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This week on The Financial Confessions we’ve got the one and only Stefanie O'Connell Rodriguez! On this episode, Stefanie provides us with some can’t miss insights about wedding planning, small business finance, the FIRE movement, and how to get into those rich people gym classes – on the cheap.

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Hello, everybody.

I am Chelsea Fagan. I am the host of The Financial Confessions and the founder of The Financial Diet.

And every week, we talk to people that I think are extremely interesting about my favorite topic-- money. And today, we have a very exciting guest who is a friend of mine, someone I've known for years now in the personal finance community. Fun fact.

She also lives basically downstairs from where I go to Pilates-- very much just like in my life orbit. Her name is Stefanie O'Connell. You may have heard of her, especially if you watch The Financial Diet on YouTube.

And she is someone who quite possibly loves talking about money more than I do, which is a rare distinction. But before we meet Stefanie and talk to her all about money, I want to talk quickly about the amazing partner that we create this show with every week-- Intuit. It, as you guys may know by now, is the creator of several amazing products that completely changed the way I personally do my money.

One of the first steps I ever took with managing my finances was downloading an app called Mint, which I now use basically every day to track my budget and my spending. They also make QuickBooks, which I also use every day to manage my business finances. They make TurboTax, which I'm sure many of you have used in the past, which is like the only program I've ever found that makes taxes easy to do.

But basically, Intuit is like a little mini CFO in your own pocket that helps you manage basically every financial decision that you'll come into contact with all throughout your day no matter what you do. And if you just can't wait to learn more about all of Intuit's awesome products, check out the link in our video description and show notes. So as I mentioned, we have a very cool and special person here in studio today, and that is Stefanie O'Connell.

Hello. Hey, Stephanie. Hey, Chelsea.

Hi. So welcome. Thanks for having me here.

I'm so excited to have you. And I feel like I know you so well. But for those who may not know you, tell like a little bit about yourself.

Yeah, like you said, I love talking about money. I like to write about money. I like to think pass the tips and tricks.

I mean, that's all good. We need all that. But at the end of the day, I want to think about how money actually plays into our lives.

What does it mean to have a good credit score? Well, it means I can actually qualify for the apartment I want to live in with my husband. So I like thinking about money in those terms and thinking about how I can use it and help others use it to align with my value systems and their value systems and kind of the future that we want to build for ourselves and the people around us.

How did you first get into to talking about money as a profession? So I started from a point of pain. And I think this is probably really common in the blogging community of I had this money issue.

And for me, it was really making very little money and not having a consistent income that were constant sources of stress and constantly limiting. And I just felt like, wow, how am I ever supposed to build toward anything if I have zero control? And writing about it seemed to kind of make me feel like I had a sense of control over something.

And through the process of writing about it, I started to learn. And I started reading. And I started creating space and time for this thing.

And that in and of itself, like creating a money practice like you might have your Pilates practice, just dedicating energy and time to it really just change my relationship with money. And it went from kind of just stressing about money all the time to actually managing it. And through time, through my own journey and through my own pain and through my own writing, I was like, oh, this is actually amazing.

Then I started taking classes, like official financial classes because I was like now I'm obsessed. Do you have any certifications? So I never finished my certified financial planning certification because you have to spend two years working at an investment bank.

And I have no interest. No thanks. Pass.

No thank you. Well, that's so-- I find I very much agree in the sense that money used to be by far the most taboo subject for me. I use to feel an incredible amount of shame around it.

And interestingly, even if you're not doing anything really to change your behavior at first, there are actual studies-- I don't know the stats, so I won't throw out some stats that are probably wrong-- but it's something like people report being like 30% more-- feeling 30% better about their money when they just admit that they feel bad, when they talk about it, particularly because for so many people, as you said, money is not just money. It never is. It's the life that it enables you to live.

And, for example, if you're not able-- if you don't have enough money to go out with your friends, for example, most people are not going to feel OK with saying I can't afford to go to your birthday party. They're going to be like, I'm sick or whatever. And they're going to-- you get yourself into these webs of lies and self-deception and excuses and all of this stuff.

And the moment you're just like, I'm broke, it all goes away. Yeah, totally. And once I embrace that, actually, it's funny.

It's like everyone around-- not everyone around me understood-- but everyone around me gave me a little bit more grace. I remember when my now husband first asked me out. I was like, I don't care what we do as long as it's cheap because I'm on a budget.

And I just kind of set the precedent that I'm going to talk about this from day one, and it changed everything. We have fights about a lot of things, but it's never about money. I'm not going to pretend and be like, I have a perfect relationship.

I don't. Spoiler. But it's not money related.

And I just think that's such a great example of just the power of talking. Yes. And you just got married.

I did just get married. How was that? Oh, man.

You know what? It's so funny because it's not something that I really like daydreamed about growing up. I didn't even know if I wanted to get married for a long time.

But then I was-- my fiance-- or what the hell was he? He was my boyfriend and then my fiance when he proposed. And I was like, OK, yeah, like this is a partnership.

And if I think about marriage and those terms rather than like what people have traditionally defined marriage as like property, that's something I'm on board with. And when that happened, I was like OK, let's think about what our version of partnership is starting with the wedding. And I was like I can't imagine spending all this money on a wedding.

But then as I started to do it, I was like, wait, I actually do value having these people at my wedding. I actually do value having live music. I actually do value being able to feed everyone, not just one meal, but having like a weekend of festivities.

And all of a sudden, I went from, oh, weddings are a waste of money to like, oh, this is actually totally in alignment with my values. And I don't care if I have to spend $40,000 to do it. Is that what you spent?

That is what I spent on my wedding. Very cool. You know what?

I actually don't know the exact total of what we spent, but it was much less than that. But we had a 27-person wedding, which was a very conscientious choice in that regard because I'm very much like that, like I splash the fuck out even when it's just Friday night at my house and having two people over for-- have you ever seen my-- what is it? My Crazy Ex-girlfriend?

Yes. You know that song, it's like having a few people over-- Oh my God, no one's going to know this reference. We're going to Youtube that next.

