Many people working past 70 didn’t plan to—they had to. From underestimating healthcare costs to delaying savings, here are 9 money mistakes that can keep you stuck working in retirement.
Some people dream of retiring in their sixties, traveling the world, and spending their days on hobbies. But for many, retirement keeps getting delayed.
Why? Often it isn’t about wanting to keep working. It’s about needing to.
Money mistakes compound over time, and by the time you hit 70, the consequences are hard to ignore.
These are the nine most common financial missteps that leave people still working when they’d rather not be.
1) Underestimating healthcare costs
Medical expenses are one of the biggest wild cards in retirement.
Many people assume Medicare will cover everything, but it doesn’t. Long-term care, vision, dental, and hearing aids often fall outside the scope of coverage.
Out-of-pocket costs can eat through savings quickly.
I remember talking with a retired neighbor who thought he had “plenty” saved. Within a few years, the bills for prescriptions and treatments changed his entire budget.
He ended up back at work part-time, not because he wanted to, but because the numbers didn’t add up.
Planning for healthcare means overestimating, not underestimating. If you prepare for higher costs, you won’t be caught off guard.
2) Delaying retirement savings
The earlier you start saving, the more time compounding works in your favor.
But many people push it off. Maybe they tell themselves they’ll start after the kids are older, or when the mortgage is smaller, or when they get a raise.
The problem? Decades slip by. By the time retirement nears, there isn’t enough runway left to let investments grow.
I’ve mentioned this before in another post: procrastination is expensive. It doesn’t just cost you money, it costs you freedom.
3) Carrying too much debt
High-interest debt is like an anchor tied around your financial future.
Credit card balances, car loans, even unpaid medical bills—these obligations don’t just disappear with age.
Some retirees still carry mortgages or significant lines of credit into their seventies.
Imagine having to keep working simply to cover monthly interest. That’s the reality for many.
Paying down debt early isn’t glamorous, but it’s one of the smartest moves anyone can make if they want a shot at a stress-free retirement.
4) Relying too heavily on Social Security
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Social Security was never meant to be the sole source of retirement income.
Yet plenty of people bank on it. They assume their monthly check will cover living expenses.
What they don’t realize is how modest those checks really are, especially once inflation eats into buying power.
A family friend once told me his plan was “to live off Social Security.” Now, at 72, he’s still working security shifts on the weekends because the numbers just don’t cover rent and food.
Social Security is a supplement, not a strategy. So, stop relying in social security.
5) Not diversifying investments
Putting all your eggs in one basket—whether it’s a single stock, one piece of property, or a narrow type of fund—is risky.
Markets fluctuate. Industries change. Companies collapse. If all your money is in one place and it tanks, you’re left scrambling.
The boomers who diversified investments—stocks, bonds, real estate, maybe even a side business—are the ones with more options. The ones who didn’t are the ones still clocking in past 70.
Diversification isn’t exciting, but it’s protection.
6) Ignoring inflation
If you think $500,000 is enough to retire comfortably, it depends entirely on when and where you retire.
Ignoring inflation quietly erodes the value of money. What felt like a large nest egg in 1995 doesn’t stretch nearly as far today.
I once read a behavioral economics study showing how people consistently underestimate the long-term effects of inflation.
It’s not just about today’s costs, it’s about how prices double—or triple—over decades.
Failing to factor this in leaves people forced to work simply to keep up with rising costs.
7) Failing to downsize
Hanging onto the big house might feel comforting, but it’s often a financial drain.
Taxes, maintenance, insurance—it all adds up.
For many, downsizing earlier would have freed up cash and reduced expenses, but the emotional attachment kept them from making the move.
I saw this firsthand when an older relative insisted on keeping a four-bedroom home long after the kids had moved out. Utilities alone were sky-high.
By the time she admitted it was unsustainable, most of her savings were already gone.
Sometimes financial freedom comes from letting go of the things you think you need.
8) Underestimating longevity
Here’s the thing: people are living longer.
That’s great news if you’ve planned well. It’s tough news if you haven’t.
Many boomers assumed they’d live to 75 or 80. Now, with life expectancies stretching into the late 80s or 90s, their money has to last a lot longer than expected.
Without enough savings, they keep working because they have to.
It’s not about being pessimistic. It’s about planning for the best-case scenario—you live a long life and still have enough money to enjoy it.
9) Neglecting financial literacy
The last big mistake? Not learning enough about money in the first place.
Too many people assume they’ll just “figure it out” or that financial planning is only for the wealthy.
But basic financial literacy—knowing how compound interest works, how to budget, how to invest—makes a huge difference.
I’ve met people who didn’t understand their retirement accounts until their sixties. By then, missed opportunities had already cost them decades of growth.
The truth is, you don’t need to be an expert. You just need to be curious enough to learn and disciplined enough to apply what you learn.
Final thoughts
Working into your seventies isn’t inherently bad. Some people love their work and choose to keep going. But for many, it’s not a choice—it’s necessity.
And more often than not, that necessity comes from avoidable money mistakes.
The lesson for all of us? Start early, plan realistically, and never underestimate the power of small financial decisions compounding over decades.
The future isn’t built in one big move. It’s built in the choices you make every day.
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