5 Biggest Financial Regrets of Older Americans — And How You Can Avoid Them
Written by
David Nadelle
Edited by
Amber Barkley
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As one continues down the road of life, it’s a journey filled with unique experiences, challenges and opportunities for growth, shaping who you are and what you become. Enjoying the adventure isn’t without its difficulties, however, and many can’t help but regret the things they didn’t do along the way.
Regrets might be inevitable, but you can’t let them consume you. It’s always best to get a head start and avoid things you feel could come back to haunt you when you’re older. But even if you’re already “up there” in age, it’s never too late to practice sound financial strategies.
Business Insider asked over 1,000 Americans between the ages of 48 and 90 their views on retirement regrets, and their insights shed light on how challenging retirement and planning for it can be. People retire at different ages and for different reasons, but here’s what Business Insider and others had to say about five common financial retirement regrets, starting with under-saving for their retirement years.
Not Having Enough Retirement Savings
Not surprisingly, not having enough money to enjoy a comfortable lifestyle in retirement was the biggest regret most retirees have, according to not only Business Insider but the 2022 working paper “Financial Regret at Older Ages and Longevity Awareness,” published by Abigail Hurwitz (Hebrew University of Jerusalem) and Olivia S. Mitchell (University of Pennsylvania’s Wharton School).
Not saving more was the biggest regret for 52% of Hurwitz’s and Mitchell’s survey respondents.
Saving early and consistently through your working years is the smartest course of action, but it’s really never too late to get started learning and earning. If you’re retired, you can try to play the market and up the risk in your investment portfolio, but it might be a better idea to adjust your spending and find ways to increase your income.
Taking Social Security Benefits Early
Assuming it still exists when the time comes for you to retire, Social Security is one of the steadiest income streams and inflation hedges you can have later in life. However, unless you have serious financial or health difficulties or expect to live a shorter life, starting Social Security early decreases the amount of benefits you’ll get over your lifetime.
According to Transamerica’s 24th annual retirement survey, the median age at which retirees began receiving benefits is 63, and nearly three in ten retirees began receiving benefits at age 62, the earliest age available, resulting in a significantly reduced payment. Only 4% of retirees waited until age 70 to receive benefits.
If you’re nearing the age where you can start claiming Social Security, holding off until you’re 70 should be a goal you take very seriously.
Not Pursuing Education More
Many respondents to Business Insider’s survey expressed regret about not pursuing education and were uniformed of the benefits of education in planning for retirement. While many Americans believe a college degree isn’t worth the financial burden, education still matters when it comes to earning more at any age.
According to the Bureau of Labor Statistics’ latest jobs report, Americans with a bachelor’s degree or higher had an unemployment rate of 2.6% in March 2025, while those with only a high-school diploma had an unemployment rate of 4.1%. The unemployment rate of those with less than a high school diploma was 5.8%.
While a college degree is a significant expense, it might be worth the investment to advance your career. Look into scholarships for nontraditional students and consider starting with community college to decrease the cost.
Making Poor Career Decisions
The quote “complacency is a slow death” is most often attributed to motivational speaker and author Rasmus Ankersen and is used as a cautionary tale for any aspect in one’s life, from relationships to health to career choices.
Regarding the latter, complacency in your job can be a killer. If you’ve been stagnating for years, or even decades, recognizing it is the first step — doing something about it is the second.
According to Business Insider’s survey, many respondents regretted not aggressively pursuing higher-paying positions and promotions and building marketable skills and networks.
To avoid the pitfalls of complacency, adopt a mindset of continuous learning and improvement by taking on stretch assignments, embracing change and staying engaged. If honing your skills doesn’t get you ahead in your current company, find another that will appreciate your efforts.
Regretful Retirement Mistakes
Many retirees regret not having a transition plan for when they stop working. Catherine Collinson, CEO and president of Transamerica Institute, told Yahoo Finance, “Many of today’s retirees lacked the awareness, know-how and access to resources needed to successfully prepare themselves for retirement.”
Retirement is a significant life adjustment that can trigger positive and negative changes. To live a comfortable life for decades after you retire takes real financial planning and knowing how to maintain your wealth when the unexpected happens. If things like how your income will change when a spouse dies or if you’re retiring with too much debt are long-standing elephants in the room, you need to finally address them.
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