Boomers Are Struggling To Retire: 23 Reasons Many Are Working Longer
Retirement at 65 used to be a given. Work hard, save a little, then kick back and enjoy the golden years. That version of retirement is long gone.
These days, more people are working into their seventies, not because they want to, but because they have no choice.
A 2024 Equitable Survey found that 47% of Americans no longer see retiring at 65 as realistic. Instead, they expect to work until 74, thanks to rising costs, shrinking savings, and an economy that makes stepping away harder than ever.
So, what’s really going on? We’re breaking down the biggest reasons why retiring at 65 isn’t the norm anymore. Understanding why can help you rethink what retirement actually looks like and what it takes to get there.
If 65 isn’t the finish line anymore, what is? Let’s get into it.
Table of Contents
Rising Living Costs
Everything is more expensive than it used to be. Housing prices have skyrocketed, groceries cost more than ever, and medical bills can wipe out savings in a blink. Inflation hasn’t just nudged prices up, it’s shoved them into the stratosphere.
While wages have crawled, expenses have sprinted ahead, making it harder to stash money away for the future. A lot of people assumed that, after a lifetime of work, they’d have enough to live comfortably.
Instead, they find themselves working longer just to keep up. The Equitable Survey found that 68% of Americans blame the rising cost of living for their delayed retirement plans.
If money is disappearing faster than you can save it, stepping away at 65 doesn’t just seem unrealistic, it feels impossible.
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Fear of Insufficient Savings
No one wants to outlive their money. The idea of spending your last decades stressing over bills isn’t exactly the dream retirement people imagined. The reality is, most Americans aren’t saving enough.
Pensions have largely disappeared, 401(k) plans are hit-or-miss, and Social Security isn’t the safety net it used to be. A lot of people think they’ll have more time to save, but life gets in the way, kids, mortgages, medical emergencies.
The survey found that 66% of Americans fear they won’t have enough to retire on. That fear keeps people working longer, hoping to build up their accounts before stepping away. But for many, the finish line keeps moving further out of reach.
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Lack of Guaranteed Retirement Income
Once upon a time, pensions guaranteed a steady paycheck for life. Those days are gone. Today, most retirement accounts are tied to the stock market, which means savings can vanish overnight.
The idea of a “guaranteed” income in retirement is a relic of the past, and it’s making a lot of people nervous. According to the survey, 39% of Americans say the uncertainty of their financial future is a major reason they’re delaying retirement.
Without a pension, there’s no safety net. People keep working because it feels like the only way to make sure there’s enough money to last.
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Boomerang Adult Children
It’s not just about supporting kids through college anymore. A growing number of adult children are moving back home—sometimes with their own kids in tow—because of high rent, job struggles, or student loan debt.
Parents who thought they’d be empty nesters are instead footing bills for extra groceries, utilities, or even car payments.
This unexpected financial strain eats into retirement savings fast. Instead of winding down at 65, many are working longer to keep the household afloat while their grown kids get back on their feet.
It’s not the retirement dream they had in mind, but family comes first, and that means the paycheck has to keep coming.
Obsolescence of Skills
The job market moves fast, and skills that were valuable 20 years ago don’t always cut it today. Tech advancements and automation have left some older workers scrambling to keep up.
Retraining isn’t cheap or quick, and ageism in hiring doesn’t make it any easier to pivot to a new career.
Without relevant skills, many can’t land jobs that pay enough to build a retirement fund. So, they stick with what they know, working longer in roles that might not pay well but are at least familiar.
It’s not about giving up—it’s about staying in the game when the rules keep changing.
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Pressure to Maintain Social Status
Nobody likes to admit it, but keeping up appearances is a real hurdle. After years of building a certain lifestyle—nice house, annual vacations, decent car—downsizing for retirement can feel like a step backward.
Social circles and family expectations add pressure to maintain that image, even when the money’s running thin.
Rather than cutting back and risking judgment, many keep working past 65 to afford the life they’re used to. It’s less about greed and more about pride, but either way, it’s a reason retirement stays out of reach for those who can’t let go of status.
Inadequate Social Security Benefits
Social Security was supposed to provide a reliable cushion in retirement. Now, it barely covers the basics. The maximum benefit doesn’t stretch nearly as far as it used to, and concerns about the program’s long-term stability don’t help.
With rising costs and longer lifespans, many people are realizing they can’t rely on Social Security alone. That’s a huge reason people keep working past 65, they simply can’t afford to stop.
Escalating Healthcare Costs
Getting older means more doctor visits, more prescriptions, and bigger medical bills. Medicare helps, but it doesn’t cover everything. Out-of-pocket costs for things like dental, vision, and long-term care add up fast.
Even a single health issue can wipe out savings, leaving retirees scrambling. The fear of high medical expenses keeps many Americans in the workforce longer than they’d like. They need the income, the health insurance, or both.
It’s not just about saving for retirement anymore, it’s about saving for the inevitable healthcare costs that come with aging.
High Levels of Debt
Retirement was supposed to be a time of financial freedom, but a lot of Americans are still carrying debt into their later years. Mortgages, car loans, credit card balances, even student loans, for themselves or their kids, are weighing people down.
The idea of living on a fixed income while still making payments every month? Stressful. Working longer isn’t about staying busy, it’s about paying off what they owe before they can even think about stepping away.
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Stagnant Wages
For decades, wages have barely budged while everything else has gone up in price. A dollar today doesn’t stretch as far as it used to, and that’s left a lot of workers struggling to save enough for retirement.
Even those who have been diligent about putting money away are finding that their nest egg isn’t growing as fast as they expected. If income isn’t increasing, but expenses keep climbing, the only solution is to work longer and try to make up for lost time.
