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A Week in Her Wallet: A 63-Year-Old Preschool Director Who Is Saving for Her “Rich Enough Old Lady” Future

Haley Paskalides  |  May 1, 2026

After a divorce at 58, she became her own CFO, and she hasn’t stopped learning about personal finance since.

Ann has a goal. She calls it her “rich enough old lady future self,” and everything, every homemade iced coffee, every no-spend day, every little savings game she plays with herself, is in service of it.

At 63, Ann is a full-time Early Childhood Director in Westchester County, New York, earning over $100k a year. She’s in a long-term partnership, has kids and grandkids she sees as often as possible, and has been living alone since her 36-year marriage ended a few years ago. She’s also had one of the lowest-spending weeks in the history of this series — just $408.79 total.

“It’s probably more than I would’ve spent, believe it or not,” she told Jean. “That just happened to be a week where I went out twice with friends. Highly unusual for me.”

Here’s how the week unfolded.

Day 1: No Spend 

💸 Total Spent: $0

Ann’s week began exactly the way she likes it: with nothing leaving her wallet.

She left the house at 6:30 a.m. with a homemade breakfast, packed lunch, and snacks. And after recording her voice note, she trimmed her own hair.

“I try to have as many no-spend days as possible during the week,” she said. “I am on a mission to save for retirement.”

That mission has a name: her “rich enough old lady future self”. Ann hopes to retire in five to seven years, ideally at 70, so she can maximize her Social Security and keep saving. She recently signed another five-year contract at her job, which she loves, and she’s keeping her options open.

“If I’m healthy enough to continue doing it, that is my plan,” she said.

For Ann, no-spend days aren’t about deprivation. Cooking at home, skipping the takeout coffee, and working out in her living room serve a dual purpose. They save money and, as she’s quick to point out, they support the weight loss journey she’s also on.

“Not only does it save money, but it helps me reach my weight loss goals,” she said. “I actually enjoy cooking as well.

Day 2: Dinner with the Girls 

💸 Total Spent: $54.34

Tuesday was a low-spending day: $23.14 for gas after work and $31.20 for dinner with her girlfriends, a monthly tradition she looks forward to.

But what Ann really wanted to talk about on Tuesday was something harder to put a dollar amount on: the guilt.

“I have a combination of life experiences that make it really challenging for me to spend money on what I call wants,” she said. “I come from a scarcity mentality. I was raised in a home where, throughout my whole life, I heard ‘scrimp and save.’ And so I have that in my mind at all times.”

The guilt doesn’t just show up around big purchases. This week, it was window treatments, something she’d been saving for deliberately for two years, had the money for, and still felt terrible about spending.

“I spent the money, and now I feel like a wreck about it,” she told Jean. “Even though I know it was there. It was not a surprise.”

Jean’s response: “Our home, our nest can be an experience,” Jean said. “I want you to feel okay about these window treatments.”

Ann’s solution to the spending guilt is what she calls her “All About Me” account. Every month, she deposits a few hundred dollars into it. That money is hers to spend, guilt-free, on whatever she wants: a dinner out, a plane ticket somewhere warm in the winter, something fun with the grandkids.

“It gives me the deep breath I need to say, ‘This is good,’” she explained. “I can save and still do the other things in life that I want to do.”

Day 3: The Little Savings Games 

💸 Total Spent: $220.68

Wednesday was what Ann called a “medium spend day.” She stopped at the ATM for $135 cash for her cleaning woman, who comes about every six weeks, and her cell phone bill hit for $85.68.

On the cleaning: she’s unapologetic. “I work full-time, I work hard, and I just don’t want to do that,” she said. “I’d rather spend the free time with my boyfriend, reading a book, being with my grandkids, or in the garden. I feel like I’ve earned it.”

She used to have someone come once a month. Stretching it to every six weeks saves a little money, and, of course, the difference goes straight into the All About Me account.

Which brings us to one of Ann’s favorite topics: the little savings games.

The coffee math came up first. She used to spend around $200 a month on takeout coffee. One day, she sat down, did the math, and stopped. Now that $200 goes into her All About Me account every month. She even brings her reusable Dunkin’ Donuts cup everywhere, filled from home, with coffee ice cubes so it doesn’t get watered down.

