• Some Americans "oversave" for retirement and end up sacrificing during their working years.
• Financial planners advised balancing savings with enjoying life to avoid regrets in retirement.
• This is part of an ongoing series on older Americans' regrets.

Joshua Winston, 70, did a pretty good job preparing for retirement: He ran two successful veterinary clinics, made smart investments, and lived frugally.

But a week after he retired in May, he was diagnosed with cancer. Now, Winston said, he regrets working such long hours during his career, often missing out on trips and date nights.

Winston is one of a few dozen respondents to an informal Business Insider survey who said they worked too hard during their careers or focused too much on saving for retirement, sacrificing family time, travel, or other leisure activities when they were younger. They're among the more than 3,600 older Americans who shared their life regrets through surveys or direct emails to reporters. This story is part of an ongoing series.

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Some survey respondents thought they were behind on retirement goals and chose to bypass larger purchases, only to realize they were well-prepared and too cautious about getting there. A few said traumatic experiences, such as the death of a loved one or a catastrophic medical diagnosis, made them anxious about saving money in case of another emergency. Interviews with five Americans who thought they were too frugal point to the difficulties of knowing how to best prepare for retirement.

Dylan Tyson, the president of retirement strategies at Prudential Financial, described the mindset of an oversaver: "You're cutting back on living — not taking that extra trip or going to that concert or ball game with family and friends — because you're worried that you don't have enough saved."

Saving for an anticlimactic retirement

Winston, who lives in Arizona, spent much of his career in veterinary work. Throughout his life, he drove modest vehicles, lived in an upper-middle-class house, and was cautious about making larger purchases.

He retired with about $3 million but wished he'd spent some of that money on an assistant for his practice so he wouldn't need to work nights running an emergency vet helpline.

"That sucked up a lot of oxygen in my life. I never could watch a movie when I went out with my wife because I would get a dozen phone calls," Winston said, though he acknowledged the helpline helped make his practice successful.

He planned to spend some of his savings in retirement, but he was diagnosed with lung cancer in May and said life has "been hell" since then.

"I have enough money to live until 95 and go on vacations. I have a whole life ahead of me, and this is what happens," Winston said. "I have cancer, and I may not even enjoy the money I worked hard to save."

Tyson said that while a lot of retirement is "guesswork," people should try to determine how much lifetime income they'll need to achieve their retirement goals while balancing their spending needs, wants, and wishes.

"With millions of Americans facing uncertainty, we see the smartest of them taking action to create financial plans that focus squarely on the things that matter most," Tyson said. "Then they are protecting those goals by ensuring that they have secure, predictable income to fund their retirement needs and wants — freeing them to worry less and pursue their greatest wishes."

Working too hard and missing out on friends and family

Ruth Mills, 63, said she began saving later in life but amassed seven figures through frugal living and careful investing. The Minnesota resident had children in her early 20s and finances were tight. As a single mom, she held multiple jobs, working odd jobs as a part-time in-home personal care assistant in addition to full-time work. She worked her way up to a senior accounting officer for the state.

She said because she worked so much and cared for her children alone, she missed opportunities to go out with friends or travel more with family. She said a part of her wished she'd forgone some savings so she could have worked one less job or had hobbies.

"I did well saving for retirement, but so much so I was too frugal along the way and did not enjoy as much while younger as I worked too much," Mills said.

Mills said she pushed back a trip to Ireland that she's no longer physically equipped to take. She recently downsized her house and hopes to retire soon and use her retirement years to spoil her grandchildren and have an active lifestyle.

"Having all the money in the world is great, and I don't have that, but if you don't have the friends and people to spend it with at the end, it's a trade-off," Mills said. She added, "Having made the necessary sacrifices to save and invest earlier, I am looking forward to having the financial security to be able to afford the basic necessities and share adventures and experiences with the grandkids."

Ryan Viktorin, a financial consultant and CFP at Fidelity, said she sees three categories of "oversavers": people who experience an unfortunate event that keeps them from spending the money they've saved, people who worry they'll never have enough because of healthcare costs or market volatility, and people who continue working because they haven't mentally prepared for retirement, fearing it's monotonous or isolating.

She also said that baby boomers retiring now grew up hearing stories about their parents or grandparents going through the Great Depression.

"Sometimes I hear from my clients who have saved really well who say it's in their bones to continue to be frugal, and they feel like they can't really enjoy themselves or live their lives because they have to keep saving," she said.

Missing out on key family moments

Kirk, 75, said he didn't realize he was doing such a good job of preparing for retirement. The retired California attorney, who asked to use only his first name for privacy concerns, worked for various financial institutions and maxed out his 401(k). He amassed over $1.1 million in tax-deferred retirement savings. However, he feared an emergency or market crash would derail his plans for a comfortable retirement.

