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Hey everyone. Welcome to Her Money. I'm Jean Chatky and today we are diving into another installment of our special series A Week in Her Wallet where we follow real women from our community as they track their spending and unpack the emotions, values and trade offs behind every dollar. Because when it comes to money, the what is important, but the why is where it gets personal. This week we are heading to Westchester County, New York to meet Ann. She is 63 in a long term partnership and has spent her career pouring her energies into the next generation. She's a full time preschool director and has had one of the lowest spending weeks in this series, only about $400. Over the course of the week, Ann showed us what it looks like to be on a real mission, not just tracking dollars, but actively engineering her life toward what she calls her rich enough old lady future self. From no spend days and homemade iced coffee to meeting with a financial advisor who finally gave her peace of mind, Ann's week is full of wisdom. Let's get into it. Ann, thank you so much for doing this with us.
D
My pleasure. Thank you for having me.
C
Of course. What made you wanna track your spending for a whole week? I mean, I don't think this is something that's on everybody's top 10 list
D
so it is on mine. I'm a tracker anyway and a fan of yours as you know. And in listening to the different podcasts I thought, well, I track anyway. I might as well make it formal and talk to Jean about it and and see how it makes me feel. And I loved it. Quite honestly it was great.
C
Oh, I'm so glad to hear that. Before we get into the nitty gritty of your week, tell us about the big picture. What's the lay of the land?
D
Sure, it's pretty simple for me. I still work full time as an early childhood director. At the moment I don't have any extra income coming in. Although I am thinking about starting or restarting a tutoring business that I did as a side hustle this summer. So we'll see where that takes me.
C
And you said to us, and we love this, that you are saving for your rich old lady future. Sounds like a fabulous thing to be saving for. What does that mean to you and when does that actually start?
D
So hopefully it will start in the next five to seven years. I just signed another five year contract at my job so I'm excited about that. We'll see at the end if I decide to go another year or two. It could, I may. I love what I do and if I'm healthy enough to continue doing it, that is my plan to go till I'm 70 so that I get the most out of Social Security and I can save more. That's where I'm at right now.
C
That sounds terrific. Are you ready to get into your week?
D
I am.
E
It's Monday, day one of a week in her wallet. Today was a no spend day for me. I try to have as many days as possible during the week that are no spend days. I am on a mission to save for retirement for what I call my rich enough old lady future self, hoping to retire in about five to seven years. And I look for ways to cut back on spending and save as much as I can. So today for example, I packed my own breakfast from home, lunch and snacks. I cook for myself during the week. Not only does it save money, but I'm also on a weight loss journey so that helps me reach my weight loss goals. I actually enjoy cooking as well. I don't pay for a gym. I work out at home. Before going to work, I cut my own hair. So after I'm done recording this, I will be trimming my hair. I need a little trim up and I will occasionally go to a salon to get a haircut probably every three or four months. But I'm able to do it myself and save money that way. And yeah. So that's it for today.
C
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D
So I'm a planner in probably all aspects of my life and I'm pretty organized and when I look at my budget I'm always looking at ways to be able to cut and one of the main places that I spend money is food. So I tend to have a certain amount of money that I spend each month on food. I rarely go out. If I do, it's a treat. I think that comes up later in my week. But I'm a planner so I'll buy a certain amount of food I food prep and I find that that saves me a lot of Money, including my iced coffees. Not spending that five or seven dollars. A little things really add up.
C
Do you make iced coffee from home?
D
I do, I do every day.
C
Do you turn your leftover coffee into ice cubes so that the coffee doesn't get weak?
D
I do that as well. I even have my reusable Dunkin Donuts cup that I bring with me everywhere I go. So yeah, I do.
C
And when you're cooking and meal prepping, is it just for you or are you cooking for your boyfriend as well?
D
It depends on the week. Mostly it's for me. So I'll do the bulk of my cooking on Sundays for the week and I'm fine with eating the same thing every day. When I cook, it's usually delicious. So I'll have it for dinners and lunches. And if I'm seeing my boyfriend, then I'll cook for him as well. I'm Italian, I always cook extra. So there's some for him, some for me, some for the week, some for everyone.
