10 Greatest Retirement Regrets, According to Reddit

Unlock the secrets to a regret-free retirement from those who've been there.
Updated May 8, 2024
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Retirement can be a time of great fulfillment, especially if you have goals and a plan for this new chapter.

But many retirees also admit to having regrets about their expectations for retirement compared to reality.

So, before you retire, here are some things to consider that could potentially lead to regret after you stop working.

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They didn’t have a flexible financial plan

Rido/Adobe senior couple planning their investments

It can be easy to say you have enough money to retire and quit your job, but it’s important to not only consider how much money you have now but will in the future.

“Keep your plan updated and flexible,” one retired Reddit user suggested. “If the market has several bad years, then I can move my SS sooner to provide more stability in cash flow and investment depletion.”

They didn’t account for the mental changes

Monkey Business/Adobe depressed senior woman

It can be exciting to quit your job and have days and days ahead to do whatever you want.

But it’s important to also consider the mental changes of retiring.

“I wouldn’t do anything different, but I think the transition for me has been more mental than I thought it would be,” one Redditor said. “Just getting past the initial relief and fatigue took longer than I anticipated.”

They went from all work to no work

chartphoto/Adobe elderly man has anorexia

You may think you’re ready to just stop working, but some retirees suggest thinking about easing into less work instead of no work.

You may want to think about transitioning to part-time work rather than a cold quick to help you ease into the financial and mental changes.

“Wish I had done something part time,” one Redditor said. “Suddenly 40 hours to zero was hard.”

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They didn’t have new goals

fizkes/Adobe exhausted senior businesswoman

You may be goal-oriented when you’re working at an office by setting deadlines to get a project done or reaching specific performance metrics.

When you retire, however, you may have to transition to new ideas about how to set goals or what you want your goals to be.

One Redditor is “thinking now ( after two years) of some major goals which I wouldn’t have had the energy for before.”

They didn’t think about the social aspect of work

pikselstock/Adobe senior man looking out of window at home

Some days, you may see your co-workers more than your family. So it can be jarring when you retire and don’t have that daily social interaction with others.

One retired Redditor said after retiring, “things were too quiet,” and decided to make an effort to meet new people to fill the social part of the day that used to be filled with work.

They didn’t prepare sooner

Astarot/Adobe african american senior man reviewing bills

It’s important to see the long-term benefits of saving now so that money can help you retire, or you could end up working longer than you expected.

“Our only regret was not preparing earlier in life where finances were concerned,” one Redditor said.

You need to set boundaries

Cookie Studio/Adobe corporate lady showing stop

You may think retirement means you have plenty of time that can now be filled with friends, volunteer work, helping out family, or any other activities.

But you also could get overwhelmed by committing to too many things with the belief that you’re retired and have plenty of time for everyone.

“You have to set boundaries and be prepared to say no,” one Redditor suggested.

They lost touch with family

annebel146/Adobe  lonely senior man

You may be excited to move somewhere else that’s warmer or has more activities. Perhaps you’re even thinking about retiring in another country.

Moving somewhere to start over in retirement can be a great idea, but you also have to consider the family and friends you may be leaving behind.

One Redditor said, “We moved to another city 150 miles away from family. It's been a really tough go.” They even decided to start a new job to get more social interactions.

Not everyone is retired

SB Arts Media/Adobe unhappy old senior man

You may have a goal to retire early and spend all those extra hours with your family and friends, so it can be difficult when you retire, but they’re still working.

One Redditor mentioned that they realized it’s hard for family to spend as much time with you because they’re busy with work or school.

“All of our adult children and working friends are still very busy with their schedules,” they said.

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They thought retirement was for everyone

Elnur/Adobe meditation balls on the desk

You may think the natural progression of your professional life is to work and then retire, but one Redditor called retirement the “worst three months of my life.”

So be prepared to give work a second chance or reevaluate whether you really want to retire before leaving your job. It’s OK to decide to keep working if you want.

Bottom line

goodluz/Adobe senior couple wearing glasses

Retirement is a major transition in your work life, just as starting your professional career or changing careers can be a major transition.

It’s important to be willing to adapt to your retirement, especially if you decide to retire early and have additional financial concerns.

You should also consider planning for different possibilities depending on changes as you go through retirement and decide what to do with your days once you’re retired.

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Author Details

Jenny Cohen Jenny Cohen is a freelance writer who has covered a bit of everything, from finance to sports to her favorite TV shows. Her work has been featured in The Wall Street Journal, USA Today, and FoxSports.com.

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