- Many older Americans regret some career choices that affected retirement plans and job prospects.
- Regrets include not prioritizing education, frequent job changes, and involvement in office drama.
- This is part of an ongoing series about older Americans’ regrets.
For millions of Americans, retiring at 65 is just a dream.
Since September, BI has heard from older Americans about their career regrets in two surveys it conducted.
Over 3,000 people between the ages of 48 and 96 completed a voluntary BI survey or emailed reporters about their life regrets. In a separate survey, over 300 recently laid-off Americans over 50 shared their career regrets. We followed up with 13 interviews to learn more. This is part of an ongoing series.
Some common themes people discussed included not prioritizing education, switching jobs too frequently, and struggling to navigate office politics. Many also cited age discrimination — data from AARP found that 64% of those over 50 have either seen or experienced age discrimination in the workplace. Nearly all said they were passed over for some roles in favor of younger applicants with lower pay expectations, particularly in white-collar roles where hiring has slowed.
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Bureau of Labor Statistics data found that 18.9% of Americans 65 and older — about 11.4 million people — still work, many for financial or social reasons. Some returned to work after retiring, citing financial concerns.
Not prioritizing or getting the wrong kind of education
Lou Nelson, 63, was an executive assistant in the medical devices industry for 25 years but faced two layoffs since 2021. She hasn’t had luck securing work since January.
For most of her career, she had few regrets about not having a bachelor’s degree because she worked for top healthtech companies and said she was well respected. However, after sending out over 50 applications, she suspects not having a degree has impeded her search.
“Nobody wants to hire someone that’s 63 years old, and I don’t know if it’s because of pay or experience,” said Nelson, who lives in Texas.
A college degree is still a big boon to finding and holding a job. The Bureau of Labor Statistics’ latest jobs report showed that Americans with a bachelor’s degree or higher had an unemployment rate of 2.4% in November 2024, while those with only a high-school diploma had an unemployment rate nearly twice as high, at 4.6%.
Grover McBeath, 79, said not having either limited his career options. He struggled through school and dropped out in eighth grade.
He joined the Air Force and worked in electronics for most of his career, but he lacked job satisfaction. Though he traveled the world for work and his salary peaked at $38,000 a year, he said he had an “unstable, nomadic lifestyle.” McBeath took Social Security at 62 and relies on the $1,108 a month he receives. He lives in affordable housing in Nevada and receives SNAP benefits to help pay for food.
“I was in a career field that I didn’t have an aptitude for, and many times, I just felt so lost in what I was doing, which is why I bounced around a lot,” McBeath said, adding he wished he prioritized education.
Still, many believe a college degree isn’t worth the financial burden. A Pew Research Center survey of US adults conducted at the end of 2023 found that just 22% of respondents believed a four-year college degree would be worth it if they had to take out loans.
Some older Americans BI spoke with agreed that their degrees haven’t helped further their careers. Lynda Namey, 54, was a healthcare business manager for two decades, making $62,000 a year at her peak. However, after a divorce that put her in debt, she said she panicked and returned to school for her master’s and doctorate degrees in counseling from Liberty University. She had no strong desire to pursue the degrees but did it because she expected them to help her land higher-paying roles.
That hasn’t panned out. The Alabama resident removed her doctorate from her résumé to not appear overqualified. While searching for a full-time job, she’s held part-time consulting, life coaching, and independent contractor roles. She also teaches meditation.
“I’m a middle-aged woman who has to completely support myself. I pay for my own insurance, and I’ve got to think about my future,” Namey said. “I can’t afford to take a job that pays $17 or $18 an hour. But those are the only jobs I get interviewed for.”
Switching jobs frequently instead of building a cohesive career
Though a few job seekers regretted not looking enough for new roles, dozens said they regretted bouncing between jobs and career paths and not being more intentional about growing their networks.
After working in various industries, Dawn Habbena, 63, fell in love with human resources. But after her company was sold, she took a job in compliance for a wealth management company, which wasn’t as satisfying as HR.
When Habbena faced a layoff during the pandemic, she struggled to get back into HR. Six months later, she got an HR job for a manufacturing plant, but she took another HR role after moving to help her aging mother. She described that role as “absolutely horrible,” and she’s since struggled to find another position — even as a grocery checker — after sending out over 1,000 applications.
