MoneyLion
Oct 21, 2026

The Biggest Retirement Regrets People Over 60 Admit Too Late

Written by David Nadelle
|
Edited by Ashleigh Ray
The Biggest Retirement Regrets People Over 60 Admit Too Late

Retirement is meant to be a celebration of years of hard work, however, many people find that it also brings the harsh realization that they wish they had done things differently when they were younger.

The decisions you make earlier in life can have a bigger influence than you imagine. Once you turn 60, it can be difficult to correct mistakes from the past, like underestimating healthcare costs, saving too little or waiting too long to develop a realistic retirement plan as you age.

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Experts have varying opinions, but those that MoneyLion reached out to felt that the biggest retirement regrets people over 60 admit too late were wishing they had started planning sooner and missing out on enjoying their non-working years.

Underestimating expenses in retirement is natural. You can — but probably won’t — have your finances managed down to the penny years before your work end date. However, there are significant changes to your lifestyle and psychological aspects to consider before you stop working.  

“The biggest regret I see is people who retire and enter a life without structure,” said Frazer Rice, director with the Next Vantage wealth advisory group and president of consulting firm Wealth Actually.

“There are many cases where successful people go from being important at work to functioning without purpose and drifting toward the TV or internet to fill the days.”

So, how can you avoid having those regrets? Like pretty much everything in life, the answer lies in the boring, but all-important, exercise of planning.

“Some of the biggest regrets many retirees express are underestimating how much planning is typically required to maintain their lifestyle once they retire,” said Brianna Rodgers, the director of investor education at Madison Trust Company.

“Not saving enough or waiting too long to prioritize retirement savings can be considered difficult to overcome later when retirement is nearing.”

Trevor Houston, financial advisor and CEO at ClearPath Wealth Strategies, agreed and added that retirees should be focused not only on savings, but also on how to keep the income coming in when they stop working.

“Hopefully, you’re saving along the way, but now’s the time to pull it all together,” he said. “I’ve seen too many situations where individuals didn’t have an integrated retirement and life strategy in place when their careers took an unexpected turn in their early 60s.”

Plenty of people stumble on the way to retirement by tapping a 401(k) too early and neglecting tax implications. But the regret that comes up most often is quieter. Many people get so focused on building wealth that they forget to live along the way.

“I think of wealth as a way to fund your life,” said Houston. “Yes, you should be saving for retirement, but hopefully you’re living life along the journey as well. Money is a tool that allows us to live well today while being prepared for our future.”

“Older clients rarely put it that plainly, but I can feel it in the room, and I hear it in the way they talk about the years they were healthiest,” said David Talley, founder and lead advisor of Talley Wealth in Johnson City, Tenn.

“They saved carefully for a version of retirement that showed up later and shorter than they expected, and they spent the best years of it holding back.”

It was a common refrain among the experts we spoke with, and it points to the same thing: people regret skipping the experiences that matter most.

Talley put it bluntly when he said, "Go on that trip. Give the kids the money now, while a down payment or a tuition bill is what they're staring at. Buy your wife the expensive, slightly ridiculous thing, because you can afford it and you'll wish you had done it years earlier.”

Retirement hits differently. You’re older and wiser, but that doesn’t mean you’re ready for what’s next.

Rice recommended giving yourself a head start. “Having a detailed schedule for the first year after retirement starts to help mitigate these problems," he explained.

In a Next Vantage blog post, Rice made the case for planning your post-exit identity, meaning who you are when work no longer defines your days. That means organizing your finances and also deciding how your daily activities, family time and meaningful interactions will look.

Your spreadsheet can handle the withdrawals. Tuesdays are on you.

This article was provided by MoneyLion.com for informational purposes only and should not be construed as financial, legal or tax advice.

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David Nadelle
Written by
David Nadelle
David Nadelle is a financial, technical and music writer based in Ottawa, Canada. After working in the energy industry for 18 years, David started writing full time in 2017, bringing an engaging style and a passion for helping people make more informed decisions about their personal finances.
Ashleigh Ray
Edited by
Ashleigh Ray
Ashleigh is an editor specializing in personal finance and banking content, with four years of experience — first at GOBankingRates, then at MoneyLion — turning complex financial topics into advice readers can actually understand and use. She holds an MFA in Creative Writing from the University of South Florida and brings that same care for clarity and voice to every piece she edits. She's based in Tampa, Florida.