C
Do you have go tos that you make every week or do you mix it up?
D
I mix it up, but it's seasonal. During the winter I'll do a lot of soups and stews. In the summer it's mostly salads. My go to is turkey chili, turkey meatballs, things that are healthy, satisfying. I'm a hungry girl so I like a hearty meal.
C
The Pierre Frenet turkey chili, that recipe from like the 1970s in the New York Times is my favorite favorite turkey chili. It is so good.
D
Oh, you'll have to share it with me. I love to try new things.
C
Absolutely. Tuesday was also a low spend day. $54.34 in total.
E
It's Tuesday evening around 8:35pm Day two of a week in her wallet. I was thinking today as I was driving home how a combination of life experience experiences make it really challenging for me to spend money on what I call wants. So to prevent the feelings of guilt that I I frequently feel about spending and not saving money, I have an all about me account. I fund it every month with a couple of hundred dollars. And this is the money I set aside that I can spend guilt free on anything I want. Whether that be dinner with my friends or a plane trip to somewhere warm in the winter. It might be something I'm doing with my grandkids or a trip with my kids and grandkids. Basically whatever I want to spend money on and not have to think about. Today was a low spend day. I had to get gas after work $23.14. And then I had dinner with my girlfriends. We usually go out about once a month. Tonight was our dinner date together and that was $31.20. So total today for spending was $54.34. And we'll see what tomorrow brings.
C
What I want to talk about is the emotional side of spending because you shared that you have really complicated feelings when it comes to spending money on yourself, particularly on things that are wants. Tell me a little bit more about that.
D
I do. It's a real struggle for me. I come from a scarcity mentality. I was raised in a home where throughout my whole life I heard the term scrimp and save. And so I, I have that in my mind at all times. And I really struggle with spending. I will give you an example this week I have saved for the last two years for new window treatments for my home. And I had the money and I had someone come in and I spent the money. And now I feel like, like a wreck about spending the money even though I know it was there and I planned for it and it was not a surprise, but I did it. And now I'm saying to myself, you're going to love those window treatments when they come in and you're okay, you can keep going.
C
You are okay, you can keep going. And I want. When you think about how you enjoy spending your time, do you enjoy being in your home?
D
Very much so. My home is my sanctuary. I live alone. I've lived alone since the end of my marriage six years ago. It is the most luxurious thing to me. I love being home. I love my house, I love my yard, I love my garden. It's where I'm most at peace.
C
I did an interview many years ago with a researcher named Lois Vitt. She developed this tool called a life values index. And it was a questionnaire. You can actually find it online where you went through a series of questions and it produced an answer that told those things that you value. And we always hear from people that we should be spending our money on experiences rather than things. But what this taught me is that's A, not true for everyone and B, our home, our nest can be an experience. So I'm kind of like you, like, I'm a throw pillow person. And although I enjoy a good vacation, I want my home to be someplace that I feel great. And so I have convinced myself that it is okay to spend the money on the window treatments and that's okay to sometimes spend $200 on a throw pillow if it's a throw pillow that I am going to absolutely love. And so I want you to feel okay about these window treatments because it's just going to increase your enjoyment about being in this house. And you're right. You have the money. So try to go easier on yourself.
D
I will, I will. Thank you. And I know once they're in, I'll enjoy it, but it's just the idea of spending it. But you're right. And I also agree, if I'm spending my money, it's either on my house or some kind of experience.
C
Yeah. And you have this account that you created called an all about me account to help you get over the spending guilt. Does it work?
D
It does. It really does. It's my pot of money that I know that I can spend on a plane ticket or going to the museum with my grandson or the window treatments. It sort of gives me the deep breath that I need to say, this is good. I can do this and still save and still do the other things in life that I want to do. And if I didn't have it, I know me, I would just save to the point that I would not enjoy things.
