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You heard about it here. Again, that's longangle.com. Hello and welcome to another episode of All The Hacks, a show about upgrading your life, money and travel all while spending less and saving more. I'm Chris Hutchins, and I'm thrilled to have you on my journey to optimize my life, and I couldn't be more excited for the conversation I'm about to have with Stephanie O'Connell-Rodriguez.

She's the author of The Broken Beautiful Life. She's the founder of Statement Event and Statement Cards and the host of the incredible podcast Money Confidential. She has a wealth of knowledge about finance, and her work has been featured in The New York Times, The Wall Street Journal, CNBC, and she's appeared as an expert on ABC World News, Bloomberg and so many more places.

In our conversation, we'll talk about some great hacks for expensive cities, whether you live there or just visiting. We'll talk about some of the ways we've tried to change things up around the holidays for gifting, both to save money and to get back to the true spirit of giving, and we'll dive into some fascinating things Stephanie's been learning about money from the first season of her podcast, where she's gone deep to solve some real money issues for her listeners.

All right, let's jump in. Stephanie, thanks for being here. Oh, man, it's been a long time coming. I know. So we met in 2018, and I've only really known you as a money person. This is kind of what you've been doing. But as I researched this podcast, I realized you did not grow up and start your professional career with the aspiration of being a financial expert.

So I would love to understand how you went from, you know, I'll let you tell the story, but to becoming this financial expert. Yeah, like you said, talking about money for a living was the farthest thing from my mind as a young teenager millennial with a lot of dreams in the nineties.

Right. So I went to college with the aspiration that I was going to be a Broadway performer, and it was so much of that narrative of like, you know, pursue your dreams, follow your passion, and everything's going to work itself out. You know, this naive notion that we all had growing up a little bit like American dream for the millennial generation, and then I actually did work in the arts for about five to seven years full time.

And when I say full time, you know, I made money performing, but I also, you know, waited tables. I was a personal assistant. I basically did anything I could do to make money in legitimate ways in between my jobs, because I would go out and I'd be on a tour for like a year.

And I was always interested in the money aspect of it, the money making aspect of it. And I would just squirrel away everything I earned and we would get per diem. And I'd be like, Ooh, this is not taxable income. Let me save as much of this as I can.

And then I would come home and be like, I can't bear to spend any of this money I just made. It took so much work. Let me go find all of these side hustles. And basically the reason I got into money was that cycle was completely unsustainable. It was exhausting.

I was tired of making very little. I was just feeling like I was never going to get ahead. One of the big turning points for me was having an accident with no, not an accident, an incident with my teeth. It's like, oh, you go to the dentist one day and then they're like, you need to have a dental implant.

That's going to cost two thousand dollars. And I just sobbed. I sobbed in the dentist chair in front of the dentist like a lunatic because I couldn't fathom where that money was going to come from. And I was like, this is the worst feeling. I am totally at the mercy of the money that I do not have and I do not like it.

And I want this to change. And that got me very into personal finance like the nerd that I have become with my spreadsheets and my personal finance books. And now eventually into a career where I cover personal finance full time. And one thing you didn't mention is that all of this was happening in New York City, not not the cheapest city in the country or the world, probably one of the most expensive.

I think this is the hard thing about a lot of low paying careers is that they're centered in very expensive cities. So think about the arts, right? It's New York or L.A., generally speaking. If you think about fashion, if you think about PR, even these are careers that are very notoriously poorly paying in some of the most expensive places in the world.

And so what I did find to be really helpful was that I wasn't alone in my pursuit of trying to make it and actually leaning on community of people who are similarly not making a lot of money in these big cities was a huge help because for me, status quo was not having my own apartment in the financial district where it costs three to four thousand dollars a month.

Status quo was having four roommates and subletting your room whenever you can to make extra money and, you know, splitting things and living out in Inwood or in the Heights or wherever else to cut costs. So I think part of it was just having an understanding of what your version of normal is.

For me, it's been at 35. I've never lived alone. And that's normal. And that that perception has saved me a lot of money over time. Yeah, I started my career in New York as well. I had a job that paid more, but not enough to really live that kind of life that you want to live.

I actually worked as an intern for the first nine months of my professional post college career. And that's a story for another day. But interns don't make the most. But what's interesting, and I'm curious if you had the same experience, is a lot of the things that I did to save money early on living in a city.

Yes, they were. Some of them are things that I probably don't do anymore, but a lot of them carry through. And I think as we've talked over the past few years, I've learned neither one of us wants to have a crappy experience in life. Like we want to like do the things you you worked in the arts.

You want to participate in that. You want to go to shows. We both like food. I'd love to just dig into some of the things that you did either before or even continue to do in a city to make it kind of an amazing experience, but to still spend less money and save more and be really responsible.

Yeah, as you mentioned, I love to go out. I love to see things. I love to have really fantastic experiences. And the wonderful thing about cities is they are just bastions for free cultural enrichment. And there is just endless calendars of workshops. You can go to performances. You can go to things you can do that literally cost zero dollars.

