From selling a business to hitting $100k in investments at 30, four women get real about what retirement planning looks like across the generations.
Do we have enough to feel comfortable in retirement? And how do we make sure the women who come after us feel financially empowered?
Those are the questions Jean Chatzky has been saving for the third and final episode of From First Paycheck to Forever Paycheck, HerMoney’s series in collaboration with AARP.
According to a recent AARP survey, the majority of women voters 50 and older say they are worse off financially than they were just one year ago. And when asked about retirement? Only 11% say they feel very confident.
“Let that sink in,” Jean said. “We are talking about women who’ve worked hard their entire lives, raised families, built careers, cared for aging parents, and navigated every curveball life threw at them. The majority of them don’t feel secure. But they really should be giving themselves more grace.”
Because what those numbers don’t capture, she says, is the decades of compounding disadvantages that got us here. The stubborn wage gap. The access gap; nearly half of all US workers don’t have a way to save for retirement at work through their paycheck. The fact that caregiving responsibilities most often fall to women. And the investing gap, because for too long, women were left out of the financial conversation entirely.
But the good news, Jean says, is that younger women are adapting, investing earlier, and building wealth differently.
She sat back down with Hannah Williams of Salary Transparent Street, Viviana Vazquez of OverGenPoverty, Ashley Parker of The Atlantic, and Carly Roszkowski, Vice President of Financial Resilience at AARP, to ask what “enough” actually looks like at every age, and how we build a life that gives us financial peace.
Here’s what they said.
What Does “Enough” Actually Mean? Four Very Different Answers
Even though she’s only 30, Viviana said, “I feel like I already have enough. Having $100,000 invested that is going to grow to a million dollars by the time I’m 67, that’s more than I could have ever imagined.”
She also introduced a concept that resonated deeply with the table: mini retirements. “That’s kind of what I’m doing now,” she said, “Taking a career break, working on my business, testing out what it feels like to take money from savings and use it.”
For Hannah, “enough” is harder to pin down, and she was refreshingly honest about why. “I struggle to think of what is enough because it really doesn’t feel like there is ever enough, especially with goalposts moving,” she said. She pointed to the American healthcare system as the biggest wildcard in her retirement planning. “One big catastrophe — we’re one big diagnosis away from bankruptcy.”
Having enough is less about a number and more about a feeling of independence for Ashley. “I always want to feel that if something were to happen — an unexpected death, an unexpected divorce — I have the ability in terms of my savings and my income and how I’m planning my life to be okay on my own. I would not get into that free fall that I can’t pull myself up out of.”
And for Carly, “enough” means stability. “It’s options,” she said. “You can choose to have that splurge or make that memory. I don’t wanna feel that stress of going to the grocery store or paying for gas in your car. That would be very peaceful.”
Solving The Retirement Planning (And Spending) Problem
The 4% rule — the conventional wisdom that says you can safely withdraw 4% of your retirement savings each year — is flawed, Jean and Carly agreed. And the emotional reality of retirement spending is even more complicated than the math.
Jean illustrated it with a story about her own mother. After Jean’s father died, her mother had a nice balance in her retirement account, along with his teacher’s pension, Social Security, and some dividend income. She spent the income happily, but she could not bring herself to touch the principal.
“When she died, 20 years after my father died, she had slightly more than she had when he died,” Jean said. “And she had three kids telling her, ‘We don’t need your money. This is your money. You should spend it.'”
The research behind Jean’s new book, The Forever Paycheck, gets to the heart of why this happens, and why retirement planning needs to include not just a plan for saving, but a plan for spending as well. “People who have a pension, a paycheck that lasts the rest of their lives, spend twice as much as people who have the exact same amount of money in an investment account,” Jean explained.
It’s a revolutionary reframe for retirement planning: the goal isn’t just to accumulate enough. It’s to build income that lasts, and a framework that lets you enjoy it.
What Financial Peace Means Across Generations
Jean closed the series by asking every woman at the table what financial peace actually feels like to them today.
Hannah admitted that she’s still working towards that peace. But to her, “being educated and informed about how my money can multiply, having a plan and sticking to it. Being as prepared as possible is the closest I can get.” And Viviana agreed that the first step is “making a plan and getting to the point where you know that past you looked out for future you, and now present you can take care of that situation.”
For Ashley, the definition of financial peace is not being able to worry about splurging on things for her kids, such as pitching in for her stepdaughter to get highlights. And Carly believes that financial peace starts with being informed. “Don’t rely on your spouse or your partner or a friend to tell you. Make sure that if you had to do it on your own, you knew enough to make informed decisions,” she said.
And Jean, who has spent her entire career making retirement planning accessible and actionable for women, put it best: “Listening to conversations like this is what it takes to bring a lot of women along.”
MORE ON HERMONEY:
- What Four Women Across Four Generations Really Think About Money, Financial Literacy, and Building Wealth Today
- The Widow’s Tax Penalty: What Happens When You Go From Married To Single
- Five Retirement Myths Busted
This is the third and final episode of From First Paycheck to Forever Paycheck, a three-part series in collaboration with AARP. Listen to the full episode on the HerMoney podcast feed and watch on YouTube. And if you haven’t listened to episodes one and two yet, go back and start there; this conversation builds on everything we’ve covered.
Jean Chatzky’s new book, The Forever Paycheck: The New Retirement Strategy to Spend More, Worry Less, and Never Run Out of Money, is available for pre-order now and publishes September 8, 2026.
Whether you’re looking to save money, manage debt, or prepare for retirement, AARP has resources and tools to help you prepare for your financial future and reach your goals. Get started at www.aarp.org/retirementreadiness.
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