Skipping Estate Plan Reviews
Retirees set themselves up with a will that one time in '98 and never looked at it again. A surprising number of people forget to update wills, trusts, powers of attorney, and beneficiary designations after major life events. Don’t be one of those people.
Seriously. Don't be that person. Update your paperwork.
Seriously. Don't be that person. Update your paperwork.
Neglecting Fitness
The promise of “getting in shape” is perhaps one of the most common ones among retirees. And possibly the one most broken. Eventually, their ambitious hikes get replaced with ambitious walks to the fridge. Start getting those daily steps in!
Not Volunteering / Giving Back Sooner
If you’re waiting for the right time to give back to your community, it was yesterday. The regret here is twofold: missing the personal satisfaction of giving back, and missing the chance to build a meaningful social network. Whenever you start this, you’ll wish you had started sooner…
Ignoring Their Passion
That dusty guitar stuffed in the corner, the half-finished painting, the novel outline document open on the laptop. They said, "When I retire." But by then, the enthusiasm has waned, the fingers are stiff, and Netflix and YouTube seem like much easier options…
You really thought healthcare was not that expensive, didn’t you?
You really thought healthcare was not that expensive, didn’t you?
Underestimating Healthcare Costs
They thought Medicare was some sort of magical force field (it isn’t). Retirees consistently regret not preparing for the high cost of supplemental plans, prescriptions, and dental work. What they’re left with is a medical expense slush fund instead of a retirement fund.
Claiming Social Security Early
Ah, the panic move. Many retirees decide to take the money and run, sacrificing years of higher payments just because they couldn’t wait. Now they receive a smaller cheque every month; a constant, nagging reminder of their short-sightedness.
Ignoring Debt Payoff
Mortgage, credit cards, and student loans for a degree they barely used. According to retirees, the biggest financial face-palm is carrying a debt into retirement. In the end, they find themselves off the job, still making payments, and wondering why their fixed income feels so... fixed.
Not Taking a Sabbatical
A year off to recharge, learn a new skill, or just be? "Too expensive," they declared. But a year off in your 50s could prevent burnout and provide you with a low-risk trial run for retirement. Consider taking that strategic break to recharge and reevaluate your retirement plans.
Fancy a gig at your local hardware store? The retirees didn’t either…
Fancy a gig at your local hardware store? The retirees didn’t either…
Lacking Income Diversity
Many retirees wish they had done some kind of side hustle in their 50s - writing, consulting, starting a business selling artisanal cat sweaters… anything to bring in a little "fun money" without the grind. Instead, they were left competing for the coveted store greeter position.
Skipping a Retirement Budget
Oh, they did budget. The regret here is that they budgeted for everything except retirement. They knew how to save, but learnt how to spend responsibly. They also underestimated the costs of the "fun" part of retirement (all those mid-week lunches!).
Ignoring Part-Time Work Options
After giving multiple decades to their work, most retirees can’t wait to get out. They fantasize about a clean break. Zero work, beer, and TV all day. Until the “retirement honeymoon” period vanishes, and they’re bored, lonely, and realize they should have taken that low-stress, part-time gig.
Avoiding Money Talks With Spouse / Partner
Both just assumed the other one had it handled. And then one day, they’re retired and constantly bickering about money because they had massive, unaddressed differences in expected spending. This conversation might be awkward, but it’s necessary.
You need to talk to someone about this. No, not your dog. An actual human being.
You need to talk to someone about this. No, not your dog. An actual human being.
Investing Too Safely
Getting scared of the market is one of the most common regrets among retirees. Most pulled everything out and stuffed it into a savings account earning 0.0001% interest. Inflation ate their capital alive, and they missed the last decade of growth, all thanks to a portfolio that simply failed to outrun inflation.
Not Stress-Testing the Retirement Plan
They ran one perfect scenario in their heads where everything went right: markets soared, they never got sick, and inflation stayed low. But they didn’t consider this one little thing called the economy. Most retirees recommend testing your plan against multiple "worst-case" scenarios.
Overgiving to Adult Children
Many retirees felt the parental obligation to fund their adult kids’ down payments, weddings, debts, or even lives was not a good idea. Once they got on a fixed income, they realized the trade-off of sacrificing their own security for their kid's short-term benefit was not worth it.
Delaying Downsizing
Retirees who struggle with fixed income and maintenance costs deeply regret not downsizing in their 50s. They clung to their house that had high taxes, endless maintenance, and three unused bedrooms. Now they’re paying a fortune to maintain it and can barely climb the stairs.
Sell the empty house. Buy a cool condo. Use the cash.
Sell the empty house. Buy a cool condo. Use the cash.