Of course, at this point in my life, I am very happy to pay for these experiences, too. But as you mentioned, you know, early on, there just wasn't the money for an entertainment budget, to be honest. But what I used to do is I would go to the New York Public Library website where they have a very comprehensive list of all of the events that are coming up and the exhibitions that are coming up and the concerts and talking series, almost all of which are completely free.

And this is not a New York specific things. Almost every town or city has a parks department calendar, has a library calendar, has like a chamber of commerce or town calendar where they have so much programming that is either free or low cost or has a lottery system or tickets or things like that.

So I was always getting in on whatever was available on those calendars. And then I also worked a lot of really cool events. So one of my side hustles was just being a greeter or somebody who's helping distributing materials for a pop up conference or a concert. I think I saw A-Rod give a talk during a I don't even know.

I think it was like a fancy baking event. And I was like, OK, I'm going to just stand inside. And then at the end, I would be the person who would go pass the mic to people who wanted to ask their questions for him after he was done with his interview.

So I have found a lot of creative ways to access some of the things that I would never be able to access if I had to pay for it out of my own budget. How did you find these side hustles? Because I feel like, you know, it's one thing to find a way to make some extra money.

It's another thing to find a way to make extra money while doing something that you otherwise could never do or like you might not even be able to buy tickets to some of these events or shows, even if you had the money. So part of it really is what I was mentioning before about community.

If you have a lot of people who are in a similar circumstance, you already have a network of people who have a similar need, probably a similar interest and are well connected enough to their own opportunities that that when, you know, another body is needed to cater this event that I don't know J-Lo is singing at, like you can get the call if you're honest and open and vulnerable enough with people to be like, listen, I need money right now or listen, I'm looking for work.

So I think you just honestly need to be up front about the fact that maybe you do need extra money or you do need side hustles or maybe you're just interested in certain things so that you become the person people think of and call when those opportunities arise. I think the other piece of it is I really leveraged social media and this is early days.

This is like I want to say late 2000s, early 2010s. And so social media was a little bit different back then, but I remember I would post things on Facebook or I would search Facebook posts and see if people were around in a given city. For example, I picked up a babysitting gig once on my day off on a tour because I was searching for friends who live in, I think it was Seattle.

And I searched that person's post and the person said, oh, my goodness, I'm looking for people who are in the Seattle area and I need them tomorrow for a babysitting gig. And I was like, I'm on it. And I would also find access to opportunities that way. So, you know, when we went to Vegas, I was like, hey, I'm headed to Vegas.

Who do I know? And somebody was like, hey, I work at Cirque du Soleil. Do you want free tickets? So I can be pretty shameless about where I am and what I need. And that has actually served me pretty well. That's amazing. I want to come back to one thing that you so briefly mentioned that I took advantage of in New York, which was all the theater lotteries.

So for anyone who doesn't know, almost every stage production, Broadway, off Broadway, has some system, whether it's a lottery or show up and get standing room only tickets, where for usually and you are way more connected to the theater industry than me for 20 or less dollars, you can usually get tickets.

Sometimes they're the front two rows. I know we've seen Wicked and Book of Mormon and Hamilton and Rent all on lottery tickets where we paid, you know, 20 bucks, 30 bucks and got tickets. And most of them were all front row seats. My first date with my now husband was front row Book of Mormon.

We entered the lottery two hours before the show. We won the lottery and we got that those seats for like, yeah, 20 bucks, maybe 30 bucks inflation. Who knows what it was, what it is now? But it's cheap. It's really cheap. And my husband works on Broadway, so I get a couple extra connections through that.

But I think part of it is, again, just being willing to ask, let people know and tap into your own network, too. And, you know, you mentioned the lotteries, but there's also, you know, free performances that come up. And this is where the social media aspect comes in. Hamilton was, I think, doing something where they were filming a show and they needed to fill the audience for the taping.

And so, you know, on their Twitter, they posted something and you could then be like, oh, I want that ticket. And you like filled out the Google form and they notified you. But you, you know, you have to move quickly. So part of it is just keeping on the pulse of what's going on and following the shows or the museums or whatever it is you want to do on Twitter.

I mean, that's a goldmine for free stuff. Yeah. A couple other good hacks here. So one I learned about when we were trying to see Hamilton before we got a lottery ticket was if you notice on a lot of sites like StubHub, if you're out a week, two weeks before the show, it's really expensive.

And then within like the last hour, everything gets really cheap because people are sitting on these tickets. They're trying to make money. And so if you just find and in New York, it's great. Almost all the shows are right near each other. And so what we would do is we would look like 30 minutes before and we would just go to like a FedEx Kinko's to print off the tickets.

This is oftentimes they're not always able to be digital. And which is to your advantage, right? If they're digital, you can go to the last second. If they're not, those last 30 minutes, people will drop the price significantly because they just need to sell the tickets. So we would do that.

There's also a lot of shows and especially live tapings where I'm not sure why they don't charge because they seem there seems to be a lot of demand. But we went to the Colbert report. We went to SNL. That kind of stuff was all free. It's all sign up.

