The golden years were ne'er meant to beryllium tarnished by regret.
Yet that’s wherever immoderate retirees find themselves aft making purchases that seemed good successful nan infinitesimal but turned retired to beryllium a drain connected finances aliases didn’t warrant nan money spent connected them. In nan aftermath of these missteps, retirees often ponder what they should’ve done differently.
“When I inquire [my retired clients] what they wish they had done instead, nan reply is consistent: sphere costs and liquidity, fortify guaranteed income, trim taxes, and support flexibility,” Linda Jensen, laminitis of retirement-focused Heart Financial Group, told The Independent by email.
“Retirement intends location is nary paycheck to retrieve from awesome mistakes and we each cognize that affectional decisions tin permanently harm semipermanent income and stability.”
While cipher tin foretell nan future, knowing communal regrets among retirees tin thief those successful their aureate years debar costly mistakes.

Timeshare despair
Timeshares - fractional ownership properties often utilized for vacations - are 1 of nan apical regrets among retirees.
“The acquisition that clients astir regret is simply a timeshare,” said Marguerita Cheng, a certified financial planner and master contributor astatine Annuity.org.
Fluctuating fees and deficiency of elasticity are 2 main reasons why timeshare purchases are often a determination retirees wish they could return back, Cheng told The Independent.
Industry investigation confirms Cheng’s observations. Some 87 percent of timeshare owners regret their purchase, pinch yearly attraction fees driving that regret, timeshare exit specialists Alpha Timeshare Consultants said successful a 2025 analysis.
Annual attraction fees mean complete $1,200 per owner, Alpha said. Additionally, 63 percent of timeshare owners person trouble booking nan clip and locations they prefer.
Making a measured determination astir a timeshare pinch nan thief of a master tin ward disconnected impulse timeshare moves that could sting later.
“Don’t unreserved into decisions,” Cheung said. “Allow yourself time. Working pinch a (certified financial planner) master tin thief you navigate these scenarios.”
Homebuyer’s remorse
Another regret retirees often person is buying a 2nd location aliases a picnic home. As bully arsenic a beachside bungalow aliases mountaintop hideaway whitethorn seem, it’s not ever a awesome idea, said Daniel Bleich, a committee personnel of self-directed IRA patient Madison Trust.
“When imagining retirement, a picnic location aliases 2nd location successful a desirable location whitethorn look for illustration a bully idea,” Bleich said successful an email to The Independent. “In hindsight, galore retirees often regret purchasing a 2nd residence. While getting distant whitethorn beryllium enjoyable, often, nan costs of taxes, security and attraction [tends] to creep up arsenic a hindrance.”
That hindrance tin go moreover much prevalent erstwhile unexpected costs, specified arsenic aesculapian emergencies, popular up.

“Combining this pinch paying 2 mortgages tin perchance beryllium overwhelming,” Bleich said. “Instead, galore retirees would person preferred to designate a information of their status savings to recreation arsenic opposed to a imperishable destination.”
“To debar this type of regret, see renting a spot first to get a consciousness for what nan committedness mightiness beryllium like,” said Dr. Deon Strickland, a financial advisor astatine flat-fee financial advising patient Scholar Advising.
“Instead of buying something, rent it,” Strickland told The Independent. “If you deliberation you want a upland house, rent a upland location for a year. Test it. Experiment earlier you make a large leap.”
Risky business
Retirement investments tin beryllium an affectional rollercoaster, arsenic relationship balances whitethorn spot important rises and falls complete time.
Those feelings - including regret - tin beryllium exaggerated erstwhile retirees allocate money to riskier, less-diversified investments erstwhile they’re already retired of nan workforce, Bleich said, particularly erstwhile they recognize they didn’t understand nan specifications of their decision.
“Retirees who are investing to perchance make returns for status thin to regret jumping connected finance opportunities earlier genuinely knowing [their] afloat scope,” he said.

Riskier investments thin to request much clip to make returns, and retirees whitethorn not recognize that erstwhile they invest. As a result, financial emergencies whitethorn unit them to rate retired their finance amid losses.
“Once an investor hits status age, watching their finance up and down tin beryllium stress-inducing, arsenic there’s little clip disposable for recovery,” Bleich said. “On reflection, investors whitethorn wish they allocated their costs crossed a wide assortment of sectors and didn’t over-concentrate their savings connected a azygous promising endeavor.”
To debar nan regret that higher-risk investments tin trigger, retirees should make judge each of their basal expenses are covered first, Bleich said.
Ensure you person capable money to meet your regular needs, apical disconnected your different finance and savings accounts, and group speech immoderate money for nosy things for illustration hobbies. Then, usage nan remaining costs for high-upside, high-risk investments, Bleich said.
“Working broadside by broadside pinch a financial advisor tin thief retirees find which expenditures are worthwhile, and really to champion sphere their savings to past nan agelong of their retirement,” he said.
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