But anyway, so that is very much my thing, and I knew I would feel that way about my wedding. So I was like, I have to limit the quantity of people and give them the best week of their lives. And it was a full week.

We put everyone up in a-- it wasn't a chateau but this beautiful place. And it was just like-- you really have to pick what was important. Do you have any regrets from how you spent?

I really don't. My wedding was so beyond perfect that it's, again, like not something I ever thought I would say. And even the experience of it, I was kind of stressed but loving it.

And then I saw the pictures afterwards, and I was like, wow, that is a really fun wedding. All these people are dancing. Everyone's having a good time.

The space is beautiful, even though I bought 0 flowers. So it's just like-- I don't know. And it's funny.

I talk about having a $40,000 wedding. And some people are like, how did you do it for so cheap? And other people are like-- Well, those people are psychos because you should not be spending $80,000.

But then some people are like, that's an insane decision. And I'm like, I guess I see both perspectives. What is the average?

It's like $30,000. It's 30 something. And I got married in New York City where the average is about closer to $80.

Yeah, the difference between a tri-state area wedding versus elsewhere in the country. We're planning our wedding right now, and I just keep having to reiterate like it's a party. We're having a party, like this isn't a [INAUDIBLE]..

Yeah. No, I mean, it is. And I think-- you know what's funny?

My approach to this and I think part of the reason why I was very able to go way lower on the number of people at my wedding was because I'm so into just like having big parties all the time throughout life. I try to have a few a year. That it's like, it just naturally took a lot of pressure off of that event because I'm like I know for our 10-year anniversary, I'm flying everyone to freaking Trinidad or whatever and having a week-long party on the beach or whatever.

You know what I'm saying? So I mean, not everyone is going to operate that way. But it allows you at least to put it in perspective of this is one party amongst, hopefully, many amazing ones that you'll have in your life.

I have some regrets for spending, though, if I could share. Oh, yeah. Cake.

I like-- Had to do that. Yeah. Every time I'm at a wedding-- half the time I'm at a wedding, I forget to eat cake because I'm already on the dance floor.

Mark and I, we are on the dance floor from the second it's everyone on the dance floor to the second everyone's turning the lights up. So I never am just like in the cake zone. And so often, I'll forget.

Sometimes, I'll take it home and eat it the next morning, which is the best way to do it in my opinion. But at my own wedding, I was like-- it was quite expensive. Cakes are very expensive.

And I do love a cake. But you're so overwhelmed in the moment. You've already had-- we had like a six-course meal.

And I was like, no thanks to cake. And so I don't know. I regret spending cake money.

We had family members make torts. So I'm Ukrainian. And we did a lot of Ukrainian traditions.

And so we had a lot people make the traditional torts. What pissed me off-- so there were things I don't regret spending money on, but there are things that pissed me off that I had to spend money on-- was the fact that it cost money for my caterer to cut the cake that I provided. Oh yeah.

That is the scam of all scams. But it's like there's nothing I can do about it at this point, right? I've already committed to the caterer.

And that's so much of wedding planning, like the ice package. I was livid. Oh, this is what I regret.

OK, I got one. I'm not spending money. It's about spending time.

So I was so mad about all these little up charges. And one of them was this ice package. It's like $5.00 per person for us to provide ice.

And I was like no, I'm done. And I went to the Upper East Side, which is where I got married the week of my wedding. And I went to all the grocery stores and bodegas to see if they had ice that they would deliver and how much it would cost.

And so I did that for my wedding, and I think I saved $20. Meanwhile, I spent like three hours on this little venture. And the ice didn't show up until about five minutes before all my guests started coming.

And [INAUDIBLE] hauling up these bags of ice in this beautiful mansion where we got married. It's dripping all over the floor. And in that case, it was like, I should have just spent the money.

You should have. But I feel like that's often-- that's what gets you in weddings or any big celebration is that you realize that the most precious thing during that celebration is your attention and time. It's what can you focus on.

And the more you're focused on little bullshit like x or y thing isn't being delivered, the less you're focusing on what you should be focusing on, which is this beautiful celebration with your family. And I will say for those who have ever been inclined to have a very small wedding, that is one of the nicest things about it because, at that scale, very little can meaningfully go wrong because even if you run out of something or you don't have something, that's still a number of people where someone can just run to the store. It's not a number of people that makes everything a mass bulk order.

And so that does relieve some pressure. Also, my wedding dress was $80, and I will never regret that as long as I live. That is really impressive.

I literally ordered it off of some random store online, tried it on. It fit great. Got it hemmed.

It was actually half as expensive to get hemmed as it was just to buy the dress. And I'm so glad because I-- first of all, white's not my color. Let's be clear-- but also, I felt like if I knew I was not going to wear that dress again, reasonably, which I wouldn't have for any wedding dress and I probably won't even for that one unless I get it hemmed or something, I could never justify that.

My ring I wear every day. A dress-- you wear it once. I would rent a dress if I wanted a really fancy one.

You what's interesting? The dress is another one of those things that I was like never had any kind of like, oh, I have to have this such and such dress. But then I tried on this fricking designer dress, and I was like, oh gosh, all bets are off.

They got you. They got you, Stef. I found it on Tradesy.

What is that? I went home and Googled it. So Tradesy's like Poshmark.

It's a secondhand site. And so the dress was new with tags, half the price. So it's still like $1,000, which is a lot but.

I'm trying to sell it now, so I'm hoping it'll be a couple hundred. Well, you looked stunning. So money well spent.

Again, something I was like, oh, I never thought that I would think this was worth it. But now that I wore it, I was like, wow, that was shockingly I'm glad I had that. I don't know why.

So for every time that expense wound up being more than I wanted it to be, I also kind of like countered it with something. I was like, OK, would do I really, really not care about? And I know flowers are a big thing for people.

But I went to the New York City Flower District the day before my wedding. I bought $200 worth of wholesale flowers. And I made a bouquet and some centerpieces.

And it was just like, OK. That paid for my wedding dress-- that trade-off. So I was kind of always thinking about it that way.