Usually for SNL, you sign up like a year in advance or something. And then they just send you an email. They're like, hey, you have two tickets to this thing. And by the way, if you ever do go to a live taping of SNL, the way it works is everyone lines up in the lobby of 30 Rock and there's people that just walk through that line and select the people who are going to sit on the floor.

And so my wife thought I was such a crazy person because I was like, every time this person comes near us, let's just start laughing and let's just like be funny. And like three times in a row, I was like, all right, now, now, now, now. So this woman walks by and I'm just like, my wife just starts laughing.

She's like, you're an idiot. This is so we look ridiculous. And then the fourth time she walked by, she was like, can you two please come in this line? And so we moved into the floor seat line. So that's my my little mini hack for for getting floor seats at SNL.

But yeah, I feel like I've tried everything I can to have this awesome experience in cities without having to pay for it. And if I do have to pay for it, great. But, you know, if there's a museum you want to go to, yeah, you can pay to go to it.

And then there are like days of the month where locals are either free or I remember for a while, Bank of America, like if you had a Bank of America debit card, you got in free on a lot of days. Oh, yeah. Check those credit card rewards. If you have an Amex, you can do so much.

Yeah, they used to do a lot of pre-release movies before they come out. There are actually I don't know if this is still a thing. Covid probably kind of tampered this down. But when I first moved to San Francisco, I found all these websites where you could sign up to go see pre-release movies and they would just all the time have free movie tickets to go see movies like the week before they came out.

And I always assumed they were going to ask me some survey to learn about the movie. They never were. I have no idea what was in it for them. But I probably went to the movie theater and saw like eight movies or 10 movies in my first couple of years here.

Totally free. Any other city hacks, maybe on food or anything else that you think makes makes high cost of living a little bit lower? I mean, I think when it comes to the necessities, one of the things I did for medical care for a long time was I made use of the schools.

We have excellent schools here. So I went to NYU Dental School and they have seriously discounted dental work that you can get. Even if you have health insurance, you might not have dental coverage. So that was a big thing. We have a lot of great clinics here, public health resources.

Again, those tend to be pretty concentrated in cities. So that's where there's a big benefit. Obviously, it'd be great to have benefits that you don't need that stuff. But in case you don't, it's a good thing to have. And then even stuff like salon services. I can't remember the last time I actually paid for a haircut because there's all these schools here that are cosmetology schools.

So they offer free haircuts. It's called SalonApprentice.com and it's I think it's dot com. If you Google Salon Apprentice, you'll find it. It's in a lot of cities. And you can just see if like a student is looking for somebody for a cut, for a color. If it's not free, it's super discounted.

So there's just so much of that kind of stuff where you can even take some of your essentials and find ways to hack them. Yeah, I remember being at the time I remember it was like called a hair model or something. It's like, oh, but the only catch was for some of them, it's like, I want to work on this type of haircut.

So you have to make sure you don't pick someone that's like, I want to learn how to completely shave someone's head. That might not be what you're looking for. That is true, though. I will give everybody some assurances that I have never had a horror story and I've probably done it 50 times.

Wow. Yeah. And women's haircuts are much more expensive than men's haircuts. So, yeah, to be fair, I'm not too concerned about how I look, but I do care a little bit. I do television. So it is I can't look like totally out there. Yeah. OK, so, you know, we very rarely talk about high cost of living hacks because especially in the industry, because so many of these bloggers are, you know, I read all these fire blogs that are like, oh, I'm trying to be financially independent.

Here's my hack so that you can live on ten thousand dollars a year. And I'm like, OK, I don't think I've seen an apartment that goes for ten thousand dollars a year in all of San Francisco. So I think it's I think it's cool that there are actually ways to make make expensive, higher cost of living cities a lot cheaper.

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So check them out today at allthehacks.com/peak, P-I-Q-U-E. And these cities have a ton of value they provide. I hate when we reduce these conversations just to the expense alone as opposed to thinking about what's the total value of the experience, right? Yeah, it costs a lot of money to live in a big city, but if it connects you to a cultural circle that you care about, a community that you care about, career opportunities that you care about, as it does for me, as it does for my husband, who's a Broadway stage and like being in New York has an enormous value.

And my career would not be where it is if I did not live here. That's not to say that you can't have really wonderful career opportunities elsewhere and that I may not have found success in other ways. But I attribute so much of the income gains that I've had and the career growth that I've had by the sheer fact that I am in the city where it happens, in the room where it happens so much of the time.

So one of the things that Covid has kind of brought up is this kind of so-called exodus from all of the cities. And I know so many people that are now trying to geo arbitrage. They're like, oh, I'm going to move to the middle of Nebraska and I'm going to work remotely.

I'm going to make my Bay Area salary and pay Nebraska rent and it's going to be fantastic. And, you know, I still live in San Francisco. You still live in New York, presumably for a similar reason to what you just described, which is I believe that the career financial life upside of being in the middle of where an industry that you're a part of is is happening.

And I think for me, that's worth it. And like you, I've seen a lot of benefit in the past. Do you think that benefit keeps coming or do you think anything major has actually changed in the way we work such that that value proposition is is less now in a post Covid world?