After retiring from his full-time job at 67, he realized there were opportunities he missed out on because he held back on spending. He regrets not going on a weekslong trip to France with his brother in his 60s; now, his brother has cognitive challenges that make travel difficult. On a trip to Hawaii, he signed his two children up for a helicopter tour but didn't go himself to save money.

"It would have been a great experience to have shared with them and talked about for years to come," Kirk said. "I could now pay for a dozen helicopter rides and not miss the money."

Viktorin said it's important to look at the gap between expenses and income and figure out where there's some wiggle room in your budget beyond saving for retirement, which may help alleviate some of these anxieties older Americans have.

"When you build out a financial plan, you can build out the 'what ifs' and see what it looks like," Viktorin said. "What if we took an extra trip and spent more money? What if we flew business class rather than coach or economy? What if we started to help our children more?"

Are you an older American with any life regrets that you would be comfortable sharing with a reporter? Please fill out this quick form.

• Tamara Ponzo Brattoli's retirement plans changed after her son's sudden death in 2018.
• Brattoli took a job at Costco to pay her bills, but she worries about her financial future.
• Many older Americans face financial struggles after losing loved ones, which affects their retirement.

Tamara Ponzo Brattoli, 57, was set on retiring comfortably in her 60s. She raised three children with her husband and worked as a professor at a community college in a Chicago suburb.

However, when her son died suddenly, she said, in addition to the grief, she became much more worried about her retirement.

Her son Anthony was a college student who died after working abroad in the summer before his senior year. His death hit the family hard, and Brattoli struggled to return to work. After taking a leave of absence to grieve and returning for a few semesters, she retired from teaching, took her pension early, and got a job as a warehouse manager at Costco to help her make ends meet.

She's proud of herself for lessening her financial burden and for getting back to work in a role she could handle, even though it was in a completely different industry.

Though she makes enough to live comfortably, she said she's worried her pension won't keep up with inflation, which could make her finances tighter down the line. She wishes she had more resources and guidance to solidify her finances after Anthony's death and had saved more money earlier in life in case tragedy struck.

"I regret not maximizing my options during that awful time," she told Business Insider. "I needed better help to make decisions but did not know where to turn, and I do not feel like my former employer, or my union, or my therapists really knew how to help me."

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Brattoli is one of a few dozen older Americans who told BI through interviews and a voluntary survey in recent months that losing a loved one affected their finances and retirement plans. Some respondents said losing a spouse, a parent, or a child made them panic and make poor financial decisions. Others said they had to quit working or take lower-stress jobs to cope with the pain.

Read a letter Brattoli wrote to her younger self about what she would have done differently or kept the same. Her story continues below.

Raising a family as a college professor

Brattoli grew up in a middle-class family in Sacramento, California, and was the first in her family to graduate from college. She got a master's degree in English and found work teaching at a community college outside Chicago in 1993, where she also ran its study-abroad program.

She and her husband had three children and invested much of their money in them. She taught extra classes to keep their finances stable and fund vacations.

Brattoli supported her children's musical passions, including financially. Anthony played the tuba and enrolled at Brown University. He won the Brown University Orchestra Concerto Competition and had a concentration in English and Slavic studies. In 2018, he got a job in Prague translating Russian legal documents into English.

"I had this job that allowed me to be flexible during the day, but then so I would run around, take the kids to their appointments," Brattoli said. "And then at night, I was up grading papers until really late."

Grieving and working

While in Prague, Anthony suffered a brain hemorrhage and was in a vegetative state for a month. Brattoli traveled there and stayed with Anthony for three weeks, and they flew him back to the US, where he lived the last days of his life. The university's insurance paid for the flight back, though she regretted not investing in good travel insurance as a backup in case Brown didn't cover it in full.

Brattoli went on leave after Anthony's death but returned to work starting in spring 2019 — including remote teaching before and during the pandemic — to pay her bills.

"I was completely incapable of teaching, and I forced myself to get through it for a time, but I could not function," Brattoli said.

She said because of the grief, she did not prioritize long-term financial planning, adding that she didn't know where to turn for help beyond her therapists or employer. She wishes she would have spoken with a financial advisor or sought retirement resources to make her savings go further.

While winding down her teaching career at 54, she took a job at Costco, first as a seasonal clerk packing e-commerce orders, then in an administrative role handling accounts payable and scheduling truck routes. She was promoted to facilities supervisor at a distribution center, which paid about $65,000 annually. She said that she's still financially stable and that her Costco salary allowed her to somewhat comfortably pay her bills.

Her husband, who is a few years older than her, worked after Anthony's death but lost his job during the pandemic. He also pivoted to Costco, working at a warehouse.

