Do You "Think Like a Breadwinner?"

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I'm pretty sure it was all those games of Monopoly that made me love business from my very early days.

I don't actually remember how often I won, but I do remember buying and selling hotels with abandon, not to mention the feeling of colorful piles of cash in my hands. 

As it turned out, I didn't end up as a developer or a hotelier or even the owner of a big business.

But I did learn to think like a breadwinner. 

That's why, when I heard the title of Jennifer Barrett’s new book, Think Like a Breadwinner: A Wealth-Building Manifesto for Women Who Want to Earn More (and Worry Less), I knew I had to have her on my podcast.

In Think Like a Breadwinner, Jennifer reframes what it means to be a breadwinner.

Think Like a Breadwinner by Jennifer Barrett

By dismantling the narrative that women don’t—and shouldn’t—take financial responsibility to create the lives they want, she reveals not just the importance of women building their own wealth but the freedom and power that comes with it, whether we end up the main earner in a relationship or not.

With practical tools, and insights from her own journey, Jennifer encourages women to embrace, and rejoice in, breadwinning like never before.

In this podcast episode, we talked about what that “breadwinner” mindset is, why women are not socialized to take responsibility for themselves and the role confidence plays in all of this -- that’s a thread that is woven into almost everything I’m thinking about and teaching these days.

Listen (here or below) and learn.... 

If you like what you hear, find more "money" resources here:

And here's the transcript of my conversation with Jenn...

Ilise Benun
When I heard the title of Jennifer Barrett's new book, I knew I had to have her on the podcast and I couldn't even wait to read the book first. It's called "Think Like a Breadwinner," and it made so much sense to me on so many levels that I am thrilled to share this conversation with you. We talked about what that breadwinner mindset is why women are not socialized to take responsibility for themselves, and the role that confidence plays in all of this. That's a thread that is woven into almost everything I'm thinking about and teaching these days. So listen, and learn.

Hello, Jenn, welcome to the podcast.

Jennifer Barrett
Thanks so much for having me. My pleasure. I'm Jennifer Barrett, and I'm the chief Education Officer at Acorns, which is a saving and investing app with about 9 million users and counting. And I'm also the author of the new book, "Think Like a Breadwinner," which is a wealth building manifesto for women who want to earn more and worry less well.

...and who wouldn't want that? Very cool. And full disclosure. I have not read the book yet. But I can't wait to and I just wanted to have you on even before I read the book, because I love the title. And I loved your TED Talk. And I loved the conversation that we had. And I just feel like there's a lot we can talk about. Maybe after I read the book, we'll do a part two, based on what I found there. But let's begin by talking about the title of the book, think like a breadwinner, what does that mean to you?

Well, thinking like a breadwinner really means making the kinds of money choices that will ensure you can support yourself throughout your life, and maybe others too. And one key element of that is investing to build wealth. And you know, for most women, we have not been taught or encouraged to invest or even really given the message of how critically important that is. So that's a big part of it. And then even, if you step back, I mean, even though more women than ever before are moving into the main earner or breadwinner role, we are still being socialized for the most part not to think of ourselves as breadwinners, as wealth builders.

And that is to our detriment. So even if we end up in that role, we often feel unprepared. And either way, we're really missing out on reaching our full earning and wealth building potential, if we don't think of ourselves in those terms, and really focus on not just earning enough to pay the bills, but building enough wealth to support the lives that we want.

I'm inclined to kind of use myself as the example here, and maybe tell you a little bit about my take on this from my past. Maybe you can comment and support it with some ideas, and keeping in mind that my listeners are for the most part, self employed creative professionals. One of the problems I have with a lot of the money, tips and guidance that's out there, especially for women, is that it's all about having a job and negotiating salaries. And I have a big chip on my shoulder about that. So I'm constantly trying to translate it all for the self employed woman who actually is in a position to do more than I think she would be able to do in a job. Do you agree with that?

