The Rubber Duck Rule of Retirement Tax Planning

A bright yellow toy with a cheerful squeak, the rubber duck has long been linked to children’s playtime. But what if that little duck could also help you uncover surprising questions about your retirement tax plan?

If the idea sounds strange, you might not have spoken with a computer programmer in recent decades.

A book, “The Pragmatic Programmer,” written in 1999 by Andrew Hunt and David Thomas, tells how a rubber duck can help solve some pretty sophisticated issues.

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Since the book’s publication, millions of programmers have learned that if they explain a problem piece of computer code to a squeaky confidant, they may well spot errors and find a solution.

Though the rubber duck technique started in programming, its value goes far beyond debugging code.

Studies show that simply talking through your thought process, whether to an actual rubber duck or just out loud, can uncover hidden flaws or assumptions in your thinking.

And when it comes to retirement tax planning, for example, where rules can be complicated and personal situations vary, the rubber duck rule might help you catch mistakes or missed opportunities before they impact your wallet.

Here’s more to know about how the “rubber duck rule” may help with your retirement tax planning.

How does the Rubber Duck Rule of retirement tax planning work?

“Rubber duck debugging” is actually an application of an older psychological phenomenon: The “self-explanation effect.”

By methodically explaining a problem to an inanimate object like a rubber duck, you can cement knowledge in your brain, identify gaps in your understanding, and potentially discover new insights.

That's because talking to a non-judgmental listener can help people explore ideas more freely without the fear of seeming silly or incompetent, according to a Michigan Technological University computer news blog. (You'll likely only seem silly to yourself for talking to a rubber duck.)

Thus, it stands to reason that this retirement “rule” could be useful when it comes to common tax planning skills like:

Challenging assumptions. By visualizing what a new learner might ask about a problem, you may challenge your own assumptions on a subject.

For example, some folks assume there’s a specific age when you stop paying Social Security benefit taxes. But there’s no such cutoff. In actuality, up to 85% of your benefits can be taxable if your combined income exceeds a certain amount.

A new, novice listener might challenge that assumption by asking, “Wait, aren't Social Security benefits taxed?"

Uncovering gaps. When a problem only exists in your head, it’s easy to get murky on details. Verbalizing the reasoning behind your retirement tax plan ideas can prompt you to clarify areas you hadn’t thought about before.

Imagine you’re explaining your retirement plan to a friend, and they ask, What if one of you passes away — what happens to the IRA? Suddenly, you realize you’ve never thought through whether the survivor should roll it into their own IRA or keep it as an inherited account. The difference could mean paying taxes sooner versus later.

Talking it out forces you to notice that gap before it impacts your tax burden.

Finding new insights. Explaining your retirement tax plan to an outside listener can help you to structure your planning into easy-to-follow steps.

This may produce new insights, as some research shows talking aloud also activates different parts of your brain than silent thinking alone.

Kiplinger interviewed three financial planning experts to gain further insight into how retirees can identify potential issues with their retirement tax plans before consulting a tax professional. Read on.

Challenge assumptions on RMDs, SS, 401(k), and Medicare

If you aren’t sure whether you have any underlying assumptions when it comes to retirement tax planning, you might try the rubber duck rule. Vocalizing your thoughts to a tiny sentinel (aka whatever object of your choosing) can help you uncover deeply ingrained speculations — even those that aren’t true.

Steve Parrish, JD, professor of retirement planning at The American College of Financial Services, highlights common, incorrect assumptions people often make regarding retirement tax planning.

One assumption is that retirement taxes work similarly to employment taxes.

In fact, retirees have greater flexibility regarding when to withdraw income and often receive a wider variety of income sources than those who are still employed. That flexibility underscores the idea that “retirement is not only a journey in time, but also an event,” as Parrish told Kiplinger.

For example, taking a 401(k) as a lump sum, or failing to file for Medicare on a timely basis, can “increase expenses for the remainder of the retiree’s life," Parrish explains.

Dave Alison, CFP®, president of Prosperity Capital Advisors, adds that folks may be tempted to assume they’ll be in a lower tax bracket in retirement, but that isn’t always the case.

Items like Required Minimum Distributions (RMDs), Social Security benefits, and Medicare surcharges can push you into a higher effective income tax bracket than initially planned.

Three retirement tax plan gaps to avoid in 2026

Talking through your retirement tax plan with a patient listener may also help you discover whether you are “missing something.”

As Alison points out, “It might surface the question of, ‘What happens to our taxes if one of us passes away?’ or ‘How would this Roth conversion affect our income?"

Those or similar questions may lead you to uncover potential retirement “surprises” that can impact your tax bill.

Alison notes some retirement planning areas that people often overlook:

• The “Widow’s Penalty.” Taxes can significantly rise for the surviving spouse after their spouse's death. This typically occurs through tax bracket creep. (e.g., Alison notes your bracket could jump from 12% to 22%.) The widow/widower can also see a dramatic increase in Social Security benefit taxation, resulting in a high income tax burden.
• “IRMAA Shock.” Medicare premiums can be tied to events that significantly increase taxable income, like selling a highly appreciated home or executing a large Roth conversion. Retirees may be surprised by a spike in higher Medicare premiums two years after the event happened, and feel blindsided by surcharges.
• Missed Charitable Giving Opportunities. Retirees who donate sometimes miss out on making Qualified Charitable Distributions (QCDs) once they reach age 70½. As Kiplinger has reported, this direct contribution from an IRA may lower taxable income in the current year while meeting RMD requirements.

In short, by explaining your retirement tax plan to an outsider, even a rubber duck, you may uncover some of these (or similar) gaps in your retirement tax plan.

Tax planning in 2026: Discover your best retirement strategy

New insights might lead to the discovery of an important “truth” in retirement tax planning.

“The truth is that retirement tax planning is less about minimizing taxes in a single year and more about smoothing taxes across a lifetime," Alison says. "A proactive approach — like strategically timing Roth conversions or coordinating withdrawals across different account types — can help retirees avoid unpleasant surprises and create more predictable outcomes.”

But a duck (or even a family member) may only get you so far.

All three of the experts interviewed by Kiplinger warned against relying solely on trusted confidants for new insights.

• Alison points out, “Strategic tax management is not intuitive….advice from friends or family, though well-intentioned, may not apply to [your] situation.”
• Parrish adds a word of warning: “Talking with a spouse or friend may help in understanding the issues, but unless they are professionals, they may still be providing bad advice.”

Last but not least, Dean Shahan, CFP®, executive vice president at CapWealth, describes how some expert advice may be only available through financial advisors due to the technology they possess.

“[We] visually show clients that, based on their current assets and savings plan, they can retire at X age and spend X dollars a year. I also test clients’ situations using 1,000 different potential investment returns.”

Shahan told Kiplinger that this specialized advisor technology can take worst-case investment returns into consideration, giving clients a “tremendous amount of peace" about their financial situation.

So while starting with a rubber duck may be beneficial, ending with a qualified tax planner could be the best way forward.

At the very least, you’ll have the duck to thank for the important questions you ask at your first (or next) financial advisory meeting.

Read More

• Three Creative Ways to Lower Your Retirement Taxes
• How the IRS Taxes Retirement Income
• Retirees Should Watch These Four Key Tax Changes in 2025
• Will You Get a ‘Surprise’ Tax Bill on Your Social Security Benefits?