C
You mentioned coffee before and it's interesting. That money that you're not spending on coffee turns out to be $200 a month that you told us you now put into this all about Me account. Are there other versions of this game that you play with yourself?
D
I do. And it's funny, I play these games all, all the time. So I'm a big like Amazon person or I'll go and I'll look at something I love to thrift and I'll do the 24 hour rule. Like I'll put something in the Amazon cart that I think I really want that next pair of let's say Adidas or whatever they are. And then I'll wait 24 hours and then if I really want it, I'll go back and get it. But if I don't, I'll take that money and I'll put it in my all about Me account. So I always have this little game, this contest with myself. How much can I save and put in that account and have it add up so that I can spend it on my big wish or my big want.
C
Wednesday was what you called a Medium Spend day. $220 and change.
E
It's Wednesday, day three of a week in her wallet. I left the house as usual this morning at around 6:30am with my homemade iced coffee. Today for me was a medium spend day. I Guess I stopped at the cash machine on my way to work. I needed $135 for my cleaning people who are coming tomorrow. I have a wonderful cleaning woman who comes in about once every six weeks. It is a splurge, but it's also a need because I work so many hours that I really don't want to clean my house, not into spending my free time cleaning. So $135 for that. And then my cell phone bill came due today. That was $85.68. So a total today was $220.68.
C
So you stopped at the ATM to get some cash for your cleaning person who comes about every six weeks. I love that you called that both a splurge and. And a need. Definitely a need in my book. But talk about that.
D
As I mentioned, I'm very organized. I love a clean house and I'm very clean. But quite frankly, I don't want to do the deep cleaning. I'm just not interested in spending my free time that way. But I find that when my house is not neat and clean, I just. I feel very disconnected. I don't know if it's OCD or whatever they call it, but it just. It feels to me like such a luxury to have someone and come and do that for me. And I feel like I earned it. I work full time, I work hard, and I just. I don't want to do that. I'd rather spend the free time with my boyfriend or reading a book or being with my grandkids or in the garden. So it's a little bit of both. I used to have someone come once a month, and I felt like that was a little too much. Every six weeks works, but it saves a little bit of money. And that goes into the all about me account.
C
Thursday, you said you were listening to our episode with Hannah Horvath about money anxiety, and it really resonated with you.
E
It's Thursday, day four of a week in her wallet. I was listening to Jean's episode, I think it was 5:20, her latest episode with Hannah Horvath, about the money behaviors that show up when economics anxiety takes hold. And it just got me thinking that I recently hired a financial advisor to manage my portfolio because I had a whole lot of anxiety about my personal economy, whether I'd have enough money to retire. Have I done enough? Am I doing enough? And it just got to the point where it was really taking over my thoughts. So much so that my son said to me, mom, I think you have a problem So I think the money that I'm spending to have this financial advisor take care of my affairs is well worth it. Seems like he's doing a great job so far. I just feel like a huge weight has been taken off my shoulders. Prior to hiring him, I was DIYing it for about probably the last four years and I was figuring it out, but I would always second guess myself. Am I really optimizing growth? Am I really buying when I need to buy? So this is just money again, well spent to me. Today I haven't spent much money at all. I bought a ticket for an event tonight at work. It's a fundraiser. A ticket was featured, $52. I have my friends joining me, so I'm really excited about that. Very rare for me to be out two nights in one week, but again, it's a fun event. We're making challah together and I'm looking forward to it. So today was definitely a low spend day. $52.
C
Why do you feel that way and what have you done to calm some of that anxiety, particularly around retirement?
D
So I'm not sure if I mentioned, but my marriage ended. My 36 year marriage ended when I was 58 in 2020 and I had to become my own CFO. I really, I was busy raising children during that marriage, building my career. I didn't know much about finance. My former husband paid the bills. I really was in the dark and I had to learn very quickly. Things that people might seem are basic were not basic to me. So I had to really, as I said, become my own cfo. That has been very empowering. I feel like I've learned a lot. I do a lot of independent study, listening to your podcasts and others. I'm really self educated and it's just given me a sense of confidence and really control and a much better forecast of what my future old lady self can and will look like. And it's calmed me a lot. It's calmed my anxiety a lot.