I would agree, I think that there are still some very real external barriers within corporate America to women, you know, women who are ambitious, and who want to move up the ranks, and especially if we want to do that, and also have a family. So it's not just the socialization that we get, but it's very real barriers in terms of workplace bias in terms of women being paid and promoted less and in terms of policies that really reinforce those outdated assumptions. And I think what you see and what we're seeing right now is that a lot of women are leaving corporate America and becoming solopreneurs entrepreneurs, small business owners, because there's more freedom there. There's more possibility, the sky's sort of the limit. And not only that, but what I saw when I interviewed a lot of them is that we then create the kind of companies that we wish we were a part of. We learn from our experience in corporate America, that's where we started. And we try to do better when we create our own company.

So I think a lot of these women led companies are really leading the way in creating a more inclusive workplace culture and a better balance between life and work and will ultimately create a model that I hope the rest of corporate America follows in the future.

So I may have said this -- I am totally unemployable. First, it was because I just don't like other people telling me what to do. Then, eventually, after now, 33 years of being self employed, I'm to a point where nobody can match my salary and the potential for what I can earn, the sky's the limit. I mean, that is the reality if I wanted to focus on that.

And yet, here's the interesting thing: in my opinion, after 33 years supporting myself, I'm not married, I have no kids, I have a dog, she's not all that expensive. I have a lot of freedom. And yet, it wasn't until maybe five years ago, that it occurred to me that I really got that I can take care of myself. In other words, I had been taking care of myself for, let's say, 28 years. But still, in the back of my mind, there was always this, "Oh, someone else should take responsibility for x." There wasn't even a person there. But there's this fantasy that someone else is supposed to take care of me.

So when I think about my past, and growing up, it was certainly my father who taught me -- I remember very clearly watching him pay the bills, write those checks. He would let me write everything but his signature. And so I kind of learned, and I remember getting my first checkbook. And yet and I still did not get the message that I will be able to take care of myself, even though I was learning some of the practical skills.

So respond to that, if you would.

Yeah. And I'd be curious to hear more about what happened five years ago to to shift your mindset around that. But to answer your question, I think and I experienced this myself growing up is, there's a lot of research around how parents speak differently to their girls than to their boys, and the kinds of conversations they have tend to center more around budgeting and spending smartly. I think you can even include paying the bills and managing a budget. And they speak more to their boys about building credit and building wealth.

Those are critical skills for everyone. And this is not to play down the importance of being able to manage a budget. But managing a budget is only one piece of it, right? What I'm talking about with the breadwinning mindset is so much more expansive. It's not just about paying the bills, it's about asking yourself, "what kind of life do I want? And what do I need to do in order to afford it?"

You know, if you're in a career, it's asking, "what kind of income? What career path do I need in order to make the kind of income to support the life I want?" If you're starting a business, it's asking, "how am I going to bring in the revenue I want to? And how is this business going to allow me to have the life the lifestyle that I want? And how am I going to build wealth on the side in order to ensure that I can cover our midterm goals, retirement, all of these things?"

I think when you're self employed, those are even bigger questions, because it's really on your shoulders, it's all on your shoulders, paying taxes, saving for retirement, saving for midterm goals. All of that really rests on your shoulders. And so you need to be that much more proactive. But I think most of us just weren't brought up to think about money that way, to think about wealth building, to think about what is the career path? Or what is the business I want to start that will generate the revenue to support the life that I want.

And so it often takes a while before that clicks into place. And to your point, you know, I don't think we're like waiting around for Prince Charming to save us anymore, necessarily. But if you look at the data out there on women and money: women invest less and later and we save less than men. We have more credit card and student loan debt. And we have lower credit scores. I could go on, you know, the gender wage gap is 18%. The gender wealth cap is 68%.

So you look at those numbers, and it's hard not to think, "are we waiting for someone to rescue us," because we are often not making the kinds of financial choices that will allow us to support ourselves throughout our lives.

So there is I think there is something very deep in our subconscious. And a lot of that comes from the cultural conditioning that we have gotten, which has said women's income is less important, which has said the man will be the breadwinner, which has said the prescription is, get a job, get a career, maybe start a small business, get married, save a little for a rainy day, save for retirement -- but it leaves out all the decades in between.

So I would say we shouldn't blame ourselves for that, because a lot of this really is the way that we have been socialized to think of ourselves in relation to money. And it takes a real conscious effort, if that is the way that you have been brought up. And it's been reinforced by pop culture to recognize that and then shift your mindset to believe, "I am capable of doing this, I am a wealth builder, I am a breadwinner, I am a successful business owner," to reinforce those beliefs and take some conscious reconditioning sometimes.

