Roth Conversions: The Tax You Pay Today To Own Your Future
Photo by Kirill Lazarev
Estimated Read Time 5 Minutes
What if the biggest threat to your retirement is the IRS waiting for you at age 73?
Most people assume taxes will drop once they retire.
They dream of beach mornings, slow coffee, and lower tax brackets.
But here’s the truth we don’t say out loud:
If you’ve saved diligently in 401(k)s and IRAs, retirement doesn’t mean lower taxes.
It often means forced income through RMDs, Social Security taxation, and Medicare surcharges that quietly siphon away your freedom.
You did the hard work. You played the long game.
But the tax system has its own schedule… and it doesn’t care when you want to stop working.
The Shift
Enter the Roth conversion. Not as a technical strategy. Not as a tax trick.
But as a choice.
A choice to trade known taxes today for unknown taxes tomorrow.
A choice to control your income later instead of being controlled by RMDs, Congress, or Medicare formulas.
Think of it like moving your money from a noisy neighborhood (tax-deferred) into a quiet one where it will never be taxed again (Roth).
Yes, the move costs something.
But once you’re there, life is calmer. Predictable. Yours.
Why This Matters (More Than You Think)
Here’s what’s coming down the pike for many pre-retirees:
RMDs that push you into higher brackets, just when you thought your taxes were going down.
The 2026 “tax cliff,” where today’s lower rates are scheduled to vanish.
IRMAA surcharges: Medicare penalties for having “too much” income.
Social Security taxes triggered simply because you took money you were forced to take.
The government has a plan for your retirement income.
Roth conversions are how you write your own plan.
The Longevity Angle
At Longevity Wealth Strategies, we talk about wealthspan, which are the years you get to live with freedom, health, and purpose.
Roth conversions aren’t about paying more tax.
They’re about buying back those years.
Less taxable income later = Less stress later, Fewer government penalties later and More control later.
Roth conversions create:
Freedom
You choose when income shows up, not the IRS. Build a strategy that supports your life.
Resilience
Markets can drop. Congress can raise rates.
A Roth doesn’t care. If invested properly, it just compounds.
Legacy
Your heirs get tax-free dollars instead of inheriting a tax problem wrapped in a 10-year distribution rule.
Optionality
Retire earlier.
Delay Social Security longer.
Avoid IRMAA entirely.
Tap Roth funds tax-free when you need them most.
A Roth isn’t about today. It’s about giving your future self the widest possible runway for the life you want to live.
So… What Does a Smart Roth Conversion Strategy Look Like?
1. Use Your “Low-Income Window.”
The years between stopping work and starting RMDs, usually ages 55 to 73, are golden.
Income drops.
Opportunity rises.
That’s where the magic happens.
2. Fill (Don’t Spill) Your Tax Brackets.
Convert just enough to stay in the 22% or 24% bracket, without spilling into a higher one.
Precision beats guessing.
3. Fund Taxes with Cash, Not Your IRA.
Every dollar you use from the IRA to pay taxes is a dollar that stops compounding.
Let your Roth grow untouched. Forever.
4. Pay attention to IRMAA.
Cross the line by a single dollar and Medicare surcharges hit you for two full years.
Roth conversions are powerful, just don’t accidentally make them expensive.
5. Build a Conversion Ladder.
Convert in steps, not leaps.
A yearly rhythm.
A predictable plan.
A five-year clock for each step, unlocking tax-free access to principal… right when early retirees often need it.
6. Use Down Markets to Your Advantage.
If the market drops, convert while prices are low.
It’s the one time taxes go “on sale.”
And If You Want to Retire Early…
A Roth ladder becomes your bridge.
Each conversion becomes accessible penalty-free after five years, long before Social Security arrives.
Your freedom date moves closer, not farther away.
The Heart of It
Roth conversions are not about the IRS.
They’re about agency.
About reclaiming control in a system designed to take it away.
About shrinking future tax bills so your wealth funds life, not government obligations.
About building a retirement that breathes, without surprise income spikes or forced withdrawals.
Your Next Step
Start now.
Not when the tax bill hits.
Not when the TCJA sunsets in 2026.
Not when RMDs show up like an unexpected houseguest.
Now, while you have the most choice, the most leverage, and the most to gain.
Run the numbers.
Map the brackets.
Build the ladder.
Write your next chapter with intention, not inertia.
Longevity isn’t just living longer. It’s living better.
A smart Roth conversion strategy is one of the most powerful ways to make that happen.
Interested to see how you could benefit you? Setup a Wealthspan Review™.
Your Next Step
Schedule Your Wealthspan Review™Disclaimer: The information provided in the linked resources is for educational purposes only and does not constitute investment, tax, or financial advice. Consult with a licensed professional before making any financial decisions.
