, and they love the self. It's about the self. It's about your money, your choices, your responsibility, your bootstraps.

It's all about you. And I feel like I don't want to get to a place where it's just like I'm trashing that, because I'm not in the sense that I think that it can provide-- I have no doubts that Timothy Ferriss's books have profoundly helped maybe millions of people, and people can get lots out of it. But I do wonder, when we put this out in the culture, and when this is such a prominent narrative of just extreme self optimization as if you were a computer program with no real express goal of what that time is used to do, what does that teach?

You know what's messed up is it's almost like-- basic bitches get such a bad rap, right? But basic bros don't. Oh my god, but Timothy Ferriss is the ultimate basic bitch.

He is the most basic, basic bitch on the planet. For what a bro is. These people are shallow motherfuckers.

Yes, I hear what you're saying. If his interest, instead of being fine scotch and surfing with Steve Jobs or like-- I know Steve Jobs is dead. That's like his fucking dirty Martini blowout from the dry bar.

Exactly. It's like if it were rosé champagne and a blowout, you'd be like, oh, get it together, lady. Go work some charity.

Ugh, you're so shallow. So we have a quick few, just real quick rapid fires from our audience before we get into your rapid fires. So you don't have to be one word on these, but we want to keep them zippy.

A lot of people saying you changed their life. What would they like to know about how I changed their-- One person says, what money issue do you wish you hadn't spent so much energy stressing about in your 20s or 30s? Oh, I think I should have had a clothing budget, honestly.

You bought a lot of clothes? No, I don't buy clothes at all. I mean, you're wearing some, so-- [INTERPOSING VOICES] I feel like you-- I don't know.

I never really budgeted-- I feel like it always says, in budget books, budget in clothing. And I never allowed myself that luxury. I was always like, no.

Clothing is the last-- that's the last frontier. That's funny. But I was still going out to eat.

I see, but same. I was still blowing money on other things. I just like food a lot, and I don't care about clothing.

Yeah, that would be the last to go in my budget, is dining. I will say this. Buying one totally stupid overpriced thing per year-- just saying, that's going to be my one thing-- the day that I lost my job at the place went under-- I was out, and I was at Betsey Johnson buying a $300 dress.

I totally couldn't afford it. I think I bought two $300 dresses that day. Oh my gosh.

I was just like, fuck it. I didn't know that we were about-- and I got home, and the answering machine-- press play. It was like, you don't have a job anymore.

You're a writer who writes a cartoon, but you don't know how to draw. That's your skill. Your skill is to write cartoons without the skill of drawing.

But yeah, these boots, which I just honestly found in my closet-- That's the third time she's done that since she's been here, by the way. It's important for everyone to see them. Wait.

You've got to see the other one. Wow. It's important to see both of them, OK?

These are Fry boots. Love Fry. They're quite comfortable.

I bought them in New York. And I immediately walked around New York, like, I can't wear these in New York. You have to walk too far.

But these boots were expensive. And I just walked into Fry one day. It's New York.

I'm in New York. I'm going to buy myself something amazing. Buying one overpriced thing per year, even when you're poor, I think is a good thing to do.

It sounds indulgent. That sounds a little out of touch. Well, it depends on how you define overpriced.

But I think having one-- I don't know. $400 seems like too much. I mean, I will say that if you're-- the thing is that I'm going to be the wet blanket here and say that you should budget that into your yearly budget and just give yourself $100 or a couple hundred bucks and say that money, whenever the hell I want on whatever the hell I want, I can drop it. I don't like budgets, I have to say.

All right, well, get the hell out of here. The time has come for the famous-- Uh-oh. --Financial Confessions rapid-fire questions. Oh, god.

So rapid fire, but, you know. You can skip-- [INTERPOSING VOICES] I'm a slow person, if you haven't noticed. What do you invest in, versus what are you cheap about?

Oh, god. What do I invest in? Not Apple.

Do you mean literal investments? No, it can be anything. I invest in food that I eat.

Same. Does that count? I mean, yes.