I have so many thoughts. I'm just gonna choose one. Because I've been thinking a lot about the role of confidence in all of this, and to say, "just shift your mindset to become a wealth builder," easier said than done, obviously. And so what I'm thinking about is what's the role of confidence? And in my own personal experience, it's taking actions and building skills, that bring the confidence that build the confidence. It doesn't come from just thinking a certain way.

And so that got me thinking, I was trying to remember when I put my first $100, in my Fidelity SEP IRA. I couldn't even find it on the website. It's been that long, but nobody told me to do that. I only had two jobs and none of them had an IRA or any kind of retirement plan associated with it. So I don't even know why, at a certain point, I decided to just start putting $100 a month into a SEP IRA. But I do remember, I had a client, I was doing bookkeeping for him, he was a psychiatrist. And he had Fidelity Contrafund, and I was like, "Okay, well, he's making money at that, I'm gonna do that."

And so I just started putting $100 into Contrafund, and for years and years it's been building.

So like, what is that action also? And where is the confidence, like, "Yes, I can build a business and save for retirement at the same time, not all of my money has to go to the same thing." 100%, I agree with you. And I think to your point, when we just start implementing those habits, even if we're saving a little bit, investing a little bit at a time, it starts to build our confidence. So one of the most important things is just to get in the game, is just to start investing, it's less important, what you're investing in.

And I always say, if you are feeling intimidated about the stock market, and I think a lot of people, men and women, still are, but you see that more in women than in men, then just to invest in an S&P 500 index funds. That gives you exposure to 500 of the biggest companies that represent more than 80% of the total market value. So you're basically in many ways, investing in the market itself -- one investment in one fund over time that has returned about 10% per year on average, or seven to seven and a half if you take inflation into account. And that is a nice rate of return.

So if you do nothing else, start there. And I think, to your point, when you start investing, and you start to see that money growing, it has a really incredible effect on your psyche and your confidence. Because there's something about actually seeing the numbers and seeing your wealth grow, that will increase your confidence, that will increase your sense of security, all of these emotional benefits to it. And we see this in Acorns, too.

So at Acorns, people can start investing with their change literally -- we will you connect your card and you use your card and we round up your purchases, take the change, and when it hits $5 we invest that for you. And so people who start there, and there are a lot of people who do start there, invest about 30 to $35 a month on average. So we're talking about around $400 a year but what we find is that they start there, and then after a few months, usually when the market is going up which it has been for the most part for you know several months now, their confidence builds and they start adding more. So they add $5, $10. And then they continue to increase their contributions. I think that's actually the way it works for a lot of people, if we're a little tentative about jumping in.

So the most important thing is to just get started and get in the habit so that every time you have a new client, for example, you're automatically thinking, "Okay, I need to take this amount, from whatever payment I get to put toward taxes, and I need to take this amount to put toward my investments." A SEP IRA is a great vehicle because you can deduct those contributions. So it helps you in more than one way, you know, you're already building your wealth, and you're saving money for retirement, but you're also saving money on your tax bill.

Excellent. I want to give you more time to tell us more about what's in the book in terms of the actual strategies that people can use and implement. So what would you say? Where else would you go with that?

So I took the the breadwinning mindset, and I used it as a filter to look at kind of every aspect of our finances. And one place to start is credit. I think anyone who's ever taken a loan out for their business is well aware of the importance of having good credit, in order to get the best terms. But again, the way that credit has been marketed to everyone, but really predominantly to women, since we are tend to make most of the consumer decisions and the household, is that credit is a way to close the gap between the life that you can afford and the life that you want. And that is such a dangerous message.

But what the breadwinner mindset would say is looking at credit as a way to get the best terms on the loan that you will want to invest in something that you think will increase in value. So for example, looking at your credit cards as a way to build your credit score, so that when you get a mortgage or business loan, you'll get the best terms.

I have some research in the book that shows that if you have the highest range credit scores and can get the best terms, that can save you over $42,000 over the course of a traditional 30 year mortgage loan for an average priced home. That is significant when you think about building wealth and the kind of money that you can set aside $42,000 makes a huge difference, especially if you're able to invest that money versus paying it in interest.

