The golden years were never meant to be tarnished by regret.
Yet that’s where some retirees find themselves after making purchases that seemed good in the moment but turned out to be a drain on finances or didn’t justify the money spent on them. In the wake of these missteps, retirees often ponder what they should’ve done differently.
“When I ask [my retired clients] what they wish they had done instead, the answer is consistent: preserve funds and liquidity, strengthen guaranteed income, reduce taxes, and maintain flexibility,” Linda Jensen, founder of retirement-focused Heart Financial Group, told The Independent by email.
“Retirement means there is no paycheck to recover from major mistakes and we all know that emotional decisions can permanently damage long-term income and stability.”
While nobody can predict the future, knowing common regrets among retirees can help those in their golden years avoid costly mistakes.
Timeshare despair
Timeshares – fractional ownership properties often used for vacations – are one of the top regrets among retirees.
“The purchase that clients most regret is a timeshare,” said Marguerita Cheng, a certified financial planner and expert contributor at Annuity.org.
Fluctuating fees and lack of flexibility are two main reasons why timeshare purchases are often a decision retirees wish they could take back, Cheng told The Independent.
Industry research confirms Cheng’s observations. Some 87 percent of timeshare owners regret their purchase, with yearly maintenance fees driving that regret, timeshare exit specialists Alpha Timeshare Consultants said in a 2025 analysis.
Annual maintenance fees average over $1,200 per owner, Alpha said. Additionally, 63 percent of timeshare owners have difficulty booking the time and locations they prefer.
Making a measured decision about a timeshare with the help of a professional can ward off impulse timeshare moves that could sting later.
“Don’t rush into decisions,” Cheung said. “Allow yourself time. Working with a (certified financial planner) professional can help you navigate these scenarios.”
Homebuyer’s remorse
Another regret retirees often have is buying a second home or a vacation home. As nice as a beachside bungalow or mountaintop hideaway may seem, it’s not always a great idea, said Daniel Bleich, a board member of self-directed IRA firm Madison Trust.
“When imagining retirement, a vacation home or second home in a desirable location may seem like a good idea,” Bleich said in an email to The Independent. “In hindsight, many retirees often regret purchasing a second residence. While getting away may be enjoyable, often, the cost of taxes, insurance and maintenance [tends] to creep up as a hindrance.”
That hindrance can become even more prevalent when unexpected costs, such as medical emergencies, pop up.
“Combining this with paying two mortgages can possibly be overwhelming,” Bleich said. “Instead, many retirees would have preferred to designate a portion of their retirement savings to travel as opposed to a permanent destination.”
“To avoid this type of regret, consider renting a property first to get a feel for what the commitment might be like,” said Dr. Deon Strickland, a financial advisor at flat-fee financial advising firm Scholar Advising.
“Instead of buying something, rent it,” Strickland told The Independent. “If you think you want a mountain house, rent a mountain house for a year. Test it. Experiment before you make a big leap.”
Risky business
Retirement investments can be an emotional rollercoaster, as account balances may see significant rises and falls over time.
Those feelings – including regret – can be exaggerated when retirees allocate money to riskier, less-diversified investments when they’re already out of the workforce, Bleich said, especially when they realize they didn’t understand the details of their decision.
“Retirees who are investing to potentially generate returns for retirement tend to regret jumping on investment opportunities before truly understanding [their] full scope,” he said.
Riskier investments tend to need more time to generate returns, and retirees may not realize that when they invest. As a result, financial emergencies may force them to cash out their investment amid losses.
“Once an investor hits retirement age, watching their investment fluctuate can be stress-inducing, as there’s less time available for recovery,” Bleich said. “On reflection, investors may wish they allocated their funds across a wide variety of sectors and didn’t over-concentrate their savings on a single promising endeavor.”
To avoid the regret that higher-risk investments can trigger, retirees should make sure all of their necessary expenses are covered first, Bleich said.
Ensure you have enough money to meet your daily needs, top off your other investment and savings accounts, and set aside some money for fun things like hobbies. Then, use the remaining funds for high-upside, high-risk investments, Bleich said.
“Working side by side with a financial advisor can help retirees determine which expenditures are worthwhile, and how to best preserve their savings to last the stretch of their retirement,” he said.
