287 | Self-Worth, Solo Aging, and Smart Money Moves with Jean Chatzky

[00:00:35] Hilary Hendershott: Well, hello, Money Lover. Welcoming to the show Jean Chatzky, CEO and Co-Founder of HerMoney. She’s the former financial editor of NBC’s Today Show, she’s a coach on the PBS show, Opportunity Knocks, a New York Times and Wall Street Journal bestselling author, the financial ambassador for AARP, and the host of the HerMoney Podcast. Through decades of reporting on personal finance, she learned that, A, the jargon-filled speak of the financial industry was created largely by men to sell you stuff you don’t need and, B, if you eliminate the jargon, there is absolutely no rocket science to money.

[00:01:12] What a breath of fresh air. She knows that a full successful financial life is within every woman’s grasp. And with the HerMoney team, she’s on a mission to help you get it. Jean Chatzky, welcome to Love, your Money^®.

[00:01:25] Jean Chatzky: Thank you. Thanks for having me.

[00:01:27] Hilary Hendershott: Yeah. It sounds strange for me to say that I’m looking forward to talking about the ways women are uniquely challenged when it comes to achieving financial freedom, and I’m hoping to get your unique perspective on that–even funding a secure retirement–but, here we are. How do you think we can have the conversation about the pitfalls of being female be empowering for women as opposed to discouraging?

[00:01:51] Jean Chatzky: I think we pair solutions with problems. And I find that to be true of any challenging conversation. Whether you’re talking about making a change in your financial life, whether you’re talking about trying to build new relationships, whether you’re talking about trying to make a change in how you’re managing your health, identify the problems. And then you try to come up with potential solutions that can get you through each one, because it’s knowing that there is possibility on the other side that makes the daunting seem less daunting, at least to me.

[00:02:37] Hilary Hendershott: It does. And do you think there’s a difference in focusing on sort of the macro issues versus the micro issues? I mean, a lot of the data about where women are financially isn’t so great, and yet each woman has her own individual financial situation. How do you view kind of how women should grapple with the differences between those two?

[00:02:59] Jean Chatzky: I say this all the time. There is so little that you and I can do about the economy. There’s nothing that we can do about the economy, right? Interest rates? Can’t change them. The markets? Can’t control it. Inflation? Not up to me. But what I spend, what I save to some degree, what I earn, I can do that, right? I can manage my own personal economy and make a big difference in my own life without making a difference necessarily in the economy of the country or the world. So, this is how we become resilient. We focus on controlling those things that we can control and challenging our brains to let go of those things that we can’t control. And that’s how we get stronger financially and, in general, in life.

[00:04:04] Hilary Hendershott: Sounds like good life lessons. Yes.

[00:04:05] Jean Chatzky: Yeah.

[00:04:07] Hilary Hendershott: So, I think the most obvious issue for women is just that we’re like one, maybe two generations into cracking the, “It’s okay for women to have a serious career and earn serious money” code. This has seriously shifted since, like, for example, my mom started her career in the 1970s, but to some degree, we’re still changing hearts and minds. What challenges do you think come along with that?

[00:04:32] Jean Chatzky: I think the challenges are both sort of external and internal, right? There is still a massive gender wage gap. It’s so frustrating. I’ve been reporting on this for decades now, and it’s so frustrating to see it not even moving penny by penny. It moves by such small fractions. It feels like you’re…

[00:04:57] Hilary Hendershott: Whoa.

[00:04:58] Jean Chatzky: Yeah. It feels like you’re constantly trying to push this boulder up a hill, right? We can try to impact that as much as we can by advocating for pay equity in our companies. Some of this is gonna be a matter of educational trends as women get more college degrees which we are and have been for a number of years than men did. The pay gap will slowly, slowly, slowly, slowly start to change. So, there’s that. But to a micro degree, we have to become comfortable ourselves with the idea that we are worth this money, that we deserve to be valued on the basis of our skills and our achievements and those skills and achievements are as valuable as those that men provide.

[00:05:50] So, of course, we should be paid the same amount, if not more, depending on what we bring to the table. I know that you know, I run a large community of women. We’ve got 20,000 women plus in our HerMoney Facebook group, and sometimes I see threads where people are still feeling that they don’t believe they should be asking for more, that they have a hard time asking for more. I had a hard time asking for more earlier in my career, and all I can say is it gets easier with practice. If you can get yourself to the table to do it once or twice then you can do it the third time and the fourth time and the fifth time, and it does get easier. You fake it until you believe it yourself.

[00:06:42] Hilary Hendershott: That’s my experience as well. And with your macro view, are there specific trends that you see shifting more quickly? Anything particularly inspiring to you in terms of progress that you see?

[00:06:54] Jean Chatzky: I think educational progress is inspiring. I mean, the last time I looked at the numbers for every 100 men that graduated college, 132 women graduated. Women are getting more graduate degrees when you look across the line in many, many fields. I think those educational trends are going to drive changes in the way the world works. When we look at family structure, when we look at pay equity, just when we look at the landscape, we’re seeing it already.

