Stefanie O’Connell is a millennial money expert for women. She is a nationally recognized millennial money expert and author or the book, ‘The Broke and Beautiful Life’. Stefanie has appeared on CBS News, Fox & Friends, ABC World news, and the Dr. Oz Show. Her work has been featured in outlets like The Wall Street Journal, The New York Times, Glamour, Success Magazine, and Oprah Magazine.


Stefanie went from the life of a struggling artist in New York City to feeling fed up with being constantly broke, to tracking all of her own personal finances and becoming an expert in the field. She now has an audience of millennial women that she helps take control of their finances.


Tune into this interview to hear how to: 

  • Get out of the pattern, both financially and mentally, of simply struggling with money.
  • Use any transformation if you’ve had in life to teach others to heal their own struggles.
  • Manage your money while self-employed or around your side hustle.
Stefanie O'Connell is a millennial money expert for women. Here's her journey out of the struggling artist persona and into entrepreneurship and personal finance expert.


Podcast Episode


Transcript of Episode

Leah Gervais:

You’re listening to Your Biggest Vission. I’m your host and this show is designed to expand your vision of your business, your lifestyle, and of course what’s possible. Enjoy the latest episode and thanks for tuning in.


Hey visionaries. Welcome back to the Your Biggest Vision Show. I am your host Leah, and I’m very excited that we have Miss Stephanie O’Connell here today with us. Stephanie has a fabulous story that she’s going to share with us about pursuing  her vision, building a business and really staying true to herself. Stephanie and I, we live across the park from each other, actually. We are both NYU alumni and the biggest differences, your musical theater career made it a heck of a lot further than mine, which ended in like singing in the shower when I was 14 so I’m excited to hear more about it. Thanks for being here.


Stefanie O’Connell: Thank you for having me.


Leah Gervais: So I’m just going to read a quick introduction to you and then we’ll hear from you. So Stephanie is a nationally recognized millennial money expert and she is the author of the book, “The Broke and Beautiful Life”. She’s appeared on CBS News, Fox and Friends, ABC World News and the Doctor Oz show. Her work has been featured in outlets like the Wall Street Journal, The New York Times, Glamour, Success magazine, and Oprah. Congratulations. So Stephanie, you didn’t go to NYU for finance?


Stefanie O’Connell: No, definitely not.


Leah Gervais: So walk us back a little to what you thought your life was gonna look like when you were in high school?


Stefanie O’Connell: Oh my gosh, it’s crazy. I saw some 16 year old kids the other day and I was like, wow, that was half a lifetime ago. Everything I thought was going to be is so not what I thought it was going to be. It’s so different and yet it’s so good. So basically in high school I just thought like I was gonna be quote on quote “starving artist” with hopefully these moments of success where I would hopefully do some Broadway shows and then kind of hustle in between and live that dream of the actor life even if that wasn’t totally glamorous. Then fast forward, I don’t know, five years and I’m out of school and actually doing it, and it was great in a lot of ways. I did get to live that dream a lot. I got to see the world. I got to sing on stages all over America and Asia and I worked on a cruise ship.


I mean I did so many fun things and I have no regrets about them. But the lifestyle of that constant hustle and not hustle in a way that you’re feeling like you’re making progress but hustle in a way that you feel like you cannot survive if you stop for a second. That sucked. It was constantly like, oh, I don’t know if I can go to your wedding because I don’t know if I can afford it. So it wasn’t just about like what I couldn’t do for myself, like pay medical bills. It was about what I couldn’t be a part of with my family, my friends and my community and the things I really valued. So it really taught me that, you know, doing what you love is not the same thing as having a lifestyle that you love and that really started the shift for me and to recognizing the value of money, having it, and then wanting to understand more about it.


Leah Gervais: Great. So walk us through that moment and I’m sure it was maybe several moments, but when you start to realize this isn’t going to work, like this isn’t going to be my career. It takes a lot of bravery to pivot like that. Especially when you did go to school for something and in probably a lot of your peers eyes, you had, you made it, you know, you were doing so well. So was it scary and what were the signs that lead you toward making that decision?