There's been nothing more powerful in my career than face to face interactions, and I do not foresee that changing. I do believe there will be more opportunity for hybrid work, for flexible work, but it is really hard to recreate the experience of being in a room with somebody, not just because of just the physical interaction, but it just facilitates a night, right?

Like, you're not just meeting for the hour that you have coffee with somebody or for the networking thing. It's like, OK, let's go get dinner. Let's go get drinks. Let's go see a show. And I do think that building relationships, even whether it's for personal or professional reasons, I think it requires that amount of spontaneousness.

And I think it requires that interaction if you're going to create a level of depth. And in my experience, it's depth of relationship that really creates the opportunities that have created the most benefit for me. Now, I'm not going to say there's no value, obviously, in having that off the grid lifestyle.

Of course, that's high value. And if you're in a place in your career where you feel really confident and secure and you don't really have much interest in pivoting into something else, great. Go do it. But I do think there's a lot of risk that hasn't been talked about in going out and like living 300 miles away from wherever you are now and just assuming that you're going to be stable for the rest of your life under the same conditions that have brought you to where you are in your career now.

Yeah, I I totally agree. I think maybe the type of work you do could matter, I think, in in in a world where relationships are really important to your job, if you're in sales, like it just seems really important if you are an engineer and that's just what you want to do and you found a company and you want to work there for 10 years.

Yeah, you might be able to save a significant amount of money. I know at least on the rent side, you could save a significant amount of money leaving the Bay Area. But if your aspiration is to start a company, if your aspiration is to run an entire organization or a team, I think it's I think I personally think you're missing out on value by being where it happens.

But I am jealous of the people who took the last two years to move somewhere else and just completely geo arbitrage their income while all of those room where it happens are closed. Let me tell you one thing about that, because I spent almost a year of my pandemic in upstate New York in a beautiful place with my family, and it was wonderful in many ways.

I could not be happier to be back in New York City. And I think part of this is also knowing yourself. I think some people are more attuned to the value proposition that a city provides, and some people are more attuned to the opposite. And I think sometimes we romanticize both.

And I think part of it is about getting really honest with yourself about what you care about. And at the end of the day, I care about having access to delivery and take out of good food 24/7. Yes, huge value. OK, so you just mentioned family and there's a lot of stuff I want to cover.

But a thing that I realize is I spent the last week talking with family on both sides about what are we doing for Thanksgiving? What are we doing for Christmas? And one of the things that I've heard you give advice about, I think you've been on like Good Morning America talking about is gifting and the holidays.

And I'm just wondering, as we approach this time of year, are there any hacks you have around finding gifts for people, buying gifts, deals, shopping, any of that stuff that people might want to use? So I'm of the philosophy that my time and energy is not particularly well spent by going deep into the weeds of couponing and comparison shopping.

That said, I am interested in anything I can do that easily facilitates a discount. So, you know, installing a browser extension that searches for deals and coupons automatically when I'm buying things online or cashback portal where you go in and it's like, oh, you get five percent cash back if you shop at J.

Crew on this day and I'm shopping for J. Crew anyway. Great. Happy to do that. That's pretty easy, pretty seamless, pretty low lift for an easy reward. So that's the kind of hack that I'm interested in. The other thing is, like, I have really no issue with opting out of things.

And I know that's very difficult for most people. I think a lot of holiday stuff and this is probably true for anything related to family. You know, you're talking about family, things like weddings, things like birthdays, anything where there's a sense of obligation, where things get emotional, where they get sticky.

I think it's the emotional piece of it where people get really carried away. And that's where things get out of hand. So I think part of it has been for me just kind of interrogating what is this really for? What is the gifting really about? What am I trying to do with the gift?

And that has really made me realize that, like, for me, gifting and the holidays is about spending time with my family. It's not about, you know, making sure that I'm partaking in the office Secret Santa because everyone else is doing it. I can tell you that I rarely partake in any kind of ancillary gifting groups and it has made no difference in the quality of my network or experience.

And it's not like I'm a Grinch and, you know, I think that you all should not be doing this and or I'm a cheapskate. It's just there's just not enough value that comes out of the experience. And that sounds super cold. But to me, it's like, OK, do I want to spend like fifty dollars on 10 different group gifting circles or do I want to buy a plane ticket so I can go visit my family?

That's not a difficult exchange. I think we're just not being honest about how much of leakage there is through this little stuff that adds like no value. And then also just a little soapbox, I'm very against like decor and candy of all kinds. Wow. I just don't find that it's like this this little junk that is so expensive as it collects.

And then like you have to deal with it afterwards versus like if I don't buy any of that, what I can do is get you. I don't know, not an Apple Watch, nothing that expensive, but something like actually useful, maybe a subscription to like Broadway HD, because my mother loves Broadway and Broadway's been closed so she can stream it for the next year.

So again, for me, a lot of money stuff is not necessarily about the numbers so much as it is about the value and then like really getting clear on what's the purpose of the thing I'm trying to do. And honestly, spending fifty dollars on candy canes for like a hundred different people is not a good value for me.