Job Insecurity
Gone are the days when someone could stay at the same company for 40 years and retire with a pension. Today’s job market is unpredictable. Layoffs happen without warning, industries shift overnight, and finding work past a certain age isn’t easy.
Companies prefer younger, cheaper workers, leaving many older employees struggling to hold onto their jobs. The fear of getting pushed out before reaching financial security forces people to stay in the workforce longer than planned.
It’s not just about saving more, it’s about making sure the paycheck keeps coming in.
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Generational Wealth Gap
Older generations had a different financial reality. Houses were affordable, jobs were stable, and pensions existed. That’s not the case anymore.
Younger generations struggle with student loans, high rent, and lower wages, which means they rely on their parents for help well into adulthood. On top of that, many middle-aged workers are also supporting their own aging parents.
Juggling these financial responsibilities makes it harder to save for retirement. Instead of stepping away at 65, many people keep working because they’re still financially responsible for family members on both ends.
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Limited Access to Employer-Sponsored Retirement Plans
Not everyone has access to a 401(k) or employer-matched contributions. Gig workers, freelancers, and those in lower-paying jobs often have no structured way to save for retirement. Without an automatic system in place, many struggle to build up enough savings on their own.
Retirement plans used to be a workplace benefit, but now, for millions of Americans, they’re a personal responsibility. That gap leaves many unprepared, forcing them to work longer to compensate for years of missed contributions.
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Economic Recessions and Market Volatility
Anyone who watched their retirement savings shrink during a market downturn knows how quickly things can change. The 2008 financial crisis wiped out years of progress for many, and recent market dips haven’t helped either.
Stock market-based retirement plans come with risk. When investments drop, people rethink retirement altogether. Instead of cashing out at a loss, many choose to stay employed, waiting for the market to recover before making a move.
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Increased Life Expectancy
Living longer sounds great, until you realize it means stretching savings over more years. People used to plan for a 10- to 15-year retirement. Now, many are looking at 25 to 30 years, sometimes more.
That’s a lot of time to cover expenses, and most retirement plans weren’t built for that kind of longevity. To avoid running out of money too soon, many people keep working well beyond 65, making sure they have enough to last through their later years.
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Impact of Divorce Later in Life
Divorce at any age is expensive, but later in life, it can be financially devastating. Splitting assets, losing a second income, and covering expenses alone changes retirement plans fast.
Those who planned to retire as a couple suddenly find themselves needing more money to maintain the same lifestyle. Instead of downsizing their dreams, many stay in the workforce longer, trying to rebuild what was lost.
For some, retirement at 65 was possible, until divorce made it impossible.
Delayed Parenthood
More people are having kids later in life. That means college tuition, teenage expenses, and all the costs of raising a child are hitting right when they should be ramping up retirement savings. Instead of planning vacations and relaxing, they’re still paying for school, braces, and first cars.
With those financial commitments still in play, walking away from work at 65 isn’t realistic. Many parents keep working to support their kids before they can even think about supporting themselves in retirement.
Financial Support for Grandchildren
A growing number of grandparents are stepping in to raise or financially support their grandchildren. Life circumstances, such as single-parent households or parents struggling to make ends meet, have led to more grandparents taking on major financial responsibilities.
Raising kids wasn’t in the retirement plan, but for many, it’s now part of daily life. That added cost means staying employed longer to ensure the family’s needs are met before even thinking about personal retirement goals.
Underestimating Retirement Needs
Plenty of people think they’re on track for retirement, until they run the numbers and realize they aren’t even close. Many underestimate how much they’ll actually need to maintain their lifestyle.
Inflation, rising medical costs, and unexpected expenses make even a solid savings account feel smaller over time. What once seemed like plenty doesn’t go as far as expected.
Instead of retiring too soon and struggling later, many workers choose to stay on the job longer to add to their savings.
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Prolonged Work Life for Enjoyment or Purpose
Not everyone works past 65 because they have to. Some do it because they want to. Work provides structure, purpose, and a reason to get up in the morning. Without it, days can feel long, and social connections can fade.
Many people realize they actually like their jobs or at least like the financial security that comes with them. Rather than walking away completely, they stick around, working fewer hours or transitioning into roles that give them flexibility while still bringing in income.
Lack of Long-Term Care Planning
Most people don’t think about long-term care until they need it, and by then, it’s too late. Nursing homes, assisted living, and in-home care are expensive, and Medicare doesn’t cover everything.
Without a solid plan in place, those costs can eat through retirement savings fast. To avoid that risk, many choose to work longer, building up a bigger financial cushion so they don’t end up relying on family or struggling to cover medical care in their later years.
Financial Illiteracy
Not everyone grows up learning how to manage money. Many Americans reach their 50s or 60s and realize they didn’t save enough, invest wisely, or plan ahead. A lack of financial knowledge can lead to missed opportunities, poor investment choices, and costly mistakes.
Without a strong understanding of money management, a lot of people find themselves playing catch-up well into their later years. Instead of retiring, they keep working, trying to make up for past financial missteps.
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Evolving Retirement Expectations
Retirement doesn’t look the same as it did for previous generations. Some people don’t want to stop working entirely. Instead, they shift into part-time jobs, consulting, or passion projects that bring in extra income while keeping them engaged.
The idea of a hard stop at 65 is becoming outdated. More people are taking a flexible approach, working longer but on their own terms. For them, retirement isn’t about quitting, it’s about finding a balance between financial stability and personal fulfillment.
Retirement at 65? Think Again
The old idea of retiring at 65 is fading fast. Rising costs, unpredictable markets, and longer lifespans have pushed the finish line further out. Many are working longer, not because they want to, but because they have no choice.
Others are redefining retirement, choosing flexibility over a full stop. The reality is, there’s no set age anymore, it’s all about financial security and personal goals.
If 65 isn’t the answer, the real question is: what’s your plan?
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