Stefanie O’Connell: So I had a lot of moments, like you said, it wasn’t like a single moment that made me think, oh, I need to pivot. It was just the constant having to opt out of things. I did have a few major things, like I had an incident with my teeth were, I had to get a dental implant and I couldn’t afford it and it was like $2,000 and I’m just like in the dentist chair crying because of money and I couldn’t stop myself. And I’m sitting there, all these people are looking at me and I’m like, I was so overcome with overwhelm about how to deal with that and I felt so helpless and at the mercy of my money and I was like, God, I don’t want to feel this way ever again. I had a lot of moments like that. You know, I was in a relationship and I wanted out and we lived together because he know in New York it’s much cheaper to live with somebody. You split the cost 50, 50, but then I couldn’t afford to pay 100% of our rent by myself. I just hated that feeling of being trapped all the time. I would say that in terms of feeling fear, I think acting was one of the best lessons in facing fear because there’s constant uncertainty, constant rejection and because of that, everything else is easier. Not that it’s easy, but I have no qualms about being myself out there. Or doing something that might feel like a little risky and I know that’s a big thing for people, but life was already so unstable, everything else was just much simpler. *Unable to transcribe*.


It’s like, well, if I didn’t do a Broadway show then I failed at this and that’s hard to accept. So how I’ve thought about it is that I don’t *unable to transcribe*. I’m still in the actor’s union, any day that I feel like it, I can wake up and go to an audition. I just never feel like it. That said, I did do a show last year after five years because I had done it before and they just asked if I could do it again at the audition. But that was just like such a manifestation of this idea that it’s not about choosing between two things. It’s about continuing to pursue just another facet in tandem with its other part of me. And that made it a lot less daunting to walk away from or really not walk away from.


Leah Gervais: I love that. That you didn’t really have to choose at all. So do you counsel any other musical theater people or actors here in New York because the struggling artist thing is real. Do you ever sort of give advice to people and if so, what advice would you have to someone who like is broke, over it, you know, just not knowing what to do?


Stefanie O’Connell: Yeah. So I talk mostly personally to my friends and colleagues. So I’m still really involved in the community and there are a couple things, but they mostly have to do with mindset. This whole idea that, that you have to struggle to be an artist or that pursuing anything for money is inherently bad or makes you less of an artist. That’s something that I definitely dealt with and I kind of accepted like the starving artists as my status. But I never looked for jobs that were not babysitting or personal assisting or waitressing. And those are fine jobs, but they’re not going to make you wealthy. They’re not going to like build you a scalable income that really you can control. So I didn’t realize I could do that even if I were pursuing acting, in fact, a friend of mine, he’s still a full time actor, but he runs a full business with 12 employees and they give tours around the theater district about about shows in different theaters. So it’s like a Broadway walking tour and that’s such a great example of somebody leveraging their skill set and their knowledge as an actor and using it to build something that’s going to be more sustainable and it’s going to allow them more freedom to pursue their artistic endeavors.

Leah Gervais: Yeah. Amazing. I love that. I love the thinking out of the box and I hope that it’s becoming more prevalent in any industry that has, or really any community that has this praise of poverty mentality in whatever form it manifests that you can actually make money in a lot of different ways and still do what you really love. So you are at this point now where you’ve been featured in the New York Times, you’ve been on lots of TV shows, you’re a nationally recognized expert in personal finance, especially for women. Was there a moment where you thought, this is what I could do with my career and really set out to start your business and that really intentional way, or was it just a result from you on your own personal finance journey that then people started picking up? My guess is that it might be a little bit of both, but just walk us through that time.


Stefanie O’Connell: Yeah, so I initially started getting into personal finance for myself and trying to learn along the way. In doing that, I discovered the world of blogs and blogging and this is around like 2013 and I did not know that personal finance blogs were what they were, I just thought it was, I just thought it was my novel idea to chronicle my experience live, online. So yeah, it was a personal thing. But then when I started doing that, I started finding other blogs and I thought, wow, people actually make a living by talking about this stuff. That opened my eyes up to the opportunity that was available if I kept telling my story and they didn’t really know what that would look like, I didn’t know how it was going to be a business. I just kind of wrote about my journey for a year before I probably made a dollar. But I’ve seen other people and I was seeing how they were monetizing their blogs and all I did was focused on getting to know them and I just like I and I would start conversations with her and that wound that being a really powerful foundation for my business when I did decide to start venturing into actually making money.


Leah Gervais: What about you are going through that path, do you think you could help other people? Like, so yours was about personal finance and your journey and how you went from being a struggling artists to you know, having your own business. If someone else said, hey, I also have a journey, maybe not personal finance related, but something they went through. What about your path and what advice would you give them on how they could maybe turn it into a business or something they could monetize or just some sort of platform because maybe they just aren’t even sure where to begin sharing something like that.


