Craig Wear, CFP®Craig Wear, CFP® | Expert in Roth Conversions & Tax-Efficient Retirement Strategies for IRA Millionaires

Are You Making This Retirement Tax Mistake

23 Apr 2026 · 1 min

Watch on YouTube

0:33

In this excerpt from Craig Wear, CFP®, the speaker explains a common retirement planning error: assuming that the tax filing status and brackets will remain unchanged throughout retirement. He highlights that while income may stay constant, the tax environment can shift dramatically, especially when a spouse dies. The loss of a filing‑joint status instantly halves the tax bracket, moving the surviving spouse into a higher tax rate—a situation Wear calls the “widow’s trap.” This oversight can lead to hundreds of thousands of dollars in unnecessary taxes, underscoring the need to plan for potential changes in filing status and tax structures during retirement.

A lot of people build their retirement plan around what they know today.
And as long as things stay the same, the plan works. And, you know, things stay the same all the time.
Yeah, exactly. But retirement doesn't stay static. To your point, people plan around current income without thinking about how the tax structure changes. The income stays, but the tax environment can change literally overnight. Like when a spouse passes away. Bingo. The tax bracket gets cut in half immediately. So if I pass before your mother, she files single taxpayer for the rest of her life.
So the mistake is assuming the tax structure just stays the same and that you'll just file jointly forever.
Yes, it's what we call the widow's trap, and it can cost hundreds of thousands of dollars of taxes unnecessarily.