I Asked ChatGPT What Retirees Will Regret Most in 10 Years: Here’s How To Avoid These 8 Mistakes
Written by
Jordan Rosenfeld
Edited by
Molly Sullivan
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Retirement regrets rarely come from one big mistake. More often, they build slowly from small habits, lack of information or procrastination. When retirees look back a decade later, several themes consistently surface.
To get a sense of the common regrets retirees have, I enlisted ChatGPT’s help to comb through research and data from sources like AARP, the Pension Research Council, Plan Advisor and more.
It found the following eight regrets and offered solutions to avoid these mistakes, too.
1. Not Saving Enough Early Enough
Many retirees wish they had contributed more money to their retirement accounts during their peak earning years, ChatGPT said. The longer your timeline, the better compounding works for you to grow your money. This benefit slows dramatically once withdrawals begin and inflation erodes purchasing power faster than expected.
How to avoid it: The AI suggested automating contributions, increasing savings rates with every raise, and maxing out catch-up contributions are great ways to get ahead.
2. Claiming Social Security Too Early
Taking benefits at the earliest age of 62 often locks in an unnecessarily lower income, ChatGPT warned. Ten years in, retirees realize that even a few hundred dollars more a month would have made a huge difference, especially as healthcare and living costs rise.
How to avoid it: Run “breakeven scenarios” with a planner, the AI suggested. If possible, fund your early retirement years with savings first to delay benefits toward full retirement age or 70, the age at which Social Security benefits are maxed out.
3. Underestimating Healthcare Costs
Healthcare is consistently one of the largest retirement expenses, ChatGPT pointed out. Many regret not preparing for Medicare premiums, supplemental coverage and supremely costly long-term care needs.
How to avoid it: Build healthcare costs into retirement projections, ChatGPT said. Also, be sure to compare Medicare options annually and consider long-term care insurance or self-funding plans.
4. Not Maintaining Enough Equity Exposure
While nobody wants to take too big of an investing risk, conversely, playing it “too safe” leaves some retirees underinvested, the AI warned. Over a decade, portfolios that were overly conservative might not keep up with inflation.
How to avoid it: Use a diversified, risk-appropriate allocation that includes equities, ChatGPT recommended. Rebalance annually to avoid drifting too conservative. And always consult with a financial planner.
5. Overspending in the First Five Years
It’s easy to reach retirement and lose track of your spending without the goalposts of careers to simplify spending. Early overspending is one of the leading causes of running short later, ChatGPT warned. Lifestyle creep in the first retirement phase can create long-term strain.
How to avoid it: Use a flexible withdrawal rule (such as 4%, adjusted for market conditions) and track spending quarterly.
6. Failing to Downsize (or Waiting Too Long)
Your big house might seem fine until you’re spending every day in it and still making a hefty mortgage payment in retirement. ChatGPT said that many wish they had sold their homes earlier, before maintenance costs increased, mobility decreased or the housing market shifted.
How to avoid it: Review housing needs every two to three years. Compare options such as downsizing, renting, relocating or aging-in-place with modifications.
7. Letting Taxes Become an Afterthought
If you’re not planning ahead, you’re possibly missing out on important tax advantaged strategies. Errors can lead to unnecessary taxes on withdrawals, required minimum distributions (RMDs), Social Security benefits and investment income.
How to avoid it: Establish a withdrawal strategy well in advance that coordinates taxable, tax-deferred and tax-free accounts. Consider Roth conversions during low-tax years but do so carefully and with the help of a financial advisor.
8. Not Having a Clear Estate Plan
An estate plan isn’t just for people with huge financial legacies to pass on. Anyone who wants to control how their assets are passed on to heirs after death will want to make sure to get this underway. Family conflict, probate delays and unintended tax burdens are common consequences of outdated or nonexistent estate documents.
How to avoid it: Keep wills, beneficiaries, trusts and powers of attorney updated. Review every three to five years or after major life changes.
A bit of planning today can help you sidestep these regrets and build a retirement you’ll feel confident living in 10 years from now.
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