As in inexpensive groceries, or as in going out to-- Yes, all food. All food. All food is a huge expense.

And what am I cheap about? I'm cheap about furniture, sadly. And I'm cheap about clothes.

I'm really cheap about clothes. Nice. A little less now, but I have a uniform.

That's cheap, to have a uniform. Well, it's a good uniform. What has been your best investment and why?

Best investment-- a husband with a PhD-- Nice. --and, oh, who's tenured, I should probably add-- He's tenured. --because the PhD is not the thing. What has been your biggest money mistake and why? Gotta be selling Apple in 2003, right?

I don't consider that a mistake because the quality of life that I gained by having a house was massive. All right. I mean, it was an important trade-off.

It's a lifestyle thing, right? Oh, when I bought that house, though, I had this year that I was like, this is my year of luxury. And I took money out on a HELOC.

What the hell is that? It's a home equity line. Oh, got it.

I took out cash on my house and bought a used Lexus with the cash from my house. Whoa. That was psychotic.

And the Lexus was a lemon. I mean, I loved driving that goddamn car. I miss it.

I drive a Honda CRV now. I'm like 20 years older. So sad, so sad.

Whatever. I never gave a shit about cars. But my dad, when he died, had a Lexus, and I drove it around town right after he died.

Lexuses are nice cars. And in LA, you're in your car a lot. I had an RX 300.

It was amazing. Driving that car was incredible. It was like floating on air.

It was $36,000 for a seven-year-old car. I mean, it was so excessive. What is your biggest current money insecurity?

College, paying for college. Still paying those loans? No, no, no, for my kids.

Oh. Saving for college. Oh, at least you don't have student loans.

No, no. I don't have any student loans. But my dad was a professor at Duke, and I went to Duke, and it was paid for.

Nice. All right, sounds like those kids are going to UCLA, where dad is. UCLA does not pay for-- it's a public college-- I'm sorry, public university.

No. If we moved to a private university-- They would pay for it. --that's different, yeah. What is the financial habit that has helped you the most?

Saving in an SEP-- is it SEP IRA, they call them? Self-employed. Saving in a self-employed IRA.

For every single year, I put the maximum in. That's awesome. And lastly, when did you first feel successful, and what does that word mean to you?

Success to me means choosing your work, like choosing the work that you love the most and being able to do it and live off of it, right? Choosing the work you want to do, which as a writer is rare, being able to say no to shit you don't want to do and say yes to the stuff you do want to do. And I would say that started two years ago.

Well, congratulations. Yeah, it's great. I love it.

Well, thank you so much for being here. It's been so fun. I want to stay.

It has been fun. This has been so enjoyable. I want to live here.

So where can people find more of you? OK, so I write Ask Polly. It's on The Cut, which is New York Magazine's fashion website.

It's amazing. And Ask Polly is there every week. I'm on Twitter @hhavrilesky.

So you just have to do a little search, because that's a long last name. And I also am on Instagram. I'm not so good at Instagram.

I'm figuring it out. And I have a newsletter called Ask Molly. Molly is Polly's evil twin.

Oh. And so Molly's into some dark shit. And Molly is a lot of fun.

Subscribed. So one of the things we talked a lot about with Heather today is the idea of buying a home and what that can mean financially. And one thing that you will definitely want to do if you are in the position of maybe wanting to buy a home in the near-ish future is to get a really good bird's eye view on all of your financial health.

And Turbo is a really cool, free app that allows you to get that perspective. It will teach you all different things about your credit score, your credit utilization ratio, your debt-to-income ratio, your net worth, give you all the key information you need for things like when you're seeking a loan or your credit worthiness, essentially a higher-level, more nuanced view of your overall financial health. Because your financial health isn't just about having a good budget.

It's also about making sure that you know all of the big numbers under which that budget falls. Because ultimately, what good is a budget if you're not reaching toward a bigger goal? So if you're thinking about that bigger goal and want to make sure that you have all of your ducks in a row going into something like, for example, potentially signing up for a mortgage, you should check out Turbo at the link in our description or our show notes. [MUSIC PLAYING]