By George McFadden

After more than 25 years helping retirees create guaranteed income, I’ve learned that market risk isn’t the only thing that can derail a retirement plan—taxes can too. For many households in the “retirement red zone” (ages 55–75), a Roth conversion is one of the most effective ways to reduce future taxes and create the flexibility to spend confidently for life. 

In this article, I break down how Roth conversions work, when they make the biggest impact, and how we build them into a broader plan that protects your income and your peace of mind.

Short version: Pay a known tax now, control your income later. That tradeoff—done thoughtfully—is often worth six figures over a lifetime.

What Is a Roth Conversion (and Why It Matters)

A Roth conversion moves money from a pre-tax IRA or 401(k) into a Roth IRA. You pay income tax on the converted amount now; future qualified withdrawals are tax-free. It’s not an investment product, it’s a tax strategy that complements your retirement income plan by giving you more control over your future tax brackets and required minimum distributions (RMDs).

Why Retirees Care

• Lower future RMDs: Converting reduces the size of pre-tax accounts that will be subject to RMDs—helping you avoid getting pushed into higher brackets later.
• Medicare IRMAA control: Smaller taxable income in later years can help you avoid surcharges on Medicare premiums.
• Tax-free income for life: Roth withdrawals don’t count as taxable income, creating flexibility for big purchases, healthcare, or legacy planning.

Timing Is Everything: Your “Roth Window”

For many people, the most powerful window for conversions is:

• After you retire (income often drops)
• Before RMDs begin (currently age 73 for most)
• While you’re in a lower tax bracket (fill it, but don’t spill over)
  

This is where we see the biggest lifetime savings because you can “prepay” taxes strategically at lower rates today and avoid higher rates later. In fact, many clients between 55 and 75 are in the sweet spot for conversions, with enough time to compound tax-free growth and meaningfully reduce RMDs.

Important deadline: Conversions must be completed by December 31 to count for this tax year—there are no extensions. This is not like filing your return in April.

“Bracket Stuffing”: Convert Just Enough

One of the smartest ways to convert is called “bracket stuffing.” We calculate how much room you have left in your current tax bracket and convert just enough to fill it without “spilling” into the next bracket. This way you shrink future RMDs and future taxes, without paying a higher rate today.

A Quick, Real-World Example

The situation: Linda, 67, recently retired. She expects Social Security next year and RMDs at 73. She has $900,000 in pre-tax IRAs and $60,000 in a brokerage account. This year, her taxable income is unusually low.

Our Approach

1. Bracket analysis: We identify how much room remains in her current bracket and convert that amount (e.g., $65,000) before December 31.
2. Multi-year plan: We repeat this “fill the bracket” process for 4–6 years, reducing future RMDs and Medicare IRMAA exposure.
3. Protected income overlay: We pair her tax plan with a guaranteed income foundation—so her essential expenses are covered without market risk—while maintaining growth potential on the rest. (This is the “protected” vs. “market-driven” distinction many of my clients prefer.)
   

The outcome: Linda locks in tax-free Roth dollars for future spending, trims the size of her RMDs at 73, and keeps her Medicare premiums in check. Her future self will thank her for using this low-income year wisely.

Common Myths (And the Reality)

Myth #1: “Roth conversions just mean a bigger tax bill today.”

Reality: Yes, you’ll pay tax now. But the goal is to lower your lifetime tax bill and create decades of tax-free income later. That’s especially valuable once Social Security, RMDs, and legacy goals enter the picture.

Myth #2: “I’m in my 60s…am I too old?”

Reality: Not at all. Ages 55–75 are often ideal. We frequently help clients in their 60s reduce RMDs, lower future taxes, and build tax-free income streams.

Myth #3: “I’ll just wait and see what taxes do.”

Reality: Waiting often wastes your lowest-tax years. If you’re retired and pre-RMD, doing nothing can leave valuable “low-bracket space” unused; that’s opportunity you don’t get back.

Who Should Consider a Conversion This Year?

Use this quick checklist. If you answer “yes” to two or more, let’s talk:

• Are you 55–73 (pre-RMD window)?
• Do you expect RMDs and don’t want to be forced into a higher bracket later?
• Do you want tax-free income flexibility in retirement?
• Are you concerned about legacy taxes for your heirs?

How We Implement Roth Conversions (Without Guesswork)

My process is educational and numbers-driven. We start by mapping your income timeline, your current and future brackets, and your RMD estimates. Then we design a multi-year conversion schedule that:

1. Fills but doesn’t overflow your current bracket (bracket stuffing)
2. Coordinates with Social Security timing and healthcare costs
3. Pairs with a protected income plan so your essential spending is covered regardless of markets (My core philosophy: Protect the money you can’t afford to lose, and generate the income you can’t outlive.)
   

I’m focusing heavily on Roth conversion education because it tends to attract higher-intent, better-fit clients who are serious about managing taxes and retirement income the right way.

Deadlines, Details, and Next Steps

• Deadline: Conversions must be finished by December 31 to count for this tax year; no extensions.
• Partial conversions: You don’t have to convert everything. We can convert some each year to manage your tax rate efficiently.
• Coordination: We’ll align your conversion with your broader income plan (pensions, annuities, Social Security) for a smooth, tax-smart retirement paycheck.
  

Compliance note: Roth conversions are tax-sensitive. I’ll run the planning analysis and coordinate with your CPA or tax professional to finalize amounts for your situation.

Plan Now. Spend Confidently Later.

Roth conversions aren’t about paying more tax; they’re about paying tax on your terms. If you’re 55–75 and staring down future RMDs, the window from now until age 73 is often the best time to act. Lock in tax-free income, reduce uncertainty, and keep more of what you’ve earned—for your lifestyle and your legacy.

The Retirement Protection Solutions team is here to help. Book a call and learn how you can get a 40 boost to recover your taxes. 

Let’s run your numbers before December 31. Schedule a 15-minute Roth Conversion Review online here. If you’d rather, email george@retirestressfree.com or call (216) 272-2333.

About George

George McFadden is the principal at Retirement Protection Solutions, a financial advisory firm in the Greater Cleveland area focused on guiding clients in the “Retirement Red Zone”—those nearing or entering retirement who need protection, reasonable growth, and guaranteed retirement income. With over 25 years of experience working alongside top financial advisors across the U.S., George saw a significant gap in traditional retirement planning. His mission is to fill that gap by helping clients protect their hard-earned savings and create a reliable retirement paycheck that lasts for life.

Many advisors offer a broad array of investment services that expose clients to market risk, often leaving those approaching retirement vulnerable. George’s value proposition is different: he emphasizes protection, ensuring clients don’t lose their principal, and offers guaranteed retirement income solutions to provide lasting confidence and peace. In partnership with Retirement Realized, George brings clients strategies that focus on safety and security, designed specifically for those who want to retire stress-free without relying on risky market-driven approaches. George is passionate about educating retirees on their income options, answering their questions, and separating fact from fiction. He believes the best benefit he provides to clients is a guaranteed retirement income that lets them sleep soundly at night.

Outside of the office, George enjoys golfing, biking, hiking, fly fishing, and boating. He is also deeply committed to supporting research for a cure for Type 1 Juvenile Diabetes, inspired by his daughter’s battle with the disease. To learn more about George, connect with him on LinkedIn.