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Every one of us can recall mistakes or regrets we have experienced at various stages of our lives. For me, I can vividly remember two of my biggest financial regrets as follows:
- Buying a brand-new sports car for $25k in my second year of working after my college graduation and thus exhausting all my savings!
- Buying an expensive beach home in 2005. My wife and I regret paying too much for this beautiful home at the height of the 2nd home real estate market. The real regret set in 12 years later when we sold this beach home for significantly less than our purchase price.
Financial regrets can and do happen at any stage of our lives. I try to think of how I might reflect later about a decision to save or spend money and the reasons for my actions.
If you are trying to map out the right course of action for your financial future, learn from us retirees who wish they had made different decisions. Here are just a few of the regrets, including some non-financial regrets.
1. Not Saving Enough
This is unfortunately the most common regret I’ve experienced myself and heard about from friends and colleagues. While my wife and I did an excellent job of saving a sizable portion of our paychecks during our prime earning years, I can’t help but think what the $25k that I foolishly spent on a new sports car in 1982 would be worth today.
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The average annualized return since adopting 500 stocks into the S&P 500 Index in 1957 through Dec. 31, 2023, was 10.26%.
Based on an average stock market return of 10%, the additional savings I would have generated 42 years later would have been a staggering $1.4 million!
2. Overspending In Retirement
Per my budget analysis (as I am a strong advocate for budgets in retirement), I would say my wife and I are spending about 5 percent more than anticipated.
As we navigate our new city of Philadelphia, we are eating out more often, enjoying lots of nearby shows, concerts, and sporting events, and dealing with the higher inflation over the past three years.
But most retirees get carried away with how much they spend, the consequences of which are tripled once you account for the rising cost of living and inflation.
3. Claiming Social Security Too Early
Since I turned sixty-two in December 2021, I needed to decide whether to start collecting Social Security benefits immediately. We discussed this with our advisor to lay the groundwork over twelve years before when I was age fifty.
To increase my benefits overall, I chose to delay my Social Security benefits until at least my full retirement age (FRA) at age sixty-six years and ten months, which will occur in only two years in 2026.
There is no “perfect strategy” to maximize your Social Security benefits over your lifetime and your spouse’s. My best advice is to set up an online Social Security Account, which allows you to review estimates of your monthly benefits under various assumptions. It is a great planning tool.
4. Not Working Longer
To be honest, I do not share this regret, as I am incredibly pleased with the career I enjoyed over forty years. The question that I am often asked in podcasts is, “Would I have done anything different in my career?”
My answer is not much as I loved my work at Hershey and Illinois, but I would have switched to academia sooner as I enjoyed the “giving back” aspect of teaching very much.
However, one of the pitfalls of quitting active work too soon is losing out on additional savings and employer benefits like health insurance. The day to day socializing also takes a dip, and you experience less human interaction than usual, making retirement seem lonelier than ever.
5. Not Planning for Long-term Care
As life expectancy and access to medical facilities prolong our lifespan, the need to opt for long-term healthcare, including care at home or in living facilities, increases.
As I can attest, I do not know anyone who has never made any mistakes with their finances, so do not worry about aiming for perfection. But if you are prone to making certain errors on this list – like overspending, for example – it might be a clever idea to devise a game plan now (e.g., develop a budget) so you can avoid the same mistakes once you reach retirement age.
Let us now turn our attention to several nonfinancial regrets of retirees.
Nonfinancial Regrets
1. Wishing you hadn’t worked so hard
As I share in my book, Checkmate: Tips & Lessons to Help You Make the Right Moves to Achieve Happiness, it was exceedingly difficult for me to be living away from my family (due to work) when we lost three male family members in a challenging ten-month period from April 2020 through January 2021.
In all honesty, I have some regrets about working in Illinois and being 700 miles away during this period of grief for my family in Pennsylvania.
From time to time, we get so caught up in our work and busy lives that we forget some of life’s simple pleasures, such as family time. As you reach the final stages of life, while monetary comforts will support you, it’s the memories and warmth of social connection that will sustain you every day.
2. Wishing you had stayed in touch with your friends
We all have friends with whom we have not stayed in touch for a myriad of reasons…whether there has been a falling out or, more likely, life getting too busy. I encourage you to reach out and talk (not text!) to your friends to let them know you are thinking of them.
If they live far away, you can meet them or take a vacation to spend time with them. It is particularly important to have an in-person connection.
