Millions of Americans are asking these questions, and some told Business Insider what they learned from a voluntary reader survey. Over the past two months, more than 1,700 Americans between the ages of 48 and 90 shared their biggest regrets with BI. (This is part three of an ongoing series.)
Several dozen of these respondents talked about mistakes they made during their retirement years.
Regrets included retiring too early, withdrawing Social Security benefits prematurely and depleting retirement savings too quickly. Others said unpredictable life events, such as the death of a spouse or a medical emergency, work against them. Many wish they could keep their jobs longer or better understand 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.
Kathleen Rudd, 74, regrets retiring when she did and running out of cushion when her health deteriorated.
Rudd spent her career running a catering company and later worked as a chef. By 2008, she had saved about $60,000 in a 401(k). That account lost 40% of its value during the Great Recession, and she said it never recovered.
Although she had retirement accounts, she said more nuanced retirement planning wasn’t really on her radar.
“I don’t think I’ve thought about retirement until the last ten years, and that’s because I don’t have any children or anyone that I was worried about leaving a legacy behind,” Rudd told BI.
At age 62, she retired on nearly $60,000 a year and opted to take Social Security early. She received $1,290 per month, about $400 per month less than if she had waited until age 67. Due to Social Security income restrictions, she opted for a job as a private chef, which paid about half as much as her previous job, and part-time gigs as a sales associate until she was 70.
Now she has just $40,000 in savings and is counting on eventually selling a house she bought with her sister in Colorado when she originally retired. Hospital admissions due to a collapsed lung, a brain haemorrhage and intestinal problems have made income particularly tight.
“I should never have left that job, and I should have kept working,” Rudd said, referring to her role as chef.
David John, a senior strategic policy advisor at AARP, told BI that older Americans’ retirement expectations often don’t match reality. Even those preparing for retirement often don’t know when to do so or how to handle it financially.
“There’s the old saying, ‘Act hastily, repent at leisure,’ and that certainly seems to apply to a lot of these situations,” John said. “In practice, retirement is essentially a foreign country. We can read about it. We can talk about it. But until you actually achieve it, until you actually retire, you’re not fully aware of the reality.”
Misty Miller, 65, said she retired too early. A week later she regretted it.
Miller worked as a paralegal and legal analyst in the private and public sectors before retiring at age 58 with approximately $700,000 in her retirement accounts. She lived frugally while working, drove the same car for 26 years and rarely spent money on luxuries like going to a salon. She calculated her expenses for the coming decades and retired with a monthly pension check for about $4,000. After her retirement, however, she said her frugal habits disappeared.
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 suburban Sacramento, paying five times as much in property taxes as the first property in Sacramento.
“I’m house rich and cash poor, so I had to go back to work,” Miller said. “Until now I have lived frugally, but after that I have gone crazy.”
Because those home purchases and other expenses reduced 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 worried her pension wouldn’t cover all her expenses.
“I plan to keep working until they carry me out in a casket,” Miller said, adding that she wishes she would never retire.
John from AARP said retirees make three common mistakes during the process. The first is that they withdraw more from their pension investments than necessary, which in the long term does not leave them with enough money to meet their daily needs. The second is the opposite: working longer and saving more than necessary, depriving oneself for fear of not having enough. The third was common among BI survey respondents: assuming they can delay financial decisions until it’s too late, for example by waiting to set aside an emergency fund or relying too heavily on Social Security.
“They have to make certain decisions as they get older, and they find that they no longer have the flexibility, that is, the financial resources, necessary to make those kinds of decisions,” John said.
Sharon, 77, took advantage of Social Security too early, prompting her to withdraw from her pension to cover the costs.
The Atlanta native, who asked to use her middle name for privacy reasons, worked as a teacher but retired in 2001 after a divorce and the death of her parents. In the 2000s, she worked a few temporary jobs and invested much of her inheritance in the market. When the market crashed in 2008, she lost almost half of her $725,000 fortune.
“I became very afraid of the stock market, afraid of what to do, I didn’t trust the advice I was getting from people and made a lot of bad financial decisions,” Sharon said.
To dig herself out, she took benefits at age 62 instead of waiting until age 67. She said her financial situation worsened when she reached her mid-60s, so she went back to work as a teacher, earning “very little pay.” A series of health problems and home damage have meant that her $936 in Social Security benefits each month have not gone far, and she has less than $100,000 in liquid assets.
“If someone had just said, don’t take Social Security early, don’t invest your money this way,” Sharon said. “If I had someone who would have really put me in charge, maybe I wouldn’t be in this terrible situation because I will easily run out of money in 2030.”
John said that about 22% of people had a financial plan before retirement, while only 33% had one after retirement. “People regularly don’t do this, in part because they’re more comfortable with a vague concern than with hard facts to consider,” John said.
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 imagine retirement as sitting on the beach or playing golf, John says many still have the itch to return to the office.
“So many people have a social network that is closely tied to their work, and once they get out of that, a lot of people just get lonely and aren’t part of the discussions anymore,” John said.
However, some respondents had a more positive view of the way retirement was upending 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 since 1990 and receives disability compensation from Veterans Affairs. For years, the Arizona native lived as a single mother of three children. She made financial mistakes, such as spending too much of her income, although she gradually developed cost-saving strategies.
However, one of her biggest regrets was not putting herself first.
“I am the type of person who has always put other people first and never thinks about myself,” Kohli said. “There are times in my life when I never bought clothes for myself, I didn’t take care of myself.”
In her retirement years she has learned to reprioritize herself. She spends hours every week reading financial books, doing pro bono legal work and being active in her community.
“Strangely enough, my biggest challenge now is rediscovering my purpose, because in the past I have helped people in every way possible,” Kohli said. “Many 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 regrets in life that you would like to share with a reporter? Please fill this in fast shape or email nsheidlower@businessinsider.com.
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