Same goes for a business loan. So having a higher credit score actually makes a huge difference. You can also leverage credit cards to actually make money once you are comfortable paying off your credit card bill every month, you can start using credit cards to get cash back to get rewards points. You know, there are fantastic deals on some of these business credit cards. But it's a different way of looking at credit. It's really like you don't want to pay for the privilege of using the card. You want to leverage credit to actually make money and build wealth. So that's one area.

The other area, again, is looking at investing from day one as a way to decrease your dependence if you are in a regular job, to decrease your dependence on paycheck. And building wealth on the side is a way to give you that cushion that could allow you to leave a corporate job and start your own business.

In fact, last night, I did an event with Luminary and Kate, who is the founder and CEO of Luminary, was telling me that she had been investing for the goal of having a child. They were going through a lot of fertility treatments and she had saved aside all this money and they ended up not having a child. But she had all this money, so she used the money to start Luminary.

So it's really thinking about building wealth to support the goals that you might have in the future and to give you the freedom of choice. Right. And that's a very different way of looking at it. Same with savings. I mean, I think we often think of savings and it's been sort of pitched us as like saving for an upcoming purchase like a expensive handbag or a getaway with our girlfriends, which is not to say that those aren't wonderful things to save for too.

But savings is so much more than that. It's like having savings is having peace of mind, it's giving you choice. It's knowing for example, if you have savings, if you suddenly get a tax bill, if you underestimated what you need to pay, having that savings there gives you that security that you're going to be okay. If you're starting a business and oh my god -- the pandemic. I mean, some people lost 50 - 80% of their revenue in the pandemic. Having savings allows you to ride those times and so your business will be okay and you'll be okay. So it's so important to just think about all those different areas of your finances as really supporting the life you want and giving you as many choices as you can have in the future.


Actually the last line of your TED Talk is the one that I told you I was going to be quoting you immediately, because it has a corollary in my work.

So you said, "There is nothing more empowering than being able to bring the future you want to life. And to know you have the savings and the wherewithal to walk away from any situation you don't want."

So I translated that to, "There is nothing more empowering than being able to bring the business you want to life. And to know that you have the marketing in place, and the pipeline, and the wherewithal to walk away from any client or project you don't want." What do you think of that?

I love that. I love that so much. I really do. I think that's so important. And the book is not necessarily written for entrepreneurs and small business owners. But I think the lessons apply. And if you translate the breadwinning mindset to an entrepreneurial mindset, it really is having the confidence that you can do this, that you have the skills that you have the pipeline, and you have the marketing capabilities to weather these storms.

And I mean honestly, there's nothing more powerful than being able to say no to a client, to be able to walk away from a client who's toxic. I mean, I've talked to so many people who have businesses and feel like when they're starting, they have to put up with so much. But as they start to build their business, build their wealth, they say, "This is an amazing, this is an amazing moment for me when I can say no to a client who's just a pain in my butt and I don't want to have to deal with them."

That's a wonderful feeling to be in that builds confidence. That by itself, I think, can build confidence. Yeah. Cuz think about how you'll show up the next time you're negotiating with a client when you know that you can walk away. I mean, that's the first rule of negotiation, right? Yep, the most effective way to negotiate is knowing in your mind that you can walk away, and it gives you so much leverage in a conversation and negotiation.

Alright, my last question for part one of our conversation. I think a lot of people want to talk about talking about money, because that's something I teach, I have a new presentation, actually, I'm giving a version of it tonight, called "Show Me The Money: Learn to love the money conversation," because I think one of the ways people, not just women, men and women I see, get in their own way is just by not bringing it up in the first place. So do you have any tips from the book or from your own experience about talking about money?

Well, number one is talk about it. To your point, I think that we often feel shame, or embarrassment, or whatever it is, especially when we have questions about money, how to invest or things that we think we ought to know. But in reality, you know, very few people in this country get a really solid financial education. It's not part of the curriculum in most schools. So a lot of people have a lot of questions well into their career. And so there's no shame in asking questions. So that's important.

But the other aspect of this, especially if you have your own business, is to talk to other business owners and get a sense of what they're charging and have those conversations. I mean, it's sort of the equivalent, you know, in our careers, when I've talked to other people about what they're earning, what their income is, and boy are those eye opening conversations.