C
For those women in our community who are worried about the cost of an advisor or whether they have enough money to justify it, what do you say to them?
D
Negotiate. So I negotiated with this financial advisor. It's not inexpensive, but in the long term, for my own personal mental health, I think it's the best money I am ever going to spend. Rather than going to a therapist, this was my therapist.
C
Fantastic. We are going to take a quick break. When we come back, we're diving into Anne's weekend. A surf and turf dinner, a visit to some brand new great grandparents and why her Honda with 115,000 miles on it is one of her proudest financial decisions. Lately, I've been thinking more about what I actually reach for in my closet. The pieces I wear on repeat versus the ones that just hang there. Spring always makes me want to simplify. And that's exactly why I've been loving quints. The quality feels genuinely elevated, the fits are flattering, and nothing is overpriced. My producer Emily just stopped me the other day to ask about my cotton cashmere rib tank in heather oatmeal. It's this beautiful warm neutral that's just distinctive enough for people to notice. Refresh your every day with luxury you'll actually use. Head to quince.comhermoney for free shipping on your order and 365 day returns. That's quince.comhermoney for Free Shipping and 365 day returns quince.com Summer's almost here and I don't know about you, but I want to be thinking about where I'm going on vacation, not lying awake wondering if I can actually afford it. That's the difference between having a financial plan and just hoping for the best. And Monarch is what makes that possible. Monarch is the personal finance app that tracks everything accounts, investments, saving goals and spending. Get your first year of Monarch for half off just $50 with promo cod her money. What I love is that Monarch doesn't just show you what you've already spent, it helps you plan ahead. My producer Hayley uses it every single day and once you have that kind of clarity on your finances, you really can't go back. Use code hermoney@monarch.com to get your first year half off at just $50. That's 50% off your first year at monarch.com with code hermoney we are back. We're talking with Ann.
E
It's Saturday, day six of a week in her wallet. It was a very chilly day here in New York, but the sun was out and my boyfriend and I went for an eight mile walk. We love to walk and on the weekends since we're both off from work, we do a whole lot of walking. So today was a really nice day. Last lots of walking followed by going out to lunch. He's wonderful. He always pays for lunch. Today I just offered to pay the tip, which was $6. Then we went to the grocery store. We wanted to pick up a few things because we were making a nice dinner. We had a surf and turf dinner this evening and as I was Walking around the supermarket, I love to people watch and and I love to look in people's carts to see what they buy. I think you can tell a lot about people by what they buy in the grocery store. I was also thinking about ways that I try to trim my own grocery bill. I live alone, so my grocery bill is not high. But with the price of food, I'm always looking for ways to trim my food bill. I find that I do look at what's on sale and I basically eat whatever is on sale. So if it's chicken or fish, that's what I will cook that week. I'll look at whatever fruits and vegetables are on sale and I'll buy those. I tend not to buy too much junk food, but when I do want snacks, I'll go to Trader Joe's just because they're healthy and the prices are right. I will very often order my groceries online as well and have them delivered. I definitely spend less money doing that. Although there is a delivery fee, it's a nominal charge compared to going into the supermarket and just buying things that I don't really need or shouldn't be eating since I'm on this health journey. So today was six dollars for the tip. At lunch, I bought a twelve dollar gift for my boyfriend's aunt and uncle. We stopped by to visit them. They just became great grandparents. So I bought a little pretty plants and then I was charged $35.75 by my home security service. That's my monthly charge. And the total today was $53. 70.
C
Saturday sounds like it was lovely. Eight miles of walking with your partner. He picked up the tab for lunch. Surf and turf, dinner at home, a quick stop for groceries, and a small gift for your boyfriend's aunt and uncle who just became great grandparents. That is a lot of joy packed into a day where you only spent about $50. How do you and your partner navigate finances together?
