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Tax

9 Tax Decisions That Quietly Haunt Retirees Years Later

July 3, 2025
By Travis Campbell
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Image Source: pexels.com

Retirement should be a time to relax, but tax decisions made years earlier can come back to cause stress. Many retirees find themselves facing unexpected tax bills, reduced benefits, or complicated paperwork because of choices they made without realizing the long-term impact. These tax mistakes are easy to overlook, but they can quietly chip away at your savings and peace of mind. Understanding these pitfalls can help you avoid them, or at least prepare for what’s ahead. Here are nine tax decisions that often haunt retirees, and what you can do to avoid them.

1. Claiming Social Security Too Early

Many people start Social Security as soon as they can, often at age 62. But claiming early means your monthly benefit is permanently reduced. This lower payment can also push more of your Social Security income into the taxable range if you have other income sources. Waiting until full retirement age, or even later, can increase your benefit and reduce the chance of paying taxes on it. Think carefully about when you start Social Security, because this decision affects your taxes for the rest of your life.

2. Ignoring Required Minimum Distributions (RMDs)

Once you turn 73, you must start taking RMDs from most retirement accounts, like traditional IRAs and 401(k)s. If you forget or delay, the IRS can hit you with a steep penalty—up to 25% of the amount you should have withdrawn. Missing RMDs can also push you into a higher tax bracket, increasing your overall tax bill. Set reminders and work with a tax professional to ensure you take the correct amount each year.

3. Overlooking Roth Conversion Timing

Converting a traditional IRA to a Roth IRA can be a smart move, but timing is crucial. If you convert in a year when your income is high, you could pay more in taxes than necessary. On the other hand, converting during a low-income year can save you money in the long run. Some retirees regret not spreading conversions over several years to manage their tax bracket. Plan your Roth conversions with care, and consider the tax impact each year.

4. Not Factoring in State Taxes

Many retirees focus on federal taxes but often overlook state taxes. Some states tax Social Security, pensions, or IRA withdrawals, while others do not. Moving to a new state without checking the tax rules can lead to higher-than-expected bills. Research state tax laws before you move or start drawing down your retirement accounts. The difference can be thousands of dollars each year.

5. Failing to Plan for Medicare Premium Increases

Your Medicare Part B and D premiums are based on your income from two years ago. Large withdrawals from retirement accounts or capital gains can push your income over certain thresholds, causing your premiums to jump. This is called IRMAA (Income-Related Monthly Adjustment Amount). Many retirees are surprised by these higher costs, which can last for a full year. Plan large withdrawals carefully and be aware of how they affect your Medicare premiums.

6. Forgetting About Taxes on Pension Income

Pension income is usually taxable at the federal level, and sometimes at the state level too. Some retirees are caught off guard when they receive their first pension check and see how much is withheld for taxes. If you don’t have enough withheld, you could owe a big tax bill at the end of the year. Review your pension withholding options and adjust them if needed to avoid surprises.

7. Not Using Qualified Charitable Distributions (QCDs)

If you’re 70½ or older, you can give up to $100,000 per year directly from your IRA to charity. This is called a Qualified Charitable Distribution (QCD). QCDs count toward your RMD and are not included in your taxable income. Many retirees miss this opportunity and end up paying more taxes than they need to. If you give to charity, consider using a QCD to lower your tax bill while also meeting your RMD.

8. Overlooking the Impact of Part-Time Work

Some retirees take part-time jobs to stay active or supplement their income. But extra earnings can push you into a higher tax bracket, make more of your Social Security taxable, or increase your Medicare premiums. Before taking a job, estimate how the extra income will affect your taxes and benefits. Sometimes, working just a few hours less can keep you in a lower bracket and save you money.

9. Not Updating Beneficiary Designations

Failing to update the beneficiaries on your retirement accounts can lead to tax headaches for your heirs. If your beneficiary is not a spouse, they may be required to withdraw the entire account within 10 years, resulting in a substantial tax bill. Review your beneficiary designations regularly, especially after significant life changes, such as marriage, divorce, or the birth of a child. This simple step can save your loved ones from unnecessary taxes and stress.

Small Tax Choices, Big Long-Term Impact

Tax decisions in retirement are easy to overlook, but their effects can last for years. A little planning now can help you avoid costly mistakes and keep more of your hard-earned savings. Review your tax strategy every year, and don’t be afraid to ask for help when things get complicated. The right choices today can make your retirement more comfortable tomorrow.

Have you faced any tax surprises in retirement? Share your story or advice in the comments below.

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Travis Campbell

About Travis Campbell

Travis Campbell is a digital marketer/developer with over 10 years of experience and a writer for over 6 years. He holds a degree in E-commerce and likes to share life advice he's learned over the years. Travis loves spending time on the golf course or at the gym when he's not working.

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