Stefanie O’Connell: Yeah. So I think the biggest thing is to start because there’s so much about what opportunities are available that you don’t really know until you actually start doing it. Like I said, when I started blogging, I didn’t know personal finance blogging was a thing, let alone a business opportunity. So I could not have imagined the career I have because I didn’t know those were options when those options only became available and clear and within my line of vision as I started taking action. And that is still true today. I don’t even know where my business is going to be in five years because I don’t know what it looks like to be an influencer for a 40 year career path. Nobody does. So all I can do is focus on my next step. And if you’re just starting, your next step is telling your story, figuring out what you do and who you are and why that matters to somebody else. I’d say the other big mistake people make is that while it is largely about your journey, why you start, ultimately if you’re going to grow it into a business, your message has to be about what you’re doing for other people. So I think what happens is we’re all like, oh well this is, this is me and this is my life and this is what this. But, but people don’t just want to know about you. They want to know about you in relation to them. What are they taking away that’s going to add value to their life from your writing or your story, your video, whatever it is. So I think getting really clear on who you want your audience to be. You know, what kind of person is it that that’s going to be consuming your content or your product that’s going to tell you so much about how to serve that audience and what kind of content or product you should be creating and how you should be reaching that audience.


Leah Gervais: That’s great advice. Do you think a lot about the girl that you were before you knew how to build wealth or how to start a business or anything, do you feel like you create a lot thinking back on what you would have wanted to know? Or how do you channel the service portion of your work?

Well, when I was first starting, I would think a lot about my first steps in terms of what I wanted to know. But at this point in my business, I do have an audience and I do have people finding me. But my best resource is the people on my site and who engage with my Instagram. And I spend a lot of time talking to those people not in person, it’s an online business. I do find out what their questions are, what are they struggling through, what are they working on? I have a free challenge that has a private Facebook group where people pop in and ask questions and it’s just like a gold mine of market research to tell me what I can talking about and doing to better serve those people’s needs.


Leah Gervais: So what, what is your biggest, or what are some of your biggest “why’s” these days? Like what keeps you really excited about your business? I know that you just said that you don’t always know what’s going to be career wise down the line in five years. And I get that and I love that actually. I think when people are like very confused about their future and they freak out about it, it’s like that you’re sucking the fun away from being an entrepreneur. So I liked that you embrace it so much. What vision do you still keep that really keeps driving you and keeps you driven?


Stefanie O’Connell: I love what I do. I think it is so fun. I mean, are there things I hate? Yes. I just did my taxes and I’m glad that’s over. And it’s funny because I even have an accountant, so that takes out half of the work, but still. So even as a finance writer, it’s not like that suddenly makes taxes easy. Anyway, I really, really enjoy it. So, for me, you know, there’s an excitement every day about getting to engage with my audience and also my inbox. Like what surprises are going to come into my inbox because my business is now at a point where I get a lot of requests about people who want to work together, whether it’s a brand, whether it’s a fellow influencer or whether it’s a media company. So I do a lot of news interviews like you said, and I never know what’s going to happen from day to day and from week to week. And it’s really exciting. But I think in terms of the bigger picture, what is really exciting to me in terms of where I think I’d like to go, is kind of looking at how do we make this talk about wealth and lifestyle design and bringing that all to there. How do we make that more of a mainstream conversation? So for me that’s something that I’m trying to do through more TV and video and social and I’m trying to bring my business there so we can get on those platforms where people talk about you know, health every day or those lifestyle topics that you hear about all the time. Fashion, you know, I want money to be as big as any of those other things and so that’s kind of my goal in the next few years.


Leah Gervais: Beautiful. I love that. If you could pick one piece of advice or one big takeaway for, I’m just going to say the women in New York since that’s where we live, who want to stop feeling like they have to make decisions on themselves based on money. What would that advice be?


Stefanie O’Connell: I guess I would ask for a little bit of clarity on the question.


Leah Gervais: I can clarify for you. I know it’s a big question. I just love where you started with this and just feeling like that image of you kind of at the dentist is such a good example of how often we, as a society feel at the mercy to our income and your situation was a bit more extreme because you were an actress who didn’t have a huge income, but I feel like because the conversation’s a bit behind in the work you do can really address any woman who’s in pretty much any fixed income that’s still feels like her decisions are based on, you know, whatever money she has. How do you think people can just become more financially free or be able to feel more in control of their income even if they have a decent amount. Does that make sense?


