Boomer’s remorse: The 5 big purchases you might regret in retirement — and how to avoid making these financial mistakes

Boomer’s remorse: The 5 big purchases you might regret in retirement — and how to avoid making these financial mistakes
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One surprise that often hits retirees in their first few years is that even without the costs of working and contributing to retirement accounts, they end up spending more than when they held down a job.
Some financial planners cite three retirement phases: Go-Go, Slow-Go and No-Go. In the Go-Go years, typically 65 to 75, many healthy, young retirees spend big to check lifelong dreams off their bucket list — and make big purchases they may end up later regretting.
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A study from AARP (1) found that there are five spending categories retirees tend to regret splurging on, which you should be mindful of if you’re in (or approaching) retirement.
Here’s what you should watch out for, and what you can do to benefit your wallet instead.
1. Splurging on fancy cars
For many, middle age is a time to drive sensible cars and SUVs that can handle the daily commute and carpool lane. But when retirement is on the horizon — and teen drivers are in the rearview mirror — you might decide the time is right for an upgrade to the car you always dreamed of.
Unfortunately, the value of any car declines as soon as you drive it out of the dealership. And taking on monthly car payments can be tricky now that your income is probably lower than it was during employment. Not only that, but the costs of gas, maintenance and insurance are typically higher for luxury cars.
If you do decide to treat yourself to a fancy ride, you could save yourself a few bucks by shopping around for better insurance rates.
According to Experian data, the national average cost of car insurance is $2,290 annually, or $191 per month (2). But luxury and antique cars come with much steeper premiums, making it incredibly valuable to comparison shop for the best rate.
By using OfficialCarInsurance.com, you can easily compare quotes from multiple insurers like Progressive, Allstate and GEICO, to ensure you’re getting the best deal.
In just two minutes, you could find rates as low as $29 per month.
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2. Upsizing to a dream house
Whether you’re tired of making do with cramped quarters or you’re just done dealing with the frustrations of an outdated house, upsizing to your dream home holds plenty of appeal. Just add an extension here, a brand new kitchen there, and your dream house starts to take shape.
The downside is how quickly the costs of all those home improvement projects can add up, which is not an ideal scenario when you’re on a fixed income. If you’re not careful, your dream house can turn into a money pit, leaving you more stressed than when you started.
However, for those who have plenty of cash for the upgrades — and are disciplined enough to stick to a budget — creating a dream house could be a viable option.
But making these upgrades can cost big, so if you are set on the dream house, you’ll want to make sure you’re saving money on other home expenses.
Homeowners insurance is an essential cost that can increase at any time, so it’s always important to ensure you’re not overpaying here. The average single-family homeowner already pays $2,370 in yearly premiums (3), but to make matters worse, 47% of policyholders saw their rates increase in the past year, according to a 2025 study by JD Power (4).
This is bad news for those who simply auto-renew with their current provider every year. In such a quickly shifting landscape, it can pay to take two minutes to shop around for better rates.
OfficialHomeInsurance.com makes it easy to ensure you have the best price available. The platform will quickly compile all the rates available to you, so you can skip the hassle of calling multiple providers for quotes.
Just fill out a few details and you could save an average of $482 a year — money you can put toward that dream home improvement project.
3. Purchasing a timeshare
After decades of working and providing for your family, retirement offers an opportunity to kick back and enjoy a well-earned extended vacation. Many retirees purchase timeshare properties with those perks in mind — a guaranteed vacation spot to share with family and friends.
But the reality of timeshares is less than idyllic. Beyond the initial investment, you’ll be shelling out cash for an annual maintenance fee, utilities and taxes — all of which can rapidly drain your retirement savings. And if you try to surrender your timeshare, you’ll typically only get pennies on the dollar compared to what you originally paid.
If you want to enjoy more vacation time in retirement, you may find better value in staying at local hotels than buying into a timeshare.
A better way to spend that timeshare money is to invest it, so you can use the returns to fund those future vacations.
With real estate platforms like Arrived, you can gain the benefit of investing in a vacation home, rather than end up stuck paying someone else for the use of a timeshare.
Backed by world-class investors like Jeff Bezos, Arrived makes it easy to fit these properties into your investment portfolio regardless of your income level. Their flexible investment amounts and simplified process allow accredited and non-accredited investors to take advantage of this inflation-hedging asset class with ease.
To get started, simply browse through their selection of vetted properties, each selected for appreciation and income generation potential. Once you choose a property, you can start investing with as little as $100.
4. Indulging in impulse buying online
Time on your hands plus money in your bank account can equal trouble if you’re not paying close attention. With the magic of the internet, just a few clicks a day can quickly deplete your accounts and even leave you with a mountain of debt — not to mention a pile of stuff you probably don’t need.
Are you really going to use that exercise bike you saw in a pop-up ad? Specialty cleaning gadgets may look like miracle workers, but soap and a cloth often achieve the same results. And prepackaged meal kits may be convenient, but the meals you make yourself are probably tastier (and much cheaper).
If you find you struggle with impulse buying and don’t always know where your money’s going each month, a budgeting app could help you curb this spending.
Monarch Money’s expense-tracking system makes managing your finances simple. The platform seamlessly connects all your accounts in one place, giving you a clear view of where you may be overspending.
By linking your credit card accounts, you can monitor your payment progress in real time, create specific goals to get out of debt and set limits to keep your spending in check.
And, for a limited time, you can get 50% off your first year with the code WISE50.
5. Giving to adult children
It’s natural for parents to want to see their children succeed, and sometimes that means helping them over a financial hurdle. Perhaps you want to pay off their student loans, buy them a car or gift them the down payment for a home.
But while well-timed financial gifts can be meaningful, too much financial assistance can leave you unprepared to face your own future. And if you opt to give them a loan — and don’t get the money back — it can lead to family discord and financial regret.
That’s why it can pay to speak with a professional financial advisor before making any decisions around significant amounts of money. The right advisor can help you crunch the numbers, figure out what you can and cannot afford to give on a fixed income and make a plan that works for your retirement.
Wondering how to find an advisor you can trust? Advisor.com makes it easy.
Just enter a few details about your finances and goals and the platform’s matching tool will connect you with a qualified expert best suited to your specific needs.
Schedule your free initial consultation today with no obligation to hire to see if they’re the right fit for you.
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Article sources
We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
AARP (1); Experian (2); ICE Mortgage Technology (3); JD Power (4)
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.