And I would say like the biggest expense we had was that we fed people eight meals over the course of the weekend. So that's all included in that $40,000. And I was like that wasn't about the food.

It was about the community and the time that those meals created for us to all be together for 72 hours. And for me, framing it from that perspective was totally worth it. I'm always blown away by people for whom the wedding food is kind of an afterthought.

It's a dinner, and its fundamental iteration. How many times have we had bad wedding food in our lives? And you're like the amount of money that you people are spending on this, I am sure that your dress costs just as much as everyone's meal.

And we're all sitting there eating really rubbery chicken and cold mashed potatoes or whatever. And it's like, wouldn't you want to spend the money on one of the few things that everyone gets to enjoy and partake in and remember? And it's also like-- that's another thing where it's like this is an opportunity to support local, small businesses.

My caterer was like Brooklyn-based local organic place. And I was like, OK, so not only am I giving people good food, but I'm also supporting local business. And that's the other thing about weddings is like unless you're going to a wedding factory, I mean, it is an opportunity to inject some money into local businesses.

We had-- we just did the thing where we just closed a restaurant for the day. And it was so sweet because the owners of this little restaurant in this part of France and the husband and wife owned it. The husband is the sommelier, like one of the lead sommeliers for the whole region.

It's a wine-producing region. The wife is the chef. Their daughter's the manager of the restaurant.

And their son is like business person accounting person. And so they were all-- we met with them a couple of times over the week before the wedding. And they were all like, we're refreshing the weather thing every single day because it was outside.

And they were so into it. They brought out all these special things. They brought out a big magnum of champagne to saber and all these extra desserts and stuff.

They'd never had a wedding in their restaurant before. They were so proud of everything because it was their family's stuff. And like you said, we'd never had a chance to really interact with a small business like that, but it was so meaningful.

It was wonderful. One interesting thing though I will say about you Stefanie is that you changed your name. And it's interesting because you're amongst the most, what I would say is stereotypically feminist people I know-- and I mean that as a compliment-- and you're also one of the only women I know who has.

And I know a lot of women, including myself, who've been married in the past few years. Explain your decision. Yeah.

So I decided to do an add on. I went from Stefanie O'Connell to Stephanie O'Connor-Rodriguez. And I wonder-- I think about this a lot-- I wonder if it was because my mom kept her name.

And it was just so difficult logistically growing up being like who is Natalie Danish. And it was that's my mom. And I had to convince people.

So that's part of it. And then I don't know. I just-- I don't really have a good-- I don't have a good story behind that.

Yeah, I feel like I hate this debate more than any other debate. And I ask, by the way, in a completely value neutral way. I'm going to change my name legally because I've never used, since I've been an adult, my actual last name.

Go ahead, creeps. My real last name is Chelsea Hunt. But there's a zillion of us, so good luck finding my old information.

But anyway, so I've used my middle name for like a decade, so my last name has no real meaning for me anymore. So I thought, why not? Because I feel like it should be, if anything, about the stronger association between a couple.

But as many smarter people than me have pointed out, like even if a woman keeps her last name entirely, it's just her dad's name. So it's not-- there's no escape from the patriarch. I know.

And then the hyphenated is also weird. I see people do it with their kids. But then it's like-- What are they going to have 17 names by the time they have multiple different children.

I think there's no right or good way to do it. And I wish I had some really strong conviction about why I'm doing something, and like I really don't. Queer couples usually run into this discussion.

And my now standard response is that you should just make something up, like we'll be Mr. And Mr. Fireworks.

Well, I like the idea a new name for a new family. That's kind of cute. Yeah.

Yeah. I just feel like there's been a-- I feel like it's kind of died down a little bit as a debate, but there was a while there where every other woman with a platform is writing a manifesto about why she wasn't changing her name. And the thing is that all that really does is inherently put an enormous amount of judgment on anyone who does change their name.

Right. And as you said, I genuinely was curious as to why you did. But the thing is, you don't really have a very compelling reason-- I don't. --for doing it, and I don't really have a very compelling reason either.

And the people I know who didn't, they also don't really have a-- it's all arbitrary. [LAUGHS] Yeah. There's no right answer here. Exactly.

That's how I feel about pretty much everything. There's no right answer to anything. There is no right answer. [LAUGHS] So speaking of things that people tend to be very opinionated about-- There we go.

So as I mentioned to you guys, Stefanie and I are from a very similar personal finance media world. And very prominent in this world is a community of people, often kind of umbrella referred to as the FIRE community-- although that doesn't entail a lot of it. But basically, these are people who aspire to reduce their costs of living to what many would define as a rather extreme extent in order to retire early or just to achieve financial independence, meaning that they no longer have to work if they don't want to.

There are many iterations of this. Some people do it with more flexibility, some people with less. But it's just essentially a way of recentering your life around the idea of needing and using much less in order to have more and more freedom.

Would you say that's a fair definition? I think that's right on. Yeah.

I know some of you guys are going to scream at me in the comments-- Yeah. Of course. --no matter what I say. Of course.

But listen, fudgers-- We're talking about FIRE. We're just opening that door. Yes.

So you are not FIRE. No, definitely not. Definitely not?

Tell me why. I really love my life. And I-- I love the implication that FIRE people don't, which I think is true.

Well, yeah. [LAUGHS] I just think the entire premise-- so much of the premise of FIRE is kind of also saying that I will be happy when I accomplish this. Right And I know that a lot of people are going to come at me for that. But I just see that play out again, and again, and again.

And I'm like, well, why are you not going to your friend's wedding so that you can hit this benchmark? Is that really a trade-off that makes sense? It's one thing if you don't go to your friend's wedding because you have, like, $100,000 in medical debt and you're just sort of like, that will only give me stress.

But if you're like, oh, I have $500,000 in the bank, and I want it to be $500,000 plus $100, that's why I'm not going to the wedding, that doesn't feel like a good trade to me. Some people would be like, oh, you live in New York City, that's a waste of money. I don't think it's a waste of money.

