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5 Tax Mistakes To Avoid In Your Initial Retirement Years, #323

Retire With Ryan

Release Date: 09/15/2026

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More Episodes

As you transition into retirement, tax planning might not be at the top of your to-do list—but overlooking it can lead to costly mistakes. This week, I break down the five biggest tax pitfalls new retirees face, from unexpected taxes on Social Security benefits to costly Medicare premium surcharges and missed Roth conversion opportunities. I’m also sharing a few of my favorite strategies to avoid unnecessary state taxes and manage your retirement distributions with confidence. 

 

You will want to hear this episode if you are interested in...

  • [01:45] Without planning, your risk of unnecessary taxes and penalties increases
  • [04:25] Managing taxes on Social Security benefits
  • [08:32] Understanding Medicare Part B premiums
  • [10:25] Understanding and strategizing state-specific tax breaks for retirees
  • [13:15] Roth conversions and required distributions
  • [14:09] Planning retirement account distributions

 

Smart Tax Planning Can Save You Money 

Without proactive tax management, retirees can encounter unexpected tax bills, costly penalties, and unnecessarily complex financial situations. These are the five biggest tax mistakes that people make in the initial phase of retirement—find out how you can avoid them to enjoy your golden years with peace of mind.

 

1. Failing to Withhold Taxes on Social Security Benefits

Many retirees are surprised to discover that Social Security benefits can be taxable. In fact, most will owe some federal tax on these benefits. The IRS calculates the taxable portion based on your combined income—that’s your adjusted gross income, non-taxable interest, plus half of your Social Security benefit. Depending on your filing status and total income, between 50% and 85% of your Social Security can be taxable.

 

2. Accidentally Triggering IRMAA Premiums

If you’re on Medicare, your income affects your monthly premiums for Part B and Part D. Exceeding certain income limits results in an “Income-Related Monthly Adjustment Amount” (IRMAA)—an unwelcome increase in premium costs. For singles, the first threshold is $109,000, and for joint filers, it’s $218,000. Exceeding these levels can raise your premiums by hundreds of dollars per month.

One pitfall is making large IRA withdrawals or cashing out retirement accounts in a single year, inadvertently pushing your income above an IRMAA threshold. By spreading withdrawals over several years or strategically withdrawing from different account types (pre-tax, Roth, or brokerage accounts), you may be able to avoid higher premiums. 

 

3. Paying Unnecessary State Income Taxes

Where you live has a significant impact on your tax liability in retirement. Some states, like Florida, Texas, and Nevada, have no state income tax. Others offer exemptions for certain types of retirement income, such as pensions or Social Security. However, states without income tax may offset this advantage with higher property or sales taxes.

Research the tax landscape of your home state and potential destinations if you’re considering relocating. Even if you aren’t moving, understanding thresholds for tax exemptions or reduced rates based on income can help you plan withdrawals to minimize your state tax exposure.

 

4. Waiting Too Long to Make Roth Conversions

Roth IRAs provide the benefit of tax-free withdrawals in retirement, making them a powerful planning tool. If you have significant pre-tax IRA balances, converting some of this money to a Roth during your retirement’s early years—especially before claiming Social Security—can make sense. Those years often bring lower income, keeping your conversion tax rate modest.

Unfortunately, many retirees delay Roth conversions until it’s too late. Once required minimum distributions (RMDs) kick in during your 70s, Roth conversions become less practical and may push you into higher tax brackets. 

 

5. Mismanaging Retirement Account Distributions

Without a distribution plan, retirees risk withholding too little or too much tax from IRA and 401(k) withdrawals. Setting proper withholding ensures compliance with the IRS “safe harbor” rules—generally, withholding 90% of current-year liability or 100–110% of last year’s taxes, depending on your income. You can meet this requirement with quarterly estimated payments or through withholdings on distributions, even waiting until year-end if needed.

Careful tax planning with a financial advisor or CPA will help you project your taxable income and avoid penalties. And, when doing Roth conversions, it’s always preferable to pay taxes from outside funds, maximizing the amount that becomes tax-free.



Resources Mentioned

 

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