Yeah, so I've gotten in a little bit of trouble in the last few years with my family perspective on gifting. I've always thought that the idea of creating a list of the things that I want and sending it to family and having them buy the thing on the list is like my nightmare because things in my world either fall into I really want them or I don't.

And if I want them, I'm going to find a way to buy them. And a lot of times I'll buy them on Facebook Marketplace or I'll wait for them to go on sale and I'll use cashback portals and all this stuff. If someone else buys them, the thing that I could have gotten for thirty bucks, they're paying fifty dollars.

And that drives me crazy. The other thing that drives me crazy is everyone's always asking like a month out. They're like, what do you want? So then you go do some research and you're like, well, here's seven things that I want to buy. Now I just want them. So it's like the whole gifting for me got so stressful because I'd find a thing that I finally like, yes, I want this shirt.

And then it's like now I've got to wait five weeks to have the shirt and I know you're going to overpay for the shirt. And all I really wanted was like some kind of gift that was meaningful. Like I care much less about the fact that you're willing to spend fifty dollars on me than I do that you spent a little bit of time trying to find something that you thought would be cool.

And so I proposed that. We just do away with lists and everyone thought that was crazy. And so then I went one step to the extreme to try to make my point. And this is where it kind of went off the rails. I said, look, if we're all just going to buy each other things off each other's lists, what if we just made a spreadsheet and we all typed in how much we were going to spend on each other?

And then we just netted it out. So if you were willing to spend eighty dollars on me and I was willing to spend seventy dollars on you, you could just Venmo me ten dollars and we just call it a day. And they're like, well, that takes the fun out of it.

And I was like, I know, but it's already not fun. Oh, my gosh, that's so funny. But I told, of course, it didn't go well. I totally get it. You know what I wish for gifts? I wish I could buy gifts when I see something and I'm like, oh, that's perfect for so-and-so.

And that's it. I don't buy them any other gifts any other time. I just get the thing when I'm like, oh, that is the thing for this person. So that's so when you talk about opting out, it's interesting. We finally got to a place with families that, you know, we don't see both sides of the family for Christmas every year.

So we just said, hey, look, on the years that we're not going to see you guys, we're opting out and everyone actually opted out. So we just don't do gifts there. And then on the years that we do, we actually just have a there's my wife has two sisters and parents.

So there's four kind of groups. We just everyone gets one person. We get them one gift and like we call it a day, except for kids. Everyone under like 10 is opted in every year. The kids get some gifts because it's exciting. But all the adults have kind of gotten to a point that they opted out, which has actually worked incredibly well.

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I was going to ask you how you are feeling about navigating all this now as a parent, because I do not have children, but I think it would make me crazy if people kept buying my kid just garbage. So the number of gifts we've already thrown out is like, I can't count on my hand because everyone's like, "Oh, I sent you this thing." And it's like, we got this one stuffed animal and it was like covered in like this smelly glitter.

And it just seemed like it was the cheapest thing ever. And if someone put it in their mouth, they would probably get some toxic chemical. And so I do think that, you know, registries for kids is one of these hysterical things where you're like, "Here are the 20 things we need for our kid." And they're like, "I'm so glad you sent that list.

I got you this other thing that I thought you would want." And I'm like, "No, if I wanted it, I would have put it on the list." Every now and then, it's a really cool sentimental thing, but for the most part, they're not. But your dream is something my wife and I have decided, which is we no longer do birthday and Christmas gifts for each other.

We just, throughout the year, when we see something really exciting for each other, we buy it and we just have random gifts. It's like, "Hey, we're at dinner." And I'm like, "I saw this book. I thought you'd love it." And a cool book that I will actually share, which I think is really cool, is this website or book or company called Adventure Challenge.

So the whole premise is you get this book and it's like 50 dates, but you don't know what they are and you have to scratch them off and you commit to doing them and they give you some requirements. So it's like, "Tonight, you're going to need two hours. It needs to be dark out and you need 30 bucks." And then you just see this thing and you're like, "All right, you're ready?

We're going to scratch this off and that's the date." So that was a recent gift and we've only gone on one date and it sent us to Target to make like little scrapbooks for each other with stickers. It was like, it sounded like the dumbest thing ever. And then we did it and we went to like a bar and got some beers and we were like putting these stickers in.

We felt like we were designing our trapper keepers back in the day. But I shout out to Adventure Challenge because I thought that was a really fun gift that keeps on giving, I guess. I love that. I've also taken to having the best gifting experience with my husband, which at this point is really just treating ourselves to extravagant meals and trips.

And I honestly, if that's what gifting was, I would be much happier. Yes. I think we both share that love for travel. Okay. So we haven't talked at all about the biggest thing that I think you're working on right now, or maybe there's multiple, but you know, last, in the middle of the pandemic, you started a podcast and it was something that I don't think I'd really seen recently, which was talking to people kind of off the record, confidentially about their money issues and trying to solve them.

And so I'd love to hear a little bit about how that came together and some of the interesting things you've been learning that maybe you were surprised by. Yeah. So the podcast is produced in partnership, well, it's their podcast. It's Real Simple Magazine. And so they hired me as the host and I'm a producer on the show.