I love living in New York City. It brings me joy every single day. Does it mean that I probably don't have as much in savings as someone who is FIRE?

Yeah. I don't have as much in savings as someone who is FIRE, but I'm also happy every single day. And I think there's just so much about this idea of deferred gratification in FIRE that, to an extent, that is not necessary.

And I think it puts so much pressure on your FIRE date to be everything, to be all the things you wanted to be, like you're going to self-actualize when you hit that number, rather than kind of self-actualizing along the way. I think that's very accurate. And to be fair, obviously many people who live in areas with much lower cost of living can be brought joy by that place as well every day.

Oh, absolutely. Yeah. Although, I will say people feel uniquely liberated to shit on New York City to New Yorkers while in New York.

I know. I've, had relatives be like I could never live in New York, while in New York with me. And I'm like, oh, really?

Because I could never live in your shithole suburb, Aunt Who I Will not Name. It's also my mom constantly says, why don't you move back home? Think of the money you could save, think of blah-blah-blah.

But it's, like, both me and my fiancee's jobs can be done in maybe three cities on the Earth. And I wouldn't be able to make what I'm making. And it's none of your business why I'm doing it.

It's truly none of your business. I like where I live. When you come visit it, tell me the things you like, and keep to yourself that you're like, it's dirty and I don't like the subway.

Well, OK, I don't like driving, and your town has nothing going on. [LAUGHS] Yeah. And I would never independently volunteer that information. When I go to areas that I would not necessarily live in, I go out of my way to try and find nice things about it, you know?

But yeah, people feel really uniquely able to shit on New York. But I will say, with regard to the FIRE thing, I totally agree with you. I also think that it really takes, as a non-negotiable given, that we have no such thing as a dignified retirement in this country.

Mhm. In so many other wealthy countries, the idea that everyone gets to work, and then gets to enjoy many years of their life with financial security and dignity, that's just a fundamental social agreement that we're all living with. And here, we don't have that.

And for many people, something like a FIRE is a necessity, especially if you have higher aspirations for what you want to do in retirement. I don't think we should all be just accepting that as a given. And I don't think that the answer is just operate around that as much as you can.

And I don't think the answer is at all just kind of accepting that and radically redefining your life without, at the very least, interrogating how we could maybe move past that as a need. Because things like a really comprehensive social security don't materialize out of nowhere. They happen because we demand them and other societies demand them.

And I don't think it's out of the realm of possibility for us to have those things. But I think the more we focus on how you can maximize your individual success within a broken system, the less we're focusing on what should be I think-- because I think everyone should have access to a life that is somewhat balanced between those things. But I also think that where I really agree with you and I have a lot of thoughts is this idea of framing your life as almost a before and an after, as a working-toward a living-with.

And I feel like, as you said, life is going to be full of opportunities, and moments, and joy that may cost money-- more than you want to spend-- at an inopportune time. And if your entire life is being framed through a prism-- even subconsciously-- of this is when I'm sowing and this is when I'm reaping, life isn't that way. You can't time your joy.

There's also the people who are like, travel a ton, do not not travel, you have to have kids by the time you're 30. Also, you should be doing FIRE. Also, please don't spend on-- and it's, like, yes, I want a mix of those things that's right for me.

But I feel like whenever anybody names their philosophy, there's a judgment for everybody who doesn't and looking down on, like, well, I'm FIRE, so I'm going to be fine. OK, well, that's right for you. And I'm really happy for you.

But for me, my life has to have a mix of those things. I have to be able to travel, have some security, eventually have kids. I don't want it to seem like we're passing judgment on these people.

I also just don't want anyone to pass judgment on the reasons why I wouldn't do that. Right. I think one of the flaws in FIRE for me, too, is that it always assumes there's going to be more time.

And to me, time is the most precious resource that any of us have. And you could die before your FIRE date. Exactly.

We could die before our FIRE date. We could come down with a chronic illness, such that we are just completely unable to do all the things we had kind of deferred for FIRE by the time we hit it. We could get a divorce and see all that wealth we accumulated just kind of go away.

And I don't know that-- FIRE doesn't seem to kind of take into account a lot of those things, and it also just assumes that you're going to be healthy and have time forever. Of course, I know that's not true in every case. But I just see kind of, in the dialogue, around it, that's the assumption that's built in.

And I think it's a really scary assumption. I agree. And I think also that when you think about-- so I understand, on a purely intellectual level, why FIRE the most popular framing amongst a lot of personal finance writing.

And obviously that's anecdotal. I don't have the data to back it up. But being in the industry for a long time, I think we can both say that, as far as a prism through which to view money and to view your choices with money, it's at least amongst the most popular approaches.

And there's a lot of overlap as well with the minimalism, for example. Mhm. And I understand why that is.

I understand that we live in a situation where, for many people, living that way is one of the only sure pathways to the kind of retirement that I think a lot of people would want. And let's be honest, a lot of people hate their jobs and would like to reach a place where they no longer have to work at that job every day. But I also think, when it comes to something like, for example, wanting to not have to commit to your job through what would be a normal retirement age-- like you want to stop working maybe at 35-- I wonder why it's not a more popular framing or interrogation to say, well, what if I were to find a job that I didn't hate as much, and would feel more content with doing for a longer period of time, and could, therefore, a little bit better diversify the amount of spending I was doing at various points in my life, and not be so dependent on that number?

Because for many people, it's maybe not even a different industry. It could a different workplace. It could be maybe finding a job that allows you to work from home more frequently or finding a job that has a better work-life balance.

My husband used to work in an industry that was really, in many ways, destroying his mental health. It was very taxing. He traveled on a plane four days a week.

And he thought that he hated a lot of what he did. And he realized, when he got a new job that use many of those same skills and was similar in some ways, but didn't have those elements, that it was really the context of that job. And at that time, when he was working that job, he himself was very interested in FIRE because he was like, I would like to be 35, 40 and be able to be free of this.

And now he's like, I don't know what I would do if I didn't have-- I love my team. I love what I do, you know? Yeah.

