• Unexpected medical crises have derailed retirement plans for many older Americans.
• Many regret not preparing financially for sudden medical expenses, while some wish they worked less.
• This is part of an ongoing series about older Americans' regrets.

Vera Steward, 64, earned over $60,000 a year at the peak of her career. But since having a stroke at 48, she hasn't returned to work and is just scraping by.

She's one of many older Americans who shared with Business Insider in recent months how an unexpected medical crisis derailed their retirement plans and what they wish they'd done differently. As of publication, over 3,300 readers between the ages of 48 and 96 have responded to an informal online survey or emailed reporters about their biggest life regrets. This is part of an ongoing series.

While many medical diagnoses are unpredictable, dozens of respondents, including Steward, said they wish they'd been better prepared financially. Their regrets include not being more cautious with spending or savvier with investments when they were healthier, not prioritizing routine medical appointments, not factoring medical expenses into retirement planning, and not having robust insurance.

Eleven said in interviews that a medical diagnosis at the peak of their careers led them to retire early, and as a result, they rely on federal government checks to get by.

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Steward is one of them, despite having a master's degree and working since she was a teenager. After her stroke almost 20 years ago, she began receiving slightly over $1,000 in monthly Social Security Disability Insurance; she now receives $1,688 in Social Security after cost-of-living adjustments. Nearly half of her benefits go toward rent, and she only receives $23 monthly in SNAP benefits to help buy food. Some months, she decides between getting a haircut or buying groceries, and she's relied on her daughter for financial assistance.

"I've always been middle class, and now I guess I'm no class," said Steward, who lives in Columbus, Georgia. "I'm in this house almost 24/7. The only time I leave is to go to the doctor. I have nowhere to go."

Not prioritizing health in younger years and asking for what you need

Anita Clemons Swanagan, 59, wishes she'd spoken up for herself more during her working years to be paid what she's worth. While employed at prisons and hospitals, she was on her feet all day often working 12-hour shifts — in addition to second jobs as a gig worker — so she could raise her three daughters.

Swanagan injured her back and developed arthritis. She had a stroke at 45 and worked again for a decade until she had a second stroke in 2021, which affected her walking, speech, and cognitive functioning.

In addition to wishing she'd asked for better pay and more health accommodations, she said she could have done more to grow her wealth, such as saving more and giving less to others. She also wished she'd prioritized her health and took more time off while sick, but she said there's little use looking back on what might have been. She lives in her SUV in rural Illinois on $1,500 a month in Social Security before Medicare deductions.

"People think they have enough money, but all they have to go through is one major illness that could wipe out everything," Swanagan said.

Swanagan is one of dozens BI spoke with who are battling health conditions, unable to work, and relying on government assistance to keep them afloat. Because of their medical conditions, most rely on two federal programs colloquially called "disability": Social Security Disability Insurance and Supplemental Security Income. Many said it isn't enough to pay their bills.

SSDI benefits are based on your work history. In 2024, the average monthly payment was $1,537, with a maximum payment of $3,822 a month. SSI, which is allocated to people with disabilities and limited incomes, will be capped at $967 a month for an eligible individual in 2025.

Retirees' reliance on these programs has risen while the benefits have barely kept up with the cost of living. The average inflation-adjusted Social Security payment for disability insurance in December 1999 was $1,413 a month; at the end of 2023, it was $1,537, SSA data showed. While 3.2% of workers covered by Social Security in 1999 were disabled workers who received Social Security insurance, this rose to 4% in 2023.

And it's becoming more difficult to qualify for these benefits, said Steve Perrigo, the vice president of sales and marketing at the law firm Allsup. SSDI processing times have doubled over the past few years while approval rates have fallen to historic lows.

In fiscal year 2023, 61% of disability claims were rejected initially, while 85% were denied in reconsideration, according to Social Security Administration data and information provided by Allsup. About 45% of people are approved in hearings, which come after denials of an additional application and reconsideration.

Perrigo said he encourages clients to try to find work before, during, and after receiving benefits if they're able to.

"We see individuals who have to go through foreclosure and tap into their 401(k) and bankruptcies," Perrigo said of the long wait times to receive benefits.

For some, including Paula Mastro, returning to work isn't an option.

Mastro, who's 65 and lives on just under $1,100 a month in Social Security benefits, worked part-time in restaurants and catering jobs while raising her daughter and spent years as a full-time caretaker for her parents. She told BI she regretted working odd jobs that didn't provide a pension and not contributing to a 401(k). She also said it was a mistake to not properly document some of her income on tax forms, which hurt her Social Security allotment.

In 1991, Mastro received about $200,000 in a divorce settlement, most of which she spent on a home and car. She said often lived paycheck to paycheck and didn't prioritize investments.

Mastro developed back problems in the late 1990s after a car accident and was diagnosed with fibromyalgia over a decade ago. Earlier this year, she developed an inflammatory skin disease that prevented her from returning to work.

She said that last year, her public assistance covered only a fraction of her medical expenses, putting her thousands of dollars in debt. She lives in a low-income condo she inherited from her sister and barely has anything in savings.

"You expect in your golden years to be traveling, going on vacation, bringing your grandchildren to the theater," Mastro said. "I didn't do any of that because I couldn't. I should have saved up for retirement."