Staying Financially Uninformed
Most retirees blindly trusted "their guy" and didn’t dedicate time to learn about fees, asset allocation, or market cycles. Now they’re retired, poorer than they should be, and vaguely suspicious that everyone else knew something they didn't. They did.
Ignoring Long-Term Care (LTC)
"That'll never happen to me!" is a common phrase for many retirees. That is, until it does, and they’re left facing the horrifying reality of having to live under potential extended care that could cost them thousands of dollars.
Not Acquiring Healthy Habits
Retirees say they ate like teenagers, slept like babies (very unhealthy babies who pulled all-nighters), and considered "walking to the car" their daily exercise. Now their habits are so ingrained that they can't break them, resulting in their body staging a full-scale rebellion.
Skipping Health Screenings
They skipped that colonoscopy, ignored that unusual mole, and assumed that chest pain was just indigestion… Only to get preventable illnesses that were significantly harder (and more expensive) to treat. Remember, preventative care is cheaper than emergency care.
Just going to the doctor won’t be enough, though. Time to start working on your habits!
Just going to the doctor won’t be enough, though. Time to start working on your habits!
Skipping Catch-Up Contributions
Many retirees wish they had fully utilized the IRS catch-up contributions (available at age 50) for their 401(k)s and IRAs. They had the income and the time, and they just... didn't. It is one of the most powerful last-minute tools for boosting a nest egg, and sadly, missing it is a common theme.
Poor Stress Management
Their jobs were taking a toll on them, but they kept pushing. All that chronic stress ate away at their body, mind, and soul. And when they finally did retire, they realized the constant high-pressure environment chemically altered their bodies and minds. Perhaps that promotion is not worth it…
Those procedures you’re postponing could be crucial…
Those procedures you’re postponing could be crucial…
Delaying Elective Procedures
Are you living with blurry vision, nagging joint pain, or dental issues? So did many retirees, thinking, "I'll deal with it later." When their "later" finally arrived, they were either too frail for surgery or the problem had escalated into something far worse. Take the hint…
Underestimating the Health-Retirement Connection
Many retirees confess that no amount of money meant a thing when their health failed. They thought that money was the key to a good retirement. But all those financial plans are moot if you’re too sick to enjoy them. Make sure you can get out of bed before you think about splashing money on that expensive RV.
Neglecting Non-Work Friendships
Are you maintaining and nurturing friendships outside your office that have nothing to do with your career? If not, you'd better get on it. Many retirees often find themselves socially isolated after leaving the office and realize the only person they have to hang out with is their spouse…
Skipping Their "Bucket List" Adventure
Many retirees thought they’d climb a mountain, backpack through Southeast Asia, and learn to surf. Now they whine about being too old and are left with memories of that one time they had a pizza party in the office. Take that adventure!
Drifting From Spouse / Partner
After decades of using work as a shield, many couples retire and realize they were essentially roommates who were treating their marriage like a logistical partnership. Then they end up retired, stuck together 24/7, without much in common.
Have you settled that silly argument you had decades ago?
Have you settled that silly argument you had decades ago?
Not Healing Family Rifts
A silly argument from 20 years ago that they can’t even remember… Retirees who lost family members before resolving a conflict carry immense regret and wish they had prioritized peace over pride. You'd better pick up that phone and get dialing.
Staying in a Dead-End Job
If you’re in your 50s, still working extra hard at that job you don’t like and waiting for that “magic number”, you’ll keep waiting for a long time. Many retirees advise making a switch if your job isn’t interesting to you.
Missing Their Grandchildren’s Childhood
The desire for "one more promotion" or "one more big bonus" often meant less time for the grandkids. This also meant that they missed all the recitals, games, and everyday moments. You can always make more money, but you’ll never witness precious childhood moments again.
The memories are finite. Don't trade them for a spreadsheet!
The memories are finite. Don't trade them for a spreadsheet!
Ignoring Mental Health
It is shocking how nearly every person struggles with this (and knows it), yet does not give it the proper importance it deserves. If you’re bottling up stress, ignoring anxiety, and pretending everything is fine and is magically going to fix itself… it won’t. You need to deal with your emotional baggage. Head on.
Postponing Travel
Perhaps the biggest regret of retirees is putting off travel. Now their knees can barely climb ten steps, and the thought of a long flight gives them hives. If you’ve got the opportunity and the capability to travel, do it. You’ll never regret it.
Not Having an Identity Outside of Work
What happens when a retiree's entire self-worth is tied to their job title? They retire and, overnight, turn into a nobody. They have no hobbies, no passions, and no idea who they are without a corporate badge hanging off their neck.
Regrettable Purchases
Apparently, the ridiculously expensive RV and boat (both of which they only used twice) don’t look so good covered in 2 separate layers of dust. If you want to spend money, do it on something you’ll actually use.