And I think that just makes it more accessible. A lot of the way people who are FIRE spend their time is exactly how I spend my time. The only difference is I don't have $5 million in the bank.

I do need the money. Yes. But once again, if I were to just prioritize having $1 million in the bank kind of at the expense of everything else I spend my money on, I don't know that I would have the quality of life and the joy that I have along the way.

And that's not a trade I'm willing to make. And I think asking people to kind of just defer this gratification, it is maybe not necessary. To your point, maybe it's just a change of work culture.

Maybe it's much more simple and much more accessible. And I think that's the other piece of this puzzle where I think the criticism of fire is legitimate, is that a lot of this is not accessible to a lot of people. If I'm not coming out of college and making a six-figure salary and with no cost of living-- there are people who do it.

I'm not going to say that there's no pathways, but there's a lot of privilege that goes into that. And I think that's the other part of FIRE that can be really dangerous and make it feel really hopeless to people who can't access it. I think also that it's important to consider, when you're talking about solutions to financial problems, how scalable is it?

And I'm sorry, but just on a purely functional level, you couldn't have 100% of the population stop working at 35. That doesn't make sense. Yeah.

But the idea just on a societal level-- and you could debate this with things like universal basic income, but I don't think that nearly would address the fundamental issue that a society in which 100% of the people stop working around the age of 35 just doesn't scale. It doesn't make sense. It's not possible.

And it's also, as you mentioned, not a necessarily desirable life choice for huge portions of the population. So what you're really kind of inherently saying with this kind of advice or this kind of approach is that this is for a certain elite. This is for a certain number of people who can do it, but it doesn't rethink in any way how we get to the place where something like that might be necessary or what the vast majority of people could do-- including, as you mentioned, people who have things like massive debt and really low income.

Right. So I think when I-- and again, this is no judgment to people who might approach life that way. I think I have a lot of philosophical disagreements with it, but I just wish it weren't, as much as it is, such a prevailing narrative because I think it leaves a lot of people cold.

And speaking of how we talk about money, it's really important that we don't just talk about it, we have the right tools to master it. And one of the best tools you have on your side for everyone from a full-blown small business owner to someone who's just doing some side hustling and freelancing in their off hours is something called QuickBooks, which I personally use every single day. It is an amazing tool that has an extremely easy-to-understand-- even for idiots like me-- interface that shows you all of the different parts of your business' financial health.

It shows you what you owe, who owes you, your cash flow. It helps track and sort your expenses for things like tax time. Basically, it just makes what is an honestly overwhelming task, which is managing the finances of any small business-- and if you are freelancing, you are also a small business, and one whether you like it or not-- into something that feels actually manageable.

And I very sincerely could not do any of what I do at TFD everyday if I didn't have it. So check out QuickBooks for yourself at the link in our description and our show notes. So clearly, neither of us ascribe to the FIRE philosophy, but what philosophies of money do you ascribe to?

Hmm. So I don't-- [LAUGHS] I don't mean this in a minimalist way, but I could almost say that my philosophy on money is a little bit [INAUDIBLE]. Mmm.

And I really like to spend money on things that bring me joy, and I really don't spend money on anything else. That's interesting. I spend money my necessities.

So is joyful for me to pay for health insurance? Not really, not in the traditional sense that we think of it. But being able to go see a doctor without stress, that's how I think about it.

That brings me joy, especially because I've been in a position where that was not the case. So yeah, it brings me a lot of joy. Peace of mind brings me joy.

My apartment that I live in with my husband on the Upper West Side, where I live between two parks, every day, I live in that. And I'm like, this is the best thing ever. I can't believe this is my life.

It's like a dream. Other stuff I'm pretty ruthless about. I haven't paid for a haircut in 15 years.

I go to a beauty school and have somebody cut my hair. So it's just-- Lucky for you to be able to do that, because not everyone has that hair type, also. Yeah.

No, totally. But it's like I'm just into what I'm into, and I'm not into the other stuff. So that's really kind of like a driving philosophy.

But all of that also is just made possible that I'm at a certain level of income. That was not a philosophy that would have worked on my income when I was just starting out, right? My income was so low that I was kind of just trapped.

There was nothing more than necessities. There was, like, no room for joy. So I think the other big thing for me is income really matters.

And we can talk about managing our money all day long, and I think that's really important, obviously-- I write about it for a living. But you can't out-frugal your way to rich. I think I said this at a talk we were at.

Yes. It's true. But I always come back to that.

It's like, unless you're earning a threshold amount of money, there really isn't the flexibility to move past that just constant level of stress to really start aligning your spending with your values. That requires a certain threshold of income. So I'm very, very bullish on earning.

Yes. I agree, absolutely. I think it's always easier to add a revenue stream than it is to further and further reduce down your expenses.

Obviously, on some level, you should do both. But I do think that it's very important that you not ever get to a place where you're actively sucking the enjoyment out of your day-to-day life in service to a financial goal if it is an option-- because it's not for everyone. Exactly.

But if it is an option to increase some revenue. I very much agree with everything you said. I feel the same way.

I'm very much, though, I will say-- my prevailing philosophy with money is that it is meant to be shared in every sense, whether that's in terms of-- and we'll talk about the finances of business, but whether it's in terms of paying people fairly that work with you, or hosting people, helping people, buying them tickets to things, especially like, for example, if you have members of your family who maybe you don't have as much to make sure that they can-- or friends, that everyone can participate, inviting people places, doing things. And I'm very extroverted. I very much enjoy spending time with other people.

But however that manifests, I think keeping a situation in which your money is as much going around you as it is to you keeps you grateful, a little bit staves off that lifestyle inflation-- which is very important to me, personally, because I'm easily sucked in by it-- but also, really, to me, what else is money for? You know, it's really interesting you say this. Because one of the things I really struggled with as I started earning more money was being able to spend it.

And I-- Not me. [LAUGHS] --my husband, now, he really helped me with this because we were kind of different. He always spent what he earned, and I was like, save, save, save. If I mistakenly dropped a $20 bill somewhere or spent money I didn't need to spend, I would have a full-on breakdown.

