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Home / Roth Conversions
Grow tax-free, protect what you've built, and take control of your retirement taxes — with simple, safe strategies designed around your goals.
A Roth conversion allows you to move money from a tax-deferred account — such as a traditional IRA, old 401(k), or other qualified plan — into a Roth IRA. You pay income taxes on the amount you convert today in exchange for long-term benefits that can significantly improve your retirement plan.
Instead of hoping tax rates stay low in the future, a Roth conversion lets you pre-pay taxes now at known rates and shift more of your retirement income into the tax-free column — giving you more control and greater long-term predictability.
Most advisors offer only one way to do a Roth conversion. We offer many — all designed to be simple, safe, tax-smart, and completely transparent.
Our Mirror Roth Conversion Strategy uses one annuity contract that holds your traditional (pre-tax) dollars and allows you to convert part or all of the balance into a mirrored Roth side over time. You choose how much to convert each year—partial or full—so you can build tax-free retirement income without market risk, confusion, or new surrender charges.
Moved into annuity structure
Within the same annuity
Same allocations, no added fees
Both accounts exist within the same annuity structure. When you convert funds from the traditional side to the Roth side, you pay taxes on that converted amount. Once converted, that money grows tax-free in the Roth account. Both accounts receive the same benefits from the annuity's allocations—whether indexed or fixed rates. There's no market risk or downside in either account, and importantly, there are no new surrender fees when you convert between the two mirrored accounts. You control the timing and amount of each conversion, staying in your optimal tax bracket each year.
Adjust the numbers below to see a rough estimate of your long-term tax savings when converting part of your IRA or 401(k) to a Roth IRA.
Assumes you pay conversion taxes with outside funds so the full amount can grow tax-free.
After setting up your two-account mirrored system, you can choose to convert everything at once, or move smaller portions each year. Each method offers unique advantages depending on your tax bracket, goals, and timeline.
Convert everything at once
Best for: Those with large cash reserves to pay conversion taxes, or those in temporarily low-income years
Convert gradually over time
Best for: Most retirees who want to minimize annual tax impact while systematically building tax-free wealth
The Mirror Strategy supports both approaches. You can convert everything at once, move funds gradually over 5-10 years, or adjust your strategy year-by-year based on your income, tax bracket, and retirement goals.
The right Roth conversion strategy can dramatically improve long-term tax outcomes. Here are the planning approaches we use most often — designed to be simple, strategic, and tax-efficient.
Converting smaller amounts over several years prevents you from jumping into higher tax brackets — making each conversion more efficient.
Ideal for retirees not yet taking Social Security or RMDs. We "fill up" your current bracket without crossing into a higher one.
Converting when markets are temporarily lower reduces your tax bill — letting recovery happen tax-free inside the Roth.
Beneficiaries face strict 10-year distribution rules. Strategic conversions can reduce their tax burden and leave a more efficient legacy.
We schedule conversions to avoid unnecessary spikes in Social Security taxation or Medicare IRMAA premiums.
Every situation is different — but when used correctly, these strategies can reduce lifetime taxes, increase your flexibility in retirement, and strengthen the legacy you leave behind.
Many people assume their Traditional IRA is worth the number they see on the statement — but they forget the IRS owns a portion of it. Tax rates change, RMDs increase income, and anything left to your heirs is fully taxable.
By waiting, you've lost control over when and how those taxes are paid. Future tax increases, RMD impacts, and a forced 10-year distribution rule for beneficiaries can all reduce the value of your retirement savings.
One of the biggest misunderstandings people have about Roth conversions is how the money moves. Many assume there are fees, penalties, or risks. Good news — that's not the case.
Your funds move directly from your current custodian to the new Roth account — you never take possession of the money.
There is no cost to transfer or convert your funds. This is an IRS-approved process that avoids penalties when done correctly.
A transfer is not a taxable event. Only the amount you choose to convert becomes taxable — and you control that amount.
You decide how much to convert and when to convert it, whether all at once or gradually over time.
Our team at O'Rourke Life & Retirement helps complete all transfer and conversion forms quickly and accurately.
This process is simple, safe, and efficient. Most clients are surprised at how easy it is once we guide them through it — with zero cost, zero hassle, and no disruption to their accounts.
Most Roth conversion strategies involve market risk, unpredictable fees, or unnecessary complexity. Our approach is built for safety, clarity, and long-term tax efficiency — without the losses or fees tied to typical brokerage-based conversions.
Your conversion dollars are protected from market downturns — a major advantage over stock-based Roth accounts.
Unlike RIAs or brokerages, we don't charge portfolio management fees. Every dollar stays in your account working for you.
Your Roth grows with fixed or indexed strategies, not speculative markets.
Move funds all at once or gradually — without fear of losses interrupting your plan.
Some of our Roth conversion solutions offer upfront bonuses, giving you more value on day one.
No confusion, no jargon, no complicated investment reports. Just clean, easy tax-smart planning.
O'Rourke Life & Retirement's goal is to give you a safer, simpler, and more predictable Roth conversion experience — one that protects your hard-earned retirement money while maximizing long-term tax-free growth.
