You’ve heard of the idyllic notion of “Freedom 55” — retiring early and enjoying the later part of your life on your own terms. But what about its lesser-known, anxiety-inducing counterpart, the “Troubled 25?”

That is, the 25% of women in a recent CNO Financial Group survey who said they are “not at all confident they'll have enough money to live comfortably in retirement.” And while the survey found that a third of all middle-income Americans aged 50-85 feel less confident about their retirement than they did a year ago — due to fears around inflation and outliving their savings, among others — only 13% of men reported the same level of concern women held (1).

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“I think that [the women’s] instinct around these things tends to be a little closer to the mark,” Scott Goldberg, president of CNO’s consumer division, told Moneywise. “If the women are worried, that's usually a sign that we all should be worried.”

And the CNO survey isn’t an anomaly. An AARP report also released earlier this month found that 55% of women over 50 aren’t certain their finances will last them through retirement (2). And 2024 reports from both the National Council on Aging (3) and the National Institute on Retirement Security (4) confirmed similar sentiments.

Marcia Mantell, founder of Mantell Retirement Consulting, isn’t surprised at the insecurities women hold around money and retirement.

“All the financial talk has been in the back room with the cigars and the whiskey. The ladies weren't welcome there,” she told Moneywise. “The history of women and money is so recent that we've never had a chance to build up, as a whole cohort, this acumen and this natural way of thinking about not only money, but investing for the future.”

Mantell points to the lack of financial education traditionally afforded to women, beginning in childhood, as a main driver behind the current-day middle-aged women’s retirement insecurity.

“No one ever talked to us,” she said. “If you were offered 25 or 50 cents to babysit for an hour, you just took it. You didn't know you could negotiate that: ‘I actually charge 25 cents per kid.’ None of that.”

Meanwhile, Lynn Toomey, whose online “retirement readiness” platform Her Retirement helps women strategize for their post-work future, told Moneywise that many younger women today suffer the opposite problem.

“I think the average 20-year-old today is concerned because they have so much more access to information in social media,” she said. “The media really highlights, ‘Oh, you need a million dollars’ … and people are like, ‘I don't have anywhere near that.’ So I think the access to the information makes it really scary.”

From a practicality standpoint, the gender wage gap — which research shows is narrowing — still means that women, on average, make around 85% of what men earn (5). And then there’s what Mantell calls “popcorn careers”: Women tend to pop in and out of the workforce to raise children and act as caregivers to older relatives, losing years of earnings in a process she calls financially “catastrophic.”

There’s also the career impact of the transition to menopause, which wealth planner Elinor Bantock described as occurring during “the age bracket where workers are expected to hit their highest level of earnings.”

Mantell noted how women, during the lead-up to menopause, are expected to reach for the brass ring while physically, mentally and emotionally exhausted, and often dealing with the difficult transitions of empty nesting and caring for aging parents.

“So, it is not a formula for success,” she added. “It is also uniquely female. The men have none of this.”

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All of that said, there are strategies that women can engage in to ease stress and better prepare themselves for retirement.

“I think our society, in some respects, probably spends more time planning vacations than they do planning their retirement,” Toomey said. “So I think there are some behavioral things that can be done.”

Our experts agree, and offered the following tips:

Get educated: Toomey believes that the women who are most secure about retirement aren’t the wealthiest, but those who educated themselves most. She and Mantell agree that learning about investments and tax strategies, when to take Social Security — and the various claims you can make related to ex-spouses, widowhood, etc. — can pay huge dividends in your later years. Working with a financial advisor or certified financial planner can help expedite this learning process.

Keep working: For women considering early retirement, or who are stressed about their retirement savings, Goldberg advises that “The number one thing you can do is to not retire early” due to the chance to earn compounding returns on wages that “can be worth multiples of that on the back end of retirement.” And don’t forget, delaying Social Security now means a bigger payout later.

Build communities: Mantell suggests that women going through menopause connect with others online to build communities, share career or savings tips, gain support and simply feel less alone during that transitional stage in their lives.

Squeeze those lemons: Another way to ease retirement stress is learning to, as Toomey says, “squeeze more juice out of the lemon” — meaning making some drastic changes to grow your retirement savings relatively late in life. Her suggestions include leveraging your home equity, cutting unnecessary spending or considering co-housing with family or friends, among other options. “It really is not too late,” Mantell added. Though it’s true, she said, that “If you weren't able to save all along, you are going to have to make some trade-offs.”

Prepare, don’t despair: That said, simply mapping out your financial situation can offer some clarity for how to achieve your retirement goals, making the process less scary moving forward.

As Toomey said, “It's not about perfection, it's about preparation.”

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CNO Financial Group (1); AARP (2); National Council on Aging (3); National Institute on Retirement Security (4); Pew Research (5)

This article provides information only and should not be construed as advice. It is provided without warranty of any kind.