I would cry. And I was just so trapped in feeling like there's never enough. And even as I started earning more, I was still trapped in that to the point that I just kind of was a hoarder of money.

And it was so unhealthy, and it brings me back to kind of what we're talking about-- trends in personal finance in general. I actually see this trend a lot in a lot of personal finance literature. It's as if money wasn't meant to be spent or shared.

And that's another narrative that I think is really destructive, and I've done a lot of work to really work on myself and be OK with spending money. I don't file my taxes in another state. I file my taxes in New York City, and I know that that comes with a lot of added expense.

But at the end of the day, I believe that it's worth supporting my city resources. I run in Central Park every day. That's not free, right?

Yeah. No, absolutely. So that's really changed my mindset personally about everything from tax rates to how I'm personally spending.

I don't pay people overseas $2 an hour. Everybody on my team makes at least $20 an hour. I have people who make a lot more.

And there are ways to do things cheaper, but to your point, money is meant to be spent and shared. And especially when you're in a position when you can afford it, you should. Yeah.

Obviously, another common example of that is donating money. And also, by the way, I think, in many cases, donating time or physical resources is more valuable. So if that's not something that's accessible to you, giving your time is also a great way.

But it doesn't have to be that literal. And I think even if it's something as simple as a friend of yours had a really terrible day at work, and you take them out to a nice dinner, and you say don't worry about it, moments like that, to me, are what people remember. It's what makes people feel like they're not as alone.

And money should not be a love language, in the sense that it should not be the currency by which you communicate your love. But if it can facilitate you making both your and someone else's life more joyous, less stressful, any of these things-- we've spoken to people on this show who the first thing they did when they got a big amount of money, if they came from families who didn't have a lot, was buy something for their mother-- buy their mother a house, buy their mother a car, nice clothes to be able to wear to work. And I guarantee you that every penny spent on that felt infinitely better than anything they've ever bought for themselves, you know?

And I agree with you that a lot of the framing of money, and how we handle it, and how we manage it is so atomized. Yeah. It's so about you, your network, your personal-- and I don't want to die with $10 million and no friends or no one who could ever say that I was a positive influence or that, you know-- because I remember what it felt like to have no money and to feel deeply ashamed and isolated.

And I remember what it felt like when I made my first friend who was wildly outside of my income bracket. I started by working for her. That's how I got to know her.

And I just remember how much she never made me feel badly about it. She always compensated for that differential. She was always putting herself out there and making sure that I didn't ever have to feel embarrassed about it.

And in many ways, that changed my life, having a friendship like that. I'll also point out that you have to work within a budget. Don't ever spend what you don't have, but there are times when spending money in a way that is enjoyable can also be an investment, not just in your personal life.

There are co-workers that I'm friendly with. We obviously have boundaries of being co-workers. But if you can go to dinner with them once a month, and just check in, and be like, how is it all going, what products are you working on-- if you can take people out around the holidays to be like, hey, we're going to do a holiday dinner or whatever on me-- people that you work with, clients, family members, people you want to network with-- and not make it so that it's like, oh, can I pick your brain, get you a cup of coffee, can you answer all these questions over email, but actually make it something that you're having fun, you're having a good time, you're also sort of networking and making friends.

Building out that network can be going to see a Broadway show together or a movie together. You might have spent that money on something fun anyway, but creating a network of professionals who are genuinely friends with each other and interested in each other's work has changed my entire life. And that has been the thing that I've been so happy about because I meet all of those friends because I genuinely wanted to be friends-- they were only my friends.

But it's also a lot of people have come to me and been like, do you want to collaborate on this? Or I can go to people and say, hey, I know you're really good at this. Can you help me in my small business, get this done?

And creating those relationships, it's fun, and also it's a good way to build up some sort of like foundation for yourself professionally. And I think a lot of the time that gets overlooked because you just go on Mint, and you see that I went to this many restaurants. And you're like, well, I can't go out to eat anymore.

And it's like, well, some of those were a good investment. Oh, yeah. Totally.

I think the ultimate thing-- and this is exactly what you said at the beginning. Money is essentially just a means to live a life that is meaningful to you and hopefully can be positive for others. But the more we think about money just in terms of the raw dollar amount, the more we lose the picture of what it's actually doing for us.

One thing I like to say in alignment with that is, if you have the money to afford your basic life expenses and you have a little bit of flexibility, the bottom line isn't the number. The bottom line is the value. And so if we kind of reframe the discussion from that point of view, I think that's really going to encompass a lot of these little bits and pieces we're talking about.

Yeah. And you'd mentioned earlier, we wanted to touch on, a little bit, just kind of the finances of running a business. And one thing that I've really learned is that putting more money just into your own pocket often exacerbates any stress that might be involved in a business.

Because in many ways, when you're running a business, when you're building something, when you're investing in something, that money in your own pocket is where it's going to do the least good. It's going to have the least impact. Yeah And I'm curious.

I know you're someone who's very big on investing in yourself, investing in your business. Do you feel like it took you a long time to figure out what was and wasn't a worthy way to spend your money, business-wise? You know it's really hard about figuring out what's worth it in your business, is that every time-- hopefully, your business is constantly upscaling.

And so what's worth it is always going to be different. And it's like, for me, I find-- I know if you find this-- it's a constant learning process. Yeah.

And I have a lot of things that I've learned about my personal finances. But when it comes to small business finances, I feel like I am on a roller coaster ride every single day. Really?

Yeah. Because business is great, but cash flow is just so difficult. And to your point, I love to invest in my business.

I love to hire people. I love to-- to what we were talking about with weddings, I love to infuse money into the shared space and into the shared objective. And I don't think that's a waste of money.

I've had a lot of growth and things are going well, but it definitely creates a lot of stress about, OK, well, if this amount of money is going out on a monthly basis, but then this client payment isn't coming in for 90 days-- if they stick to their terms-- [LAUGHS] then how do we balance all that? And do these investments make sense now, or do we make them later? And once we're at later, we might be at a different point in our business, where we have a different objective.

