7 Biggest Regrets People Have About Retirement

Mature woman using laptop in the living room.
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Looking forward to the day you retire? It’s fun to daydream about all the hobbies you’ll have time for and the trips you’ll take, but preparing for retirement is another thing entirely.


Failing to do so can lead to regrets, as a 2021 Coventry Direct study revealed that 26% of retirees don’t have the lifestyle they wanted during retirement. What are the biggest regrets people have about retirement and how can you avoid them? GOBankingRates spoke with the experts to get the answers.

Not Diversifying Investments

According to the study mentioned above, 52.8% of retirees regret not saving earlier, and 32% aren’t sure whether or not they’ll be able to live comfortably for the remainder of their retirement.

Richard Ricciardi, an estate planning attorney and partner at Powell, Jackman, Stevens & Ricciardi, encourages people to diversify their investments long before retirement. This helps to limit the risk of losing money. When one or two of your investments are doing poorly, others may be performing well to make up for it.

He also recommends moving to less risky investments as you get closer to retirement.

“The volatility of the real estate market and the stock market can ravage a person’s financial safety,” he said. “In retirement, the character of investments needs to change to less risky strategies concentrated more on income than investment growth.”

Not Seeking Professional Financial Help

Thanks to many self-help investment options, some people prefer to handle their own investments without the help of a financial planner. But Ricciardi says this may be a mistake.

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“A comprehensive financial plan can give you great insight into how far your money will take you in retirement,” he said. “I believe evaluating different strategies and listening to professional advice is key to successfully planning for retirement.”

Not Preparing for Diminished Capacity

At some point in your life — hopefully far down the road — you’ll likely need more help with certain tasks or decisions. Not planning for this can lead to regrets.

“Powers of attorney, healthcare directives, and wills and trusts should be put in place prior to or early in retirement,” Ricciardi said. “That way, there’s a plan in place if a person loses the ability to manage their own affairs.”

Not ‘Practicing’ Retirement First

As you get closer to retirement, consider practicing what you want your life to be like. Patti Black, a certified financial planner at Bridgeworth Wealth Management, says one of her clients did this by taking longer vacations in their RV as they neared retirement.

“They learned how much time traveling was just right — not too long, not too short,” she said. “They also determined how to spend time together when they were at home and not on the road.”

This helped Black’s clients discover which experiences worked for them and which didn’t.

“They didn’t just wake up on day one of retirement and fall into an ideal routine,” Black said. “They tried many things, talked about what was working and what wasn’t, and made adjustments.”

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Not Having a Purpose for Retirement

It’s easy to look forward to retirement because you get to leave behind the 9-to-5. But if that’s your only focus, you may be disappointed when you finally retire.

“Spend time thinking about your purpose in retirement,” Black said. “Who are you and what are you going to be doing now that you’re not working? Playing golf is not a purpose!”

Not Having Enough Non-Work Friends

If all your friends are from work, you may find the transition to retirement a bit jarring. A 2021 study found that persistent loneliness in retirement was associated with morbidity, disability, and more advanced biological aging. The researchers concluded that having social connections may promote healthy aging.

“Check out volunteer groups, clubs, and classes that interest you that may be a source of new friends,” recommended Black. “People may feel out of the loop in retirement. It takes time and effort to find a new tribe.”

Not Communicating With Your Partner About Expectations

Black encourages couples nearing retirement to be patient with each other and communicate openly about their expectations for daily life.

For example, will you and your spouse eat lunch together every day? Will you spend time on hobbies together each day or have independent routines? Will you invite others over regularly?

“Spouses need to talk to each other about expectations regarding how much they’re willing and able to babysit grandchildren and how work around the house will change, too,” Black said.

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