A successful Roth conversion isn't about converting everything at once — it's about converting the right amount each year so you stay in your preferred tax bracket and avoid triggering costly Medicare premium increases.
IRMAA stands for Income-Related Monthly Adjustment Amount — it's an additional charge added to your Medicare premiums if your income exceeds certain thresholds.
If you convert too much in one year, your modified adjusted gross income (MAGI) can spike, triggering IRMAA surcharges that can add thousands of dollars to your annual Medicare costs.
📊 Bottom Line: Strategic planning reduces taxes, avoids surcharges, and protects income.
Depending on your goals, you can choose a Roth conversion strategy with an upfront bonus or a clean non-bonus structure.
We compare both choices side-by-side so you can make a confident, informed decision.
These rules are often misunderstood, but they're simple once explained clearly — and they shouldn't stop you from completing a Roth conversion when it's the right strategy for your tax future.
Each Roth conversion—whether partial or full—starts its own 5-year clock, and the IRS treats that clock as beginning on January 1 of the same tax year the conversion is made (even if the conversion happens later in the year). Your converted principal is always income-tax-free after conversion but may incur a 10% penalty if withdrawn within its 5-year window and before age 59½. Roth earnings become tax-free only after you are 59½ and your first Roth account has been open at least five tax years.
Heirs must empty the entire Traditional IRA within 10 years, and all withdrawals are fully taxable. This forces large taxable distributions during their peak earning years, potentially pushing them into a higher tax bracket.
Heirs still must withdraw within 10 years, BUT all withdrawals are 100% tax-free. They keep the full value without any tax burden, as long as the original owner’s Roth met the 5-year rule before death.
We structure your conversions so your funds grow tax-free and the timing aligns with your retirement goals. You stay in control, avoid surprises, and maintain simplicity in your plan while protecting your family from harsh tax consequences.
A Roth conversion isn't just a tax strategy — it's a family strategy. By converting now, you remove future tax uncertainty and leave your loved ones a more valuable, tax-free asset that's easier to manage and inherit.
When you pass away, your retirement accounts become part of your legacy. Here's why a Roth IRA is dramatically better for your heirs than a Traditional IRA:
Once funds are converted into your Roth structure, you have the option to turn a portion — or all — of your Roth balance into predictable, tax-free retirement income. This can create long-term financial security without relying on market performance or portfolio withdrawals.
Interested in turning your Roth into guaranteed tax-free income? Let's discuss how this strategy fits your retirement goals and timeline.
Get a simple comparison of full vs. partial conversion strategies, tax impacts, and long-term benefits — customized to your goals.
Compare My Roth Options
Let’s design a simple, safe, and tax-smart Roth Conversion Strategy tailored to your goals, income, tax bracket, and retirement timeline. No market risk, no fees, and no complicated jargon — just clear guidance and a personalized plan.
We do not provide tax or legal advice. Consult your tax professional for details specific to your situation.
O'Rourke Life & Retirement and Greg O'Rourke do not provide tax, legal, or investment advice. The information presented on this page is for educational purposes only and should not be construed as personalized tax or legal guidance. We strongly recommend consulting with a qualified tax professional, CPA, or tax attorney before making any Roth conversion decisions. Tax laws are complex and subject to change.
The Roth conversion strategies discussed involve insurance-based products such as fixed annuities and fixed indexed annuities. These products are not securities and are not regulated by the SEC or FINRA. Insurance products are backed by the financial strength and claims-paying ability of the issuing insurance company.
O'Rourke Life & Retirement is not a registered investment adviser (RIA) and does not provide securities brokerage services, investment advisory services, or portfolio management. We specialize exclusively in insurance-based retirement solutions including fixed annuities, fixed indexed annuities, and life insurance products. We work only with guaranteed fixed index products with no market loss or downside exposure. We charge no fees, and our services are always 100% free to our clients.
Greg O'Rourke — National Producer Number (NPN): 21340769.
O'Rourke Life & Retirement is not connected with or endorsed by the U.S. government, the federal Medicare program, or any federal or state agency. Information related to Medicare and IRMAA (Income-Related Monthly Adjustment Amount) is for educational purposes only.
Any illustrations or projections on this page are hypothetical and for educational purposes only. They are not guarantees of future performance. Actual tax savings, growth rates, and outcomes will vary depending on your tax situation, timing, market conditions, carrier performance, and changes in tax law.
The strategies and products described on this page may not be suitable for everyone. Suitability depends on your unique financial situation, goals, risk tolerance, and time horizon. A personalized consultation is required to determine whether a Roth conversion strategy is appropriate for you.
Helping you protect your retirement with clear, independent guidance — from a licensed professional team that you can trust!
© 2025 O’Rourke Life & Retirement. All rights reserved. Specializing in fixed annuities, life & health insurance solutions. We are not a registered investment adviser or securities broker-dealer and do not provide investment, tax, or legal advice. Insurance products offered by Greg O’Rourke, Licensed Insurance Agent & Financial Professional. Not connected with or endorsed by the U.S. government, Medicare, or the Federal Marketplace. Licenses: FL #G166831 | National Producer #21340769 | Multi-State Licensed Agent