So there's just these constant questions of reassessing, I find. It's also shocking-- this is going to sound like such a fake plug. So we've very-- it's true we very frequently use QuickBooks small business loans when we have that situation where we pay a bunch of people.

Because we always pay within 30 days, because we're respectful of other people's time and effort. But you'll have clients who pay on 90 days, and 90 days is more like 120 days. So you'll be in a situation where you have a whole month of payroll and five huge checks that aren't coming in.

And so now it's like we never ever worry about that anymore because you put in the, in this case, QuickBooks-- sorry, it's true-- loan and you get that cash immediately, and you pay it right back. But it's so hilarious how, when you most need that money, like when we were just starting out, and we had nothing, and a $5,000 loan would have been life changing, you can't get it. And obviously, I understand the machinations behind that and why it makes sense.

But if you didn't have access to something like that-- and I've known what it's like to not have access to it-- that is the biggest pain point by far because it makes every single month into a complete nail-biter. Yeah. And it's the difference-- especially when we're talking about big contracts, a difference of one day can be the difference between-- Oh, absolutely. --being able to pay 10 people and not.

Yes. And that's kind of a different level of stress and just gymnastics that I can't say I have an answer for, you know? I do build-- I have a business emergency fund.

I have a personal emergency fund that kind of serves to kind of deal those little cash flow challenges, but it's hard when something is a lot of money. [LAUGHS] I had to just straight up stop thinking about it. Because so, basically, just like running a month costs, like, 100 grand. And I'm just like, don't think about that number because it'll send you to an anxiety spiral from which you will never recover.

And you make it work, and the business builds, and these numbers become more and more abstract because it becomes more normalized. Right. But when you actually stop to think about it, you're like, holy shit, I'm on the hook to earn so much money that it seemed inconceivable.

And so you even have that lifestyle creep in a business. And to be fair, one thing that has been very helpful in business that I think is equally helpful in your personal life is taking time-- we have two budgets. We have the good month budget, where we're firing on all cylinders, where we're reinvesting a ton, we're doing a lot of nice-to-have stuff, and then the minimal budget that we can squeak by, delay payments.

Even I won't pay myself that month. I'll wait if we need to. And you know the differential, and that can help you [INAUDIBLE].

That is so smart. Yes. And so it's a huge difference.

Because we are very much where-- and I know you are as well-- we're all about reinvesting in things and making things as good as they can be. But for example, we'll spend-- I don't even know exactly how much, but probably around 10 grand a month just on social media marketing and things like that. And that stuff, some of it we're obligated to spend, but a lot of it we're not.

A lot of it is just because we want to get our stuff out there. And so that's the kind of thing that we can turn the throttle down if we need to. There's a lot of more discretionary spending.

But unless you take the time to separate that out and be like, what do I absolutely need-- like payroll, duh. We pay year-to-year in our office, so at least we don't have rent. But if we had rent, rent.

Mhm. There are certain things that are an absolute-have-- must-have. But if you don't do that, everything feels like you must have it.

Everything feels essential, and that's when it becomes much more overwhelming. Because you can't even differentiate in your own mind the value you're getting out of these things. Exactly.

And to your point, this totally applies to the personal stuff too. Absolutely. And that's basically the way I survived for the first 10 years of my adulthood, was what's my absolute most basic cost of living so that I can just break even?

So there are some skills that do transfer from personal to business, but I do think business is another ballgame and there are things, like rules of business money that a lot of people take for granted-- that revenue is not the same as your income. Oh, absolutely. Absolutely.

Right? But when you first start, when it's just you and you're writing a freelance article for someone, you think, OK, well, this $250 I just made is my income. But no, I have to pay my taxes out of that, I have to pay my web hosting fees out of that, I have to pay all my stuff.

So I think, from the start, anyone who is thinking about starting a business, or freelancing, or whatever it is really needs to start creating that separation from the very beginning. Absolutely. And if you earn any money that's freelance, keeping in mind that, again, like I said, we go out of our way to pay people in a very timely fashion, but most people do not.

And you have to get used to the idea that just because you signed the contract for something today, you may not see that money for six months. Absolutely. We've had situations where clients were literally six months late on paying something substantial.

Oh, yeah. I've been there. [LAUGHS] And we were like, listen, you're a huge corporation. We clearly have no leverage against you.

But on a personal level, this is fucked up. You don't know how hard I feel right now. [LAUGHS] It's so frustrating. Because I'm the same way.

I pay everybody immediately, and I think it's because I've been scarred by waiting on these things. But it's like the bigger the company, the longer it takes to get paid. I don't know why.

Because they know can. Because that's how these people operate, and they know they can. But so while I still have you, I have a few rapid fire questions that I love to ask all my guests if you're game.

Oh, yeah. Of course. It'd be hilarious if someone was like, no thanks. [INAUDIBLE] no, thank you.

So now for the rapid fire questions. Do do do. [HUMMING FANFARE] [GIGGLES] What is the big financial secret of your industry? I think money is a lot easier than we make it out to be.

I think a lot of people get caught up in the, oh, what's your take on the markets, and options, and swapping, and trades? And it's like, really, if you just spend time looking at your bank accounts and dedicate maybe an hour once a month to reading something about how to improve your financial life, you're going to be pretty much in a good position, right? Yeah.

Circumstantially, I can't change anything that happens to you if you get hit by a bus and your insurance doesn't cover it. Yeah, that's a real obstacle. But when we're talking about like being good at money, it's not that you have to be a math expert or anything like that.

You can be good at money just by dedicating the time to actually sit down and manage your money. Also, even the brokers can't predict stocks. I know.

And actually, a lot of people who work in finance are really terrible at managing their own money. A lot of them are dumb. They're super niche specialists at some very specific thing, but they don't even know their basic cost of living. [INAUDIBLE] common sense stuff.

Yeah. I'm always blown away when I encounter a dumb lawyer. And there are a lot more of them than you would think there are.