[00:07:32] Hilary Hendershott: So, the converse then of the challenges that women face, what do you think is the most costly? What do you think is kind of the worst challenge that we face now?

[00:07:41] Jean Chatzky: The worst challenge. That’s a hard one because I do think that there are a lot of challenges. I continue to think that balancing work and family is difficult. Until men can have babies, it will continue to be difficult, right?

[00:07:58] Hilary Hendershott: I can say that one humbled me for sure. For sure.

[00:08:01] Jean Chatzky: Yeah. For me too. And my kids are grown and flown. They’re at the age at which they will soon be looking to have kids of their own, I think. I think it’ll be hard for them too. It’s very, very difficult to be great in all areas of your life on the same day. I always felt as if I had a particularly good day at work, it was not going to be a particularly good day at home, and vice versa. Childcare, quality, affordable childcare would go such a long way to solving these issues. And it’s not even on the radar.

[00:08:45] Hilary Hendershott: Yeah. Well, since you’re here and since your children are grown and flown, let me ask you, how do you think about the choices that you did make in retrospect? I mean, in the thick of it, my daughter’s nine. She’s had cancer twice.

[00:09:00] Jean Chatzky: So sorry.

[00:09:01] Hilary Hendershott: It’s been quite a thing and I was definitely overconfident when I thought about balancing career and family and I thought, I mean, I’m a great recruiter. I’ll recruit great nannies and I’ll make sure that my child, I thought I would have more than one, would get good care. And now I’m in a community where most of the women don’t work, and so I’m envious of the time they spend with their kids. I just, I don’t know what the right answer is because I know I have concerns and I’m worrying that I’ll have regret once she’s 18 and flown and grown. How do you think about the choices you made? Can I ask?

[00:09:38] Jean Chatzky: You can totally ask. And I can relate more than you know. My oldest was born with a very serious congenital heart defect.

[00:09:48] Hilary Hendershott: Oh.

[00:09:48] Jean Chatzky: He’s had five open heart surgeries. He’s 30. He had his first at three weeks, his second at a year, and his third in kindergarten. So, I understand what it’s like to have a child who is not well.

[00:10:01] Hilary Hendershott: Yeah.

[00:10:02] Jean Chatzky: On the flip side, he is 30. He’s married. He works for the New Heights podcast which is the Kelce Brothers podcast. They have him on the air. They call him Jets Jake. But in the thick of it, I think I probably ran away a bit and ran into work maybe more than I should have and regretted a little bit later. It’s hard to juggle your ambition to be a great mom with your ambition to be good at what you do, especially when you love what you do. And I know that you love what you do.

[00:10:35] Hilary Hendershott: We both do. Yeah.

[00:10:37] Jean Chatzky: As I look back on the decisions that I made, do I regret them? Not many.

[00:10:44] Hilary Hendershott: Yeah.

[00:10:44] Jean Chatzky: I think I was there for the important stuff. I think that there was some stuff that I felt was not that important and I chose to prioritize other things in that moment, but it was hard. I lived in a community like the one that you live in, and it was really difficult to watch the people from the outside sort of judging.

[00:11:09] Hilary Hendershott: Yes. It’s quite a feat to think about yourself as one person and not two. I feel like I’m either working or I’m mom-ing, right? And so, it turns out there’s a zero-sum game in there somewhere that I can’t quite wrap my mind around. But I know that doing it the way I’m doing it takes a lot of money. I have to really focus on earning because we’ve spent, ever since she’s born, we spent near six figures on childcare on an annual basis. So, we’re both saying the same thing. It’s a difficult question to answer no matter how you answer it.

[00:11:39] Jean Chatzky: And the answers are different for everybody, right?

[00:11:44] Hilary Hendershott: Right.

[00:11:45] Jean Chatzky: I just wish, and this is why we shut down judgment at HerMoney when it comes to looking at how other women use their resources because there’s no room for that, right? Let’s just support each other in the choices that we feel are right for us and let’s not get so judgy about other people’s choices.

[00:12:09] Hilary Hendershott: I am here for that. Let’s see. I’m sure you get to hear from a really wide range of women about their financial lives, Facebook Group with 20,000 members. Do you have any particularly interesting stories or examples that would fit under, and I’m thinking about inspiring listeners, under the header “Turning Setbacks into Comebacks”? Any good turnaround stories you’ve got?

[00:12:33] Jean Chatzky: Oh, boy. We’ve got a lot of great divorce stories.

[00:12:36] Hilary Hendershott: Oh.

