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Retirement should be the least stressful chapter of your life. Yet many seniors trap themselves into an endless loop of anxiety and regret after just a few bad money moves.
In 2026, with the rising cost of living and relatively high interest rates, these bad decisions are easier than ever to fall into.
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With that in mind, here are the top five things Baby Boomers are likely to regret buying in 2026 so you can steer clear of them.
1. New cars
There’s no doubt that cars still represent freedom, especially if your mobility is on the decline. But that freedom can literally come with a hefty price tag. The average new car sold for $49,191 at the start of this year, according to Kelley Blue Book (1). Even more importantly, automakers have broadly ceased production of budget-friendly vehicles — so anything under $20,000. Meanwhile, the average auto loan rate for someone with a good credit score (781 or higher) was 4.66% in June, according to Experian data cited by (2)U.S. News (2). For those with poor credit, this rate was almost four times higher, at 16.01%.
Simply put, a new ride is expensive. And you’ll likely regret it. After all, new cars lose about 20% of their value just being driven off the lot, again according to Kelley Blue Book (3), turning that $49,191 purchase into an immediate $9,838 loss.
Buying used could be a better option, but don’t forget to shop around for a good insurance policy to cover the vehicle.
By using a comparison platform like Insurify, you can instantly view quotes from top-rated providers to ensure you aren’t paying a hidden ‘loyalty tax’ to your current insurer.
Just answer a few basic questions, and Insurify will show you the most affordable deals in as little as three minutes.
Not only is the process 100% free, but you could also save up to 15% by bundling your car and home insurance. That could help minimize regrets and maximize your savings by tackling two of the most common monthly line items for households.
2. Vacation or second homes
Real estate seems like a savvy investment, but many mom-and-pop property owners overlook the downsides.
You get to enjoy them for a while, sure, but then comes the onerous day-to-day maintenance, out-of-season repairs and potential for property value depreciation. Buying a rental property or vacation home also requires a huge down payment, prohibitive mortgage rates, maintenance fees, property taxes and, for some, tenant management.
Instead, you can invest in real estate the easy way through platforms like Arrived. Backed by world-class investors, including Jeff Bezos, Arrived allows you to invest in shares of rental properties, earning a passive income stream without the extra work that comes with being a landlord.
To get started, simply browse through their selection of vetted properties, each picked for their appreciation and income generation potential. Even better, you don’t need to bet big to see if Arrived is for you — you can start investing with as little as $100, earning monthly dividends.
3. Complicated or expensive financial products
If you’re looking to diversify away from traditional stocks and bonds, there are plenty of options.
But just because an asset class is exotic or different doesn’t mean it’s a good fit for your portfolio. It might be tempting to add cryptocurrencies, private equity or even private credit funds to your nest egg, but some of these assets come with exorbitant fees and low liquidity.
In other words, you could get trapped holding an expensive and complicated financial product that you don’t need. That’s a recipe for regret.
This doesn’t mean you shouldn’t diversify away from stocks. After all, 2025 and 2026 have brought with them uncertainty about tariffs, war and a potential AI bubble — all of which could lead to a big crash.
In 1999, the S&P 500 peaked, and it took 14 long years to fully recover.
Today? Goldman Sachs is forecasting just 3% annual returns from 2024 to 2034. It sounds bleak but not surprising: the S&P is trading at its highest price-to-earnings ratio since the dot-com boom. Vanguard isn’t far off, projecting around 5%.
In fact, nearly everything feels priced near all-time highs — equities, gold, crypto, you name it.
That’s why billionaires have long carved out a slice of their portfolios in an asset class with low correlation to the market and strong rebound potential: post-war and contemporary art.
It may sound surprising, but more than 70,000 investors have followed suit since 2019 — through Masterworks. Now you can own fractional shares of works by Banksy, Basquiat, Picasso and more.
Masterworks has sold 31 artworks so far, yielding net annualized returns like 14.6%, 17.6% and 17.8%.*
Moneywise readers can get priority access to diversify with art: Skip the waitlist here.
*Past performance is not indicative of future returns. Investing involves risk. See important Regulation A disclosures at * *Masterworks.com/cd.
4. Financial assistance for family
Nearly half of parents of adult children provide some financial support every year, according to a Savings.com (4) survey. It’s easy to see why so many young adults would need assistance navigating the affordability and jobs crisis, but you could end up sabotaging your own finances if you go too far.
Consider having an open conversation with your loved ones about boundaries and time limits on any assistance you provide. Try to set your children up for success instead.
5. Get-rich-quick schemes
It’s tempting to think that one good investment move can help you cover lost ground or boost your retirement income. But your retirement savings took decades to build, and scams can drain them in minutes. The FBI logged billions in elder fraud losses (5) last year, much of it tied to investment scams and crypto pitches promising fast riches.
If an opportunity sounds too good, your nest egg is the one at risk.
That’s why one of the best things you can do, especially if you’ve still got time before you retire, is invest steadily over the course of your working years. One of the safer options, beloved by financial wizards like the Oracle of Omaha Warren Buffett, is to sock away a little bit of money whenever you can into an ETF that tracks something like the S&P 500.
The beauty of ETF investing is its accessibility — anyone, regardless of wealth, can take advantage of it. Even small amounts can grow over time with tools like Acorns, an app that automatically invests your spare change.
Signing up for Acorns takes just minutes: Link your cards and Acorns will round up each purchase to the nearest dollar, investing the difference — your spare change — into a diversified portfolio.
With Acorns, you can invest in a dividend ETF with as little as $5 — and, if you sign up today, Acorns will add a $20 bonus to help you begin your investment journey.
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Article Sources
We rely only on vetted sources and credible third-party reporting. For details, see our ethics and guidelines.
Kelley Blue Book (1), (3); U.S. News & World Report (2); Savings.com (4); Federal Bureau of Investigation (5)
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.