'Floating through life' with no concrete plan

Jan Lovell, 73, said she should have learned more about finances during and after her marriage. Lovell, who lives in Warren, Michigan, was diagnosed with multiple sclerosis in 2005. As the disease progresses, it further complicates her financial planning.

Lovell spent 25 years as a church secretary, earning a modest salary. She only contributed about 5% to her 401(k) and let her husband handle most of her finances. An unexpected divorce in 2004 put Lovell into "float through life" mode, during which time she didn't have a financial plan and did what she could to pay her bills. Over her career, she accumulated seven retirement funds she never combined, totaling $160,000.

She went through a foreclosure in 2010, and she worked for another decade until retiring in January 2020.

She lives off about $3,300 monthly gross income from Social Security pre-deductions and a pension, but medical expenses, such as contributing $3,500 for a wheelchair, have put a dent in her wallet. After a recent hospitalization, she's planning to move to a senior living facility that she expects will deplete her savings by 2027.

"Most places I've looked at now are $3,000 a month for a 400-square-foot unit, which is twice the cost and half the square footage of a regular apartment," Lovell said. "The 'assistance' is an additional charge, depending on needs, and I'll likely need the most expensive level, at about $2,000 a month."

Relying too much on the market

D. Duane MaGee, 78, thought he prepared well for retirement, but after losing thousands in the 2008 market crash, he regretted putting too much faith in the market — and hasn't touched investments since.

MaGee made six figures as a manager at Ford. He retired in his early 50s as the plant shuttered. He'd saved money throughout his career, though not enough. To compensate for his reduced income, he worked in security at a hospital and in hotel management.

His wife had a quadruple bypass surgery three decades ago, and he became her caregiver in between his work shifts. His wife's medications ate up a portion of their savings each month. The 2008 market crash erased nearly $80,000 of their limited retirement savings — much of which was his wife's inheritance from her mother — and he wished he had been more proactive about saving while at Ford.

MaGee, who still cares for his wife, was diagnosed with Parkinson's disease six years ago. He gave up his retirement job shortly after the diagnosis, and they rely on about $62,000 a year in retirement income from Social Security and a pension. Meanwhile, rising inflation has made them even more cautious about spending.

"I don't know how I'm going to get savings now because we're getting a lot older now, and so we have things facing us now where we don't know where the money is going to come from," MaGee said.

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• Florence Pugh, 28, was diagnosed with PCOS and endometriosis at 27.
• She froze her eggs at 27 because both conditions can impact fertility.
• Pugh said a different doctor dismissed the diagnoses because of her age.

Florence Pugh has opened up about two recent diagnoses that prompted her to freeze her eggs at 27 years old.

Speaking on Dear Media's SHE MD podcast with her Beverly Hills gynecologist, Pugh, now 28, discussed the moment she was diagnosed with polycystic ovarian syndrome (PCOS) and endometriosis — conditions that can impact fertility.

The Oscar-nominated actress said it was a "mind-boggling" experience to find out that having kids may not be a straight-forward process for her, and embarking into the world of fertility preservation.

Pugh also said that another doctor back home in London, whom she did not identify, dismissed her diagnoses.

"She shook her head and she said, 'well, that's just not possible,'" Pugh recalled. She said she told the doctor about her egg count and hormone test results done in LA. Pugh said the doctor responded: "No, you're fine. And even if you do have it, you'll be fine to have kids well into your 30s."

Dr. Thais Aliabadi, the gynecologist who diagnosed Pugh, reacted to her story on the podcast: "That is what women go through every single day."

PCOS and endometriosis — the leading causes of infertility — often go undiagnosed

PCOS and endometriosis are some of the most common causes of infertility. PCOS is a condition where ovaries produce excess male sex hormones, or androgens, creating hormonal imbalances. Endometriosis occurs when the lining of the uterus grows outside of the uterus.

Common symptoms of both include irregular and painful periods, as well as bloating or weight gain. PCOS symptoms also include thinning hair, excess hair growth, acne, and darkened skin.

Pugh said she had some of the symptoms, like weight fluctuations, acne, and "hair that shouldn't be in certain places." She attributed them all to work stress and just "part of being a woman."

Pugh said she went to get a checkup after being hit by a "sudden feeling" that something was off with her body. "I'd had a few weird dreams; I think my body was telling me," Pugh said.

At the appointment, Aliabadi asked Pugh if she'd ever had her eggs counted — something Pugh said she never thought of doing because she was young.

After counting her eggs and giving Pugh a hormone test, Aliabadi diagnosed her with both PCOS and endometriosis, encouraging her to freeze her eggs in her 20s.

Pugh said she had heard of the conditions before, but didn't think they were common. 1 in 10 women have PCOS, and roughly 200 million people worldwide have endometriosis.

She also didn't expect to have fertility problems because of her family history. "My family are baby-making machines," she said. Her mother had babies into her 40s, for example. She said she was grateful to get diagnosed and freeze her eggs because she'd been wanting kids since she was a child.

These conditions are often misdiagnosed or ignored

PCOS and endometriosis are commonly underdiagnosed or misdiagnosed entirely.

Pugh said she understands that she has "privilege in areas where others won't," so if her symptoms were dismissed, other patients might take even longer to get proper treatment.

PCOS disproportionately impacts women of color, who are also more likely to be misdiagnosed due to racial bias around symptoms like weight gain.

Pugh said she believes everyone should be educated on PCOS and endometriosis because "it's something that will be the defining factor of whether you can have children or not."