[00:12:36] Jean Chatzky: Actually, so our community seems to be one where women going through divorce sometimes gravitate. And I’ve watched a lot of women sort of turn the corner, find themselves step into their power as women, as earners, as friends, as new partners in relationships that make them happier as parents. I have enjoyed watching those threads. I’ve also seen a lot of stories of women who– not doing particularly well with their money and decided that they were going to make a change, that they were going to start small, start tracking their spending, watching the flows of money, becoming more accountable to themselves, and have watched them grow into really, really strong financial women.

[00:13:31] Hilary Hendershott: There’s one thing that I’ve really been thinking about this year. I have a good number of clients who don’t have children or spouses, and so they’re left wondering, “Who’s going to care for me at the end of my life? Who’s going to make medical and financial decisions with my best interest at heart?” I can’t imagine trying to hire that role out, right? How do I navigate solo aging? Do you have particular advice for these women?

[00:13:53] Jean Chatzky: Yes. First of all, they should know they’re not alone. The number of single women is, I think, one of the fastest-growing demographic slices of the United States. It’s just for a lot of reasons when we’re talking about not just divorce statistics, but widowhood and a large number of people who’ve decided that they are going to remain single. I think you want to look at your own circle first to find those likely friends, cousins, siblings who might step in and become your healthcare proxy or take on durable power of attorney for you. But depending on those people alone I think is a mistake. And although you say you can’t imagine hiring out for this, I do think you need to have a professional choice in your back pocket because somebody that you pay to do this is going to show up.

[00:15:00] And long-term care insurance and disability insurance is so much more important for single women and sometimes we just don’t get enough of it or don’t get it in time. The last thing is I’ve seen a lot of movement among our older listeners to look at communities where they can age living independently in a community where they could eventually get the kind of care that they need down the road. And the nice thing about these sorts of places, and I’m really talking about sort of 50-plus communities where there are services…

[00:15:41] Hilary Hendershott: It’s a stratification of services. As you need more, you take more.

[00:15:45] Jean Chatzky: Yeah. The nice thing about these communities is that they’re communities and we know from our prior surgeon general how much of an epidemic loneliness is. You’ve got to do whatever you can to avoid that as you get older.

[00:15:58] Hilary Hendershott: That was a really significant letter he published. I know the letter you’re speaking of. That was very touching. I actually sent that out to clients. So, in terms of paying a professional, and I’ve definitely heard of a professional fiduciary trust–the alternative to the power of attorney–you can hire that out, can you also hire that for medical?

[00:16:19] Jean Chatzky: I don’t know.

[00:16:21] Hilary Hendershott: Research for me to do.

[00:16:22] Jean Chatzky: Yeah. Actually, I don’t know.

[00:16:24] Hilary Hendershott: Yeah. Okay. All right.

[00:16:25] Jean Chatzky: But you can be very specific with a living will. And there’s a document called The Five Wishes Living Will, that’s sort of a combo platter of a living will with a healthcare proxy.

[00:16:36] Hilary Hendershott: Yeah.

[00:16:36] Jean Chatzky: You be very specific in terms of documentation that will guide medical people, medical practitioners about what you want. And you need to make sure that your paperwork is buttoned up and that all the significant professionals in your life, actually have a copy. So, I wrote a column for AARP Magazine about hiring a professional to do these things. It’s been about a year, year and a half, but if you google it, you should find it.

[00:17:04] Hilary Hendershott: Well, we’ll google it and we’ll put it in the show notes for today’s episode. Thank you. I appreciate that. Okay. Thank you for this wide-ranging conversation. I do have, of course, a signature question that I ask everybody. This is what the Love, your Money^® podcast is about, being in a loving relationship reciprocal between you and your wealth. So, Jean, if your money was writing you a love note, what would it be thanking you or complimenting you for?

[00:17:29] Jean Chatzky: It would be complimenting me for saving it, particularly after my divorce, when I put my savings on a supercharged regimen, but it would also be thanking me for knowing how to use it to bring me joy. And that’s something that I’ve really learned over the years by just paying attention to which purchases I’ve regretted and which purchases I’ve not regretted. Those tend to be really helpful guidelines when it comes to using your money in a way to make you happy.

[00:18:14] Hilary Hendershott: Well, that’s really interesting. Can I ask you, what’s the last thing or your favorite thing in 2025 that you spent your money on that brought you a lot of joy?

[00:18:21] Jean Chatzky: Yeah. Actually, in 2025, my favorite thing is–it’s still in progress, but I know it will bring me joy–is some landscaping at my house in New Jersey, including a couple of raised garden beds where I am going to really master tomatoes.

[00:18:42] Hilary Hendershott: Whip those tomatoes into shape, Jean.

[00:18:44] Jean Chatzky: Exactly.

[00:18:45] Hilary Hendershott: Well, I hope you enjoy your outdoor space. That sounds wonderful.

[00:18:48] Jean Chatzky: Thank you.

[00:18:49] Hilary Hendershott: Thank you for your time today. Thanks for being on Love, your Money^®.

[00:18:51] Jean Chatzky: Thanks for having me.