What do you invest in versus what are you cheap about? I spend money on fitness and food. Maybe not surprising since that we've talked about our fitness routines before.

So I love-- My fitness routine. [INAUDIBLE] [LAUGHS] I also run, which is [INAUDIBLE].. [INAUDIBLE] I use ClassPass. I don't if I can say that. I use Class Pass.

So I do the cheap version of the getting the access to the really fancy classes. So it's like I pay 80 bucks a month, but I leverage it so that I get, like, five to six $40 a pop classes, and it's fantastic. She's like the annoyingly fit person in [INAUDIBLE].. [LAUGHS] Also, what do I not spend money on?

I spend almost no money on beauty. I don't get my-- Because you're so beautiful. --don't get my nails done. I was going to say, some of us don't have to. [LAUGHS] No, please.

I just mean I got my nails done for my wedding, but that's pretty much it. I don't color my hair. Every time I go to get a haircut, they're like, are you sure you don't want to cover these grays?

I'm like, I'm good, thank you. Are you going to be one of those women who very chicly goes gray and leans into it young? I love that.

Probably. Not I'll probably get more vanity with it. I follow a lot of grayfluencers.

I love them so much. And they're-- Maybe if I had a streak. Yes.

Like [INAUDIBLE] London. [INAUDIBLE] Yeah. Love that. We'll see.

My grays have this weird texture, and they pop up a little bit. Oh, yeah. It's not cute. [LAUGHTER] What has been your best investment and why?

My business. It's like the most obvious thing to say, but everything I now have I owe to my business in terms of just the peace of mind I have in my day-to-day life. Where I live, the way I am able to spend my time going restaurants and all the things I really like to do, it's because I grew my income substantially through my business.

Love it. What has been your biggest money mistake and why? Hmm.

This one is always really hard for me to answer for some reason. I feel like I just made a lot of stupid mistakes, but they weren't big. So I think for a long time, I just accepted that I was not qualified to earn any money, and I didn't-- Hmm.

Underestimating yourself. Yeah, but big time. And kind of just accepting that I didn't have the right degree, and I didn't have the right experience, and I didn't have the right connections or anything to earn more than $30,000 a year.

So I was like, well, I guess that world is not accessible to me-- the world of peace of mind. And that's not great, as in I don't have the good credit card story or whatever it is. But to me, that was the thing that most changed my life was kind of getting over that-- that I always come back to it.

I feel like that holds people back more than most things-- Yeah. --is not feeling entitled to a certain kind of life. Right. What is your biggest current money and security?

Running a business. [LAUGHS] It's funny because running a business is simultaneously the thing that's enabled so much of my financial success, but it's also my biggest source of financial stress to this point of, oh, well, we have uneven cash flow, or, is this investment going to be worthwhile, or, what if tomorrow I get sued and it all comes crashing down. [LAUGHS] There are certain things like that that I'm just like, I can't think about it. Not going to think about it. I know.

So it used to be health insurance though. OK. So coming back to my wedding-- I know we're on rapid fire, but the best gift I got was really the fact that I could join my husband's bomb union insurance.

Should have gotten a domestic partnership beforehand to get the insurance without the baggage of marriage. I tried. Wait, did you qualify for this?

Yes. I tried to get this. The union was like, we don't recognize that.

What has been the single financial habit that has helped you the most? Tracking my money. Bam.

Not to get so much of a direct plug, but it's true. It's like-- Mint? All the ways, actually.

I use the technology, I use pen and paper, and I use a spreadsheet, and I reference. Because to me, that is really a mental health practice. Because so much financially with business ownership and even before I was a business owner, with freelance and uncertain income was feeling out of control-- but tracking my money is something I can control.

Out of curiosity, what program do you use for your business? I use QuickBooks. [LAUGHS] I also have an accountant. [MAKES BUZZER SOUND] [LAUGHTER] Listen, it's true. It's the best.

Last question. When did you first feel successful, and what does that word mean to you? It sounds stupid, but I think it's one I took a cab to the airport. [LAUGHS] That is such a New York answer, oh my god.

Because I can't tell you the lengths I have gone to avoid paying for things like transportation in the past, because I was like, this is something I could do for free or for, like, $2. But now, it's like, all right, I'm going to pay 30 bucks instead of taking three trains to get to the airport. And I was like, wow, I can't believe I just did that.

If you know your New York geography-- but you could also look at this on a map if you don't-- I live in Morningside Heights. And you look at that, and then you look at where JFK is, it is an epic poem to get to JFK on public transportation. No thanks.

Paying that money. When I lived in New Jersey, I went from Jersey to JFK. I took the bus from my house to Penn Station area, got on the A train, then took the JFK tram.

It was, like, a two hour trip. Oh my god. Man, yeah, that's a no-no for me.

Yeah. Well, thank you so much for being here. Such a joy, as always.

Oh, it's so fun. I love talking to you. Where can people get more of this greatness? [LAUGHS] OK.

So I'm online at Stefanie O'Connell everywhere., Twitter, I'm all over. Awesome.

Well, thank you so much for being here. And thank you, of course, to our amazing partner, Intuit. So as we mentioned, a considerable number of times today, QuickBooks rules.

Basically, QuickBooks is the biggest tool I use on a day-to-day basis to understand the finances of my small business. And even if you are just someone who's got a couple different streams of income, that is a little, tiny business of its own. It takes everything from the process of invoicing, to tracking your expenses, to your profit and loss sheets, and makes it so much more easy to navigate and keeps it all in one very coherent place that even I can understand.

And it's one of those things that makes the rest of my day and all of the other stuff that comes with running a small business feel way easier because I know that the finances are being tracked with a tool that I can understand and that helps me make all of those little, tiny decisions and all those little tiny reminders that I can personally be liable to forget. Running a business is hard enough. And frankly, you don't want to have to add the chaos of managing your own finances of the business all by yourself without the right tools.

So I could not recommend QuickBooks anymore. If you want to learn more about QuickBooks for yourself, just check out the link in our description and our show notes. [MUSIC PLAYING]