Millions of Americans are asking these questions, and some told Business Insider what they've learned in a voluntary reader survey. Over the past two months, over 1,700 Americans and counting between the ages of 48 and 90 shared their biggest regrets with BI. (This is part three of an ongoing series.)
A few dozen of those survey respondents talked about mistakes made while navigating their retirement years.
Regrets included retiring too early, taking Social Security benefits prematurely, and draining retirement savings too quickly. Others said unpreventable life events like a spouse's death or medical emergency set them back. Many wished they held onto jobs longer or better understood how sudden costs could hurt their wallets. And a few talked about finding community — and themselves — in retirement.
Here are a few of their stories.
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Unexpected financial and medical setbacks
Kathleen Rudd, 74, regrets retiring when she did and not having a cushion when her health declined.
Rudd spent her career running a catering business and later working as an executive chef. By 2008, she had about $60,000 saved in a 401(k). That account lost 40% of its value in the Great Recession, and she said it never recovered.
Though she had retirement accounts, she said more nuanced retirement planning wasn't really on her radar.
"I don't think I thought about retirement until probably the last 10 years, and it's because I don't have kids or anybody that I was concerned about leaving a legacy for," Rudd told BI.
Kathleen Rudd regrets retiring too early from her job.Kathleen Rudd
At 62, she retired from a job paying almost $60,000 a year and opted to take Social Security early. She received $1,290 a month, about $400 a month less than if she had waited until 67. Because of Social Security earnings restrictions, she opted for private chef positions paying about half as much as her previous job and part-time gigs as a sales clerk until she was 70.
Now, she has just $40,000 in savings and is banking on eventually selling a house she bought with her sister in Colorado when she originally retired. Hospitalizations for a collapsed lung, a brain bleed, and gut trouble have made money particularly tight.
"I never should have left that job, and I should have stayed working," Rudd said, referring to her executive chef role.
David John, a senior strategic policy advisor at AARP, told BI that older Americans' retirement expectations don't often match reality. Even those who prepare for retirement often don't know when to do so or how to navigate it financially.
"There's the old saying, 'Act in haste, repent at leisure,' and that definitely seems to apply to many of these situations," John said. "In practice, essentially retirement is a foreign country. We can read about it. We can talk about it. But until you actually reach it, until you actually do retire, you aren't fully aware of the reality."
Retiring too fast and spending too much
Misty Miller, 65, said she retired too early. One week in, she regretted it.
Miller worked as a paralegal and legal analyst in the private and public sectors before retiring at 58 with about $700,000 in her retirement accounts. She lived frugally while working, driving the same car for 26 years, and rarely spending on luxuries like going to a salon. She calculated her expenses for the next few decades, and she retired with a monthly pension check of about $4,000. However, after retiring, she said her frugal habits disappeared.
Misty Miller regrets retiring at 58, prompting her to return to work shortly thereafter.Misty Miller
The Sacramento resident withdrew money from her 401(k) for a down payment on a $515,000 beach house. She and her husband then sold the house in 2020 and moved to a $488,000 home in a Sacramento suburb, paying five times as much in property taxes as the first Sacramento property.
"I'm house-rich and cash-poor, so I had to go back to work," Miller said. "I lived frugally up to this point, and then I just lost my mind."
With those house purchases and other expenses cutting her retirement savings by about a third, to $450,000, Miller returned to work for the state, where she worked before retiring. She said she was worried her pension couldn't cover all her expenses.
"I plan to stay working until they carry me out in a casket," Miller said, adding she wishes she never retired.
John, at AARP, said retirees make three common mistakes during the process. The first is taking out more than they should from their retirement investments, leaving them with not enough money to meet their daily needs down the line. The second is the opposite: working longer and saving more than necessary, depriving themselves in fear of not having enough. The third was common among respondents to BI's survey: assuming they can put off financial decisions until it's too late, doing things like stalling on putting aside an emergency fund or relying too heavily on Social Security.
"They need to make certain decisions at an advanced age, and they find that they no longer have the flexibility, meaning the financial assets, necessary to make that kind of decision," John said.
Cashing out Social Security too fast
Sharon, 77, took Social Security too early, prompting her to unretire to cover expenses.
The Atlanta resident, who asked to use her middle name for privacy reasons, worked as a teacher but retired in 2001 after a divorce and her parents' deaths. She worked a few temporary jobs in the 2000s, and she invested much of her inheritance in the market. When the market crashed in 2008, she lost nearly half of her $725,000 assets.
"I became very afraid of the stock market, afraid of what to do, not trusting the advice I was getting from people, and making a lot of bad financial decisions," Sharon said.
To dig herself out, she took Social Security at 62 instead of waiting until 67. She said her financial situation deteriorated when she hit her mid-60s, so she returned to work as a teacher, earning "very little pay." A series of health issues and home damage meant her $936 in Social Security each month hasn't gone far, and she has under $100,000 in liquid assets.
"If only someone had just said, do not take Social Security early, do not invest your money this way," Sharon said. "If I had somebody who would have just really directed me, maybe I wouldn't be in this horrible situation because, by 2030, I easily will run out of money."
John said that about 22% of people had a financial plan before retirement, while just 33% had one after retirement. "People regularly don't do this in part because they are a little more comfortable with a vague worry than with hard facts that they need to deal with," John said.
Returning to work and staying busy
For many older Americans, retirement mistakes aren't about finances. Dozens told BI they returned to work after discovering retirement was lonely or monotonous. While some may envision retirement as sitting on a beach or playing golf, John said many still have an itch to get back to the office.
"So many people have a social network intimately tied with their work life, and once they're outside that, many people just plain old get lonely, and they aren't part of the discussions anymore," John said.
Some respondents, however, had a more positive outlook on how retirement upended their social lives. Many said they took on passion projects and used their retirement to focus on themselves and rediscover their passions.
Cindy Kohli, 64, has been on Social Security Disability Insurance since 1990 and receives Veterans Affairs Disability Compensation. For years, the Arizona resident scraped by as a single mother of three children. She made financial mistakes such as spending too much of her income, though she gradually developed cost-saving strategies.
One of her biggest regrets, though, was not putting herself first.
"I'm the type of person who has always put other people first, never thinking about myself," Kohli said. "There are periods of my life where I never bought myself clothes, didn't take care of myself."
In her retirement years, she has learned to reprioritize herself. She spends hours each week reading financial books, doing pro bono paralegal work, and being active in her community.
"Oddly enough, my greatest challenge now is rediscovering my purpose because, in the past, it's been helping people in any way I can," Kohli said. "A lot of people complain that their limited income keeps them from going places like they used to. In reality, they just have to adapt and find new things to do."
Are you an older American with any life regrets that you would be comfortable sharing with a reporter? Please fill out this quick form or email nsheidlower@businessinsider.com.