And they basically had this idea of, we really want to talk to people confidentially about their money problem and then have an expert come on and explain how to solve the problem. And that's the framework they gave me. And I was like, Hmm, this could go so many ways.

How are we going to really bring it together? And one of the things that I've found in doing the actual interviews and seeing what brings it together is that it's almost never about the money. It's almost always about the feelings about the money, the shame, the fear, the everything else, the family, the friend, the husband, the wife, you know.

And almost every single person thinks they are totally alone and it makes them feel like they're a failure. Everybody else around them is succeeding and they are hopeless. And so they internalize whatever they're going through as this experience of, Oh, it's just me as an identity. I am bad with money and that is who I am.

And that is just a quality that I must have been born with or inherited from my family. And thus, there is no hope. And that is a really painful place to try to make a positive change from. You can't really hack your way out of that. You know, we talk about optimizing these things, using the deal sites and trying to set these boundaries of people in our lives.

But if you are in a place where you don't even think it's possible for you to change, if you're saying I'm bad with money, not I've made a money mistake, that's a really hard place to move forward from. And so on the show, when we're talking to people and we bring on the experts, not only do we have to go into the hacks of like, OK, here's what this means for your spreadsheet and here's what this means for your budget and your investment account and your savings account.

We also have to go into, well, here's what this means for your relationship to your mother or here's what this means for your relationship to yourself. And it is really emotional. And I don't say that to say that we're trying to be a kind of therapy podcast. We're not.

But I notice when it's confidential, people start to open up about what's really behind why the numbers on the page aren't adding up. And when people do that, you really just start to see how much of it is about shame and isolation and how much can really be helped by having these conversations that you and I are having, where we're like, I actually hate this thing that we all do.

You know, maybe we should change that, because if you don't have that conversation, you continue to feel obligated and you continue to feel overstretched and you continue to get trapped in this cycle where nothing's working out for you. So I think the coolest thing about the show has just been really talking to the listeners themselves and seeing what they've been willing to be vulnerable about and, like, realize for themselves in the process of sharing what's going on.

Because a lot of it is these aha moments that they never thought about before. They never thought about, oh, well, why isn't this working? Then, you know, the budget's not working. But as they talk it out, you can hear them start to have these aha moments. And that's super cool.

Can you walk through an example of an interview you've done and kind of some of the learnings you've had? Yeah, we had one listener on the show who called in and she said, you know, I'm really struggling to figure out how to plan for the future with my boyfriend because, you know, I make 30 percent more than he does.

Oh, no, it wasn't 30 percent more. It's $30,000 more than he does. Just a significant income difference. And she was in her mid-20s. They were both in their mid-20s. And presumably that difference could grow a lot more in the future. And so she's like, you know, I just can't seem to figure out how we're going to make it work.

And what I realized in talking to her and having her talk through how they were managing the expenses, what did it look like when the paychecks came in, what did the conversations look like around dividing expenses up, was all of their conversations were based on the premise that fair is 50/50 and there is nothing else.

And it was just an interesting assumption that equal is same. And that is not necessarily true. You know, what does equal mean in a relationship? It sounds like a super heavy topic. But if you've never really interrogated that, then you can't make a good financial plan for your relationship because the fact is almost nothing is ever 50/50 in the course of not just a moment in time, but certainly over the course of a marriage that could potentially be 20, 30, 40 years.

And so that's an example of something that it starts with, like this really simple thing. It's like, well, how do we split our rent? You know, I make $30,000 more than he does. But then if you kind of strip away all the layers, what it's really about is like, oh, well, I've been conditioned to think that like what it means to to be an empowered woman in a relationship is that, you know, it's equal 50/50.

And I'm making more. So what does that mean now that I'm the breadwinner? And where do my thoughts about this come from? And why is it creating resentment? And why is this now a point of tension in our every day? And so it's just like really wild to see what comes up when you keep digging behind the layers and asking more questions.

And what's the advice for someone like that? Is it to just talk about it? Is it, you know, how do you get past it? Is it just, you know, it doesn't have to be 50/50. So a lot of the money stuff is like what it's not about the money stuff again, like always comes back to everything else.

It's like, OK, what is your perception of what it means to be fair? What is the model of behavior you experienced growing up? Was it that your parent told you that you had to do everything and provide for everyone? Was it that it's a bad thing if you're a woman and you make more money than your spouse?

And so, you know, you should feel somehow ashamed if you're in that position. These might not be things that were explicitly said to you, but these are also things that you might need to stop and go through those memory banks to be like, wait, what are these kind of models of behavior I either witnessed growing up or the messages I got, whether they were explicit or maybe like maybe not so explicit, but you felt it.

And then you have to talk about those things with your partner because you both had totally different experiences growing up. And so you are not going to match perfectly with your finances because you have had completely different outlooks. You have had completely different histories. You had completely different models of behavior.