And it's so powerful. I was just thinking yesterday about a string and one of my network networking groups about getting paid to speak. I had been trying to decide what to charge and that string was eye opening. The range was like zero to 10, on what people were charging, and it was not necessarily a reflection of experience, or the amount of times you've spoken or your platform. It was really a lot of times about what you asked for. And having read that entire string, now I know this, this spectrum, the range, and I know how to have that conversation, I felt so much better equipped to negotiate the next talk that I was asked to give. That was hugely powerful.

I'm thinking of one friend in particular and I include her in the book. She holds these workshops to help others run strong PR firm, to help other business owners with negotiations. But even you know, she did some work for me and she said, "I hope you don't mind, but she's like, honey, I got to get paid. Like I got bills. I'll give you a friend discount. But I got to get paid."

And I thought I would never ask you to do work and not pay you. You know, but I think you can have those conversations, even in a case like that where you're working with a friend, and they say, I love you, but I got to get paid.

Well, my take on the friends and family discount is they should pay more because they know how much you're worth and they want to support you.

I told her that too. I said I'm willing to pay full price, more than willing because you're exactly right, they know more than anyone how talented you are and they will want to support that. I completely agree.

But I also think it is just so important to remember, you need to get paid, you need to get paid what you're worth, there's no way around it. And there's nothing wrong with saying, "I want to make a lot of money,"

I definitely want to make a lot of money, I'm very open about it, I want to make a lot of money so I can have the impact I want to have in the world, so I can have the life I want. And, you know, I think a lot of times, we don't talk about that enough. There's this weird shame around saying, especially as a woman, that you want to make a lot of money. And we need to get over that.

And I would say -- and then I'll get off my horse about this -- But when we talk about venture capital, I've talked to so many female entrepreneurs, and they tell me that one of the things that drives them nuts when they're raising money is that there's almost this idea of like, it's charity to put money into a female led company right now. It's like, "we ought to do it to help female entrepreneurs."

That is such BS! Invest in the company because we will make money and we will make you money. That's why you invest in a company. We're not a charity. And we have every intention of making a lot of money. And so it's even reshaping the conversation around that to like, the reason you should invest in a female led business is because we have a higher rate of success. And we are just as ambitious and talented as male founders. Not because there's some quota to fill, or because you feel like oh, I need to support female founders, but because you actually see the value in what we're doing.

All right, that would be the perfect place to put the bookmark. But I did think of one other question that I want to ask you is: Do you have a favorite female personal finance "guru" that you recommend people listen to or read?

Well, it's hard to read her, but she does have a blog, but my mom is my, she really is my hero. We talk all the time about money and investments. She will call me when she makes a good investment and makes money. So we have that kind of relationship where she says, I'm so glad I can call you and tell you about this money I made today with Baidu or Amazon or whatever. 

She has a background and a PhD in accounting. And she actually takes the time to read all these reports that companies put out and look for opportunities. That is not something that most people have the time to do, but I admire her for more than that. She is self taught and really started managing the finances after my parents were divorced. And she got remarried. And has didn't start quite from scratch, but almost and has built a really impressive portfolio in stocks and bonds and in real estate. So I have so much admiration for what she's been able to do. And she also gives just incredibly solid advice. She is the person who takes the time to research everything. And she's at

She has a blog, and she writes mostly for people who are near or in retirement. That's her focus right now because she is retired. She was an accounting professor for many years.

So interesting. And just funnily my mother also spends what sounds like all of her spare time reading all those reports and watching the stock market. She doesn't have an accounting degree, actually, so she is also self taught, and I think has been doing it probably for the last 10 years. But that's what she seems to have devoted her life to -- is teaching herself how to take care of herself -- she's now in her 80s.

That is amazing. That's so inspiring. And I think they would get along very well.

Yes. All right. So tell the people where they can find you online, also in your book.

Sure. Well, I'm at I'm on all the social platforms and feel free to reach out. And the book is "Think like a breadwinner" and it's available anywhere you buy books.

Awesome. I can't wait to get mine. Okay, so thank you, Jenn. And we will definitely have to have a part two. That sounds great.

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