A neighbor of mine retired at 63 with a solid pension and a paid-off house. Six months later, he was sitting on his porch most afternoons looking restless. "I spent thirty years dreaming about this," he told me. "Turns out I was dreaming about the wrong things."
His story isn't unusual. Surveys of retirees turn up the same handful of regrets again and again, and they're not always the ones you'd expect. Money matters, sure. But so does identity, health, and the people you didn't make enough time for. The encouraging part is that most of these regrets are still fixable, no matter where you stand right now.
Not Saving Enough (Or Starting Late)
This is the obvious one, and it tops nearly every survey. A 2023 Edward Jones and Age Wave study found that the single biggest retirement fear among Americans is running out of money. Many retirees wish they'd started putting money away a decade earlier or contributed just a little more each paycheck.
The math is frustrating when you look backward. An extra $200 a month invested over 20 years could mean $100,000 or more at retirement, depending on returns. But beating yourself up over past decisions doesn't help. If you're still earning, even modest increases to your savings rate can make a meaningful difference. Our retirement savings guide walks through strategies that work at any age.
Walking Away Too Early
Retiring at 55 sounds glamorous. Living on a tighter budget for 35 years doesn't. Some people leave their careers because they're burned out, not because they're financially ready. That's a dangerous combination.
Working even two or three extra years can dramatically change the math. You're adding to savings, delaying withdrawals, and shortening the window your money needs to last. It also means a larger Social Security benefit if you can push past 62. Plenty of retirees who left early say they wish they'd found a less demanding role instead of quitting work entirely. A career shift at 58 isn't the same as grinding it out until 70.
Losing a Sense of Identity
This one catches people off guard. You spend decades being "the engineer" or "the teacher" or "the manager." Then one Monday morning, you're just... a person with nowhere to be. That shift can feel disorienting in ways nobody warned you about.
The retirees who struggle most are the ones whose entire social circle and self-image revolved around their job. The ones who thrive tend to have interests and relationships that existed independently of work. If that doesn't describe you yet, it's worth building those connections now. Volunteering, mentoring, picking up a creative project, these aren't just hobbies. They're anchors. We've written more about this in our piece on finding purpose after 50.
Neglecting Their Health
Retirement doesn't mean much if you can't enjoy it. A surprising number of retirees say their biggest regret has nothing to do with money. It's that they didn't take better care of their bodies in their 40s and 50s.
Joint problems, cardiovascular issues, chronic fatigue, these things don't appear overnight. They're the slow accumulation of skipped workouts, poor sleep habits, and meals grabbed on the way to meetings. You can't undo all of it, but you can change the trajectory. Strength training, regular walking, and consistent sleep do more for your quality of life after 60 than almost any financial strategy. The common mistakes guide covers some of the financial side, but honestly, your health is the asset that matters most.
Not Spending Enough Time With People Who Matter
This is the regret that stings the most when people talk about it. Kids grow up. Parents pass away. Old friendships fade because nobody picked up the phone. Retirees consistently say they wish they'd been more present during the years that slipped by while they were busy building a career.
There's no trick to this one. It's just a choice you make repeatedly. Call the friend you've been meaning to call. Visit the grandkids even when the drive is long. Say yes to the dinner invitation. Time with the people you care about isn't something you can stockpile for later. You either spend it now or you don't get it back.
You Still Have Time
Here's what I've noticed after talking with dozens of retirees over the years: the ones who are happiest aren't the ones who did everything perfectly. They're the ones who recognized what needed to change and actually changed it. Saving more at 58 still counts. Starting a walking routine at 62 still counts. Rebuilding a neglected friendship at 67 absolutely counts.
Regret is only useful if it pushes you toward something better. Every item on this list is something you can start addressing today, not next month, not after the holidays. The retirees who told me their regrets all said the same thing: they wish someone had been blunt with them sooner. Consider this that nudge.