My CPA Laughed at My Roth Conversion—Until He Ran the Math
When I told my CPA I was planning a six-figure Roth conversion, he didn’t even hide the smirk.
“You want to pay more taxes on purpose?”
I get it. On the surface, it sounds insane.
But when he ran the numbers—real numbers, not gut feelings—that smirk disappeared.
And by the time he was done?
He told me I should’ve done it sooner.
Let me back up.
The Problem With “Later”
For most of my working life, I did what you’re supposed to do:
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Max out the 401(k)
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Get the employer match
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Defer, defer, defer
The logic was simple: Save taxes now, deal with them later.
But here’s what no one talks about:
“Later” often means more taxes, not less.
Once I retire, I’ll have:
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Required Minimum Distributions (RMDs)
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Social Security income
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Possibly rental income
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No big deductions
And all that income stacks on top of each other, pushing me into a higher tax bracket. Suddenly, that “tax-deferred” account becomes a tax time bomb.
So I asked myself a simple question:
What if I could pre-pay taxes at a lower rate today… and never owe taxes again on that money?
That’s when I started looking into Roth conversions.
The Math My CPA Didn’t Expect
Here’s what I brought to our meeting:
Current taxable income: $65,000
Available space in 24% tax bracket: ~$80,000
IRA balance: $450,000
Conversion plan: Move ~$70K/year from IRA → Roth IRA over 5 years
His immediate reaction?
“You want to give the IRS over $16,000 this year… for fun?”
I didn’t argue. I just asked him to run a side-by-side projection:
Scenario A – Do nothing
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RMDs at age 73 = ~$43,000/year
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Taxable Social Security + RMDs push me into a higher bracket
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Total lifetime taxes (projected): ~$290,000
Scenario B – Roth conversion strategy now
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Pay ~$17K/year in conversion taxes (total ~$85K)
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Shrink RMDs to almost zero
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Tax-free growth + no RMD headaches
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Total lifetime taxes (projected): ~$180,000
He stared at the spreadsheet. Looked up.
“Okay… wow.”
What He Missed (And Most People Do Too)
This isn’t about being clever. It’s about seeing the whole board.
Most people only focus on their taxes this year.
They never ask: “What’s my tax burden over the next 30 years?”
Here’s what the Roth conversion gave me:
✅ Tax-free growth for life
✅ No RMDs
✅ More control over my retirement income
✅ Lower taxes on Social Security
✅ Zero taxes for heirs (if I don’t spend it)
In short, I’m buying optionality.
And yes, that comes with a tax bill up front. But it’s a bill I want to pay—on my terms.
The “Ah-Ha” Moment
The real kicker for my CPA was the flexibility it gave me.
When you have all your money in traditional accounts, the government controls the timing.
They force withdrawals.
They set the rules.
They change the rules (and probably will again).
With a Roth, I can take money when I want—or not at all.
And here’s the wild part: The Roth conversion didn’t even push me into a brutal tax bracket. We were strategic. We “filled up” my current bracket but didn’t go higher.
We even used some tax-loss harvesting to offset the tax hit further.
A Few Lessons I Learned the Hard Way
If you’re even thinking about a Roth conversion, here are a few things I wish I knew earlier:
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Do it during your “gap years”
The sweet spot is after you stop working but before you take Social Security. That’s your low-income window. -
Watch out for IRMAA
Medicare surcharges kick in if your income crosses certain thresholds. Roth conversions can trigger them. -
State taxes matter
Live in a high-tax state now but plan to retire in a no-tax state? Maybe wait. Or plan around it. -
You don’t have to convert everything
Even small conversions now can save big later. -
Run the numbers, not the feelings
Your gut will say “don’t pay taxes early.” Your spreadsheet might say otherwise.
Want to see the spreadsheet I used?
Or have questions about how I figured out the right amount to convert?
Happy to share what I did. Just ask👇