Habbena wished she’d stayed focused on HR to accrue more experience and kept building her computer skills. She lives in a one-bedroom apartment with her 86-year-old mother and drives for DoorDash to stay afloat.
“I wish I had more confidence in what I did because I was easily knocked off,” said Habbena, who lives in Texas.
Many older Americans, like Chuck Smith, 60, couldn’t control how long they stayed in roles because of layoffs but wished they had settled somewhere more stable. Smith, from Massachusetts, worked in tech marketing for most of his career, making as much as six figures.
Smith was laid off in June 2023 and said he’s since applied to over 2,700 roles and landed about 100 interviews. Though he and his wife are financially comfortable, Smith said he’s worried about how quickly he’s spending down his savings without a stable income.
Though hiring has remained steady for lower-income workers, the job market for six-figure earners has slumped. New LinkedIn data found hiring has fallen 27% in IT and 23% in product management and marketing since 2018. Middle managers have also faced hiring challenges — hiring levels fell 42% between April 2022 and October 2024, data from Revelio Labs found.
To be sure, recent data reveals that switching jobs often yields financial gains. A September Vanguard report found that the median job switcher received a 10% increase in pay. Still, it also showed a 0.7 percentage-point decline in people’s retirement savings rate when switching jobs because 401(k) plan benefits can vary and people often make mistakes when rolling over retirement accounts.
AARP found that older workers who voluntarily change roles or industries in their 40s and 50s tend to retire later and have better work outcomes than their peers who stay in one role.
“They have better wage growth. They’ve experienced a higher success rate of staying in the workplace over those who might have been forced to change jobs later in their career,” said Carly Roszkowski, the vice president of financial resilience programming at AARP.
Taking a risk on a business, contract roles, or an ‘office bully’
Some respondents took risks that hurt them financially.
Michael R., 70, opened toy stores in New York throughout the 2000s, thinking they would grow enough that he could retire comfortably. However, when his businesses crashed amid the 2008 recession, he lost over $650,000 and declared bankruptcy.
“If I didn’t do the business, I would have bought a house,” Michael said, adding that in that scenario, he could’ve helped his whole family by selling his mom’s house and gifting his siblings the money.
However, he had to move in with his mother, and after she died, he rented a studio apartment. He said he works nearly every day of the week at his friend’s toy store and earns about $8,000 a month between his paycheck and his Social Security benefits.
“I’m still struggling just to pay my rent, my groceries, and my car. We don’t get a raise. We don’t get a bonus,” Michael said. “I’m grateful I’m employed, but I can’t go out looking for another job. Nobody’s going to hire somebody who’s 70 years old.”
Some regretted taking risks working in contract roles instead of prioritizing full-time work. Mauricia Day, 74, never finished her degree and said she’s held over 40 jobs — many contracted — in radio, tailoring, and office administration, making $30,000 a year at most. After a layoff in 2020, she hasn’t found secure work. She works at a nonprofit in a part-time contract role that ends in December.
Day said because she knew little about saving and investing, she lived paycheck to paycheck. She wished she’d focused on securing full-time employment in one field instead of relying on unstable income. She receives $1,136 in Social Security and $317 from her pension each month, which is slightly more than her house payment.
“I wish I had focused more on a career; it would have probably helped better with retirement and investing,” Day said, adding she stayed home for nearly 18 years raising her children. “I have a lot of friends who have been retired for 10 years, 15 years. I’m unsure why I’m still looking, but I know I’m still looking.”
A few wished they took fewer risks navigating workplace dynamics. Robbi Sera, 59, said she had a stable career as a biotech project manager and made good financial decisions, such as maxing out her 401(k). However, she said she took a few risks at work that backfired.
Sera said she gave constructive feedback to a “company bully,” which she said contributed to her layoff in February. She wished she’d stayed quiet until she locked down a different job, as she said the hiring landscape is “dismal.”
Sera, who splits her time between California and Hawaii, said even though she’s financially stable, she and her husband have cut back on spending significantly, rarely eating out or traveling. She earns $20 an hour as a contracted customer service agent for the aviation industry while searching for higher-paying roles.
“You just keep swimming and hope that something gets better,” Sera said.
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.
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