Financial pains

Brattoli contributed to her public-school retirement plan, though she said she and her husband didn't save much. She didn't track how much she put into her retirement accounts and said it was cumbersome to increase her contributions. She wishes she had set aside much more of her earnings earlier so interest would compound on them.

In the years after Anthony's death, Brattoli said her grief and lack of direction led to some financial issues. Because she gave up teaching, she cashed out her state pension early and got paid less than if she continued teaching for more years.

Since she has a public pension, a Social Security provision cuts her benefits from her private-sector work.

"I'm now at a penalty, and that'll be for the rest of my life," Brattoli said. "Even though now I'm working for Costco and I'm putting into Social Security, my Social Security is going to be terrible."

She intends to work for Costco until she's 65, when she expects to have enough for retirement, fearing she won't be physically equipped to work there much later. Costco gives her health insurance, and with her children now financially stable adults, she said she could save more for her future, putting much of her earnings into her 401(k). She said her pension would help keep her afloat after retirement.

"I feel uncertain right now because inflation has messed up my pension already," Brattoli said. "I suffered with that because I took my pension, and then inflation jumped up, and it's not like Social Security where it automatically increases based on how much inflation goes up."

Brattoli said despite the pain of the last few years, the decision to work at Costco was the best choice. Her Costco income and pension brought her to about where she'd be if she still taught full-time, and the role helped her rebuild her confidence.

"It gave me a chance to focus on something completely different than teaching," Brattoli wrote in her letter. "Now, I wear steel-toed shoes. I learned how to drive a forklift. I climb into the backs of semi-trailers and onto the roof of the building."

Are you an older American with any life regrets that you would be comfortable sharing with a reporter? Please fill out this quick form.

• Many of the 3,300 older Americans BI heard from recently regret not preparing enough for retirement.
• Financial planners described how younger people could set themselves up now to retire comfortably.
• This is part of an ongoing series about older Americans' retirement regrets.

For many Americans, their golden years can be a time of reflection — and regret.

Since mid-September, more than 3,300 older Americans have shared their retirement regrets with Business Insider through a reader survey or direct emails to reporters. Many said they wished they'd saved more, waited longer to retire, relied less on Social Security, or been more prepared for unexpected financial setbacks, such as a layoff, a medical diagnosis, or a divorce.

"I didn't really think about retirement in concrete terms," one 65-year-old wrote in response to a survey question about how people wished they planned for retirement differently. "I always felt I had time. Now I'm older, wholly unprepared, and without savings or a 401(k)."

We want to hear from you. Are you an older American with any life regrets that you would be comfortable sharing with a reporter? Please fill out this quick form.

BI talked to financial planners, wealth managers, and a personal-finance writer about what younger generations could do to avoid similar financial mistakes. This story is part of an ongoing series.

Start saving and investing as early as possible, even with a small amount of money

The amount of money Americans need to save for retirement can vary based on lifestyle and the local cost of living. In a survey conducted by Northwestern Mutual in January, the average respondent said they thought they'd need about $1.5 million to retire comfortably. Wealth managers and financial planners encourage young people with this goal — or any others — to understand their options, start early, and take advantage of employer-match programs.

Brad Bartick, a wealth planner at Baird, said Americans should begin saving for retirement while they're in college or in their early 20s. "Sobering though it may be," Bartick said, "success may require you to work a second job" or "earn a higher level of training or education."

He suggests people create a "ruthlessly honest budget" so they can identify places to cut spending and ways to pay down high-interest debt or build up an emergency fund. If money is tight, start by putting $25 to $50 per paycheck aside for retirement.

"That may not seem like much, but it is the behavior of saving — the habit, if you will — that is most important later in life," Bartick said. "Additionally, time will reward your having started early."

Bartick suggested that people whose workplaces offer retirement plans contribute at least the maximum dollar amount their employer will match and raise their savings rate as their salary increases.

A fact sheet published by AARP in December cited an estimate based on Census, IRS, and Federal Reserve data that about 56 million Americans in 2022 lacked access to retirement-savings plans at work. The vast majority of those people earned less than $50,000, meaning they may not have much surplus cash to save for retirement.

Judith Ward, thought leadership director and a certified financial planner at T. Rowe Price, said that not every employer clearly communicates which resources it offers, so workers may have to research what's available. She suggests people aim to save 15% of their salary annually.

A 72-year-old who responded to the survey implored people to "always, always, always take advantage of a 401(k) program with your employer and max it out," adding: "My mortgage was too big initially, so I didn't participate in the program for a few years. Big mistake."

Those lacking a retirement-savings plan at work can use individual retirement accounts, which most banks offer. Traditional IRAs offer tax breaks up front. Roth IRAs offer tax-free qualified withdrawals later in life. Bartick said higher earners should consider a Roth 401(k), as they're likely to be in a higher tax bracket later in life and can therefore save more money.

