7 Financial Decisions Retirees Say They’d Undo If They Had the Chance

Retirement. It’s the golden finish line after decades of work, right? Yet once people reach that point, many discover they wish they’d made different choices along the way. According to Lincoln Financial Group, more than 60% of retirees said they’d go back and do things differently when planning their retirement. We’re talking about real regrets here, not minor inconveniences.

Fidelity’s 2025 State of Retirement Planning Study showed that 38% of retirees surveyed said they would have prioritized saving earlier if they had the chance to go back in time. That’s a lot of second guessing. Let’s be real, nobody wants to spend their later years thinking “I should have known better.” So let’s dive in and see what mistakes retirees wish they could reverse. These aren’t abstract warnings. They’re actual financial missteps that left people scrambling to adjust their lifestyle when it was too late.

Not Saving Enough Early On

Here’s the thing about compound interest: it’s absolutely magical if you start early. Not saving as much as possible is a big retirement regret for many, and honestly, it makes sense. Over half (52%) of survey respondents expressed this regret of not saving more. The most common reason given (by 29% of respondents) was that they were living from day to day. Nearly as many (27%) said that they simply didn’t plan ahead. I think people underestimate just how much a few hundred dollars a month in your twenties or thirties can balloon into by retirement. It sounds cliche, but time really is money.

Claiming Social Security Too Early

Nearly one in five respondents (19%) regretted claiming Social Security before their full retirement age, and those numbers get worse when retirees reflect on how much they lost by doing so. Claiming benefits at the earliest age possible (62) can lower a monthly benefit by 30%. On the other hand, holding off until age 70 to claim can boost the monthly benefit received by 24%. That’s not chump change. Research has shown that around 7 in 10 retirees would find themselves with more lifetime income if they delay benefits until 70 instead of claiming at a younger age. The temptation to grab that check as soon as you’re eligible is real, but many later wish they’d waited a few more years.

Underestimating Healthcare Costs

This one catches nearly everyone off guard. Health care costs catch many retirees by surprise. About half of retirees told Schroders they thought Medicare would cover more of their health care expenses than it does. Medicare helps, sure, but it’s not a free pass. Fidelity’s 23rd annual Retiree Health Care Cost Estimate revealed that a 65-year-old retiring in 2024 was expected to spend an average of $165,000 in health care and medical expenses throughout retirement. That’s a staggering figure for folks expecting Medicare to handle everything. Nearly two-thirds of pre-retired investors anticipate spending at least $1,220 below the $8,600 annual estimate in costs. People just don’t budget properly for medical bills, prescriptions, and long-term care needs.

Not Purchasing Long-Term Care Insurance

One-third of the survey respondents said that if they could do it all over again, they would buy long-term care (LTC) insurance, which helps cover the cost of long-term care and is less expensive the earlier it’s purchased. Let’s think about what long-term care actually costs. A Place For Mom breaks down the 2025 costs for different levels of care: Assisted living: $5,190 per month. Memory care: $6,200 per month. Those numbers add up fast. The U.S. Department of Health and Human Services estimated that 49% of men and 64% of women turning 65 in 2022 would need significant long-term care. Yet only 27% of respondents believe they’ll need long-term care at some point in their lives. There’s a massive disconnect between expectation and reality here.

Carrying Mortgage Debt Into Retirement

Back in the day, people held mortgage-burning parties when they retired. Now? Over the past three decades, the share of homeowners ages 65 to 79 with a mortgage rose from 24% to 41%, while median mortgage debt surged by 400%. That’s jaw dropping. 44 percent of Americans between the ages of 60 and 70 have a mortgage when they retire, and as many as 17 percent say they may never pay it off. Living on a fixed income while making monthly mortgage payments creates serious financial strain. 97% of older owners with mortgages who are lower-income, have an income under $25,000, are cost-burdened, meaning they’re paying more than 30% of their income for housing. Honestly, carrying debt into retirement is one of those things that sounds manageable until you’re actually doing it.

Not Planning for Early or Forced Retirement

A lot of folks plan to keep working into their late sixties or even early seventies. The Employee Benefits Research Institute (EBRI) found 58% of respondents were forced into early retirement mostly due to a health problem or disability (38%) – though 23% reported changes or restructuring at their company. Fidelity’s 2025 State of Retirement Planning survey showed that more than half of all workers plan to continue working part-time in retirement indefinitely. The problem is, reality doesn’t always match intentions. Health issues, layoffs, or plain burnout can shove you into retirement before you’re financially ready. If your entire plan hinges on working until 68, you’re gambling with your future security.

Failing to Create a Written Retirement Plan

Here’s something wild: Only 18% of Americans have a written retirement plan, according to Fidelity. Most people just wing it with vague notions of needing “enough” money. 63% of retirees wish they had done more planning before retirement, according to the Schroders survey. More than a quarter of retirees who haven’t saved enough attribute it to not planning ahead, according to a National Bureau of Economic Research working paper. A proper plan isn’t just about saving money; it’s about understanding your income sources, your expected expenses, tax implications, and how to make your nest egg last. Without a written roadmap, people tend to drastically miscalculate what they’ll actually need. It’s hard to hit a target you’ve never defined.

Looking back on these regrets, one thing becomes crystal clear: small decisions early on have massive consequences later. The retirees sharing these stories aren’t trying to be doom and gloom. They just wish someone had explained these pitfalls before it was too late to course correct. What do you think? Are any of these surprises, or do they confirm what you already suspected about retirement planning?