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5 Roth Conversion Mistakes Retirees Make (And How to Avoid Them)

  • Will Snodgrass
  • 2 days ago
  • 4 min read

If you're approaching retirement with a traditional IRA or 401(k), you've probably heard someone say, "You should do a Roth conversion."

And they might be right. A Roth conversion — moving money from a tax-deferred account into a Roth IRA — can save you tens of thousands of dollars in taxes over your lifetime, reduce your Required Minimum Distributions (RMDs), and leave your heirs a tax-free inheritance.

But here's the problem: most people do it wrong.

As a CERTIFIED FINANCIAL PLANNER™ who works with Christian retirees every day, I've seen smart, faithful people make these five Roth conversion mistakes — and pay a heavy price. Here's what to watch for and how to get it right.

Mistake #1: Converting Too Much in One Year

This is the most common mistake I see. A retiree converts their entire $500,000 IRA to a Roth in a single year and gets hit with a massive tax bill — potentially pushing them into the 32% or even 35% bracket.

The fix: Spread your conversions over multiple years. The "sweet spot" is converting just enough each year to fill up your current tax bracket without spilling into the next one. For many retirees, that means converting $50,000–$100,000 per year during the "gap years" between retirement and age 73 (when RMDs begin). This is where having a plan matters. A Roth conversion isn't a one-time decision — it's a multi-year tax strategy.

Mistake #2: Forgetting About Medicare (IRMAA)

Here's the surprise no one warns you about: a large Roth conversion can increase your Medicare premiums.

Medicare uses your income from two years ago to determine your premium surcharges (called IRMAA — Income-Related Monthly Adjustment Amount). If your Roth conversion pushes your Modified Adjusted Gross Income above $206,000 (married filing jointly in 2026), you could pay an extra $1,000–$4,000+ per year in Medicare premiums.

The fix: Factor IRMAA thresholds into your conversion plan. Sometimes it's worth converting a little less to stay under the line — or timing conversions before you enroll in Medicare at 65.

Mistake #3: Paying the Tax from the Converted Funds

When you convert $100,000 from a traditional IRA to a Roth, you owe income tax on that $100,000. Many people pay the tax bill from the conversion itself — effectively converting only $75,000 and losing $25,000 to taxes.

The fix: Pay the tax from a separate account — a checking account, savings, or taxable brokerage account. This way, the full $100,000 goes into the Roth and grows tax-free for decades. That $25,000 difference, compounded over 20 years, could be worth $60,000 or more.

Think of it this way: the Parable of the Talents teaches us to put our resources to work wisely. Paying taxes from outside the conversion is how you maximize the talent you've been given.

Mistake #4: Not Considering State Taxes

Texas residents, you have an advantage here — Texas has no state income tax, so your Roth conversion is taxed at the federal level only.

But if you're moving to Texas from a high-tax state (California, New York, New Jersey), timing your conversion for after the move could save you 5%–13% in state taxes. Conversely, if you're planning to leave Texas for a state with income tax, converting before you move locks in the tax-free benefit.

The fix: Coordinate your Roth conversion strategy with any relocation plans. This is especially important for business owners selling a company and relocating in retirement.

Mistake #5: Doing It Without a Multi-Year Tax Projection

A Roth conversion affects your taxes this year, your Medicare premiums in two years, your RMDs starting at 73, your Social Security taxation, your estate plan, and your heirs' tax brackets. These are interconnected — you can't evaluate a conversion by looking at one year in isolation.

The fix: Work with an advisor who builds a multi-year tax projection — not just this year's return, but a 10–20 year model showing the impact on your total lifetime taxes, your spouse's survivor taxes, and your heirs' inheritance. This is exactly what we do at Matt25 Capital. We don't guess. We model it.

So, Should You Do a Roth Conversion?

For many Christian retirees in the 55–75 age range with $250,000 or more in retirement savings, the answer is yes — but only with a plan.

The right Roth conversion strategy could:

  • Save $50,000–$200,000+ in lifetime taxes (depending on your balances)

  • Reduce or eliminate RMDs that force you to take money you don't need

  • Leave your children and grandchildren a tax-free inheritance

  • Give you more flexibility to give generously to your church and causes you care about

The wrong strategy — or no strategy at all — could cost you just as much.

Your Next Step

Not sure where you stand? Take our free 20-Point Retirement Scorecard for Christians at matt25capital.com/scorecard. It takes about 2 minutes and gives you a clear picture of your retirement readiness — including whether a Roth conversion should be part of your plan.

Will Snodgrass, CFP®, is the founder of Matt25 Capital, a faith-based wealth management firm in The Woodlands, TX, serving Christian families approaching and in retirement.

This content is for educational purposes only and should not be considered investment, legal, or tax advice. Consult with your own tax professional before making any Roth conversion decisions. Dollar figures and tax savings referenced are hypothetical examples for illustration only and do not represent actual client results.

Securities and advisory services offered through Commonwealth Financial Network®, Member FINRA/SIPC, a Registered Investment Adviser. Fixed insurance products and services are separate from and not offered through Commonwealth Financial Network.

 
 
 

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