Stefanie O’Connell: Totally. Really. So, yes. So, the key word here is I think control, right? And if you don’t control your money, it’s going to control you. And I know that when things like medical emergencies happen, it’s hard. I know that when you’re not earning enough, it’s hard. And then when there are circumstances beyond your control, it’s hard. But in every situation there is some piece of your financial life that you can control. Even if it is just tracking where your money’s going, even if it’s just downloading an app and checking in with it every day to look at the numbers or writing down everything you spend and writing down everything you earn, that’s step one, right? That’s something you can control no matter what is happening. And then you get to take the next step. And that might be for you, making a list of all of your debts and creating a plan of action for how you’re going to pay that down. Or maybe it’s automating a percentage of your paycheck to go directly to savings each week. Or maybe it’s talking to your HR department to understand what your 401k is and how you can use it better. But it’s focusing on these elements of control no matter how small they are. And using those to start building confidence around your finances, because once you take those first steps, it’s like building a business. Your next steps will become much more clear, but you can’t build the pathway to wealth if you haven’t started and it’s starting that’s really intimidating. And so if you can get yourself to do that by focusing on those very simple things, you’ll start building the confidence you need to start doing those bigger things.


Leah Gervais: Amazing] advice. I love that you really pull out the control. I think that that is the, the reason that people avoid looking at their bank accounts or don’t want a budget because they just feel so out of control. So finding the control wherever you’re at is a great place to start. And Stefanie, since you’ve worked with so many people on this, what do you see differently about women and their money or maybe some tips that you’d give them in particular that you feel like men either don’t talk about or maybe they talk about and don’t include us in. What is the key difference between women in their twenties and thirties and what they need to know about money that may be we’re not as a society really talking about?


Stefanie O’Connell: Well women tend to live longer than men and they intend to earn less than men. And so between those two things, we have a major problem in terms or not problem, but rather a challenge in terms of how we’re going to build wealth that sustains us, not just now our lifestyle now, but through our lifetime. This is a crisis, it’s unfortunately not something that, that seems to be addressed enough Uf. Um, and it’s not something that, you know, if you talked to your average 20 or 30 year old woman that they necessarily feel. They might feel struggling, they might feel nervous about something. But the idea of long term wealth as a crisis of a lifetime, isn’t really on people’s radars and I think it’s really critical that we start realizing that, and I think the second piece of that is another thing I see particularly among women in their late twenties, early thirties is we tend to still plan our lives on the assumption that we’re going to have a very traditional family structure. And when we do, then we’ll have double the income and that will help us achieve our goals. We don’t really need to start thinking about putting plans in place to do the things we want until we find that partner. I always tell women, plan your life like you’re going to be single for the rest of your life because if you wait until you meet the right person to start saving for a house or to start saving for a family or a wedding, I mean, you might already be in your mid thirties and if you haven’t laid any financial foundation before, then you’re going to have a hard time catching up. And the second piece of that is you could be partnering up with somebody that has $30,000 of their own debt. So maybe, if you’re in a position that you can build a lot of savings, well that’s great, do that because you might have to dedicate a lot of that to paying off a partner’s dead before you even start getting the money you need for your down payment on a house.


Leah Gervais: Yeah. Another situation where you don’t want to be choosing things like who you’re gonna marry based on the fact that neither of you have any money. Really good advice, Stephanie. Okay. I have one less finance question for you just because it’s so useful for everyone to hear, no matter if they’re entrepreneurs or not. But with that said, most of my audience are entrepreneurs. So what basic, I’m sure you could go on about this forever, but what basic advice do you have for people that have inconsistent incomes, especially who are going from a nine to five salary, to now an inconsistent income, never having paid taxes. Also managing the fact that they have business expenses and you having to pay health insurance out of pocket. You don’t need to get into each of those individually. But are there some things that you think women or anyone really could know when they’re making that leap that maybe there isn’t a whole lot of advice out there about,


Stefanie O’Connell: Yeah, you’re right. It is, it is a lot to talk about. But I will say that one thing that’s really important is that everybody understand what their personal minimum cost of living is. I call it a make or break number. So that is the amount of money you need every single month at a minimum to meet your essential expenses. So like housing, food, anything that you basically can’t live or work without for more than a month. So I would include Internet in that. I wouldn’t include like a clothes budget in that, but you know, it’s going to be a little bit different for everybody, but it’s really necessity based. And then on top of that, I include a 10% buffer. So whatever your bare bones cost of living is, plus 10% because life is always more expensive than you anticipate. And then another 20% for savings, investing in debt, payoff goals. And then once you do that, once you find that number for yourself, you have a very clear benchmark for how much you must commit to bringing home after taxes every single month. And that’s a really good indicator of when you could afford to leave a fulltime job, for example.