Then there’s the Amazon rule. If she sees something she wants, she puts it in her cart and waits 24 hours. If she still wants it, she gets it. If she doesn’t, that money goes into the account.

“I always have this contest with myself,” she said. “How much can I save and put in that account?”

Day 4: Quelling Money Anxiety

💸 Total Spent: $52

Thursday was a low-spending day, with just $52 for a fundraiser ticket at work, where she and her friends made challah together. 

On her commute, Ann had tuned into a HerMoney episode about money anxiety and economic uncertainty, and it hit close to home. For years, she’d been managing her own investments, but never quite silencing the voice in her head that asked: Am I doing this right? Am I optimizing? Is it going to be enough?

Her son noticed before she did. “He said, ‘Mom, you always talk about money. I don’t know if you realize it, but I think it’s becoming a problem,” she recalled. “And I realized, I think he’s right.”

So she hired a financial advisor. And she has zero regrets. “It is the best money I am ever going to spend,” she said. “Rather than going to a therapist, this was my therapist.”

For women who worry about the cost, or whether they have “enough” to justify working with an advisor, Ann is direct: The weight that lifted off her shoulders when she handed over the reins was immediate and real.

“I no longer have to DIY and second-guess myself,” she said. “I’m still learning, still on that journey, but it just feels so good having someone else take care of it.”

Day 5: A Free Meal and a Home Manicure

💸 Total Spent: $0

Friday was another no-spend day. Ann got out of work early, came home, did some chores, and gave herself a manicure. 

That evening, she headed back to work for an event. One of the perks of her job is that when there’s an event, there’s always wonderful food. She took full advantage.

Day 6: Surf and Turf for Under $50 

💸 Total Spent: $53.75

Saturday was chilly but sunny, and Ann and her boyfriend logged eight miles of walking, their favorite free weekend activity. He picked up the tab at lunch. She covered the $6 tip.

Then came a trip to the grocery store, which Ann approaches as both a mission and a sport.

“I love to look in people’s carts to see what they buy,” she said. “You can tell a lot about people by what they buy in the grocery store.”

Her own cart reflects her values: whatever’s on sale. If it’s chicken that week, she cooks chicken. If it’s fish, she cooks fish. When she can, she orders online; the delivery fee is worth it, she says, because it keeps her from buying things she doesn’t need or shouldn’t be eating.

That evening, she and her boyfriend made surf and turf at home. 

The rest of the day’s spending: a $12 gift of plants for her boyfriend’s aunt and uncle, who just became great-grandparents, and her $35.75 monthly home security charge.

Day 7: The Green Lady and “Gucci Gas

💸 Total Spent: $28.02

Sunday was for family. Ann spent the day with her kids and grandkids in Connecticut, something she tries to do at least one day every weekend, with a weeknight visit squeezed in when she can.

On the way, she drove past her local gas station without stopping.

“I call them the Shell station with Gucci gas,” she said. “Their prices are outrageous.” She drove a little further, found gas for $3.79, and filled up, happy, as she often is, that she drives a modest car.

That car is a Honda with 115,000 miles on it, paid off, and beloved. She calls her “the green lady,” and she plans to drive her into the ground. “She is the first object other than my house that I have owned independently,” Ann said.

Earlier in her life, she drove luxury cars. Premium gas, expensive maintenance, the whole thing. That chapter is over. “My values have changed,” she said. “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 the sticker price anymore.”

Before heading home, she started her Sunday ritual: food prep for the week. Breakfast, lunch, snacks, all sorted, all packed, all ready to go. It saves money, keeps her on track with her eating, and it means that when she gets home from a long day of work, she doesn’t have to think about dinner.

A Week In Her Wallet: Final Reflections 

💸 Total Weekly Spend: $408.79

Ann’s week came in at $408.79, and she wasn’t even in a particularly lean week. She went out twice with friends (unusual), had a ticket to a work fundraiser, and bought a gift. A truly typical week, she says, would have been even lower.

When Jean asked what she’d want other women — especially those in their late 50s and early 60s, maybe feeling behind, maybe navigating divorce later in life the way she did — to hear, Ann didn’t hesitate.

“Trust yourself and trust your gut,” she said. “Know that you can always learn, especially when it comes to money. Educate yourself so that you feel confident to make good decisions.”

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