D
So we have an account together, our vacation account. We opened it when we decided to become a couple and we put in a certain amount, equal amounts, every month so that when we travel together, which is often, it doesn't hurt as much, the money's there. Everything else, he pretty much always pays for lunch in exchange. If he's at my house, I will cook dinner. And we just have this understanding that for the big picture items, we split. Sometimes he treats, sometimes I treat. But it's something that we talked about up front, like how do we want to handle this together?
C
And you both came out of other relationships, is that right?
D
We did. We both. Yes. Yes, we did.
C
So was it a shift for him in how he had managed money with his prior partner or spouse?
D
Yes, I think it was. I think this was a very big shift. He has shared with me that his relationship with me feels more like a financial partnership. We have very similar goals. We have very similar spending habits. We were raised almost identically and have the same values when it comes to money and life basically and exercise.
C
Sunday was all about family. You spent the day with your kids
E
the seventh and final day of a week in her wallet I spent the day today with my kids and grandkids as I normally do at least one day out of the weekend. And if I can sneak in a weekday night, I try to as well. On my way to my kids, I needed to stop for gas again. I have a local gas station closest to my house. I do not buy gas there because their prices are outrageous. I call them the Shell station with Gucci gas. So I decided to drive a little further north, headed to Connecticut where my kids live and found gas for 379. So I filled my tank or at least half filled my tank. And on days like today I'm happy that I drive a very modest car so I don't have to buy premium gas.
D
Gas.
E
My whole life when I was married I always drove very nice luxury cars which meant premium gas and expensive maintenance. And I quickly learned that is not a place I want to spend my money in. Chapter two of my life now that I'm single and no longer married, I would much prefer to drive a Honda paid off which it is I caught. Call her my green lady. She has about 115,000 miles on her. My plan is to drive her into the ground. I've saved so far about $35,000 toward my next car and when I do need to buy one it will be pre owned. I'd love to get a Mini Cooper but at the end of the day I'll get whatever I can afford that has low mileage and is a safe car. Just because my priorities have changed. I'm about to start my food prep for the week. As I mentioned, early in the week I take my own meals to work. So on Sunday nights I generally do my food prep for the week. That way I can take my breakfast, lunch and snacks. And then when I get home at night I don't have to think about making dinner. Not only does it save money, but it helps me me to stay on track with my eating plan. So that's it for today. That's it for the week. My total spend today was gas. $28 and 2 cents.
C
You spent the day with your kids, your grandkids. You try to do that at least one day a week. And on the way, you made it a point to skip the gas station near your house because the prices are, as you put it, Gucci gas.
D
Absolutely. Gucci Gas.
C
All right. How do you think about these decisions?
D
So I just. I try to just be very realistic. The gas prices were almost $6 at that gas station. Why would I do. That's crazy. It's Gucci gas. So on my way to my kids, I, you know, I found a better price and I stopped there and it was convenient. I wouldn't like, drive all over the place to save a few pennies. But why would I spend all that extra money when I can find a better price that was on my way anyway?
C
You talked about your car so fondly. It's a paid off Honda. You call it my Green lady. I do 115,000 miles on her. You gonna drive her into the ground?
D
Absolutely. I will drive her into the ground. She's in great shape. I take care of the green lady. She is the first object other than my house that I have owned independently. And she's not even the best car in the world. But she's mine and she's paid off. And every month I made a pretend car payment and it goes into my all about me fund. Even though she's paid off.
C
You said that earlier in your life you drove luxury vehicles with premium gas and expensive maintenance, and you very consciously chosen not to do that anymore. What shifted for you?
D
My financial position. My marital status, quite frankly. And my values have changed. I realize I don't want to spend the money on a luxury car. I could, but it'll cost more. And then that means I can't travel or I can't do things with my kids or that's one less thing that I can buy from my home. So it's just a matter of prioritizing and really thinking about my values. A car is a tool. It gets me back and forth to work. It has to be safe, it has to be reliable. But that's it. I don't need to have the big sticker price anymore.