I think a lot of people are scared because they haven’t done the work of actually sitting down and looking at the numbers and calculating the numbers because once you do that, well, it’s very clear what you can and can’t afford to do. There are a lot of unknowns in situations like that, but what are knowns is like your rent, right? And your health. You can look up what it would cause for health insurance. You know what your costs of food is. So again, it’s taking those elements that you know and can control and using those as a bench to ground yourself in your financial planning. In a world that’s going to be much less certain than it has been for you on a nine to five salary.


Leah Gervais: Very, very interesting. I love that equation. That’s so helpful. I think a lot of times people just think, well, if I’m making you know, as much as I was at my nine to five, then that’s enough. And a lot of times it is, but you do need to think, well you paid nine to five taxes. That was, that’s your post tax take home. That also didn’t include expenses. Really look at the difference in equations because it’s not the same thing.


Stefanie O’Connell: Absolutely. And you know, you make a good point not only about taxes but about benefits. I mean I really can’t overstate how much of a pain point healthcare and your own doing your own retirement savings is having been self employed basically my entire life. I mean that benefit alone is probably worth $30,000 maybe more. So like that’s a big thing to look up and consider before you make a leap. I’m not saying you shouldn’t make a leap. I also don’t like the word leap because I, that also implies that you can only do one thing or the other. But, you can definitely lay a foundation and start building up whatever you’re thinking about doing on the side and still have the protection of your health insurance and the benefit of your employer sponsored retirement plan while you’re building that foundation so that by the time you do leave that security, you really have so much already in place.


Leah Gervais: Right. Yeah. No, that’s, that’s such a good way to put it because this isn’t about not taking the risk, not following your dreams, anything like that. It’s just about being aware of what situation you’re in when you do so. So I appreciate that. Okay. Stephanie, thank you so much. This has been so powerful. I just have a couple lightening questions for you. What are you most proud of thus far in your pursuit of your big vision and in your career?


Stefanie O’Connell: I mean, I think it’s every time I get a message from someone about something they were able to do, whether it’s pay off their debt or save an amount or something, and, what that enabled in their life, whether that’s just a feeling of confidence or whether it meant that they could move out of their parents’ house. I mean, that is the coolest thing about what I do.


Leah Gervais: Awesome. What is a book or podcast you love and recommend?


There’s so many. I’ll go with “This American Life”. I know it doesn’t have to do with business, but I love this podcast because it’s about storytelling and I think ultimately all business is, is really about storytelling. So I know it’s really easy to get caught up in when you’re building a business in all the entrepreneurship stuff. But I always try to make sure I’m listening and reading things that bring me back to stories and human connection and empathy and the things that really make an experience like the human experience.


Leah Gervais: That’s a great piece of advice, especially in the online world of just complete like hyper technology, I love that. Okay, one thing you’re excited about in business or life. I know the answer to this.


Stefanie O’Connell: I am getting married.


Leah Gervais: Congratulations!


Stefanie O’Connell:  Thank you. Thank you. Yeah, so my wedding is this summer, so as excited as I am about it and I’m like, Oh man, I just, I just need some more time to deal with it.


Leah Gervais: I know and you just moved. Crazy. Okay, and how can people find out more about you? What handle do you prefer?


Stefanie O’Connell: Yeah, I’m @StefanieO’connell on everything on Instagram is where I’m most active. Also on Youtube and I spell Stephanie with an “f” , not a “ph”, so that’s a good tip to find me.


Leah Gervais: Perfect. All right, well thank you so much for sharing your story, Stephanie and all the great finance tips that you gave for entrepreneurs and for women. I’m so grateful for you and loved hearing your story and thank you so much.


Stefanie O’Connell: Thanks for having me on.


Leah Gervais: Talk to you soon. Bye Bye.

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