And the only way to really get on the same page about what is fair is to kind of interrogate all of those things together. And it's really uncomfortable to do that, especially when you're dating, because, you know, you don't want to sit down on the first date and be like, you know, tell me your entire family history with money and your credit score and your debt load.

You know, that's not the answer. But the answer is, right, the answer is, though, that like you can't lean out of that conversation entirely until you're after a legally, like financially obligated to somebody in a marriage, which is unfortunately, I think what happens a lot. Yeah, I saw on your website a guide of 25 talks to have with your partner about money.

So I'm going to link to that in the show notes, because I imagine that would help a lot of people get past these things. It does. And it also kind of lays out at what point in the relationship to do these things, because, again, you don't want to be that person on the first date asking about, you know, student loan balances.

Yeah. I mean, this isn't money related, but something I found was when we had our daughter, my wife doesn't have the same last name as me. And, you know, that was something that didn't matter to me. But she was kind of like, are you sure? Are you OK? And I'm like, yeah, it doesn't bother me.

So then we have to pick what our daughter's last name is. And for most people, it's just like assumed. And I think for me, I was like, well, you have a cooler last name, like your last name's Fox. That's a pretty cool name. We should give our daughter that name.

And it was just surprising how many people were like blown away by the fact that we gave our daughter my wife's last name, so much so that some people either chose to ignore it or didn't know or just assumed. And they'd like sent her like, you know, a monogrammed pillow with the wrong initials and that kind of stuff, as if, you know.

And so I just realized that her assumption of what we would do and my assumption of what we would do weren't even on the same page. And when we talked about it, it was like, oh, OK, she'll have, you know, and mine's a little more systematic. I personally, I really struggle with hyphenated names because I'm like, well, if we give all our kids hyphenated names, then all our kids are going to get married to other kids with hyphenated names.

Then they're going to have quadruple hyphenated names. And then their kids are going to have eight last names and so on and so on. So mine's more like a process and system argument for not doing that. But I think my wife also just has a much cooler last name.

And I slightly regret not taking her last name because I feel like Chris Fox, like would just be a much better podcast host, much better name on the billboard, all those things. I mean, it's never too late. So one of a few things that you touched on in that conversation was about, you know, you talk to this woman who makes more than her husband.

And I know you've been spending a lot of time digging into the data that comes around. And by data, I mean studies, research with women who make more than their husbands try to be too ambitious. And you've even kind of coined the term "the ambition penalty." Could you talk a little bit about what you've been learning and what you've been sharing?

And we'll go from there. Yeah, so I got really interested in a lot of the advice that we have been giving women in particular in order to close these really persistent gaps in pay, in wealth, in leadership, in workforce representation, because I think in the last decade or so, you've seen a lot of the Instagrammable advice of like, OK, just speak up, just be more aggressive, just ask for more, just negotiate.

And I wanted to challenge the assumption that women were not doing those things. And what happened is when I looked into the data, what I found is women actually are doing a lot of these things. They are asking for more. They are speaking up. They are trying to reach leadership positions.

But what happens is when women engage in these behaviors, there is a backlash to the behavior. So there's a lot of studies that look at, for example, a resume. And what happens if you change the name from a Howard to a Heidi is if you have all of the same qualifications, if you have all of the same perceptions otherwise other than the name, then the Howard is more likely to be judged favorably compared to the Heidi, who not only is she less likely to be judged favorably, if the cover letter is seen as somehow aggressive or self-advocating, then she's actually likely to get a backlash.

She's likely to be labeled unlikable. And this isn't just about likability. This has real tangible financial consequences. In fact, on one episode of Money Confidential, I interviewed a woman who was negotiating her salary after getting a job offer, and the job offer was rescinded as a result. So they withdrew the job offer.

That is a tangible financial penalty that woman got for trying to negotiate a raise. And that is not an anomaly. This has been borne out in the data. And that's just one example, a job offer being rescinded. This happens when women try to get promotions, reach leadership positions. There's all of this backlash, and a lot of it has a tangible cost.

And my takeaway in covering this is not that, well, we should just not negotiate or we should just not try to reach these leadership positions or whatever else it is. My takeaway is we need to broaden the conversation so that it's not so overly simplistic, because when you say, oh, just speak up, just be more confident, just be more assertive, the assumption is that somehow we're not already doing these things and that getting to pay equity is as simple as that.

And the truth is, it's not that simple. It's being borne out in the data that it's not that simple. And it also puts so much of the onus on women, especially women of color, basically anyone who's, you know, outside of the gender binary to be the person who's going to solve for what's really a structural inequity.

And so I think for all of us who are trying to navigate in this world, we need to have a broader conversation about how do we recognize these biases and then how do we manage them in the context of these conversations of negotiating, getting leadership positions, leaning in, all of that.

So. I mean, it's fascinating that a lot of times I hear these stories, but I've never dug into it, so you've actually linked out to a lot of different studies that show what's happening. And I went deep on a couple of them and like, you know, the Journal of Psychology and that kind of stuff.

What do you think someone listening today and especially for me, right, I'm on the other side of of the gender here. What can I start doing to make this better? Is it as simple as just talking about it? What can happen at work? What can we do to promote an environment that kind of makes this I mean, it's not going to go away overnight, but kind of works on making this go away.

