Retirees Reveal the 3 Biggest Money Mistakes They’d Never Repeat

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While everyone has a different path to retirement, the end goal is the same: Financial freedom and a life of enjoyment. But not all plans work out and some retirees are left reeling from lessons they wish they’d learned earlier.

As a result, some are forced to work part-time, while others live on tight budgets, rack up debt or take on side hustles. Hindsight is powerful and retirees are sharing the mistakes they made — and why they’re warning others not to repeat them.

Retire Without a Mortgage or Car Payment

Living on a fixed income isn’t easy. The average Social Security payment per month in 2026 is $2,071, according to the Social Security Administration. For those relying on it alone, covering monthly expenses can be difficult. One way to stretch your money is to pay off your house and car before retirement –something Judy Shaw, 72, learned. 

“Unless you have a trust fund or a 401(k), the most Social Security typically pays is around $4,000 a month, which is very difficult to live on if you have a mortgage and or big car payment, with taxes and insurance,” she said. “I advise people to please have their home and car paid for before they retire.”

Relying Only on Social Security

These days, Social Security alone won’t cover all your costs. As of 2024, people 65 and older have average annual expenses totaling $61,432, according to the Federal Reserve Bank of St. Louis, so other revenue streams are needed for many retirees — another thing Shaw quickly realized.

To help cover expenses and build a better nest egg, Shaw partnered with a friend and bought cheap houses to flip or rent.

“Retiring just on Social Security wasn’t enough,” she said. “At one point, we had 10 rentals, which was a bit too much, but we kept finding good deals. We eventually sold them all and that’s how I’m able to live comfortably now,” she explained. 

Entering Retirement with High Credit Card Debt

Andrew Reichek, an AWS and developer operations engineer at NioyaTech, isn’t fully retired yet, but he plans to be soon. In his 50s, Reichek accumulated around $40,000 in high-interest credit card debt over 10 years, driven by lifestyle choices and business-related costs.

“I was only paying the minimum monthly amount without realizing how terribly high the interest could grow,” he said. The debt significantly impacted his retirement savings and it took him years to pay it off. 

“I had to restructure my finances, create a strict budget, prioritize high-interest balances first, cut unnecessary expenses and commit to paying more than the minimum each month,” he explained.

Reichek admits he underestimated how quickly interest would grow, but has since adopted a new credit card policy that he sticks to. 

“I pay off the whole amount due every month and I also have a rigorous budget,” he said. “Moreover, by staying away from high-interest loans, I am not only able to save more money but also to have confidence in my retirement.”

Financial mishaps happen to everyone, but when preparing for retirement, the stakes are much higher and there’s less room for error. The key takeaway is to learn from these mistakes sooner rather than later and to have a carefully crafted retirement plan that prevents costly regrets. 

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