Bartick described investing as "the great equalizer" for young people looking to build a retirement portfolio, adding that most people can open a brokerage account and invest with few barriers. While investing can be lucrative, it involves risk and isn't a surefire way to build wealth.

Rob Williams, a managing director of financial planning at Charles Schwab, said the biggest regret he hears is that people waited too long to invest, missing out on years of compounding interest.

Retirees who didn't save or invest enough often rely on Social Security in their later years. Several older adults told BI they regretted collecting Social Security at 62 instead of 67, when their full retirement benefits would have kicked in.

A 77-year-old survey respondent who wrote that they "took Social Security too early" said they regretted cashing in on their benefit before reaching full retirement age. They added that working a lower-paying teaching job hurt their Social Security income and retirement savings later in life.

Prepare in case of a divorce or a spouse's death

Dozens of survey respondents said they regretted how they handled finances with their spouse. Some said they weren't on the same page about retirement goals, while others said the death of a partner disrupted their carefully laid plans.

Ward suggested married couples consider retirement as a household and analyze finances together, even if spouses keep their accounts separate.

"One of the biggest retirement mistakes I see is when a spouse assumes they share the same retirement vision," Ward said.

Many older adults told BI that a divorce hurt their finances. One 67-year-old survey respondent who got a divorce said they regretted "not having a 401(k) and thinking I would be OK because my husband worked hard all his life."

A study published in the Journal of Gerontology in 2022 found that from 1990 to 2010, the divorce rate for adults 65 and older nearly tripled. A BI analysis of 2023 individual-level Census Bureau data found that divorced retirees had lower average 401(k) balances, less savings, and a lower monthly retirement income than married people.

Elizabeth Ayoola, a personal-finance writer at NerdWallet, said people could protect some of their money and retirement savings with prenuptial agreements. However, prenups typically apply only to money and assets acquired before a couple ties the knot, so they provide less protection if the couple divorces later in life. She said that including major assets or money in a trust could be an effective way to secure wealth in a divorce, and she advised couples to have transparent conversations about finances at all stages of their relationship.

A spouse's death can also have detrimental financial ramifications. Older Americans told BI they struggled to get by without their spouses' paychecks or Social Security income. Others said a lack of a will threw them into a complex legal battle and probate process for their spouses' assets.

Ayoola advised couples to write a will and consider a life-insurance policy.

Build a nest egg to lessen the sting of sudden bills or loss of income

Some older Americans told BI that unexpected expenses or events, like medical diagnoses or layoffs, depleted their retirement savings.

One 78-year-old survey respondent wrote that her husband had heart problems and was recently laid off. She described wanting to reduce their housing costs but being unable to. "We are trapped in a large home living on Social Security and draining savings until it's gone," she wrote.

Dozens of older Americans said a layoff affected their retirement planning. Carly Roszkowski, a vice president of financial-resilience programming at AARP, advised older workers to continue updating their résumés and keep their skills sharp in case they're laid off.

Younger people may want to diversify their skills and prepare to pivot careers. They may also want to build an emergency fund to support themselves or loved ones if they lose their jobs.

"Build relationships with colleagues, mentors, and industry professionals. Networking can open doors to new opportunities and provide valuable support and guidance," Roszkowski said. "Reverse mentorship programs can be effective in organizations to help bridge generational gaps and build understanding and collaboration between different age groups."

Several older Americans said they stopped working or used up much of their savings because of a medical diagnosis. Healthcare researchers advise investing in routine checkups, factoring medical emergencies into nest eggs, and researching government-assistance options.

When a 69-year-old survey respondent and her husband began to struggle with health issues in their 50s and 60s, she said it took a toll on their savings: "Because of our health, I had to cash in my 401(k) for medical expenses at a very early age."

Financial planners told BI that people should analyze the value of their last-resort funding sources, like homes or life-insurance policies, so they know the total of their assets in a costly emergency. Ward said a healthy emergency fund for young people should include enough to cover three to six months' worth of expenses. As people age, they should allocate more: Retirees should have one to two years' worth of income, Ward said.

Sudden healthcare costs can drain emergency funds. Williams advised that people — whether they're young or heading into retirement — research their insurance options so they can reduce out-of-pocket costs.

Doug Ornstein, a director of wealth management at TIAA, argued that people paying high out-of-pocket healthcare costs in retirement "probably would have to live really bare-bones instead of being able to leave their kids some money or be able to do some trips and travel."

Benefits counselors can also help people determine the government aid they qualify for — the money may help them conserve savings and cover bills. The National Council on Aging estimates that up to 9 million older Americans are eligible for government assistance but not enrolled.

Ayoola said that benefits like SNAP or Medicaid could help lower-income people save money over time. "I would tell them to look around for as many government resources as possible to supplement their income," Ayoola said.

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