I think talking about it is actually more powerful than we might think it is, because as we kind of talked about earlier, a lot of this stuff isn't explicit. Nobody is out there being like, we don't want women to be leaders. We don't we want to suppress the ambitions of minorities.

Nobody is saying that. But this stuff is really deep. It's structural. And so part of it is really just bringing awareness to the ways in which we do undermine women, people of color, LGBTQ individuals when they do advocate for themselves. And if you see it happening, you know, if you're in a position of power to go ahead and say something, that means something.

If you can support that person through the process of a negotiation and be their mentor, be their advocate, that means something. I think part of this, too, especially in personal finance world, is that we have to do better. Me, myself included, I have given that advice of, you know, be more confident.

But that is really insulting to just imply that confidence alone is going to solve for what is really a structural and systemic inequity. And so I think we have to say, OK, you know, if we see a little gap in how much men and women are negotiating, maybe we should interrogate why.

What is going on there? Is it because women aren't confident or is it because they have a realistic and borne out fear of backlash? It's not just a lack of confidence. It's a real legitimate and borne out, proven fear that if I do this, I'm going to be labeled aggressive.

I'm going to be labeled unlikable. They're going to say I'm not a great fit for this company the next time that I'm in the running for a promotion. So I think part of it is really about just interrogating the assumptions we have around a lot of the career and financial advice that we are giving to these historically marginalized communities.

Are there any tactics that someone in one of these communities can use to try to lighten or reduce the likelihood that they face this backlash? Yeah, so a lot of this, you know, in my research around why this is happening, that part of it stems from our expectations around how certain communities are, quote unquote, supposed to act.

And historically speaking, women are, quote unquote, supposed to act in a way that is deferential, that is serving, that is nurturing of the community. And men are supposed to, quote unquote, act in this way that is, you know, aggressive and being the provider. And so basically what happens is when a woman asserts the qualities that we associate with, you know, heteronormative masculinity, this isn't typically a conscious thing.

But subconsciously, there's this feeling of like, oh, you know, that's just like a little bit too much. You know, there's just a little bit not the right fit. And we have this instinctive reaction around like, we don't like this person because they're not conforming to this expectation of how we think they should behave.

And so what we can do as people managing these biases, if you're a woman and, you know, you know that you're in a company where maybe there's some bias and discrimination you've seen firsthand, maybe you can think, OK, so I know that I'm in an environment where there is a lot of this bias.

What is it that I can do to advocate for myself in a way that's not going to be seen as I'm the bitch or difficult or whatever for just engaging in these very basic self-advocacy behaviors? So what I can do is frame my ambition through the net benefit to the organization.

So, for example, if I'm saying if what I really want is a raise, what I can do is instead of, you know, framing what I think I should get a raise for through just me and my contributions, I can also frame it through the perspective of what this work has done to benefit the community, the people around me, the company, and really play more into that, you know, traditional nurturing vibe, even as you're doing this self-advocacy that might be seen as more masculine, if that makes sense.

No, it makes total sense. So there is so much we could keep going. I actually have a bunch of questions that I'll save for the next conversation. But where can people who want to see some of this data and want to learn more about what you're learning find everything you're doing?

Yeah, so I've been writing a lot more in detail about the ambition penalty and sharing these firsthand accounts that women have had on my bulletin, which is a newsletter service, which you can find at ambition.bulletin.com. We'll link to that in the show notes and anything else that you're working on online or anywhere that people should look for.

Yeah, you can listen to our Money Confidential podcast wherever you're listening to this podcast and hear some, you know, not just experts, but real people sharing the real stories and like a lot of the interesting emotions and stories behind those numbers on the page, which I always find fascinating.

Yeah, I've been listening. It's fantastic. Stephanie, thank you so much for joining. What a fun time. Thank you. Wow. I always have so much fun talking with Stephanie and I hope you all enjoyed the conversation too. For anyone new here, I love hearing from listeners and especially love hearing about topics you'd love me to cover in the future or any questions I can answer in a future Mailbag episode.

Speaking of which, if you tuned into the last Q&A episode, I'd love to know what you think. So please shoot me a quick note and let me know if you want to see more or less episodes like that. You can always get ahold of me at chris@allthehacks.com or I'm @hutchins on Twitter.

And finally, if you're not already subscribed to the All The Hacks newsletter, please check that out at allthehacks.com/email. All right, that's it for now. See you next week. I want to tell you about another podcast I love that goes deep on all things money. That means everything from money hacks to wealth building to early retirement.

It's called the Personal Finance Podcast, and it's much more about building generational wealth and spending your money on the things you value than it is about clipping coupons to save a dollar. It's hosted by my good friend, Andrew, who truly believes that everyone in this world can build wealth and his passion and excitement are what make this show so entertaining.

I know because I was a guest on the show in December, 2022, but recently I listened to an episode where Andrew shared 16 money stats that will blow your mind. And it was so crazy to learn things like 35% of millennials are not participating in their employer's retirement plan.

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