C
Your total spend for the week was about $400. Sounds pretty low. Does it sound like a normal week for you as you're thinking consciously about saving for retirement?
D
It's probably more than I would have spent, believe it or not. That just happened to be a week where my bills weren't coming in, but the fact that I went out twice that week with my friends, highly unusual for me. Again, not big ticket items, but just unusual for me. Nothing about the week really surprised me though. There were no surprises financially. Everything was sort of thought out and budgeted for.
C
We have a lot of women in our community who are late 50s, early 60s. Maybe they're feeling behind on retirement. Maybe like you, they are going through a divorce later in life. What do you want them to hear?
D
I think my best advice would be trust yourself and trust your gut and know that you can always learn, especially when it comes to money and finance. And educate yourself so that you feel confident enough to make good, good decisions.
C
Thank you so much Ann. This was a great conversation.
D
Thank you Jean. Thanks for having me. It was fun.
C
And that's all for this week's episode of A Week in Her Wallet. Once again, thank you so much to Ann for sharing so openly and giving us a real, honest look at what a full week of spending actually looks like. If you want to be considered for a future episode of the series, tap the link in the show notes. We would love to hear from you. And before we go, if you love today's episode, please take a moment to leave us a five star review on Apple Podcast. Your feedback means the world to me, but it also helps other women find the show. And if you're ready to grow your investing skills and make smarter decisions with your money, come join Investing Fix, our twice monthly Women only investing club. Expert stock pickers bring ideas to the table and together we help build a portfolio. Since launching four years ago, we've built a strong track record and more importantly, a community of women who are learning and winning together. Tap the link in the show notes to check out Investing Fix today. Your first two classes are always free. Hermoney is produced by Hayley Pascalides and our music is provided by Video Helper. Thanks for listening and we'll talk soon.
Episode: A 63-Year-Old Preschool Director Saving For Her “Rich Enough Old Lady” Future
Date: May 1, 2026
Guest: Ann, Preschool Director, 63
Host: Jean Chatzky
This episode dives into the real-life weekly spending of Ann, a 63-year-old preschool director in Westchester County, NY, as part of HerMoney's ongoing "A Week In Her Wallet" series. Ann, who is in a long-term partnership and planning for retirement, offers a transparent look at her financial habits, emotional triggers around money, and the intentional decisions she makes toward her “rich enough old lady” future. The conversation is grounded in compassion, practical wisdom, and the emotional realities facing women navigating financial transitions later in life.
Relationship & Joint Finances: Uses a joint vacation account with her partner, shares expenses based on mutual agreement, with each contributing equally to shared travel and outings.
Grocery Strategies: Buys what's on sale, shops at Trader Joe’s for healthy snacks, and finds that online shopping curbs impulse buys.
Notable Moment: "I call them the Shell station with Gucci gas." (Ann, 28:53)
On saving for retirement:
“I am on a mission to save for retirement, for what I call my rich enough old lady future self.” (Ann, 04:03)
On the importance of her home:
“My home is my sanctuary... It is the most luxurious thing to me. I love being home.” (Ann, 12:50)
On dealing with spending guilt:
“It's my pot of money that I know that I can spend... It sort of gives me the deep breath that I need to say, this is good. I can do this and still save and still do the other things in life that I want to do.” (Ann, 15:02)
On managing money post-divorce:
“I had to become my own CFO. That has been very empowering... It's just given me a sense of confidence and really control.” (Ann, 20:47)
On driving a modest car:
“She is the first object other than my house that I have owned independently. And she's not even the best car in the world. But she's mine and she's paid off.” (Ann, 32:13)
“Trust yourself and trust your gut and know that you can always learn, especially when it comes to money and finance. And educate yourself so that you feel confident enough to make good, good decisions.”
(Ann, 34:21)
This episode is a must-listen for anyone rethinking their financial life in midlife, tackling spending guilt, or striving for a “rich enough” future defined by personal values rather than social expectations.