While I have lived in Philadelphia for the past three years, I still make several trips per month back to the Central Pennsylvania area to visit family, friends and ex-coworkers. There is nothing more enjoyable for me than to catch up face-to-face with others over lunch, dinner or even a coffee chat in the morning!
3. Failing to embrace a slower pace
We’re taught to constantly strive for the next upgrade, whether in our lifestyle, careers, or networks. So retirement can become a chore when you consider how much you’re “giving” up after a lifetime of constant effort and improvement.
For me, it was initially difficult to let go of the feeling that I needed to be “measurably productive” every day.
As with most of our readers, my career was a large part of my identity, and I always gave 100% to my career. Over time, my new normal developed which did not include as much hectic scheduling and the related stress. I have found it empowering to simply enjoy a cup of tea at a local coffee shop while watching others start their hectic day in their daily rat race.
Please share your regrets in the comments. The key for all of us is to learn from others’ experiences to make the best decisions possible to enjoy our retirement years!
8 thoughts on “Most Common Retiree Regrets”
I’m 68 and starting “retirement” now, which includes working about 20 hours per week. I don’t think I’m “built” for retirement, but hopefully I’ll get used to it gradually. I think it has something to do with me feeling useful to the world. Anyway, time will tell.
Thanks Nicolas for your comment as I love that you’re easing into a semi-retirement phase
by reducing your working to 20 hours per week. As a person who transitioned from a busy corporate life to a semi-retirement phase of teaching college classes for 7 years, I can appreciate this transition. Hopefully this allows you to do more of the things you want to do with your additional free time. It’s important to note that it took me 3 years to get over the “feeling useful” phase to truly enjoy my retirement. Good luck in your new phase of life!
I want to thank you as your web site and blog were a major reason I retired early. I certainly don’t regret stepping away from the hectic demands of medicine especially racing to the OR at 2 am. As far as pre retirement regrets, I got swept up in the real estate craze years ago and made a couple of financial mistakes, on the other hand I learned a lot and have made multiple good investments thereafter. I somewhat regret never acquiring a snowbird home, but given current events I think that was probably a good move and renting will work out just fine. Post retirement it’s been interesting to see that we are spending a bit more than I budgeted for and I think I had a very liberal budget. I had great plans to leap into volunteering but once I retired I really wanted to let things organically happen instead of forcing myself into action. Now in my second year I have rekindled my woodworking hobby, exercising regularly and am learning the local fishing area. My travel budget, which I considered generous could easily be increased as we both enjoy travel. I am learning to relax and I am ok with sitting and reading a good book or having a cup of coffee and looking out at the water.
Thanks DW for your comments as I love that you are learning to relax by reading a good book (I might suggest my life lessons book, CHECKMATE) over a cup of coffee while enjoying the calmness of a view of the water! Congratulations on exercising regularly as well as rekindling your woodworking hobby as I hope you enjoy it as much as I do in restarting my competitive chess journey after a 47-year hiatus. Kudos also for not jumping into volunteering but just letting things happen organically in retirement. My sincere hope is that you enjoy your increased travel and your well-deserved retirement years!
Thanks Sir Lawrence as busy careers certainly do get in the way of our hobbies. In a similar manner, my busy career stopped me from playing competitive chess for 47 years. Now in my 3rd year of retirement, I started playing in live chess tournaments again in January 2024. While I started off losing many matches, it took me almost 8 months of study & devotion to the game I love to enable me to win a tournament at age 64! Good luck with your painting & drawing!
I would say, a regret is: abandoning hobbies due to the intense demands of a medical career. In my case, as I’m getting close to retirement, I have to decide if I can pick up my old pursuit of drawing and painting. I’d have to start over again from a lower level of skill and experience. If somehow I’d been able to keep it up through the years, I’d be able to enjoy it at a much higher level.
Thank you so much for your article, it really brings to light some aspects that we may not have considered. I especially can relate to your point regrading your identification to your job, you almost become one. Also, everyone says you need to have a plan or something to do in retirement. Nothing wrong with just enjoying life, like you a cup of tea in the local coffee shop. I am sure things will come along to fill one’s time.
You are welcome Tony as I’m glad you enjoyed my article. To your point of identification to your job or career, one of the greatest challenges in retirement is to find something that defines you & makes you happy. While my wife was extremely busy as a pathologist during her career, she finds greater satisfaction in serving others by volunteering in the mailroom at a local mission that serves our city’s homeless population! If you are retired, don’t feel obligated to be productive every day as retirement is all about flexibility in doing things when YOU want to do them. Now that I’m done writing this reply, it’s time for a relaxing cop of tea while reading a good book in my local coffee shop!