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Why Working Longer Might Be Your Riskiest Retirement Plan
By Liliana Hall MONEY RESEARCH COLLECTIVE
Working longer sounds safe, but new data shows retirement rarely goes as planned.
Americans are increasingly counting on working longer to make up for retirement shortfalls. But new data suggests that strategy may be less reliable than it seems.
Confidence in retirement is slipping, with just 61% of workers reporting they feel confident they’ll have enough money to live comfortably later in life, according to the latest Employee Benefit Research Institute (EBRI) survey. That’s down from 67% a year ago and the lowest level in nearly a decade.
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To close the gap, many workers are planning to delay retirement or keep working. The problem? That plan doesn’t always hold up. According to the survey, nearly half of people who retired in 2025 — 46% — say they left the workforce earlier than expected, underscoring how unpredictable the end of a career can be.
Rising costs, mounting debt and uncertainty about the future of Social Security and Medicare are only adding to the pressure, leaving many employees with a plan to work longer, but no clear backup if they can’t.
Why working longer isn’t really a plan
The disconnect between expectation and reality is something financial experts say workers often underestimate.
“The biggest problem is that people treat working longer like it’s a plan when it’s really just an assumption,” Pam Krueger, founder and chief executive officer at Wealthramp, tells Money. “And it’s an assumption that depends on a lot of things going right.”
For many workers, the end of a career isn’t something they control. Health setbacks, layoffs or caregiving responsibilities can abruptly change even the best-laid plans, and in 2025, factors like these were behind the vast majority of early retirements, according to EBRI.
That risk shows up in the labor market, too. Data from the U.S. Bureau of Labor Statistics shows that older workers who lose jobs are significantly less likely to get rehired, with reemployment rates dropping sharply after age 55.
“The real risk isn’t just that you stop working early. It’s that you built your entire plan around something you can’t fully control,” says Krueger. “Really ask: Is this what I really want to aim for as my Plan A?”
In other words, working longer isn’t a retirement strategy; it’s a gamble. And it’s one that calls for a real Plan B.
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What a realistic backup plan looks like
A true backup plan, financial experts say, isn’t about picking a single alternative but building flexibility into how retirement actually works.
“A good Plan B isn’t one big solution. It’s in the layers,” Krueger says. That starts with understanding real spending needs, not estimates, and identifying where budgets could realistically be adjusted if retirement comes earlier than expected.
From there, it’s about building multiple sources of income — including Social Security, investment withdrawals and, for some, the option of part-time work.
Some of the preparation also comes down to stress-testing assumptions: What happens if retirement comes earlier than expected, or if markets don’t perform as planned in the early years? That kind of scenario planning can reveal gaps long before they become real-life problems.
Still, building that kind of flexibility takes preparation, not just hoping things work out.
“That’s really the goal: optionality,” Krueger says. “You don’t want to be in a position where you’re forced to keep working. You want to be able to choose it.”
She often encourages workers to think less in terms of a hard stop and more in terms of a gradual transition out of full-time work.
“Think of your plan as a dimmer switch instead of an on/off switch,” Krueger says. “Maybe you ease into something lighter, more flexible and potentially interesting — but that only works if it’s a choice.”
As retirement gets closer, the focus shifts from building wealth to protecting it, making sure a plan can hold up if retirement comes earlier than expected or if markets underperform in the early years of retirement.
Strengthening your financial footing also becomes more important. That can include reducing debt, managing withdrawals carefully and ensuring a portfolio can withstand volatility.
“None of this is exciting, but it’s what gives you financial stability,” says Krueger.
For younger workers, the advantage is time — and the ability to build flexibility long before retirement becomes reality.
“Planning for optionality instead of ‘working forever’ means you’re not dependent on one job or even one type of job,” Krueger says. “You’re building flexibility into your future.”
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Liliana Hall is an Austin-based reporter for Money, where she covers a range of topics, including financial news, policy, banking, investing, passive income, financial planning and student loan debt. Passionate about accessibility and financial literacy, she’s dedicated to helping readers navigate the complexities of money management and feel empowered to make informed decisions about their financial futures. Previously, Liliana covered all angles of personal finance as a writer and editor at CreditCards.com, Bankrate and CNET. Before she ever wrote about money, she worked in a handful of newsrooms across Austin, Texas, covering everything from the Texas Legislature to SXSW and the 2019 Men’s NCAA Swimming and Diving Championships. Her work has been featured in The Daily Texan, Austin Chronicle and KUT. A Texas native, Liliana graduated from the University of Texas at Austin with a bachelor’s degree in Journalism. When she’s offline, you can probably find her paddle boarding on Lady Bird Lake, riding her moped around town or reading for her book club.