Three Major Purchases Retirees Deeply Regret Making in Their Golden Years
Retirement should be a time of relaxation and enjoyment, but for many, it becomes marred by financial regrets over purchases that seemed wise at the moment but later proved draining. With no regular paycheck to cushion mistakes, these decisions can have lasting impacts on stability and income.
"When I ask my retired clients what they wish they had done differently, the answer is consistent: preserve funds and liquidity, strengthen guaranteed income, reduce taxes, and maintain flexibility," explained Linda Jensen, founder of retirement-focused Heart Financial Group. "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."
Timeshare Despair: A Top Regret Among Retirees
Timeshares, which involve fractional ownership of vacation properties, rank high on the list of regrets. Marguerita Cheng, a certified financial planner, noted that fluctuating fees and lack of flexibility are key reasons retirees wish they could undo these purchases.
Industry research supports this, with a 2025 analysis by Alpha Timeshare Consultants revealing that 87% of timeshare owners regret their decision, largely due to average annual maintenance fees exceeding $1,200. Additionally, 63% struggle to book preferred times and locations.
To avoid this pitfall, experts advise against rushing into decisions. "Don't rush into decisions. Allow yourself time. Working with a certified financial planner professional can help you navigate these scenarios," Cheng emphasized.
Homebuyer's Remorse: The Vacation Home Trap
Another common regret is purchasing a second or vacation home. While the idea of a beachside bungalow or mountaintop retreat is appealing, the reality often involves hidden costs.
Daniel Bleich, a board member of Madison Trust, explained that taxes, insurance, and maintenance can become burdensome, especially when combined with two mortgages. Unexpected expenses, like medical emergencies, exacerbate the financial strain.
"In hindsight, many retirees often regret purchasing a second residence. Instead, many would have preferred to designate a portion of their retirement savings to travel as opposed to a permanent destination," Bleich said.
Dr. Deon Strickland, a financial advisor, recommends renting first to test the commitment. "If you think you want a mountain house, rent a mountain house for a year. Test it. Experiment before you make a big leap," he advised.
Risky Business: Investment Regrets in Retirement
Retirees often regret allocating funds to riskier, less-diversified investments without fully understanding the implications. Bleich highlighted that such decisions can lead to stress, as there is less time to recover from losses.
"Once an investor hits retirement age, watching their investment fluctuate can be stress-inducing, as there's less time available for recovery. On reflection, investors may wish they allocated their funds across a wide variety of sectors," he noted.
To mitigate this, retirees should ensure necessary expenses are covered first, then diversify investments. "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," Bleich added.
By learning from these common regrets, retirees can make more informed decisions, preserving their financial well-being and enjoying their golden years without unnecessary stress.
